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Sample records for anthracene

  1. Growth of rhodococcus S1 on anthracene.

    Science.gov (United States)

    Tongpim, S; Pickard, M A

    1996-03-01

    Three slow-growing bacteria were isolated from a mixed culture enriched for growth on anthracene, using creosote-contaminated soil as the inoculum. Organisms were shown to use anthracene by the production of a clear zone around the colony after a mineral salts agar plate was sprayed with anthracene. All three bacteria were nonmotile, nonsporulating, gram-positive rods and stained acid-fast. Physiological and biochemical tests, GC content, and cell wall lipid patterns of whole cell methanolysates indicated that they belonged to the Nocardia-Mycobacterium-Rhodococcus group. On the basis of these characteristics and pyrolysis gas chromatography, they were assigned to the genus Rhodococcus. Growth of the isolates was slow on crystalline anthracene, giving a doubling time of 1.5-3 days, and they grew mainly on the crystal surface. When anthracene was supplied by precipitation from a solvent, doubling time was reduced to 1 day. All three isolates mineralized anthracene but not phenanthrene or naphthalene, nor could they grow on naphthalene, phenanthrene, fluorene, fluoranthene, acenaphthene, pyrene, chrysene, or naphthacene as sole carbon source. One isolate, Rhodococcus S1, was able to use 2-methylanthracene or 2-chloroanthracene as carbon source but not 1- or 9-substituted analogs. These results suggest that the initial enzyme attacking anthracene in these isolates has a narrow substrate specificity. PMID:8868237

  2. (Anthracen-9-yl(piperidin-1-ylmethanone

    Directory of Open Access Journals (Sweden)

    Hua-You Hu

    2008-11-01

    Full Text Available The title compound, C20H19NO, is a substructure of CP-640186, a potent inhibitor of mammalian acetyl-coenzyme A carboxylases. In the crystal structure, the amide group forms a dihedral angle of 87.0 (1° with the plane of the anthracene unit and the piperidine ring adopts a chair conformation. Molecules are arranged into layers parallel to (100 and adjacent anthracene units within layers form dihedral angles of 13.2 (1°. C—H...O interactions from the piperidine rings to the C=O group of the amide are observed between layers.

  3. o-Carborane-based anthracene: a variety of emission behaviors.

    Science.gov (United States)

    Naito, Hirofumi; Morisaki, Yasuhiro; Chujo, Yoshiki

    2015-04-20

    An o-carborane-based anthracene was synthesized, and single crystals, with incorporated solvent molecules, were obtained from the CHCl3 , CH2 Cl2 , and C6 H6 solutions. The anthracene ring in the crystal is highly distorted by the formation of a π-stacked dimer between the anthracene units. The crystals exhibited a variety of emission behaviors such as aggregation-induced emission (AIE), crystallization-induced emission (CIE), aggregation-caused quenching (ACQ), and multichromism. PMID:25729004

  4. Thermal and Optoelectronic Properties of Anthracene and Dibenz[a,c]Anthracene

    Institute of Scientific and Technical Information of China (English)

    MUDDASIR Hanif; WANG Zhi-ming; YANG Bing; LU Ping; MA Yu-guang

    2013-01-01

    The basic characteristics of anthracene(AN) and dibenz[a,c]anthracene(D[a,c]A) derivatives,important semiconductors,were systematically studied.Differential scanning calorimetry(DSC) shows that D[a,c]A has the reversibility of solid and liquid phases.Thermalgravimetric analysis(TGA) shows that D[a,c]A exhibits higher Td(decomposition temperature),which indicates D[a,c]A,as active layers,should be more suitable to being made into stable devices.D[a,c]A shows blue-shifted UV-Vis absorption and emission despite increased conjugation compared to anthracene due to different symmetries.Both the compounds are planar and show weak blue fluorescence in the tetrahydrofuran(THF) solution and higher fluorescence in the solid-state,due to different energy levels in solution and solid-state,explained via Jablonski diagram.

  5. Anthracene dosimeter characterization under radiotherapy photons

    International Nuclear Information System (INIS)

    New radiotherapy techniques such as intensity-modulated radiation therapy and stereotactic radiosurgery have increased the need for dosimeters that can provide measurements in real time with high spatial resolution. Organic scintillation dosimeters are able to measure with accuracy small radiation fields and fields with high gradients, besides having advantages such as water and soft tissue equivalence and the possibility to be used in vivo. Anthracene is an organic scintillator crystal with the highest known scintillation efficiency among organic scintillation materials. The objective of this work is to characterize the anthracene as a dosimeter under radiotherapy photons energies, analysing its signal against average granulosity, intern capsule diameter, absorbed dose, absorbed dose rate, photon energy and its spatial resolution; with the last one analysed under three methods (edge spread function, line spread function and modulation transfer function). The photons energies used were 1.25 MeV (60Co), 0.661 MeV (137Cs) and X-rays (effective energies of 28.4; 46.5; 48.5; 94.0 e 106.0 keV). The scintillation detection system consisted of an optical fiber with one end attached to the anthracene capsule and the other to a photomultiplier tube maintained by power supply followed by an electrometer. Once Cerenkov radiation occurs in the optical fiber, it was removed from the total scintillation signal trough the subtraction of the signal, taken irradiating the optical fiber without the anthracene attached to one of its extremity. From results obtained, one can infer that the dosimeter signal increases proportionally with average granulosity and intern capsule diameter. The signal is linearly dependent of absorbed dose, linearly dependent of low photons energies and independent for high photons energies, as well as independent of the absorbed dose rate. From the spatial resolution values obtained it was possible to infer that the one obtained through modulation transfer

  6. Anthracen-9-ylmethylene-(3,4-dimethylisoxazol-5-ylamine

    Directory of Open Access Journals (Sweden)

    Abdullah M. Asiri

    2011-09-01

    Full Text Available The title compound, anthracen-9-ylmethylene-(3,4-dimethylisoxazol-5-ylamine (3, was synthesized in high yield by reaction of anthracene-9-carbaldehyde and 5-amino-3,4-dimethyl­isoxazole in ethanol. The structure of this new compound was confirmed by elemental analysis, IR, 1H NMR, 13C NMR and GC-MS spectral analysis.

  7. Diels-Alder reactions of anthracenes with C-sulfonyldithioformates

    DEFF Research Database (Denmark)

    El-Sayed, I.; Ali, O.M.; Fischer, A.;

    2003-01-01

    C-Sulfonyldithioformates (2) (R-1 = ArSO2, R 2 = ArS) readily add to anthracene and 9-methylanthracene (1) in a Diels-Alder fashion with formation of 9,10-dihydro-10,9-(epithiomethano)anthracenes (3) which in turn may suffer thermally induced elimination of arenesulfinic acid to yield the 9...

  8. Reversible Triplet Energy Transfer between Neo- Alloocimene and Anthracene

    DEFF Research Database (Denmark)

    Gorman, A. A.; Hamblett, I.; Jensen, Niels-Henrik

    1984-01-01

    The rate constants for triplet energy transfer between neo-alloocimene and anthracene have been redetermined by a combination of pulsed laser photolysi......The rate constants for triplet energy transfer between neo-alloocimene and anthracene have been redetermined by a combination of pulsed laser photolysi...

  9. Combined Phytotoxicity of Fluorene, Fluoranthrene or Phenanthrene in Anthracene-Contaminated Soil to Crop Seedling Growth

    Directory of Open Access Journals (Sweden)

    Khanitta SOMTRAKOON

    2014-08-01

    Full Text Available The phytotoxicity of different combinations of phenanthrene, fluorene, and fluoranthrene in anthracene-contaminated soil to seedling growth was studied. Seeds of sticky rice and water morning glory were planted in soil contaminated, with anthracene alone, a mixture of anthracene with each polycyclic aromatic hydrocarbon (PAH, and various combinations of PAHs. The results showed that anthracene + fluorene and anthracene + fluoranthene were more toxic to the growth of sticky rice seedlings than anthracene alone or anthracene + phenanthrene. However, all combinations of anthracene with other PAHs were toxic to water morning glory seedlings. When there were 3 - 4 PAHs present together, anthracene + fluoranthene + fluorene was the most toxic combination for shoot length, root length, and fresh weight of both plants, but not for dry weight. Responses of dicot and monocot to the toxicity of PAH co-contamination were different when anthracene was present alone or with other PAHs.

  10. Assessing Anthracene and Arsenic Contamination within Buffalo River Sediments

    OpenAIRE

    Adrian Gawedzki; K. Wayne Forsythe

    2012-01-01

    Anthracene and arsenic contamination concentrations at various depths in the Buffalo River were analyzed in this study. Anthracene is known to cause damage to human skin and arsenic has been linked to lung and liver cancer. The Buffalo River is labelled as an Area of Concern defined by the Great Lakes Water Quality Agreement between Canada and the United States. It has a long history of industrial activity located in its near vicinity that has contributed to its pollution. An ordinary kriging...

  11. Interaction Mechanism of Anthracene with Benzoic Acid and Its Derivatives

    Institute of Scientific and Technical Information of China (English)

    HE Ying-Ying; WANG Xiao-Chang; FAN Xiao-Yuan; ZHAO Bo; JIN Peng-Kang

    2008-01-01

    Interaction mechanism of anthracene, one of the typical polycyclic aromatic hydrocarbons, with benzoic acid and its hydroxyl-substituted derivatives, o-hydroxylbenzoic acid and p-hydroxylbenzoic acid, were studied using FFIR, UV and fluorescence spectra. The experiments confirmed that there was a specific and oriented interaction between anthracene and the aromatic carboxylic acids, and the bonding mode depended on both the chemical struc- ture of reactants and acidity of solution. The π-H hydrogen bond played a main role in the interaction between an-thracene and the aromatic carboxylic proton of benzoic acid or o-hydroxylbenzoic acid when pH≤pK, and the π-π electron donor-acceptor (EDA) interaction increasingly became the main binding mode when pH>pK. The de-crease of interaction intensity of benzoic acid was observed by introducing hydroxyl at its ortho position. The spe-cial D-π-A structure of p-hydroxylbenzoic acid made it easy to form the planar multi-molecule congeries that could interact with anthracene, so the interaction between anthracene and p-hydroxylbenzoic acid always followed the π-π EDA model no matter the solution acidity. For p-hydroxylbenzoic acid, the π-π interaction mode remained un-changed when pH increased from 2.0 to 10.0, and the binding intensity was higher than that between benzoic acid and anthracene because of the formation of the multi-molecule congeries.

  12. The structure of anthracene-d10 at 16 K using neutron diffraction

    International Nuclear Information System (INIS)

    The crystal structure of anthracene-d10 at 16 K has been refined using neutron diffraction measurements [C14D10, P21/a, a = 8.37(3), b = 6.00(2), c = 11.12(4) A, β = 125.4(1)0]. Using 1105 structure factors, an R factor of 6.0% was obtained, which reduced to 3.2% when a simple one-parameter correction was made for multiple Bragg scattering, although this correction is not correlated to the crystal structure results. Constrained refinements have also been carried out which indicate significant distortions in the crystalline state from the free-molecule symmetry of mmm. The thermal-parameter analysis shows that the T tensor is reduced most on reducing the temperature from 298 to 16 K, whereas the thermal motion of the D nuclei is hardly affected. A comparison with the room-temperature result confirms the accuracy of the molecular-geometry measurement, and shows a molecular reorientation of over 10 between 16 and 298 K. (Auth.)

  13. Assessing Anthracene and Arsenic Contamination within Buffalo River Sediments

    Directory of Open Access Journals (Sweden)

    Adrian Gawedzki

    2012-01-01

    Full Text Available Anthracene and arsenic contamination concentrations at various depths in the Buffalo River were analyzed in this study. Anthracene is known to cause damage to human skin and arsenic has been linked to lung and liver cancer. The Buffalo River is labelled as an Area of Concern defined by the Great Lakes Water Quality Agreement between Canada and the United States. It has a long history of industrial activity located in its near vicinity that has contributed to its pollution. An ordinary kriging spatial interpolation technique was used to calculate estimates between sample locations for anthracene and arsenic at various depths. The results show that both anthracene and arsenic surface sediment (0–30 cm is less contaminated than all subsurface depths. There is variability of pollution within the different subsurface levels (30–60 cm, 60–90 cm, 90–120 cm, 120–150 cm and along the river course, but major clusters are identified throughout all depths for both anthracene and arsenic.

  14. Isothiouronium Salts Based on Anthracene and Pyrene as Anion Sensors

    Energy Technology Data Exchange (ETDEWEB)

    Nguyen, Quynh Pham Bao; Kim, Taek Hyeon [Chonnam National Univ., Gwangju (Korea, Republic of)

    2010-03-15

    In summary, we prepared anthracene-bisisothiouronium and pyrene-isothiouronium salts as anion chemosensors, which showed significant fluorescence enhancement upon the addition of fluoride, acetate and dihydrogen phosphate, even in an aqueous medium. Due to the isomerism that occurred, the two isomers of the anthracene-bisisothiouronium salt bound the fluoride anion in equilibrium, while the two isomers of the pyrene-isothiouronium salt bound the fluoride anion in parallel. Organic sensors have attracted much attention due to their many possible applications in analytical and biomedical research. Therefore, a variety of synthetic receptors for anions have been reported. Among them, thiourea receptors have been thoroughly exploited in the field of molecular recognition, due to their binding of anions through hydrogen bonding. The use of isothiouronium groups has not been explored very much in the area of anion binding. Such groups can enhance the acidity of the NH moieties, thereby functioning as a better binder compared to the thiourea group. However, in some cases, the investigation of the anion sensing properties of isothiouronium receptors was complicated by the presence of isomerism. In a previous report, the isomerism of anthracene-isothiouronium salts was detected at room temperature. Herein, we wish to report the isomerism of different isothiouronium structures, viz. anthracene-bisisothiouronium and pyrene-isothiouronium salts. The anion sensing properties of these structures was also examined.

  15. Excited state kinetics of anthracene-bridge-aniline intramolecular exciplexes

    DEFF Research Database (Denmark)

    Thyrhaug, Erling; Hammershøj, Peter; Kjær, Kasper Skov;

    2014-01-01

    We report on the synthesis and characterization of fluorescent halogen substituted anthracene-bridge-aniline (ABA) supermolecules that undergo structural reorganization on photoexcitation to form transient complexes. The syntheses were achieved in high yields on a large scale and the molecular st...

  16. Anthracene clusters and the interstellar infrared emission features

    International Nuclear Information System (INIS)

    The unidentified infrared bands are ubiquitous in the interstellar medium and typically attributed to emission from neutral and ionized polycyclic aromatic hydrocarbons (or PAHs). The contribution of neutral PAH clusters to these bands has been impossible to determine due to a paucity of infrared spectral data. Here we investigated neutral clusters of the three-ring PAH anthracene using FTIR absorption spectroscopy of anthracene matrix-isolated at varying concentrations in solid argon. In order to determine likely cluster structures of the embedded molecules, we also calculated theoretical absorption spectra for the anthracene monomer through hexamer using density functional theory with a dispersion correction (DFT-D). The DFT-D calculations have been calibrated for the anthracene dimer using the second-order Møller-Plesset approach. Because there is some support for the hypothesis that three or four-ring PAHs are present in the Red Rectangle nebula, we discuss the application of our results to this nebula in particular as well as to the interstellar infrared emission in general.

  17. Anthracene Fluorescence Quenching by a Tetrakis (Ketocarboxamide Cavitand

    Directory of Open Access Journals (Sweden)

    Tibor Zoltan Janosi

    2014-01-01

    Full Text Available Quenching of both fluorescence lifetime and fluorescence intensity of anthracene was investigated in the presence of a newly derived tetrakis (ketocarboxamide cavitand at various concentrations. Time-correlated single photon counting method was applied for the lifetime measurements. A clear correlation between the fluorescence lifetime of anthracene as a function of cavitand concentration in dimethylformamide solution was observed. The bimolecular collisional quenching constant was derived from the decrease of lifetime. Fluorescence intensity was measured in the emission wavelength region around 400 nm as a result of excitation at 280 nm. Effective quenching was observed in the presence of the cavitand. The obtained Stern-Volmer plot displayed upward curvature. The results did not follow even extended Stern-Volmer behavior, often used to describe deviations from static bimolecular quenching. To explain our results we adopted the Smoluchowski model and obtained a reasonable estimate for the molecular radius of the cavitand in solution.

  18. 1-(Anthracen-1-ylpyrrolidine-2,5-dione

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    Sanaz Khorasani

    2012-05-01

    Full Text Available In the molecular structure of title compound, C18H13NO2, the succinimide ring is orientated away from the plane of the anthracene moiety by 71.94 (4°. The crystal structure features three different types of intermolecular interactions, viz. C—H...O, C—H...π and π–π bonds. Molecules along the b axis stack on each other as a result of π–π interactions which have a centroid–centroid distance of 3.6780 (15 Å, while C—H...π interactions are present between neigbouring stacks. Also, acting between the stacks are the C—H...O interactions between the aromatic H atoms of the anthracene and the O atoms of the succinimide.

  19. (E-4-[(4-Nitrophenyldiazenyl]phenyl anthracene-9-carboxylate

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    François Léonard

    2008-12-01

    Full Text Available In the title compound, C27H17N3O4, the azo group displays a trans conformation and the dihedral angles between the central benzene ring and the pendant anthracene and nitrobenzene rings are 82.94 (7 and 7.30 (9°, respectively. In the crystal structure, weak C—H...O hydrogen bonds, likely associated with a dipole moment present on the molecule, help to consolidate the packing.

  20. The Use of Demulsifiers for Separating Water from Anthracene Oil

    OpenAIRE

    Zečević, N.

    2008-01-01

    The main feedstocks for the production of oil-furnace carbon black are different kinds of liquid hydrocarbons. The quality and utilization of oil-furnace carbon black mainly depends on the type of liquid hydrocarbons contained in the oil feedstocks.In practice, both carbochemical and petrochemical oils are used as feedstock sources. Carbochemical oils are fractions obtained during coal tar distillation. Anthracene oil is one of these oils. Depending on the conditions of distillation, coal tar...

  1. Density Functional Studies of Molecular Polarizabilities. 7. Anthracene and Phenanthrene

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    Humberto J. Soscun Machado

    2000-03-01

    Full Text Available We report accurate Ab Initio studies of the static dipole polarizabilities of anthracene and phenanthrene. Geometries were optimized at the HF/6-311G(3d,2p level of theory. Dipole polarizabilities were calculated at the HF/6-311++G(3d,2p and BLYP/6-311++G(3d,2p levels of theory, using HF/6-311G(3d,2p geometries. The calculated dipole polarizabilities for anthracene are compared with experiment. Inclusion of electron correlation using the BLYP procedure increases the L and M components of the dipole polarizability, but not the perpendicular (N component. Examination of corresponding BLYP results for the polyacene series benzene, naphthalene and anthracene shows that the normal component of the dipole polarizability scales linearly with the number of benzene ring units, with an increment of 20.8 au. The medium component also scales linearly with an increment of 42.8 atomic units. The long component does not scale linearly. Semi-emiprical AM1 calculations are also given for comparison; the normal component of the dipole polarizability tensor is poorly represented by such calculations.

  2. Photocatalytic Degradation of Anthracene in Closed System Reactor

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    Faiq F. Karam

    2014-01-01

    Full Text Available Polycyclic aromatic hydrocarbons (PAHs represent a large class of persistent organic pollutants in an environment of special concern because they have carcinogenic and mutagenic activity. In this paper, we focus on and discuss the effect of different parameters, for instance, initial concentration of Anthracene, temperature, and light intensity, on the degradation rate. These parameters were adjusted at pH 6.8 in the presence of the semiconductor materials (TiO2 as photocatalysts over UV light. The main product of Anthracene photodegradation is 9,10-Anthraquinone which isidentified and compared with the standard compound by GC-MS. Our results indicate that the optimum conditions for the best rate of degradation are 25 ppm concentration of Anthracene, regulating the reaction vessel at 308.15 K and 2.5 mW/cm2 of light intensity at 175 mg/100 mL of titanium dioxide (P25.

  3. Biodegradation of naphthalene and anthracene by chemo-tactically active rhizobacteria of populus deltoides

    OpenAIRE

    Sandeep Bisht; Piyush Pandey; Anchal Sood; Shivesh Sharma; Bisht, N. S.

    2010-01-01

    Several naphthalene and anthracene degrading bacteria were isolated from rhizosphere of Populus deltoides, which were growing in non-contaminated soil. Among these, four isolates, i.e. Kurthia sp., Micrococcus varians, Deinococcus radiodurans and Bacillus circulans utilized chrysene, benzene, toluene and xylene, in addition to anthracene and naphthalene. Kurthia sp and B. circulans showed positive chemotactic response for naphthalene and anthracene. The mean growth rate constant (K) of isolat...

  4. The effects of anthracene and methylated anthracenes on gap junctional intercellular communication in rat liver epithelial cells.

    Science.gov (United States)

    Upham, B L; Weis, L M; Rummel, A M; Masten, S J; Trosko, J E

    1996-12-01

    Polycyclic aromatic hydrocarbons (PAHs), many of which are known carcinogens, are derived from the pyrolysis of organic materials. A rich source of PAHs is cigarette smoke, which contains methylated anthracenes and phenanthrenes as the predominant PAHs. The tumor-promoting activity of cigarette smoke has been well documented. The down-regulation of gap junction intercellular communication (GJIC) by nongenotoxic chemicals and several oncogenes has been implicated in tumor promotion. Therefore, we determined the effects of the three isomers of methylanthracene on GJIC in WB-F344 rat liver epithelial cells. Anthracene and 2-methylanthracene did not significantly inhibit GJIC, whereas anthracene methylated in the 1 or 9 position reversibly inhibited GJIC with I50 values of 22 and 36 microM, respectively. Inhibition occurred within 15 min. In conclusion, the biological effect of methylanthracene depends on the ring position of the methyl group, and these inhibitory isomers could play a potential role in tumor promotion of methylated PAH-rich mixtures such as cigarette smoke and crude oil products. PMID:8954755

  5. The Use of Demulsifiers for Separating Water from Anthracene Oil

    Directory of Open Access Journals (Sweden)

    Zečević, N.

    2008-03-01

    Full Text Available The main feedstocks for the production of oil-furnace carbon black are different kinds of liquid hydrocarbons. The quality and utilization of oil-furnace carbon black mainly depends on the type of liquid hydrocarbons contained in the oil feedstocks.In practice, both carbochemical and petrochemical oils are used as feedstock sources. Carbochemical oils are fractions obtained during coal tar distillation. Anthracene oil is one of these oils. Depending on the conditions of distillation, coal tars contain up to w = 18·10 –2 highly aromatic fractions, which can be used as carbon black feedstock. The sulphur fraction of these oils can vary between w = 0.5 and 0.7·10 –2, depending on the origin of the coal. The availability of carbochemical oils obtained from coal tar is largely dependent on the production of coke used in the manufacture of steel. The quantities available today are insufficient to satisfy the demand for carbon black feedstock. In addition, in highly industrialized countries, production of carbochemicaloils is declining.Although, carbochemical oils are preferred in terms of efficiency, petrochemical oils are more important in terms of quantities available, particularly in the production of furnace blacks. These are residual oils resulting either from catalytic cracking processes or from the production of olefins in steam crackers using naphtha or gas oil as raw material. Nevertheless, the choice of carbon black feedstock is not determined merely by price and efficiency, but also by specific quality criteria. However, due to their origin, the feedstocks are mixtures of a large number of individual substances and are, therefore, not easy to characterize. More than 200 different components have been recorded in the range detectable by gas chromatography.Some important components of carbon black feedstock are listed in table 1.1 An important parameter for the evaluation of carbon black feedstock is density, since it increases with

  6. Flow cytometric determination of the photoinduced toxicity of anthracene to the green alga Selenastrum capricornutum

    International Nuclear Information System (INIS)

    Certain PAHs are photosensitizers and in the presence of solar radiation can cause toxicity to aquatic plants and animals. The photoinduced toxicity of anthracene to the green alga Selenastrum capncornutum was assessed by the use of flow cytometry to measure cell size, cellular chlorophyll concentration, and cell viability. Anthracene was slightly toxic in the absence of UV-A radiation. The detection of the direct toxicity of anthracene in this study at a concentration of 19 μg/L anthracene resulted from the use of sensitive flow cytometric measures. There was a significant interaction between anthracene and UV-A radiation, which, in combination, caused significant toxic effects on Selenastrum capncornutum. The most sensitive flow cytometric measure of toxicity was the stress index (SI), which was predictive of longer term effects on cell growth. The 28-h EC50 and EC10 for the SI for Selenastrum capncornutum were 16.1 and 8.3 μg/L anthracene, respectively, at 125 μW/cm2 UV-A. All combinations of anthracene and UV-A that inhibited algal growth also caused a significantly greater number of nonviable cells. The flow cytometric methods used in this study proved to be sensitive, predictive measures of the direct and photo-induced toxicity of anthracene and UV-A radiation to Selenastrum capricornutum

  7. Solubility of anthracene in binary alcohol + 2-methoxyethanol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    McHale, M.E.R.; Powell, J.R.; Kauppila, A.S.M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1996-01-01

    Experimental solubilities are reported for anthracene dissolved in seven binary mixtures containing 2-methoxyethanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-octanol, 2-methyl-1-propanol, and 3-methyl-1-butanol at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined Nearly Ideal Binary Solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the seven systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being on the order of 0.5%.

  8. Anthracene + Pyrene Solid Mixtures: Eutectic and Azeotropic Character

    OpenAIRE

    Rice, James W.; Fu, Jinxia; Suuberg, Eric M.

    2010-01-01

    To better characterize the thermodynamic behavior of a binary polycyclic aromatic hydrocarbon mixture, thermochemical and vapor pressure experiments were used to examine the phase behavior of the anthracene (1) + pyrene (2) system. A solid-liquid phase diagram was mapped for the mixture. A eutectic point occurs at 404 K at x1 = 0.22. A model based on eutectic formation can be used to predict the enthalpy of fusion associated with the mixture. For mixtures that contain x1 < 0.90, the enthalpy ...

  9. Macrocrystals of Colloidal Quantum Dots in Anthracene: Exciton Transfer and Polarized Emission

    Science.gov (United States)

    Soran-Erdem, Zeliha; Erdem, Talha; Hernandez-Martinez, Pedro Ludwig; Akgul, Mehmet Zafer; Gaponik, Nikolai; Demir, Hilmi Volkan

    We systematically investigate the exciton energy transfer from anthracene host (donor) to quantum dots (acceptor) in a centimeter-scale macrocrystal of nonpolar colloidal quantum dots incorporated into anthracene. The decrease in photoluminescence lifetime of the donor anthracene indicate a strong energy transfer with increasing quantum dot concentration in the macrocrystals. In addition, anisotropic emission from the isotropic quantum dots in anthracene macrocrystals was observed. The quantum dots inside the anthracene host acquired a polarization ratio of ~1.5 at 0 degree collection angle, and this increases to ~2.5 at the collection angle of 60 degree. Finally, a proof-of-concept application of these excitonic macrocrystals as tunable color converters was employed in light-emitting diodes. Bilkent University.

  10. Enhanced tolerance and remediation of anthracene by transgenic tobacco plants expressing a fungal glutathione transferase gene

    International Nuclear Information System (INIS)

    Highlights: → Transgenic plants expressing a TvGST gene were tested for tolerance, uptake and degradation of anthracene. → Transgenic plants were more tolerant to anthracene and take up more anthracene from soil and solutions compared to control plants. → Using in vitro T1 seedlings, we showed that anthracene-a three fused benzene ring compound was phytodegraded to naphthalene derivatives, having two benzene rings. → This is the first time that a transgenic plant was shown to have the potential to phytodegrade anthracene. - Abstract: Plants can be used for remediation of polyaromatic hydrocarbons, which are known to be a major concern for human health. Metabolism of xenobiotic compounds in plants occurs in three phases and glutathione transferases (GST) mediate phase II of xenobiotic transformation. Plants, although have GSTs, they are not very efficient for degradation of exogenous recalcitrant xenobiotics including polyaromatic hydrocarbons. Hence, heterologous expression of efficient GSTs in plants may improve their remediation and degradation potential of xenobiotics. In the present study, we investigated the potential of transgenic tobacco plants expressing a Trichoderma virens GST for tolerance, remediation and degradation of anthracene-a recalcitrant polyaromatic hydrocarbon. Transgenic plants with fungal GST showed enhanced tolerance to anthracene compared to control plants. Remediation of 14C uniformly labeled anthracene from solutions and soil by transgenic tobacco plants was higher compared to wild-type plants. Transgenic plants (T0 and T1) degraded anthracene to naphthalene derivatives, while no such degradation was observed in wild-type plants. The present work has shown that in planta expression of a fungal GST in tobacco imparted enhanced tolerance as well as higher remediation potential of anthracene compared to wild-type plants.

  11. Copolyacrylates with phenylalanine and anthracene entities prepared by ATRP and microwave irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Buruiana, E.C., E-mail: emilbur@icmpp.r [Romanian Academy, Petru Poni Institute of Macromolecular Chemistry, Grigore Ghica Voda Alley 41A, 700487 Iasi (Romania); Murariu, Mioara; Buruiana, Tinca [Romanian Academy, Petru Poni Institute of Macromolecular Chemistry, Grigore Ghica Voda Alley 41A, 700487 Iasi (Romania)

    2010-10-15

    In this study, two amino acid copolymers containing anthracene incorporated either on the one end, poly(N-acryloyl-L-phenylalanine-co-methyl methacrylate)-1 or as pendant groups, poly-(N-acryloyl-L-phenylalanine-co-methyl methacrylate)-2 were prepared directly from N-acryloyl-L-phenylalanine (APhe) and methyl methacrylate (MMA) through atom transfer radical polymerization (ATRP) and microwave-assisted synthesis. In the first case, 9-(chloromethyl)anthracene was used as an ATRP-initiator to obtain a copolymer that contains amino acid sequences and anthracene end-capped units (0.03 molar fraction). Rapid synthesis of copolymer under microwave irradiation (250 W) in the presence of 1,1'-azobis(cyclohexanecarbonitrile) used as an initiator was followed of a functionalization of the formed copolymer with an anthracene derivative yielding copolyacrylate with pendant anthracene (0.02 molar fraction). The structure of the copolymers was verified by {sup 1}H NMR, UV-Vis and FTIR spectroscopy, gel permeation chromatography (GPC), and fluorescence spectroscopy. The fluorescence quenching process of anthracene which exists in copolymers by FeCl{sub 3}, cobalt acetate, nitrobenzene, maleic anhydride, diethylaniline and nitromethane in DMF solutions shows that this involves an electron transfer between the excited state anthracene and the present transitional metal cations, more efficiently being FeCl{sub 3} for poly-(APhe-co-MMA)-1 and cobalt acetate for the latter copolymer.

  12. Synthesis, photophysical and electroluminescence properties of anthracene-based green-emitting conjugated polymers

    International Nuclear Information System (INIS)

    Anthracene-based conjugated polymers, which include carbazole and fluorene groups as host materials, are synthesized via Suzuki coupling reaction. Monomer feed ratios are varied in order to determine the effect of anthracene concentration on polymer properties. It is found that anthracene content plays a crucial role both in photoluminescence and electroluminescence properties of the polymers. All polymers exhibit efficient energy transfer from host groups to anthracene moieties in solid state. Excimer emission is observed for all polymers in devices, leading to green emission around 530–545 nm. The device structure ITO/PEDOT:PSS/Polymer/Alq3/LiF/Al based on a polymer with 5% anthracene-containing monomer produces a luminance efficiency of 1.9 cd/A. -- Highlights: • Anthracene containing conjugated polymers with host groups are synthesized. • Emission characteristics depend on the extent of energy transfer. • Polymers exhibit excimer emission, leading to green-emitting devices. • Polymer with 5% anthracene produces a luminance efficiency of 1.9 cd/A

  13. Temperature and sodium chloride effects on the solubility of anthracene in water

    International Nuclear Information System (INIS)

    The solubility of anthracene was measured in pure water and in sodium chloride aqueous solution (salt concentration, m/mol . kg-1 = 0.1006, 0.5056, and 0.6082) at temperatures between (278 and 333) K. Solubility of anthracene in pure water agrees fairly well with values reported in earlier similar studies. Solubility of anthracene in sodium chloride aqueous solutions ranged from (6 . 10-8 to 143 . 10-8) mol . kg-1. Sodium chloride had a salting-out effect on the solubility of anthracene. The salting-out coefficients did not vary significantly with temperature over the range studied. The average salting-out coefficient for anthracene was 0.256 kg . mol-1. The standard molar Gibbs free energies, ΔtrGo, enthalpies, ΔtrHo, and entropies, ΔtrSo, for the transfer of anthracene from pure water to sodium chloride aqueous solutions were also estimated. Most of the estimated ΔtrGo values were positive [(20 to 1230) J . mol-1]. The analysis of the thermodynamic parameters shows that the transfer of anthracene from pure water to sodium chloride aqueous solution is thermodynamically unfavorable, and that this unfavorable condition is caused by a decrease in entropy.

  14. Solubility of anthracene in binary alcohol + 2-propoxyethanol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    McHale, M.E.R.; Powell, J.R.; Kauppila, A.S.M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1996-03-01

    Solid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the petroleum industry, particularly in light of present trends toward heavier feedstocks and known carcinogenicity/mutagenicity of many of the larger polycyclic aromatic compounds. Experimental solubilities are reported for anthracene dissolved in seven binary mixtures containing 2-propoxyethanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 1-octanol, and 3-methyl-1-butanol at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the seven systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being on the order of 0.5%.

  15. Solution Processable Symmetric 4-Alkylethynylbenzene End-Capped Anthracene Derivatives

    International Nuclear Information System (INIS)

    New candidates composed of anthracene and 4-alkylethynylbenzene end-capped oligomers for OTFTs were synthesized under Sonogashira coupling reaction conditions. All oligomers were characterized by FT-IR, mass, UV-visible, and PL emission spectrum analyses, cyclic voltammetry (CV), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), 1H-NMR, and 13C-NMR. Investigation of their physical properties showed that the oligomers had high oxidation potential and thermal stability. Thin films of DHPEAnt and DDPEAnt were characterized by spin coating them onto Si/SiO2 to fabricate top-contact OTFTs. The devices prepared using DHPEAnt and DDPEAnt showed hole field-effect mobilities of 4.0 x 10-3 cm2/Vs and 2.0 x 10-3 cm2/Vs, respectively, for solution-processed OTFTs

  16. Low-energy ions interacting with anthracene molecules and clusters

    International Nuclear Information System (INIS)

    The interaction of slow ions (v∼0.4a.u.) with a small polycyclic aromatic hydrocarbon, namely anthracene (C14H10), is studied in the gas-phase either with the isolated molecule or with a pure cluster target. We discuss the ionization and fragmentation of the molecule with respect to the projectile charge state, i.e. for singly charged He+ ions and for multiply charged Xe20+ ions. For the isolated C14H10, single or multiple ionization of the molecule occurs under ion impact. The (multi) cation relative yields are compared with those obtained by other ionization methods (electron and fs-laser). The molecular dissociation occurs by loss of hydrogen and small hydrocarbon molecules, leading to the formation of CnHx cations. The interaction of Xe20+ with C14H10 clusters gives surprising results, i.e. the emission of hotter monomer compared to the interaction with He+.

  17. Biodegradation of naphthalene and anthracene by chemo-tactically active rhizobacteria of populus deltoides

    Directory of Open Access Journals (Sweden)

    Sandeep Bisht

    2010-12-01

    Full Text Available Several naphthalene and anthracene degrading bacteria were isolated from rhizosphere of Populus deltoides, which were growing in non-contaminated soil. Among these, four isolates, i.e. Kurthia sp., Micrococcus varians, Deinococcus radiodurans and Bacillus circulans utilized chrysene, benzene, toluene and xylene, in addition to anthracene and naphthalene. Kurthia sp and B. circulans showed positive chemotactic response for naphthalene and anthracene. The mean growth rate constant (K of isolates were found to increase with successive increase in substrate concentration (0.5 to 1.0 mg/50ml. B. circulans SBA12 and Kurthia SBA4 degraded 87.5% and 86.6% of anthracene while, Kurthia sp. SBA4, B. circulans SBA12, and M. varians SBA8 degraded 85.3 %, 95.8 % and 86.8 % of naphthalene respectively after 6 days of incubation as determined by HPLC analysis.

  18. Anthracene-fused BODIPYs as near-infrared dyes with high photostability

    KAUST Repository

    Zeng, Lintao

    2011-11-18

    An anthracene unit was successfully fused to the zigzag edge of a boron dipyrromethene (BODIPY) core by an FeCl 3-mediated oxidative cyclodehydrogenation reaction. Meanwhile, a dimer was also formed by both intramolecular cyclization and intermolecular coupling. The anthracene-fused BODIPY monomer 7a and dimer 7b showed small energy gaps (∼1.4 eV) and near-infrared absorption/emission. Moreover, they exhibited high photostability. © 2011 American Chemical Society.

  19. Alizarin red S functionalized mesoporous silica modified glassy carbon electrode for electrochemical determination of anthracene

    International Nuclear Information System (INIS)

    Highlights: • Alizarin red S-SBA15 composite was prepared and characterized. • A novel sensing platform was constructed for anthracene determination. • The proposed sensor exhibited high sensitivity and low detection limit for detecting anthracene. • This method can be applied to the practical detection of anthracene in waste water. - Abstract: In the paper, a novel and sensitive electrochemical sensor based on modification of electroactive alizarin red S functionalized mesoporous silica material SBA15 onto glassy carbon electrode (ARS-SBA15/GCE) was developed. Alizarin red S, called electrochemical probe that can selectively recognize polycyclic aromatic hydrocarbons (PAHs), as tools for the detection of tricyclic aromatic hydrocarbon anthracene. The morphology and interface property of ARS modified SBA15 (ARS-SBA15) were examined by transmission electron microscopy (TEM) and fourier transform infrared spectroscopy (FTIR). Taking advantage of the π-π stacking force between alizarin red S and anthracene, the ARS-SBA15/GCE sensor could detect anthracene quantitatively in a wide range of 1.0 pM–10.0 nM and a low detection limit of 0.5 pM (S/N = 3). Other PAHs, such as naphthalene, phenanthrene, pyrene, and benzo[a]pyrene show little interference on the detection. Consequently, a simple and sensitive electrochemical method was proposed for the determination of anthracene, which can be used to determine anthracene in waste water samples. The electrochemical method provides a general tool that complements the commonly used spectroscopic methods and immune method for the detection of PAHs

  20. Consequences of Environmentally Hazardous Polycyclic Aromatic Hydrocarbon- Anthracene Treatment on Cyanobacteria

    Directory of Open Access Journals (Sweden)

    Jignasha G Patel

    2015-09-01

    Full Text Available The study was aimed to determine the chronic toxicity of Polynuclear aromatic hydrocarbon – Anthracene in response to pigments and metabolic study on three different cyanobacterial species such as Synechocystis sp., Anabaena fertilissima, and Nostoc muscorum. Test organisms were treated at different doses and encountered LC50/Mean Lethal Concentration (at which 50% lethality/ growth reduction occur separately at 7.0 ppm for Synechocystis sp, 5.0 ppm for Anabaena fertilissima and 1.5 ppm for Nostoc muscorum. The influence of anthracene on pigments, metabolites and enzymes was carried out. The test doses caused concentration dependent and decreased pigments like carotenoids and phycobilliproteins. Depletion of carbohydrate by 65 to 80% and proteins by 58 to 78% was encountered with rise in Anthracene concentrations after 16th day exposure in case of Synechocystis sp however, phenols were found to raise by 26 to 37% with increased anthracene concentrations. Similar trend also observed in other two tested blue green algae. Thus the Synechocystis sp.is more tolerant to anthracene treatments as compare to Anabaena fertillissima but Nostoc muscorum showed highest sensitivity to anthracene.

  1. Syntheses and Chemosensory of Anthracene and Phenanthrene Bisimide Derivatives

    Science.gov (United States)

    Bogusz, Zachary A.

    2004-01-01

    As the present technology of biochemical weapons advances, it is essential for science to attempt to prepare our nation for such an occurrence. Various areas of current research are devoted to precautionary measures and potential antidotes for national security. A practical application of these precautions would be the development of a chemical capable of detecting harmful gas. The benefits of being capable to synthesis a chemical compound that would warn and identify potentially deadly gases would ensure a higher level of safety. The chemicals in question can be generalized as bisimide anthracene derivatives. The idea behind these compounds is that in the presence of certain nerve gases, the compound will actually fluoresce, giving an indication that there is a strong likelihood of the presence of a nerve gas and ensure the proper precautionary measures are taken. The fluorescence is due to the quenching of an electric proton transfer within the structure of the molecule. The system proves to be very unique on account of the fact that the fluorescence can be "turned off" by reducing the system. By utilizing the synthesis designed by Dr. Faysal Ilhan, four distinct compounds can be synthesized through photochemical reactions involving para- and ortho- diketones. The photochemistry involved is very modem and much research is being devoted to fully understanding the possibilities and alternative applications of such materials. and meta-nitro anthracene bisimide (ABI-NO2), the amine of each (ABI-NH2), a para- and meta-nitro phenanthrene bisimjde (PBI-NO2), and the amine of each (PBI-NH2). Upon synthesizing these distinct compounds, I must then purify and analyze them in order to obtain any relevant trends, behaviors, and characteristics. The chemical composition analyses that will be conducted are the procedures taken by Dr. Daniel Tyson on previous experiments. The results generated from the data will point further research in the correct direction and hopefully

  2. Comparative study of neutron and gamma-ray pulse shape discrimination of anthracene, stilbene, and p-terphenyl

    International Nuclear Information System (INIS)

    Solid state organic scintillators, such as anthracene, stilbene, and p-terphenyl were investigated on their basic scintillation properties and neutron–gamma discrimination capabilities. Scintillation wavelengths under X-ray irradiation of anthracene, stilbene, and p-terphenyl were 445–525, 400–500, and 350–450 nm, respectively. Scintillation light yields of anthracene, stilbene, and p-terphenyl under 137Cs gamma-ray irradiation were 20100, 16000, and 19400 ph/MeV, respectively. Neutron and gamma-ray events discrimination capabilities were examined and anthracene exhibited the best figure of merit among three organic scintillators

  3. Comparative study of neutron and gamma-ray pulse shape discrimination of anthracene, stilbene, and p-terphenyl

    Energy Technology Data Exchange (ETDEWEB)

    Yanagida, Takayuki, E-mail: yanagida@lsse.kyutech.ac.jp [Kyushu Institute of Technology, 2-4 Hibikino, Wakamatsu, Kitakyushu, Fukuoka 808-0196 (Japan); Watanabe, Kenichi [Nagoya University, Furocho, Chikusa, Nagoya 464-8603 (Japan); Fujimoto, Yutaka [Kyushu Institute of Technology, 2-4 Hibikino, Wakamatsu, Kitakyushu, Fukuoka 808-0196 (Japan)

    2015-06-01

    Solid state organic scintillators, such as anthracene, stilbene, and p-terphenyl were investigated on their basic scintillation properties and neutron–gamma discrimination capabilities. Scintillation wavelengths under X-ray irradiation of anthracene, stilbene, and p-terphenyl were 445–525, 400–500, and 350–450 nm, respectively. Scintillation light yields of anthracene, stilbene, and p-terphenyl under {sup 137}Cs gamma-ray irradiation were 20100, 16000, and 19400 ph/MeV, respectively. Neutron and gamma-ray events discrimination capabilities were examined and anthracene exhibited the best figure of merit among three organic scintillators.

  4. Assessment of the toxicity of anthracene photo-modification products using the topminnow (Poeciliopsis lucida) hepatoma cell line (PLHC-1)

    International Nuclear Information System (INIS)

    Many polycyclic aromatic hydrocarbons (PAHs) are acutely toxic to fish and other aquatic organisms in the presence of environmentally realistic intensities of solar ultraviolet radiation (SUVR). In this study, the cytoxicity/phototoxicity of anthracene photo-modified products to aquatic animals was assessed based on in vitro toxicity assays using a fish hepatoma cell line (PLHC-1 cell line). The results from this study showed that pre-exposure of anthracene/cell culture media to SUVR caused a significant amount of photo-modification and reduced the phototoxicity of parent anthracene compound. SUVR pre-exposed anthracene did not induce cytotoxicity in the absence of SUVR. It was shown that in comparison with anthracene, two major anthracene photo-modified products (anthraquinone, 1,2-dihydroxyanthraquinone) were significantly less phototoxic to PLHC-1 cells. Also in the absence of SUVR, these chemicals did not induce any detectable cytotoxicity to PLHC-1 cells. In conclusion, this study demonstrated that photo-modification reduced the phototoxicity of anthracene to PLHC-1 cells because major anthracene photo-modified products are not phototoxic. Also it was found that these photo-modified anthracene products were not cytotoxic in the absence of SUVR. This study indicated the need for separate toxicity assessments of individual photo-modified PAH products in both animal and plant models

  5. Long-term reproductive and behavioral toxicity of anthracene to fish in the presence of solar ultraviolet radiation

    Energy Technology Data Exchange (ETDEWEB)

    Hall, A.T. [Sandoz Agro, Inc., Des Plaines, IL (United States); Oris, J.T. [Miami Univ. Oxford, OH (United States)

    1994-12-31

    The long-term, low-level effects of anthracene in the presence of solar ultraviolet radiation (SUVR) were examined in the fathead minnow (Pimephales promelas). Adult fish exposed to anthracene exhibited reduced egg laying capacity, with altered oocyte maturation as a potential mechanism of action. Eggs and larvae maternally exposed to anthracene exhibited reduced hatching success and severe developmental abnormalities when incubated under SUVR. The combination of reduced egg output and developmental effects resulted in an inhibition in reproductive capacity in the range of 70--100%. Maternal transfer of anthracene to eggs was efficient; the BCF was 717 for maternally exposed eggs. However, anthracene deputation from eggs after oviposition with only maternal PAH exposure was rapid; anthracene half-life from eggs equaled 1.3 days. Exposure to anthracene under SUVR altered locomotor activity patterns in fathead minnows by inducing hyperactivity or hypoactivity during the light or dark phases of the photoperiod, respectively. Altered activity patterns indicated potential effects of anthracene on the nervous system and/or pineal gland. These alterations disrupted normal activity patterns and reproductive behaviors, and thus have major implications on a fish`s ability to survive and reproduce. Anthracene, a model phototoxic PAH, has many potential sites of toxic action, and any organism exposed to such contaminants will be an considerable SUVR-enhanced risk in the environment.

  6. Optical absorption of the anthracene and temperature-dependent capacitance-voltage characteristics of the Au/anthracene/n-Si heterojunction in metal-organic-semiconductor configuration

    Science.gov (United States)

    Kaçus, H.; Aydoğan, Ş.; Ekinci, D.; Kurudirek, S. V.; Türüt, A.

    2015-11-01

    An anthracene film has been deposited on an n-type silicon to fabricate an Au/anthracene/n-Si junction device. The band gap of the anthracene film has been determined from the optical measurement as Eg=1.65 eV. After the fabrication of the Au/anthracene/n-Si junction device, temperature dependent capacitance-voltage characteristics in the range of 160-300 K were studied to obtain the junction parameters of the device. The diffusion potential, barrier height, Fermi energy level and donor concentration parameters have been determined from the linear 1/C2-V curves with reverse bias at all temperatures. Both Fermi energy level and the barrier height increased with the increasing temperature. Temperature-dependence of the barrier height has been attributed to inhomogeneous barrier, traps and interface states. The ionized donor concentrations have varied with the temperature in an unsystematic manner due to the trapping/de-trapping of the charges at various temperatures.

  7. Thiophene And Anthracene Containing Polymers In Organic Solar Cells

    International Nuclear Information System (INIS)

    Organic solar cell research has attracted worldwide attention during the last two decades. Organic semiconductors are easily processable, light weight, easy to integrate in a wide variety of devices and have chemically tunable properties. These properties describe the advantages of organic plastic solar cells over that of conventional silicon solar cells. Conjugated polymers, also known as semiconducting polymers, are distinguished by alternating single and double bonds between carbon atoms on the polymer backbone. Among π-conjugated polymers, polythiophenes are promising candidates for organic solar cell research. At present, the commonly used polythiophene derivatives, as the electron donor in polymer solar cells, are mainly poly(3-hexylthiophene)s (P3HT). In this study, we investigated the effect of solvent, annealing on the performance and morphology of novel two thiophene-[P1 (MEH-PPE1-PThV2) and P2 (MEH-PThE1-PPV2)] as well as two anthracene- containing poly (phenylene-ethynylene) family of polymers [P3 (MEH-PPE1-PAnV2) and P4 (MEH-PAnE1-PPV2)] and (1-(3-methoxycarbonyl) propyl-1-phenyl[6,6]C61) (PCBM) based organic solar cells. The devices using the blends of P2 as donor and PCBM as acceptor (1:3 weight ratio) exhibited a short circuit current of JSC = 5.2 mA/cm2, an open circuit voltage of VOC 800 mV, fill factor FF = 0.4 and resulting power conversion efficiency ηAM1.5 = 1.8 %.

  8. Novel Organic Sensitizers Containing 2,6-Difunctionalized Anthracene Unit for Dye Sensitized Solar Cells

    Directory of Open Access Journals (Sweden)

    Jiann T. Lin

    2012-08-01

    Full Text Available A series of new organic dyes comprising different amines as electron donors, 2-(6-substituted-anthracen-2-yl-thiophene as the π-conjugated bridge, and cyanoacrylic acid group as an electron acceptor and anchoring group, have been synthesized. There exists charge transfer transition from arylamine and anthracene to the acceptor in these compounds, as evidenced from the photophysical measurements and the computational results. Under one sun (AM 1.5 illumination, dye-sensitized solar cells (DSSCs using these dyes as the sensitizers exhibited efficiencies ranging from 1.62% to 2.88%, surpassing that using 9,10-difunctionalized anthracene-based sensitizer.

  9. (E)-Methyl 3-(10-bromo­anthracen-9-yl)acrylate

    Science.gov (United States)

    Bugenhagen, Bernhard; Al Jasem, Yosef; Hindawi, Bassam al; Al Rawashdeh, Nathir; Thiemann, Thies

    2013-01-01

    In the title mol­ecule, C18H13BrO2, the anthracene unit forms an angle of 46.91 (2)° with the mean plane of the methyl acrylate moiety. In the crystal, the mol­ecules arrange themselves into strands parallel to [010] and, due to the crystal symmetry, there are eight strands crossing the unit cell. In each strand, mol­ecules form short C—H⋯O and C—H⋯π contacts and have their anthracene groups parallel to each other. Neighboring strands, related by a c-glide operation, are connected via C—H⋯O inter­actions and form a layer parallel to (100). The arrangement of the acrylate and anthracene groups in the crystal do not allow for [2 + 2] or [4 + 4] cyclo­addition. PMID:24046689

  10. Growth of optical-quality anthracene crystals doped with dibenzoterrylene for controlled single photon production

    Energy Technology Data Exchange (ETDEWEB)

    Major, Kyle D., E-mail: kyle.major11@imperial.ac.uk; Lien, Yu-Hung; Polisseni, Claudio; Grandi, Samuele; Kho, Kiang Wei; Clark, Alex S.; Hwang, J.; Hinds, E. A., E-mail: ed.hinds@imperial.ac.uk [Centre for Cold Matter, Department of Physics, Blackett Laboratory, Imperial College London, Prince Consort Road, London SW7 2AZ (United Kingdom)

    2015-08-15

    Dibenzoterrylene (DBT) molecules within a crystalline anthracene matrix show promise as quantum emitters for controlled, single photon production. We present the design and construction of a chamber in which we reproducibly grow doped anthracene crystals of optical quality that are several mm across and a few μm thick. We demonstrate control of the DBT concentration over the range 6–300 parts per trillion and show that these DBT molecules are stable single-photon emitters. We interpret our data with a simple model that provides some information on the vapour pressure of DBT.

  11. (E)-Methyl 3-(10-bromo­anthracen-9-yl)acrylate

    OpenAIRE

    Bernhard Bugenhagen; Yosef Al Jasem; Bassam al Hindawi; Nathir Al Rawashdeh; Thies Thiemann

    2013-01-01

    In the title molecule, C18H13BrO2, the anthracene unit forms an angle of 46.91 (2)° with the mean plane of the methyl acrylate moiety. In the crystal, the molecules arrange themselves into strands parallel to [010] and, due to the crystal symmetry, there are eight strands crossing the unit cell. In each strand, molecules form short C—H...O and C—H...π contacts and have their anthracene groups parallel to each other. Neighboring strands, related by a c-glide operati...

  12. Growth of optical-quality anthracene crystals doped with dibenzoterrylene for controlled single photon production

    International Nuclear Information System (INIS)

    Dibenzoterrylene (DBT) molecules within a crystalline anthracene matrix show promise as quantum emitters for controlled, single photon production. We present the design and construction of a chamber in which we reproducibly grow doped anthracene crystals of optical quality that are several mm across and a few μm thick. We demonstrate control of the DBT concentration over the range 6–300 parts per trillion and show that these DBT molecules are stable single-photon emitters. We interpret our data with a simple model that provides some information on the vapour pressure of DBT

  13. Interaction of atomic hydrogen with anthracene and polyacene from density functional theory

    Science.gov (United States)

    Ferullo, Ricardo M.; Castellani, Norberto J.; Belelli, Patricia G.

    2016-03-01

    The interaction of atomic hydrogen with two linear polycyclic aromatic hydrocarbons (PAHs), anthracene and polyacene (the polymer of benzene), was studied within the density functional theory (DFT). Using a proper dispersion-corrected method (DFT-D) the preferential physisorption sites were explored. The activation barrier for the bond formation between a peripheral C and the incoming H was calculated to be 58.5 and 34.1 meV with pure DFT on anthracene and polyacene at its antiferromagnetic ground state, respectively. DFT-D, although improves the description of the physisorbed state, tends to underestimate the chemisorption barriers due an artifact arising from the dispersion correction.

  14. Fluorescence quenching of anthracene by N, N-diethylaniline in the O/W microemulsion

    Institute of Scientific and Technical Information of China (English)

    郭霞; 徐慧; 郭荣

    2000-01-01

    Photoinduced electron-transfer system of anthracene-N , N-di-ethylaniline (DEA) was studied in the oil in water (O/W) microemulsuins formed by SDS (sodium dodecyl sulfate), BA(benzyl alcohol) and H2O. The time-resolved fluorescence study showed that the fluorescence quenching of the excited anthracene by DEA occurs at the interface of the O/W micreomulsions Besides as the quencher of the excited anthrace ne, N, N-diethylaniine could act as a cosurfactant to change the structures of the microemulsions, just as BA did. The quenching rate constants for the different structures of the system were determined.

  15. Efficient laser desorption ionization mass spectrometry of polycyclic aromatic hydrocarbons using excitation energy transfer from anthracene

    International Nuclear Information System (INIS)

    Highlights: ► Femtomolar detection of PAHs such as perylene and benzopyrene was achieved. ► Photoexcited anthracene molecules transferred their energy to PAHs. ► Electronically excited PAHs were then excited to be ions. ► Two-photon ionization process was necessary to complete the ionization process. ► The number of defect sites could be reduced by the annealing procedure. - Abstract: Polycyclic aromatic hydrocarbons (PAHs), such as perylene and benzopyrene, doped at amounts on the order of femtomol (∼10−15 mol) in anthracene crystals could be detected by laser desorption ionization mass spectrometry. Sensitivity was roughly 103 times higher than that of LDI method in our experimental conditions. It was revealed from the excitation power dependence of the peak intensity of PAHs on the mass spectra that two-photon excitation in one UV pulse was necessary to complete the ionization process. It was also clarified that the number of defect sites that trap excitons generated in anthracene crystals could be reduced by the annealing procedure, by which an efficient energy transfer between anthracene and PAHs became possible

  16. Efficient laser desorption ionization mass spectrometry of polycyclic aromatic hydrocarbons using excitation energy transfer from anthracene

    Energy Technology Data Exchange (ETDEWEB)

    Fujimori, Kensuke [Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji-shi, Tokyo 192-0397 (Japan); Fujino, Tatsuya, E-mail: fujino@tmu.ac.jp [Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji-shi, Tokyo 192-0397 (Japan)

    2013-06-20

    Highlights: ► Femtomolar detection of PAHs such as perylene and benzopyrene was achieved. ► Photoexcited anthracene molecules transferred their energy to PAHs. ► Electronically excited PAHs were then excited to be ions. ► Two-photon ionization process was necessary to complete the ionization process. ► The number of defect sites could be reduced by the annealing procedure. - Abstract: Polycyclic aromatic hydrocarbons (PAHs), such as perylene and benzopyrene, doped at amounts on the order of femtomol (∼10{sup −15} mol) in anthracene crystals could be detected by laser desorption ionization mass spectrometry. Sensitivity was roughly 10{sup 3} times higher than that of LDI method in our experimental conditions. It was revealed from the excitation power dependence of the peak intensity of PAHs on the mass spectra that two-photon excitation in one UV pulse was necessary to complete the ionization process. It was also clarified that the number of defect sites that trap excitons generated in anthracene crystals could be reduced by the annealing procedure, by which an efficient energy transfer between anthracene and PAHs became possible.

  17. Synthesis of pentacyclic 13-azadibenzo[a,de]anthracenes via anionic cascade ring closure

    DEFF Research Database (Denmark)

    Kristensen, Jesper Langgaard; Vedsø, P.; Begtrup, M.

    2003-01-01

    Bromine-lithium exchange using tert-butyllithium at -78 °C initiates a cascade process whereby either xanthone derivatives or pentacyclic 13-azadibenzo[a,de]anthracenes are produced in high yields. The reaction proceeds via a sequential intramolecular trapping of organolithium intermediates....

  18. Synthesis and electroluminescent properties of anthracene derivatives containing electron-withdrawing oxide moieties

    Energy Technology Data Exchange (ETDEWEB)

    Yoon, Jhin-yeong; Na, Eun Jae; Park, Soo Na [Department of Chemistry, Sungkyunkwan University, Suwon, 440-746 (Korea, Republic of); Lee, Seok Jae [Department of Information Display, Hongik University, Seoul, 121-791 (Korea, Republic of); Kim, Young Kwan, E-mail: kimyk@wow.hongik.ac.kr [Department of Information Display, Hongik University, Seoul, 121-791 (Korea, Republic of); Yoon, Seung Soo, E-mail: ssyoon@skku.edu [Department of Chemistry, Sungkyunkwan University, Suwon, 440-746 (Korea, Republic of)

    2014-10-15

    Highlights: • Blue fluorescent material is important for application in full-color displays. • We have synthesized emitters based on anthracene connected with oxide moieties. • 1C shows a highly efficient blue EL emission due to electron-injection property. - Abstract: A series of new blue-emitting materials: (4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)(phenyl)methanone (1); 9-(naphthalen-2-yl)-10-(4-((diphenyl)phosphine oxide)phenyl)anthracene (2); 9-(naphthalen-2-yl)-10-(4-(phenylsulfonyl)phenyl)anthracene (3) were designed and synthesized via Suzuki cross-coupling reaction. Multilayer OLEDs were fabricated in the following sequence: ITO (180 nm)/NPB (50 nm)/blue materials 1–3 (30 nm)/TPBi (15 nm)/Liq (2 nm)/Al (100 nm). All devices showed the efficient blue EL emissions. In particular, the device using 1 as an emitter exhibited efficient blue electroluminescent properties with a maximum luminous, power, external quantum efficiency and CIE coordinates of 0.36 cd/A, 0.90 lm/W, 0.55% at 20 mA/cm{sup 2} and (x = 0.16, y = 0.20) at 10.0 V, respectively.

  19. Photoligation of self-assembled DNA constructs containing anthracene-functionalized 2'-amino-LNA monomers

    DEFF Research Database (Denmark)

    Pasternak, Karol; Pasternak, Anna; Gupta, Pankaj;

    2011-01-01

    Efficient synthesis of a novel anthracene-functionalized 2'-amino-LNA phosphoramidite derivative is described together with its incorporation into oligodeoxynucleotides. Two DNA strands with the novel 2'-N-anthracenylmethyl-2'-amino-LNA monomers can be effectively cross-linked by photoligation at...

  20. Activation energies for fragmentation channels of anthracene dications : Experiment and theory

    NARCIS (Netherlands)

    Reitsma, G.; Zettergren, H.; Martin, S.; Bredy, R.; Chen, L.; Bernard, J.; Hoekstra, R.; Schlathölter, Thomas

    2012-01-01

    We have studied the fragmentation of the polycyclic aromatic hydrocarbon anthracene (C14H10) after double electron transfer to a 5 keV proton. The excitation energies leading to the most relevant dissociation and fission channels of the resulting molecular dication were directly determined experimen

  1. N-[(E-Anthracen-9-ylmethylidene]-3,4-dimethyl-1,2-oxazol-5-amine

    Directory of Open Access Journals (Sweden)

    Abdullah M. Asiri

    2011-12-01

    Full Text Available In the title compound, C20H16N2O, an intramolecular C—H...N forms an S(6 ring motif. In the crystal, the molecules are stacked with their anthracene ring planes in sheets along [100].

  2. Enzymatic degradation of anthracene, dibenzothiophene and pyrene by manganese peroxidase in media containing acetone

    Czech Academy of Sciences Publication Activity Database

    Eibes, G.; Cajthaml, Tomáš; Moreira, M. T.; Feijoo, G.; Lema, J. M.

    2006-01-01

    Roč. 64, - (2006), s. 408-414. ISSN 0045-6535 R&D Projects: GA AV ČR KJB6020308 Institutional research plan: CEZ:AV0Z50200510 Keywords : enzymatic degradation * manganese peroxidase * anthracene Subject RIV: EE - Microbiology, Virology Impact factor: 2.442, year: 2006

  3. Synthesis and electroluminescent properties of anthracene derivatives containing electron-withdrawing oxide moieties

    International Nuclear Information System (INIS)

    Highlights: • Blue fluorescent material is important for application in full-color displays. • We have synthesized emitters based on anthracene connected with oxide moieties. • 1C shows a highly efficient blue EL emission due to electron-injection property. - Abstract: A series of new blue-emitting materials: (4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)(phenyl)methanone (1); 9-(naphthalen-2-yl)-10-(4-((diphenyl)phosphine oxide)phenyl)anthracene (2); 9-(naphthalen-2-yl)-10-(4-(phenylsulfonyl)phenyl)anthracene (3) were designed and synthesized via Suzuki cross-coupling reaction. Multilayer OLEDs were fabricated in the following sequence: ITO (180 nm)/NPB (50 nm)/blue materials 1–3 (30 nm)/TPBi (15 nm)/Liq (2 nm)/Al (100 nm). All devices showed the efficient blue EL emissions. In particular, the device using 1 as an emitter exhibited efficient blue electroluminescent properties with a maximum luminous, power, external quantum efficiency and CIE coordinates of 0.36 cd/A, 0.90 lm/W, 0.55% at 20 mA/cm2 and (x = 0.16, y = 0.20) at 10.0 V, respectively

  4. Enhancement of fluorescence in anthracene by chlorination: Vibronic coupling and transition dipole moment density analysis

    Energy Technology Data Exchange (ETDEWEB)

    Uejima, Motoyuki [Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan); Sato, Tohru, E-mail: tsato@moleng.kyoto-u.ac.jp [Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan); Unit of Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Kyoto 615-8510 (Japan); Tanaka, Kazuyoshi [Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan); Kaji, Hironori [Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011 (Japan)

    2014-02-17

    Highlights: • Vibronic coupling analyses for chlorination effect in the S{sub 1} state of anthracene A. • Vibrational relaxation originates from the sides of A; chlorinations suppress this. • High symmetry plays an important role in suppressing the internal conversion. • Delocalized overlap density along to C9–C10 atoms increases transition dipole moment. • The findings lead to a design principle for a molecule with a high quantum yield. - Abstract: The vibronic coupling constants and transition dipole moments for the Franck–Condon and adiabatic S{sub 1} states of anthracene, 9-chloroanthracene, and 9,10-dichloroanthracene were calculated and analyzed by using the concept of vibronic coupling density (VCD). The transition dipole moments are also analyzed on the basis of the transition dipole moment density (TDMD). The VCD analyses indicate that the vibronic couplings in the Franck–Condon S{sub 1} state come from the side rings of anthracene, and introduction of chlorine atoms reduces the vibronic couplings in the side regions and the reorganization energy. The TDMD analyses indicate that the chlorination enhances the transition dipole moment and that the contribution of the chlorine atom to the transition dipole moment is the largest. Finally, we derived a design principle for anthracene derivatives with a high quantum yield: the same long acceptors should be introduced into the two central carbon atoms in the anthracene’s central ring for the derivative to keep the point group to be D{sub 2h}.

  5. Enhancement of fluorescence in anthracene by chlorination: Vibronic coupling and transition dipole moment density analysis

    Science.gov (United States)

    Uejima, Motoyuki; Sato, Tohru; Tanaka, Kazuyoshi; Kaji, Hironori

    2014-02-01

    The vibronic coupling constants and transition dipole moments for the Franck-Condon and adiabatic S1 states of anthracene, 9-chloroanthracene, and 9,10-dichloroanthracene were calculated and analyzed by using the concept of vibronic coupling density (VCD). The transition dipole moments are also analyzed on the basis of the transition dipole moment density (TDMD). The VCD analyses indicate that the vibronic couplings in the Franck-Condon S1 state come from the side rings of anthracene, and introduction of chlorine atoms reduces the vibronic couplings in the side regions and the reorganization energy. The TDMD analyses indicate that the chlorination enhances the transition dipole moment and that the contribution of the chlorine atom to the transition dipole moment is the largest. Finally, we derived a design principle for anthracene derivatives with a high quantum yield: the same long acceptors should be introduced into the two central carbon atoms in the anthracene's central ring for the derivative to keep the point group to be D2h.

  6. Enhancement of fluorescence in anthracene by chlorination: Vibronic coupling and transition dipole moment density analysis

    International Nuclear Information System (INIS)

    Highlights: • Vibronic coupling analyses for chlorination effect in the S1 state of anthracene A. • Vibrational relaxation originates from the sides of A; chlorinations suppress this. • High symmetry plays an important role in suppressing the internal conversion. • Delocalized overlap density along to C9–C10 atoms increases transition dipole moment. • The findings lead to a design principle for a molecule with a high quantum yield. - Abstract: The vibronic coupling constants and transition dipole moments for the Franck–Condon and adiabatic S1 states of anthracene, 9-chloroanthracene, and 9,10-dichloroanthracene were calculated and analyzed by using the concept of vibronic coupling density (VCD). The transition dipole moments are also analyzed on the basis of the transition dipole moment density (TDMD). The VCD analyses indicate that the vibronic couplings in the Franck–Condon S1 state come from the side rings of anthracene, and introduction of chlorine atoms reduces the vibronic couplings in the side regions and the reorganization energy. The TDMD analyses indicate that the chlorination enhances the transition dipole moment and that the contribution of the chlorine atom to the transition dipole moment is the largest. Finally, we derived a design principle for anthracene derivatives with a high quantum yield: the same long acceptors should be introduced into the two central carbon atoms in the anthracene’s central ring for the derivative to keep the point group to be D2h

  7. Design and electrical characterization of Au/Anthracene/p-Si/Al organic/inorganic heterojunction

    Energy Technology Data Exchange (ETDEWEB)

    Al-Ghamdi, Attieh A., E-mail: aaaalghamdi4@kau.edu.sa [Center of Nanotechnology, King Abdulaziz University, Department of Physics, North Jeddah (Saudi Arabia); Nawar, Ahmed M.; El-Tantawy, Farid [Department of Physics, Faculty of Science, Suez Canal University, Ismailia (Egypt); Yaghmour, S.J. [Department of Physics, King Abdulaziz University, North Jeddah (Saudi Arabia); Azam, Ameer [Center of Nanotechnology, King Abdulaziz University, Department of Physics, North Jeddah (Saudi Arabia)

    2015-02-15

    Highlights: • We have successfully fabricated a Au/Anthracene/p-Si/Al organic/inorganic heterojunction. • The calculated series resistance and the shunt resistance of the device were found to be 440 Ω and 1.47 MΩ, respectively. • The Cheung-Cheung and Norde’s models were used to investigate and determine the heterojunction parameters. • Essential junction parameters and performance of heterojunction established a photovoltaic behavior. • Open circuit voltage (V{sub oc}) 0.382 V, short circuit photocurrent (I{sub SC}) 0.72 mA and power conversion efficiency (η) of 4.65%. - Abstract: Hybrid organic/inorganic heterojunction of nanocrystalline Anthracene and p-Si was fabricated by using a conventional thermal evaporation technique. The crystal and molecular structure of the Anthracene thin films were analyzed by means of X-ray diffraction (XRD), and Fourier Transformation-Infra Red (FT-IR) spectroscopy. The morphologies of the Anthracene/p-Si were investigated by scanning electron microscopy (SEM). The dark current-voltage (I-V) characteristics of Au/Anthracene/p-Si/Al heterojunction were investigated at room temperature (293 K). The calculated series resistance and the shunt resistance of the device were found to be 440 Ω and 1.47 MΩ, respectively. The Cheung-Cheung and Norde’s models were used to investigate and determine the heterojunction parameters. The ideality factor and barrier height values of the Au/Anthracene/p-Si/Al diode were obtained to be 1.1 and 0.464 eV, respectively. The dependence of capacitance-voltage (C{sup -2}-V) for the device Anthracene/p-Si was found to be almost linear. Essential junction parameters and performance of heterojunction established a photovoltaic behavior with an open circuit voltage (V{sub oc}) 0.382 V, short circuit photocurrent (I{sub SC}) 0.72 mA and power conversion efficiency (η) of 4.65%.

  8. Impact of Anthracene Exposure on Bacterial Community Composition and Function in an Egyptian Marine Environment

    International Nuclear Information System (INIS)

    The application of bioremediation technology for pollution treatment requires more knowledge about how do microbial communities respond to pollutant exposure. The main goals of this study are to investigate the behavior of natural bacterial microflora of Suez Gulf (SGM) in response to exposure to different concentrations of Polycyclic Aromatic Hydrocarbons (PAHs) for different periods. In this study, anthracene, as a model of (PAHs) was added in different concentrations, (30,150 and 500 ppm) to fertilized Suez Gulf water in shaking microcosms to examine the possible shifts in bacterial community composition and function. Changes in bacterial community composition was followed up after different periods of exposure (0, 6, 12, and 18) days to the above mentioned concentrations of anthracene by profiling the amplified product of 16S rDNA via denaturing gradient gel electrophoresis (DGGE) of SGM in treated microcosm separately. DGGE profiles revealed remarkable changes in diversity due to exposure concentration and duration to anthracene. A diverse relationship between anthracene concentration and bacterial diversity was detected. On the other hand, changes in community function were determined by testing the biodegradation capabilities of the consortia after different exposures separately in microcosms containing 50 ppm of anthracene for 14 days. The remaining anthracene was extracted and monitored by high performance liquid chromatography (HPLC) and DGGE profiles of amplified 16S rDNA extracted from parallel biodegradation microcosms were examined to indicate the effects of pre-exposure to different concentrations for different periods to PAHs on the bacterial community compositions. The results confirm that the long term effects of pre exposure to high concentrations of PAH on the bacterial community composition, suggesting that that some organisms can be used as a bio marker indicating the exposures of the marine environment to high concentrations of PAHs. HPLC

  9. Well-defined Polymethylene-Based Co/Terpolymers by Combining Anthracene/Maleimide Diels-Alder Reaction with Polyhomologation

    KAUST Repository

    Hadjichristidis, Nikolaos

    2015-05-26

    A novel strategy towards well-defined polymethylene-based co/terpolymers, by combining anthracene/maleimide Diels-Alder reaction with polyhomologation, is presented. For the synthesis of diblock copolymers the following approach was applied: a) synthesis of α-anthracene-ω-hydroxy- polymethylene by polyhomologation using tri (9-anthracene-methyl propyl ether) borane as initiator, b) synthesis of furan-protected-maleimide-terminated poly (ε-caprolactone) or polyethylene glycol and c). Diels-Alder reaction between the anthracene and maleimide-terminated polymers. In the case of triblock terpolymers the α-anthracene-ω-hydroxy-polymethylene was used as macroinitiator for the ring-opening polymerization of D, L-lactide to afford an anthracene-terminated PM-b-PLA copolymer, followed by Diels-Alder reaction with furan-protected maleimide-terminated poly (ε-caprolactone) or polyethylene glycol to give the triblock terpolymers. All intermediate and final products were characterized by SEC, 1H NMR, UV-VIS spectroscopy and DSC.

  10. Synthesis and thin films characterization of new anthracene-core molecules for opto-electronic applications

    International Nuclear Information System (INIS)

    Two new anthracene-core conjugated molecules, 1-(9-anthrylvinyl)-4-benzyloxybenzene (AVB) and 1,4-bis(9-anthrylvinyl)benzene (AV2B), were synthesized by the Wittig reaction. Organic thin films based on these derivatives were elaborated using thermal evaporation under high vacuum. The UV-vis film spectra show an anthracene-type absorption behavior for the two π-conjugated systems with an optical gap of 2.77 eV for AVB and 2.55 eV for AV2B. These derivatives reveal practically the same photoluminescence spectra and exhibit blue emitting films. However, the electrical properties investigations demonstrate an enhancement in the electrical conductivity for AVB resulting from the high crystallinity of the film and attributed to a well intermolecular charge transfer. Finally, the conduction mechanisms in the solid state are discussed in terms of space charge limited current (SCLC) and correlated to the film morphology.

  11. Research on Synthesizing Disperser with Fraction of Anthracene Oil for Coal Water Slurry

    Institute of Scientific and Technical Information of China (English)

    WU Guo-guang; GUO Zhao-bing; WU Jian-jun; XIE Qiang; WANG Xiao-chun

    2003-01-01

    Experiment of synthesizing a disperser for coal water slurry (CWS) by using fractions of anthracene oil from high-temperature coal tar was performed. The orthogonal test was used to investigate the influence of temperature, time, quantity of sulfonation agent and condensation agent and the interaction of these factors on properties of the disperser. The result shows that the influence of temperature, time, quantity of sulfonation agent and condensation agent, and the interaction of sulfonation time and sulfonation agent has a significant influence on the properties of disperser. The optimal condition of synthesis is that in 150g of the fractions of anthracene oil, 40 mL of sulfonation agent is added and sulfonated for 3 h at 130℃, then, 10 mL of condensing agent is added and condensated for 1.5 h at 115 ℃.

  12. Inhibiting the photosensitized oxidation of anthracene and tryptophan by means of natural antioxidants

    Science.gov (United States)

    Aksenova, N. A.; Vyzhlova, E. N.; Malinovskaya, V. V.; Parfenov, V. V.; Solov'eva, A. B.; Timashev, P. S.

    2013-08-01

    It is shown that model reactions of photosensitized oxidation of anthracene and tryptophan can be used for evaluation and comparison of antioxidant activity of various classes of compounds. Inhibition of the oxidation of substrates in the presence of the familiar antioxidants tocopherol (vitamin E), ascorbic acid (vitamin C), and mixtures of these vitamins with methionine, and in the presence of reputed antioxidants dihydroquercetin and taurine, are considered. It is concluded that all of the above compounds except for taurine have antioxidant properties; i.e., they reduce the rate constants of the photosensitized oxidation of anthracene and tryptophan. It is found that the inhibition of oxidation is associated with the interaction between antioxidants and singlet oxygen. Analysis of the kinetic dependences of the photosensitized oxidation of substrates in the presence of antioxidants reveals that a mixture of vitamins inhibits the process most efficiently, and inhibition occurs at the initial stages due to more active interaction between singlet oxygen and vitamin C

  13. Monitoring cellular uptake and cytotoxicity of copper(II) complex using a fluorescent anthracene thiosemicarbazone ligand.

    Science.gov (United States)

    Kate, Anup N; Kumbhar, Anupa A; Khan, Ayesha A; Joshi, Pranaya V; Puranik, Vedavati G

    2014-01-15

    The thiosemicarbazone derivative of anthracene (ATSC, anthracene thiosemicarbazone 1) and its copper(II) complex (CuATSC, 2) were synthesized and characterized by spectroscopic, electrochemical, and crystallographic techniques. Interaction of 1 and 2 with calf thymus (CT) DNA was explored using absorption and emission spectral methods, and viscosity measurements reveal a partial-intercalation binding mode. Their protein binding ability was monitored by the quenching of tryptophan emission using bovine serum albumin (BSA) as a model protein. Furthermore, their cellular uptake, in vitro cytotoxicity testing on the HeLa cell line, and flow cytometric analysis were carried out to ascertain the mode of cell death. Cell cycle analysis indicated that 1 and 2 cause cell cycle arrest in sub-G1 phase. PMID:24328322

  14. Scintillation characteristics on anthracene-doped naphthalene crystal for 137Cs-γ ray source

    International Nuclear Information System (INIS)

    In this paper, we report scintillation characterizations on anthracene-doped naphthalene (NA) crystal. Crystals of this scintillator have been grown using the Bridgman-growth process. The peak of NA crystal emission is at 425 nm. The luminescence intensity of the NA crystal is 3 times that of pure naphthalene crystal. Naphthalene when doped with anthracene has high light output and fast principal decay constant (137Cs source), energy resolution of 18% (FWHM) has been recorded at room temperature for NA crystals coupled to a photomultiplier. The pulse height of NA is 10 times greater than the pure naphthalene crystal. The NA detector exhibited a good timing performance compared to trans-stilbene detector

  15. Scintillation characteristics on anthracene-doped naphthalene crystal for {sup 137}Cs-{gamma} ray source

    Energy Technology Data Exchange (ETDEWEB)

    Balamurugan, N. [Crystal Growth Centre, Anna University, Chennai 600025 (India); Arulchakkaravarthi, A. [Electrical Engineering Department, University of South Carolina, SC (United States); Ramasamy, P. [Crystal Growth Centre, Anna University, Chennai 600025 (India) and SSN College of Engineering, Kalavakkam 603110 (India)]. E-mail: pramasamy@annauniv.edu

    2006-12-01

    In this paper, we report scintillation characterizations on anthracene-doped naphthalene (NA) crystal. Crystals of this scintillator have been grown using the Bridgman-growth process. The peak of NA crystal emission is at 425 nm. The luminescence intensity of the NA crystal is 3 times that of pure naphthalene crystal. Naphthalene when doped with anthracene has high light output and fast principal decay constant (<30 ns). For 662 keV {gamma} rays ({sup 137}Cs source), energy resolution of 18% (FWHM) has been recorded at room temperature for NA crystals coupled to a photomultiplier. The pulse height of NA is 10 times greater than the pure naphthalene crystal. The NA detector exhibited a good timing performance compared to trans-stilbene detector.

  16. A molecular dynamics study on slow ion interactions with the polycyclic aromatic hydrocarbon molecule anthracene

    International Nuclear Information System (INIS)

    Atomic collisions with polycyclic aromatic hydrocarbon (PAH) molecules are astrophysically particularly relevant for collision energies of less than 1 keV. In this regime, the interaction dynamics are dominated by elastic interactions. We have employed a molecular dynamics simulation based on analytical interaction potentials to model the interaction of low energy hydrogen and helium projectiles with isolated anthracene (C14H10) molecules. This approach allows for a very detailed investigation of the elastic interaction dynamics on an event by event basis. From the simulation data the threshold projectile kinetic energies above which direct C atom knock out sets in were determined. Anthracene differential energy transfer cross sections and total (dissociation) cross sections were computed for a wide range of projectile kinetic energies. The obtained results are interpreted in the context of PAH destruction in astrophysical environments.

  17. Discovery of novel dihydro-9,10-ethano-anthracene carboxamides as glucocorticoid receptor modulators.

    Science.gov (United States)

    Yang, Bingwei V; Vaccaro, Wayne; Doweyko, Arthur M; Doweyko, Lidia M; Huynh, Tram; Tortolani, David; Nadler, Steven G; McKay, Lorraine; Somerville, John; Holloway, Deborah A; Habte, Sium; Weinstein, David S; Barrish, Joel C

    2009-04-15

    A series of dihydro-9,10-ethano-anthracene-11-carboxamides as novel glucocorticoid receptor modulators is reported. SAR exploration identified compounds from this series displaying a promising dissociation profile in discriminating between transrepression and transactivation activities. 17a is a partial agonist of GR-mediated transactivation which elicits potent and efficacious transrepression in reporter gene assays. A hypothetical binding mode is provided which accounts for the induction of functional activity by a bridgehead methyl group. PMID:19321341

  18. Degradation and Mineralization of the Polycyclic Aromatic Hydrocarbons Anthracene and Naphthalene in Intertidal Marine Sediments †

    OpenAIRE

    Bauer, James E.; Capone, Douglas G.

    1985-01-01

    The degradation of the polynuclear aromatic hydrocarbons (PAHs) anthracene and naphthalene by the microbiota of intertidal sediments was investigated in laboratory studies. No mineralization of either PAH was observed in the absence of oxygen. Both rates and total amounts of PAH mineralization were strongly controlled by oxygen content and temperature of the incubations. Inorganic nitrogen and glucose amendments had minimal effects on PAH mineralization. The rates and total amounts of PAH min...

  19. Anthracene derivatives of benzo(f)quinoline. Synthesis, spectra, and luminescence

    Energy Technology Data Exchange (ETDEWEB)

    Koslov, N.S.; Shmanai, G.S.; Gladchenko, L.F.

    1986-05-01

    By condensation of 9-(N-(2-naphthyl)formimidoyl)anthracene with methyl ketones under conditions of acid catalysis, 1-R-3-(-anthryl)benzo(f)quinolines have been obtained. The byproducts of the reaction have been identified: 1-R-3-(9-anthyl)-2-propen-1-ones and N-(1-(p-aminophenyl)-3-(9-anthryl)-2-propen-1-ylidene)-2-naph-thylamines. The spectral and luminescence properties of these compounds have been examined critically.

  20. DFT study of the electronic structure of anthracene derivatives in their neutral, anion and cation forms

    International Nuclear Information System (INIS)

    Anthracene and its simplest derivatives with electron-accepting (anthraquinone) and electron-donating (diaminoanthracene) properties in their anionic, neutral and cationic charge states are investigated using the density functional theory. The effect of addition and removal of the electron on the bond lengths, atomic charges, frontier orbitals, ionization potential (IP), electron affinity (EA) and reorganization energy is considered. The computed IP, EA and optical gaps are in rather good agreement with available experimental data.

  1. Enhancement in semiconducting and optical properties in doped anthracene micro crystals

    Energy Technology Data Exchange (ETDEWEB)

    Sinha, Nidhi [Crystal Lab, Department of Physics & Astrophysics, University of Delhi, Delhi-7 (India); Department of Electronics, SGTB Khalsa College, University of Delhi, Delhi-7 (India); Ray, Geeta; Godara, Sanjay; Yadav, Harsh; Bhandari, Sonia [Crystal Lab, Department of Physics & Astrophysics, University of Delhi, Delhi-7 (India); Kumar, Binay, E-mail: b3kumar69@yahoo.co.in [Crystal Lab, Department of Physics & Astrophysics, University of Delhi, Delhi-7 (India)

    2015-08-15

    Effect of CuCl{sub 2} doping on structural, optical, dielectric and semiconducting behavior of solution grown anthracene crystals has been reported. UV–vis spectra showed a blue shift of various peaks in the range of 350–390 nm. A broad peak around 760 nm of high intensity appeared in Cu{sup 2+} doped anthracene. Remarkable increase in dielectric constant and ac conductivity were observed along with a structure related phase transition at 126 °C. Different mechanisms of ac conductivity for the two temperature ranges, typically below and above 60 °C, were reported. A higher dependence of conductivity on temperature above 60 °C established enhanced semiconducting behavior in doped crystals. Change in activation energy has been reported in different temperature regions. In photoluminescence (PL) studies, three strong blue/UV emissions were obtained at 400 nm, 424 nm and 450 nm in both the crystals and a remarkable PL quenching has been observed in the doped anthracene.

  2. Crystal structure of [(1,2,3,4,11,12-η-anthracene]tris(trimethylstannylcobalt(III

    Directory of Open Access Journals (Sweden)

    William W. Brennessel

    2014-11-01

    Full Text Available The asymmetric unit of the title structure, [Co(η6-C14H10{Sn(CH33}3], contains two independent molecules. Each anthracene ligand is η6-coordinating to a CoIII cation and is nearly planar [fold angles of 5.4 (3 and 9.7 (3°], as would be expected for its behaving almost entirely as a donor to a high-oxidation-state metal center. The slight fold in each anthracene ligand gives rise to slightly longer Co—C bond lengths to the ring junction carbon atoms than to the other four. Each CoIII cation is further coordinated by three Sn(CH33 ligands, giving each molecule a three-legged piano-stool geometry. In each of the two independent molecules, the trio of SnMe3 ligands are modeled as disordered over two positions, rotated by approximately 30%, such that the C atoms nearly overlap. In one molecule, the disorder ratio refined to 0.9365 (8:0.0635 (8, while that for the other refined to 0.9686 (8:0.0314 (8. The molecules are well separated, and thus no significant intermolecular interactions are observed. The compound is of interest as the first structure report of an η6-anthracene cobalt(III complex.

  3. High-Pressure Effects on the Electronic Structure of Anthracene Single Crystals: Role of Nonhydrostaticity

    Energy Technology Data Exchange (ETDEWEB)

    Dreger, Zbigniew A.; Balasubramaniam, E.; Gupta, Yogendra M.; Joly, Alan G.

    2009-02-26

    Optical spectroscopy methods were used to examine the effect of nonhydrostaticity on the electronic structure of anthracene single crystals compressed statically to 9 GPa. Two pressure-transmitting media, nitrogen (hydrostatic) and water (nonhydrostatic above ~ 5.5 GPa), were utilized. It was found that nonhydrostatic compression generates several new features both in the absorption and fluorescence spectra: (i) formation of new absorption and fluorescence bands, (ii) deviations in pressure shift of fluorescence peaks, (iii) extensive broadening of vibrational peaks, and (iv) irreversible changes in the spectra shape upon pressure unloading. Furthermore, the time-resolved fluorescence decay curves measured at the wavelength corresponding to the new fluorescence band show clear initial increase. These new features are accompanied by inhomogeneous color changes and macroscopic lines on the (001) plane of the crystal. All of the changes are discussed and correlated with microscopic transformations in the crystal. It is demonstrated that nonhydrostatic compression in anthracene crystal introduces inelastic changes in the form of dislocations along [110] and [1 10 ] directions. These dislocations lead to the development of dimeric structures and, consequently, to various changes in the electronic response of the compressed anthracene crystal.

  4. Semiconducting Polymers Consisting of Anthracene and Benzotriazole Units for Organic Solar Cells.

    Science.gov (United States)

    Shin, Seung Ah; Kim, Ji-Hoon; Park, Jong Baek; Hwang, Do-Hoon

    2015-02-01

    An alternating copolymer composed of 2,6-dibromo-9,10-bis(2-ethylhexyloxy)anthracene and benzotriazole units, poly(An-alt-BTz), was synthesized, through a Suzuki cross-coupling polymerization, for use in photovoltaic devices as a p-type electron donor. For the reduction of the bandgap energy of benzotriazole units, 5,5'-dibromo-2,2'-bithiophene, or 2,5-dibromothieno [3,2-b] thiophene units were introduced into the polymer. Poly(anthracene-co-benzotriazole-co-bithiophene(thienothiophene))s were synthesized using the same polymerization reactions. The measured optical bandgap energy of poly(anthracene-alt-benzotriazole) was 2.62 eV. As the contents of the flat comonomer units in the ter-polymers increased, the bandgap energies of the resulting polymers decreased up to 1.95 eV. The energy levels of the HOMO and the LUMO of the copolymers were determined from the cyclic voltammetry. Photovoltaic devices were fabricated with the polymers as electron donors and PC71 BM as an electron acceptor. One of the fabricated devices showed the maximum PCE of 0.74% with 0.57 V of VOC, 2.59 mA/cm2 of JSC, and 0.48 of FF under AM 1.5G (100 mW/cm2) condition. PMID:26353683

  5. Picosecond ion-pair dynamics following CT excitation of EDA complexes of tetranitromethane with anthracene

    Energy Technology Data Exchange (ETDEWEB)

    Han, Chul Hee [Sun Moon University, Asan (Korea, Republic of)

    1995-11-15

    It was well known that CT (Charge Transfer band) excitation of EDA (Electron Donor Acceptor) complex of Aromatic compound and Tetranitromethane (TNM) produces covalent adduct as the final product; however, it was not until the picosecond study on the Anthracene EDA complexes with Tetranitromethane that the dynamics associated with the covalent adduct formation and other related processes became quantitatively evaluated. According to the current understanding of the subject, picosecond excitation of EDA complex produces Contact Ion Pair (CIP) instantaneously, and this CIP is subject to two main competing processes; Ion-Pair collapse to form a covalent adduct and separation by solvent to form solvent separated Ion Pair (SSIP). In addition to these processes, Ion-pair exchange is possible with the added salt such as Tetra-n-butylammoniumperchlorate (TBA{sup +}P{sup -}) or Tetra-n-butyl-ammonium trinitromethide (TBA{sup +}T{sup -}). Previous picosecond study on the Anthracene EDA complexes with TNM employed a series of 9-X-anthracenes, where the substituents (X) of varying electrophilic character were used to modulate the ion-pair dynamics in various solvent with or without the added salts. Their work on the solvent effect and salt effect has revealed the importance of the ionic character of CIP in its solution dynamics.

  6. Picosecond ion-pair dynamics following CT excitation of EDA complexes of tetranitromethane with anthracene

    International Nuclear Information System (INIS)

    It was well known that CT (Charge Transfer band) excitation of EDA (Electron Donor Acceptor) complex of Aromatic compound and Tetranitromethane (TNM) produces covalent adduct as the final product; however, it was not until the picosecond study on the Anthracene EDA complexes with Tetranitromethane that the dynamics associated with the covalent adduct formation and other related processes became quantitatively evaluated. According to the current understanding of the subject, picosecond excitation of EDA complex produces Contact Ion Pair (CIP) instantaneously, and this CIP is subject to two main competing processes; Ion-Pair collapse to form a covalent adduct and separation by solvent to form solvent separated Ion Pair (SSIP). In addition to these processes, Ion-pair exchange is possible with the added salt such as Tetra-n-butylammoniumperchlorate (TBA+P-) or Tetra-n-butyl-ammonium trinitromethide (TBA+T-). Previous picosecond study on the Anthracene EDA complexes with TNM employed a series of 9-X-anthracenes, where the substituents (X) of varying electrophilic character were used to modulate the ion-pair dynamics in various solvent with or without the added salts. Their work on the solvent effect and salt effect has revealed the importance of the ionic character of CIP in its solution dynamics.

  7. Hydrogenation of Anthracene in Supercritical Carbon Dioxide Solvent Using Ni Supported on Hβ-Zeolite Catalyst

    Directory of Open Access Journals (Sweden)

    Ashraf Aly Hassan

    2012-01-01

    Full Text Available Catalytic hydrogenation of anthracene was studied over Ni supported on Hβ-zeolite catalyst under supercritical carbon dioxide (sc-CO2 solvent. Hydrogenation of anthracene in sc-CO2 yielded 100% conversion at 100 °C, which is attributed to the reduced mass transfer limitations, and increased solubility of H2 and substrate in the reaction medium. The total pressure of 7 MPa was found to be optimum for high selectivity of octahydroanthracene (OHA. The conversion and selectivity for OHA increased with an increase in H2 partial pressure, which is attributed to higher concentration of hydrogen atoms at higher H2 pressures. The selectivity reduced the pressure below 7 MPa because of enhanced desorption of the tetrahydro-molecules and intermediates from Ni active sites, due to higher solubility of the surface species in sc-CO2. The selectivity of OHA increased with the increase in catalyst weight and reaction time. The rate of hydrogenation of anthracene was compared with that found for napthalene and phenanthrene. The use of acetonitrile as co-solvent or expanded liquid with CO2 decreased the catalytic activity.

  8. Antioxidant Potential of Anthrarobin (1, 2, 10 trihydroxy anthracene) and its Acyl Derivatives

    International Nuclear Information System (INIS)

    The current study explores the antioxidant potential of anthrarobin and its synthesized derivatives determined by various methods including DPPH radical scavenging ability, reducing power and superoxide scavenging activity. Anthrarobin was acetylated with acetic anhydride in the presence of pyridine to afford anthracen-1, 10-dihydroxy-2-acetate (1), anthracen-1-hydroxy-2, 10-diacetate (2) and anthracen-1, 2, 10-triacetate (3). Anthrarobin exhibited good antioxidant potential with 68 and 78% at 50 meuM and 100 meuM concentrations, respectively. Reducing power of anthrarobin increases with increase in concentration in a dose-dependent manner as could be seen from 37 and 54% activity at the concentration of 50 and 100 meuM, respectively. 3-Tetra-butyl-4-hydroxyanisole (BHA) used as standard showed 84 and 93% activities at 50 and 100 meuM, respectively. BHA and anthrarobin were compared to determine that how much superoxide radicals were scavenged in alkaline DMSO by different concentrations. It was found that 50 meuM of anthrarobin was needed to scavenge 50% radicals while 12.5 meuM of BHA scavenged 50% radicals in DMSO. It is concluded that anthrarobin has highest antioxidant potential as compared to its derivatives. It is postulated that position and numbers of hydroxyl group in anthrarobin are responsible for antioxidant potential and the activity decreases with the substitution of acyl groups at various positions in synthesized derivatives. (author)

  9. Usefulness of a Technique Based on Negative Corona Discharge for the Degradation of Selected, Condensed PAHs: Application to the Oxidation of Anthracene and Similar Structures

    OpenAIRE

    Tessier, D.; OGUIC, C.; PINART, J.

    2001-01-01

    The usefulness of negative corona discharge for oxidation of condensed polycyclic aromatic hydrocarbons (PAHs), including anthracene, naphthalene and 2,3-benzanthracene, adsorbed on a solid substrate is evaluated. In the case of anthracene, the application of corona discharge under high voltage (10-20 kV) for 10 to 180 min with a current intensity of 5-120 m A in a controlled, humid atmosphere leads to the progressive formation of anthraquinone. A kinetic study of the anthracene o...

  10. A new family of donor-acceptor systems comprising tin(IV) porphyrin and anthracene subunits: Synthesis, spectroscopy and energy transfer studies

    Indian Academy of Sciences (India)

    A Ashok Kumar; L Giribabu; Bhaskar G Maiya

    2002-12-01

    A new family of covalently linked `Sn(IV) porphyrin-anthracene’ diad (1), triad (2) and tetrad (3) donor-acceptor (D-A) systems have been designed and synthesized in good-to-moderate yields. While diad 1 possesses one anthracene subunit at the peripheral (meso) position of the tin(IV) porphyrin scaffold, triad 2 possesses two trans axial anthracene subunits at the tin(IV) centre. On the other hand, tetrad 3 is endowed with both the peripheral and axial anthracene subunits in its architecture. These D-A systems have been fully characterised by elemental analysis, FAB-MS, UV-Vis, 1H and 13C NMR and electrochemical methods. UV-Vis, NMR and redox data suggest the absence of intramolecular - interaction between the porphyrin and the anthracene/s in 1-3. Fluorescence from the anthracene subunit in 1 and 3 is found to be quenched in comparison with the fluorescence of free anthracene in four different solvents. This is not the case with compound 2. Excitation spectral data provides evidence for an intramolecular excitation energy transfer (EET) from the singlet anthracene to the porphyrin in 1 and 3. The energy transfer efficiency is in the order: 2 (almost negligible) < 3 (∼ 30%) < 1 (nearly quantitative), with the peripheral anthracene → porphyrin pathway being largely favoured. This orientation dependence of EET could be analysed using Forster’s dipole dipole mechanism.

  11. 1-[5-(Anthracen-9-yl-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

    Directory of Open Access Journals (Sweden)

    Yong-Hua Li

    2011-01-01

    Full Text Available In the title compound, C25H20N2O, the pyrazoline ring is nearly planar [maximum atomic deviation = 0.0254 (17 Å]; but the anthracene ring system is distorted from a coplanar structure [maximum atomic deviation = 0.181 (3 Å], the dihedral angle between the outer benzene rings being 10.68 (13°. The pyrazoline ring is almost perpendicular to the mean plane of the anthracene ring system [dihedral angle = 76.94 (8°], but nearly coplanar with the phenyl ring [dihedral angle = 1.63 (7°]. π–π stacking is observed between parallel benzene rings of adjacent anthracene units, the face-to-face distance being 3.27 (3 Å. Weak intramolecular C—H...N hydrogen bonding also occurs.

  12. White organic light-emitting diodes with 9, 10-bis (2-naphthyl) anthracene

    Energy Technology Data Exchange (ETDEWEB)

    Guan Yunxia; Niu Lianbin [Key Laboratory of Optical Engineering, College of Physics and Information Technology, Chongqing Normal University, Chongqing 400047 (China)], E-mail: gyxybsy@126.com, E-mail: niulb03@126.com

    2009-03-01

    White organic light-emitting diodes were fabricated by 9, 10-bis (2-naphthyl) anthracene (ADN) doped with Rubrene with a structure of ITO/copper phthalocyanine (CuPc) / NPB /ADN: Rubrene /Alq{sub 3} /CsF/Mg:Ag/Ag. Multilayer organic devices using AND and Rubrene as an emitting layer produced white emissions with good chromaticity and luminous efficiency as high as 5.93 cd/A. This performance can be explained by Foerster energy transfer from the blue-emitting host to the orange-emitting dopant.

  13. Free Volume and Gas Permeation in Anthracene Maleimide-Based Polymers of Intrinsic Microporosity

    Directory of Open Access Journals (Sweden)

    Muntazim Munir Khan

    2015-05-01

    Full Text Available High free-volume copolymers were prepared via polycondensation with 2,3,5,6,-tetrafluoroterephthalonitrile (TFTPN in which a portion of the 3,3,3',3'-tetramethyl-1,1'-spirobisindane (TTSBI of PIM-1 was replaced with dibutyl anthracene maleimide (4bIII. An investigation of free volume using positron annihilation lifetime spectroscopy (PALS, and gas permeation measurements was carried out for the thin film composite copolymer membranes and compared to PIM-1. The average free volume hole size and the gas permeance of the copolymer membranes increased with decreasing TTSBI content in the copolymer.

  14. Bioastrophysical Aspects of Low Energy Ion Irradiation of Frozen Anthracene Containing Water

    Energy Technology Data Exchange (ETDEWEB)

    Tuleta, M.; Gabla, L.; Madej, J.

    2001-08-13

    The origin of life on Earth remains a fascinating mystery in spite of many theories existing on this subject. However, it seems that simple prebiotic molecules could play an essential role in the formation of more complex organisms. In our experiment, we synthesized a class of these molecules (quinones) bombarding frozen anthracene containing water with low energy hydrogen ions. This experiment roughly simulated the astrophysical conditions which one can find in the solar system. Thus, we can hypothesize that prebiotic molecules could be created by interaction of the solar wind with interplanetary dust grains. The delivery of these molecules to early Earth may have contributed to the generation of life on our planet.

  15. Bioastrophysical Aspects of Low Energy Ion Irradiation of Frozen Anthracene Containing Water

    International Nuclear Information System (INIS)

    The origin of life on Earth remains a fascinating mystery in spite of many theories existing on this subject. However, it seems that simple prebiotic molecules could play an essential role in the formation of more complex organisms. In our experiment, we synthesized a class of these molecules (quinones) bombarding frozen anthracene containing water with low energy hydrogen ions. This experiment roughly simulated the astrophysical conditions which one can find in the solar system. Thus, we can hypothesize that prebiotic molecules could be created by interaction of the solar wind with interplanetary dust grains. The delivery of these molecules to early Earth may have contributed to the generation of life on our planet

  16. New 1,4-anthracene-9,10-dione derivatives as potential anticancer agents.

    Science.gov (United States)

    Zagotto, G; Supino, R; Favini, E; Moro, S; Palumbo, M

    2000-01-01

    The amino-substituted anthracene-9,10-dione (9,10-anthraquinone) derivatives represent one of the most important classes of potential anticancer agents. To better understand the basic rules governing DNA sequence specificity, we have recently synthesized a new class of D- and L-aminoacyl-anthraquinone derivatives. We have tested these new compounds as cytotoxic agents, and we have correlated their activity with the configuration of the chiral aminoacyl moiety. Molecular modeling studies have been performed to compare the test drugs in terms of steric overlapping. PMID:10755224

  17. Intersystem Crossing Mechanisms and Single Molecule Fluorescence: Terrylene in Anthracene Crystals

    International Nuclear Information System (INIS)

    Single molecule spectroscopy requires molecules with low triplet yields and/or short triplet lifetimes. The intersystem crossing (ISC) rate may be dramatically enhanced by the host matrix. Comparing the fluorescence intensity of single terrylene molecules in para-terphenyl, naphthalene, and anthracene crystals, we found a reduction of the saturation intensity by three orders of magnitude in the latter case. The fluorescence autocorrelation function indicates that the bottleneck state is the terrylene triplet. We propose a ping-pong mechanism between host and guest. This intermolecular ISC mechanism, which can open whenever the host triplet lies lower than the guest singlet, was overlooked in previous single molecule investigations

  18. Towards nanoprobes for conduction in molecular crystals: Dibenzoterrylene in anthracene crystals

    International Nuclear Information System (INIS)

    The miniaturization of electronic devices and structures brings along the quest for instruments that operate on mesoscopic and nanometric scales. In these structures, nano-instruments could elucidate the rich variety of physical processes, an understanding of which will be necessary to develop and to predict the function of new nanoscale devices. For this purpose, we propose to use single molecules as nanoprobes and to address the probes individually by means of optical single molecule microscopy and spectroscopy. This would allow us to study the conduction in molecular crystals. Here, we compare different material systems and show that dibenzoterrylene in an anthracene crystal is a promising candidate system

  19. Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

    Directory of Open Access Journals (Sweden)

    Kiymet Berkil Akar

    2011-07-01

    Full Text Available Efficient and stereoselective syntheses are described for the preparation of 2,3,9,10-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydroanthracenes 7, 8 and the corresponding 1,4-diol 17 by silver ion-assisted solvolysis of hexabromotetrahydroanthracene 6. Base-promoted aromatization of 7 and 8 afforded synthetically valuable tribromo-1-methoxyanthracenes 10 and 11. The reaction of 17 with sodium methoxide generated tribromodihydroanthracene-1,4-diol 27, whose oxidation with PCC gave 2,9,10-tribromoanthracene-1,4-dione (28. Therefore a selective and efficient method was developed for the preparation of compound 28 starting from 9,10-dibromoanthracene (1, in a simple four-step process. Compounds 10 and 11, and diol 27 constitute key precursors for the preparation of functionalized substituted anthracene derivatives that are difficult to prepare by other routes. The studies also reveal the broad range of reactivity and selectivity of the stereoisomeric anthracene derivatives.

  20. Synthesis, characterization, optical and electrical properties of bis(phenylvinyl)anthracene-based polymers

    Science.gov (United States)

    Mansour, Nadia; Hriz, Khaled; Jaballah, Nejmeddine; Kreher, David; Majdoub, Mustapha

    2016-08-01

    A series of bis(phenylvinyl)anthracene-based polymers containing different lengths of polar ethylene glycol groups in the main chain (P1-3) were efficiently synthesized by Wittig polycondensation. These polymers are fully soluble in volatile solvents, which helped a lot to obtain high quality films. Moreover, these semi-conducting materials exhibited semi-crystalline morphology with relatively high glass transition temperature. In this article, the UV-visible absorption and fluorescence properties of P1-3 were studied consequently both in solution and as thin solid film: tan absorption-onset at 433 nm was observed and all these bis(phenylvinyl)anthracene-based polymers (P1-3) show a blue emission in solution, fluorescence quantum efficiencies being respectively 52% for P1, 75% for P2 and 67% for P3. In addition, the HOMO/LUMO energy levels were evaluated by cyclic voltammetry measurements and indicate a p-type semi-conducting materials. Finally, the electrical properties of P1-3 were investigated by recording current-tension characteristics and these experimental results were modeled by the current space-charge-limited (SCLC) mechanism.

  1. A panchromatic anthracene-fused porphyrin sensitizer for dye-sensitized solar cells

    KAUST Repository

    Ball, James M.

    2012-01-01

    The development of ruthenium-free sensitizers which absorb light over a broad range of the solar spectrum is important for improving the power conversion efficiency of dye-sensitized solar cells. Here we study three chemically tailored porphyrin-based dyes. We show that by fusing the porphyrin core to an anthracene unit, we can extend the conjugation length and lower the optical gap, shifting the absorption spectrum into the near-infrared (NIR). All three dyes were tested in dye-sensitized solar cells, using both titanium dioxide and tin dioxide as the electron-transport material. Solar cells incorporating the anthracene-fused porphyrin dye exhibit photocurrent collection at wavelengths up to about 1100 nm, which is the longest reported for a porphyrin-based system. Despite extending the photon absorption bandwidth, device efficiency is found to be low, which is a common property of cells based on porphyrin dyes with NIR absorption. We show that in the present case the efficiency is reduced by inefficient electron injection into the oxide, as opposed to dye regeneration, and highlight some important design considerations for panchromatic sensitizers. © 2012 The Royal Society of Chemistry.

  2. 7,12-DIMETHYLBENZ(A)ANTHRACENE-DEOXYRIBONUCLEOSIDE ADDUCT FORMATION 'IN VIVO': EVIDENCE FOR THE FORMATION AND BINDING OF A MONOHYDROXYMETHYL-DMBA (DIMETHYLBENZ(A)ANTHRACENE) METABOLITE TO RAT LIVER DNA (DEOXYRIBONUCLEIC ACID)

    Science.gov (United States)

    The polycyclic aromatic hydrocarbon, 7,12-dimethyl benz(a)anthracene (DMBA) is a potent carcinogen to the female Sprague-Dawley rat, and when administered under conditions that have been shown to produce cancer, results in extensive formation of hydrocarbon-deoxyribonucleoside ad...

  3. Uptake of 7,12-dimethylbenz(a)anthracene and benzo(a)pyrene in melanin-containing tissues

    Energy Technology Data Exchange (ETDEWEB)

    Roberto, A.; Larsson, B.S. [Uppsala Univ., Dept. of Pharmaceutical Biosciences, Div. of Toxicology, Uppsala (Sweden); Tjaelve, H. [The Swedish Univ. of Agricultural Sciences, Dept. of Pharmacology and Toxicology, Uppsala (Sweden)

    1996-08-01

    It is widely accepted that UV exposure is the main etiological factor for malignant melanoma. Epidemiologic studies, however, have indicated that also chemical carcinogens may be a risk factor for the disease. Polycyclic aromatic hydrocarbons such as 7,12-dimethylbenz(a)anthracene and benzo(a)pyrene represent an important class of carcinogenic chemicals. It is known that 7,12-dimethylbenz(a)anthracene can induce melanotic tumours in various animal species, and human melanocytes in culture have been found to be capable of metabolizing benzo(a)pyrene to its proximate carcinogen benzo(a)pyrene-7,8-diol. In the present study the disposition of {sup 14}C- and {sup 3}H-7,12-dimethylbenz(a)anthracene and {sup 14}C-benzo(a)pyrene was studied in pigmented and albino mice and Syrian golden hamsters by whole-body autoradiography. The results showed pronounced retention of label in the melanin-containing structures of the eyes and the hair follicles in the pigmented animals. The labelling of the corresponding structures in the albino animals was low. Additional experiments showed that 7,12-dimethylbenz(a)anthracene and benzo(a)pyrene as well as some of their metabolites are bound to melanin in vitro. The specific localization of the polycyclic aromatic hydrocarbons in pigmented tissues due to melanin affinity, combined with bioactivating capacity of melanocytes, suggest that these substances may play a role in the induction of malignant melanoma. (au).

  4. Quinoline-Substituted 10-(naphthalene-7-yl)anthracene Derivatives for Blue Fluorescent Organic Light-Emitting Diodes.

    Science.gov (United States)

    Kim, Chanwoo; Park, Soo Na; Lee, Seul Bee; Kim, Young Seok; Lee, Ho Won; Kim, Young Kwan; Yoon, Seung Soo

    2016-02-01

    In this study, we have designed and synthesized blue emitters based on quinoline-substituted 10-(naphthalene-7-yl)anthracene. Particularly, a material exhibited highly efficient blue electroluminescence with CIE coordinates of (0.15, 0.18). PMID:27433688

  5. Electronic states of the fluorophore 9,10-bis(phenylethynyl)anthracene (BPEA). A synchrotron radiation linear dichroism investigation

    DEFF Research Database (Denmark)

    Thulstrup, Peter Waaben; Jones, Nykola; Hoffmann, Søren Vrønning; Spanget-Larsen, Jens

    2013-01-01

    The electronic transitions of 9,10-bis(phenylethynyl)anthracene (BPEA) were investigated by synchrotron radiation linear dichroism (SRLD) spectroscopy in the range 20000–58000 cm1 (500–170 nm) on molecular samples aligned in stretched polyethylene. The investigation was supported by variable...

  6. Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)[subscript 2

    Science.gov (United States)

    Charleton, Kimberly D. M.; Prokopchuk, Ernest M.

    2011-01-01

    A laboratory experiment aimed at students who are studying coordination chemistry of transition-metal complexes is described. A simple vanadyl acetylacetonate complex can be used as a catalyst in the hydrogen peroxide oxidation of anthracene to produce anthraquinone. The reaction can be performed under a variety of reaction conditions, ideally by…

  7. Formation and Stabilization of Environmentally Persistent Free Radicals Induced by the Interaction of Anthracene with Fe(III)-Modified Clays.

    Science.gov (United States)

    Jia, Hanzhong; Nulaji, Gulimire; Gao, Hongwei; Wang, Fu; Zhu, Yunqing; Wang, Chuanyi

    2016-06-21

    Environmentally persistent free radicals (EPFRs) are occasionally detected in Superfund sites but the formation of EPFRs induced by polycyclic aromatic hydrocarbons (PAHs) is not well understood. In the present work, the formation of EPFRs on anthracene-contaminated clay minerals was quantitatively monitored via electron paramagnetic resonance (EPR) spectroscopy, and surface/interface-related environmental influential factors were systematically explored. The obtained results suggest that EPFRs are more readily formed on anthracene-contaminated Fe(III)-montmorillonite than in other tested systems. Depending on the reaction condition, more than one type of organic radicals including anthracene-based radical cations with g-factors of 2.0028-2.0030 and oxygenic carbon-centered radicals featured by g-factors of 2.0032-2.0038 were identified. The formed EPFRs are stabilized by their interaction with interlayer surfaces, and such surface-bound EPFRs exhibit slow decay with 1/e-lifetime of 38.46 days. Transformation pathway and possible mechanism are proposed on the basis of experimental results and quantum mechanical simulations. Overall, the formation of EPFRs involves single-electron-transfer from anthracene to Fe(III) initially, followed by H2O addition on formed aromatic radical cation. Because of their potential exposure in soil and atmosphere, such clay surface-associated EPFRs might induce more serious toxicity than PAHs and exerts significant impacts on human health. PMID:27224055

  8. Confined growth of carbon nanoforms in one-dimension by fusion of anthracene rings inside the pores of MCM-41

    Science.gov (United States)

    Bosch-Navarro, Concha; Coronado, Eugenio; Martí-Gastaldo, Carlos; Amorós, Pedro

    2014-06-01

    We report a simple two-step procedure that uses anthracene, a cheap polyaromatic hydrocarbon with low melting point, as a molecular precursor to produce carbon nanoforms (CNFs). First, we describe the chemical synthesis of graphite from the fusion of anthracene rings at relatively low temperature (520 °C) followed by cyclodehydrogenation. Next, we extend this protocol to the synthesis of CNFs by confining the molecular precursor in a mesoporous host like MCM-41. The confined environment favors one-dimensional growth of CNFs with sizes controlled by the pores of the mesoporous host.We report a simple two-step procedure that uses anthracene, a cheap polyaromatic hydrocarbon with low melting point, as a molecular precursor to produce carbon nanoforms (CNFs). First, we describe the chemical synthesis of graphite from the fusion of anthracene rings at relatively low temperature (520 °C) followed by cyclodehydrogenation. Next, we extend this protocol to the synthesis of CNFs by confining the molecular precursor in a mesoporous host like MCM-41. The confined environment favors one-dimensional growth of CNFs with sizes controlled by the pores of the mesoporous host. Electronic supplementary information (ESI) available: Synthesis details, SEM and additional HR-TEM images, FT-IR spectra, EDAX microanalysis and pore distribution of loaded MCM41@anth. See DOI: 10.1039/c3nr06669j

  9. Photochemical Reaction of 7,12-Dimethylbenz[a]anthracene (DMBA and Formation of DNA Covalent Adducts

    Directory of Open Access Journals (Sweden)

    Peter P. Fu

    2005-04-01

    Full Text Available DMBA, 7,12-dimethylbenz[a]anthracene, is a widely studied polycyclic aromatic hydrocarbon that has long been recognized as a probable human carcinogen. It has been found that DMBA is phototoxic in bacteria as well as in animal or human cells and photomutagenic in Salmonella typhimurium strain TA102. This article tempts to explain the photochemistry and photomutagenicity mechanism. Light irradiation converts DMBA into several photoproducts including benz[a]anthracene-7,12-dione, 7-hydroxy-12-keto-7-methylbenz[a]anthracene, 7,12-epidioxy-7,12-dihydro-DMBA, 7-hydroxymethyl-12-methylbenz[a]anthracene and 12-hydroxymethyl-7-methylbenz[a]anthracene. Structures of these photoproducts have been identified by either comparison with authentic samples or by NMR/MS. At least four other photoproducts need to be assigned. Photo-irradiation of DMBA in the presence of calf thymus DNA was similarly conducted and light-induced DMBA-DNA adducts were analyzed by 32P-postlabeling/TLC, which indicates that multiple DNA adducts were formed. This indicates that formation of DNA adducts might be the source of photomutagenicity of DMBA. Metabolites obtained from the metabolism of DMBA by rat liver microsomes were reacted with calf thymus DNA and the resulting DNA adducts were analyzed by 32P-postlabeling/TLC under identical conditions. Comparison of the DNA adduct profiles indicates that the DNA adducts formed from photo-irradiation are different from the DNA adducts formed due to the reaction of DMBA metabolites with DNA. These results suggest that photo-irradiation of DMBA can lead to genotoxicity through activation pathways different from those by microsomal metabolism of DMBA.

  10. Diazaquinomycins E–G, Novel Diaza-Anthracene Analogs from a Marine-Derived Streptomyces sp.

    Directory of Open Access Journals (Sweden)

    Michael W. Mullowney

    2014-06-01

    Full Text Available As part of our program to identify novel secondary metabolites that target drug-resistant ovarian cancers, a screening of our aquatic-derived actinomycete fraction library against a cisplatin-resistant ovarian cancer cell line (OVCAR5 led to the isolation of novel diaza-anthracene antibiotic diazaquinomycin E (DAQE; 1, the isomeric mixture of diazaquinomycin F (DAQF; 2 and diazaquinomycin G (DAQG; 3, and known analog diazaquinomycin A (DAQA; 4. The structures of DAQF and DAQG were solved through deconvolution of X-Ray diffraction data of their corresponding co-crystal. DAQE and DAQA exhibited moderate LC50 values against OVCAR5 of 9.0 and 8.8 μM, respectively. At lethal concentrations of DAQA, evidence of DNA damage was observed via induction of apoptosis through cleaved-PARP. Herein, we will discuss the isolation, structure elucidation, and biological activity of these secondary metabolites.

  11. Syntheses of electroactive layers based on functionalized anthracene for electrochromic applications

    International Nuclear Information System (INIS)

    A new monomer (DTAT) was synthesized via linking 3,4-ethylenedioxythiophene (EDOT) on anthracene. The polymer, P(DTAT) was electrosynthesized by anodic oxidation of the corresponding monomer in 0.1 M LiClO4 acetonitrile (ACN) solution. The optical properties, the absorption spectra and the kinetics, were examined. Spectroelectrochemical analysis showed that P(DTAT) has an electronic band gap (due to π-π* transition) of 1.57 eV at 776 nm. Copolymers of DTAT with EDOT were prepared in ACN/LiClO4 (0.1 M) solvent-electrolyte couple by varying applied potential. The incorporation of an EDOT into the full conjugated backbone, DTAT, affects its optical behavior resulting in different colors; a claret red neutral state, gray and red intermediate states and a blue oxidized state

  12. Growth of large naphthalene and anthracene single-crystal sheets at the liquid–air interface

    Energy Technology Data Exchange (ETDEWEB)

    Postnikov, V. A., E-mail: postva@yandex.ru [Donbas National Academy of Civil Engineering and Architecture (Ukraine); Chertopalov, S. V. [Donetsk National University (Ukraine)

    2015-07-15

    The growth of organic single crystals of naphthalene (C{sub 10}H{sub 8}) and anthracene (C{sub 14}H{sub 10}) at the liquid‒air interface from a mixture of solvents has been investigated. The growth technique used in the study makes it possible to obtain single-crystal sheets up to 10 mm in size for 24 h. The surface morphology and structure of the crystals have been analyzed by optical microscopy and X-ray diffraction. C{sub 10}H{sub 8} and C{sub 14}H{sub 10} single crystals grow coplanarly along the (001) plane. A thermodynamic model of the flat-crystal nucleus formation at the liquid‒air interface, based on the analysis of the change in the free Gibbs energy, is considered.

  13. Polymorphism in Self-Assembled Structures of 9-Anthracene Carboxylic Acid on Ag(111

    Directory of Open Access Journals (Sweden)

    Bo Xu

    2012-06-01

    Full Text Available Surface self-assembly process of 9-anthracene carboxylic acid (AnCA on Ag(111 was investigated using STM. Depending on the molecular surface density, four spontaneously formed and one annealed AnCA ordered phases were observed, namely a straight belt phase, a zigzag double-belt phase, two simpler dimer phases, and a kagome phase. The two high-density belt phases possess large unit cells on the scale length of 10 nm, which are seldom observed in molecular self-assembled structures. This structural diversity stems from a complicated competition of different interactions of AnCA molecules on metal surface, including intermolecular and molecular-substrate interactions, as well as the steric demand from high molecular surface density.

  14. Investigating the anisotropic scintillation response in anthracene through neutron, gamma-ray, and muon measurements

    CERN Document Server

    Schuster, Patricia

    2015-01-01

    This paper reports a series of measurements that characterize the directional dependence of the scintillation response of crystalline anthracene to incident DT neutrons, DD neutrons, Cs-137 gamma rays, and, for the first time, cosmic ray muons. The neutron measurements give the amplitude and pulse shape dependence on the proton recoil direction over one hemisphere of the crystal, confirming and extending previous results in the literature. In similar measurements using incident gamma rays, no directional effect is evident, and any anisotropy with respect to the electron recoil direction is constrained to have a magnitude of less than a tenth of that present in the proton recoil events. Cosmic muons are measured at two directions, and no anisotropy is observed. This set of observations indicates that high dE/dx is necessary for an anisotropy to be present for a given type of scintillation event, which in turn could be used to discriminate among different hypotheses for the underlying causes of the anisotropy, ...

  15. Synthesis and characterization of Al- and Ti-MCM-41 materials: application to oxidation of anthracene

    Directory of Open Access Journals (Sweden)

    R. S. Araújo

    2007-03-01

    Full Text Available The synthesis and characterization of new molecular sieves of the MCM-41 type are presented in this study. Samples were obtained from the alkoxides of Si, Ti and Al and different long-chain amine and alkylammonium salts surfactants, by the sol-gel method, through moderate agitation at room temperature. The reactions were conducted in two steps, acid hydrolysis (pH=2 and alkaline condensation (pH=10, both taking about 90min. The synthesized crystals were characterized using infrared spectroscopy, thermogravimetry and X-Ray diffraction. Pore diameters and surface areas were measured by N2 adsorption at 77K. Catalytic tests were conducted for anthracene oxidation using different oxidants (H2O2, alkylhydroperoxide and organic solvents (benzene, tetrahydrofuran.

  16. Characterisation and vapour sensing properties of spin coated thin films of anthracene labelled PMMA polymer

    International Nuclear Information System (INIS)

    In the present article thin films of poly (methyl methacrylate) (PMMA) polymer labelled with anthracene (Ant-PMMA) prepared by spin coating are characterised by UV-visible spectroscopy, surface plasmon resonance (SPR), spectroscopic ellipsometry (SE) and Atomic Force Microscopy (AFM) and their organic vapour sensing properties are investigated. Ant-PMMA films' thickness are determined by performing theoretical fitting to experimental data measured using SPR and SE. Results obtained show that the spin-cast films are of good uniformity with an average thickness of 6-8 nm. Organic vapour sensing properties are studied using SPR technique during exposures to different volatile organic compounds (VOCs). Ant-PMMA films' response to the selected VOCs has been examined in terms of solubility parameters and molar volumes of the solvents, and the films were found to be largely sensitive to benzene vapour compared to other studied analytes.

  17. Solubility of anthracene in binary alcohol + 3-methoxy-1-butanol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    McHale, M.E.R.; Horton, A.S.M.; Padilla, S.A.; Trufant, A.L.; Sancha, N.U. De La; Vela, E.; Powell, J.R.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1997-01-01

    Experimental solubilities are reported for anthracene dissolved in ten binary mixtures containing 3-methoxy-1-butanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-methyl-1-butanol, 4-methyl-2-pentanol, 1-octanol, and 2-ethyl-1-hexanol at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the ten systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being 0.4% and 0.5% for the combined NIBS/Redlich-Kister and modified Wilson equations, respectively.

  18. Solubility of anthracene in binary alcohol + 2-pentanol and alcohol + 4-methyl-2-pentanol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    Powell, J.R.; McHale, M.E.R.; Kauppila, A.S.M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1996-07-01

    Experimental solubilities are reported for anthracene dissolved in 16 binary mixtures containing either 2-pentanol or 4-methyl-2-pentanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 1-octanol, 2-methyl-1-propanol and 3-methyl-1-butanol at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the 16 systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being 0.3% and 0.5% for the combined NIBS/Redlich-Kister and modified Wilson equations, respectively.

  19. Solubility of anthracene in binary alcohol + 2-ethyl-1-hexanol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    Powell, J.R.; McHale, M.E.R.; Kauppila, A.S.M.; Otero, P.; Jayasekera, M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1995-11-01

    Solid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the petroleum industry, particularly in light of present trends toward heavier feedstocks and known carcinogenicity/mutagenicity of many of the larger polycyclic aromatic compounds. Experimental solubilities are reported for anthracene dissolved in seven binary mixtures containing 2-ethyl-l-hexanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-octanol, 2-methyl-1-propanol, and 3-methyl-1-butanol at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the seven systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values on the order of 0.6%.

  20. Destruction of acenaphthene, fluorene, anthracene and pyrene by a dc gliding arc plasma reactor

    International Nuclear Information System (INIS)

    In this study, four kinds of PAHs (polycyclic aromatic hydrocarbons) i.e. acenaphthene, fluorene, anthracene and pyrene are used as targets for investigation of PAHs treatment process assisted by dc gliding arc discharge. The effects of carrier gas and external resistance on the PAHs decomposition process are discussed. The results indicate that the destruction rate can be achieved to the highest with the carrier gas of oxygen and the external resistance of 50 kΩ independent of type of PAHs. Furthermore, experimental results suggest that destruction energy efficiency of gliding arc plasma would be improved by treating higher concentration pollutants. Based on the analysis of experimental results, possible destruction mechanisms in different gas discharge are discussed.

  1. Preparation of non-covalently functionalized graphene using 9-anthracene carboxylic acid

    International Nuclear Information System (INIS)

    A simple way of achieving stable aqueous dispersion of graphene by non-covalent functionalization using 9-anthracene carboxylic acid has been successfully accomplished. Unlike in chemically reduced graphene, the C-sp2 network of the graphene remains undistorted and therefore of superior quality. The non-covalent functionalization facilitates the exfoliation of graphite layers in a polarity controlled combination of media. A detailed exfoliation mechanism is proposed based on the controlled experiment and is supported by the data from UV-vis spectroscopy, transmission electron microscopy, and x-ray diffraction studies. Formation of monolayer graphene has been confirmed from Raman spectroscopy. The graphene based ultracapacitor shows a high value of specific capacitance (148 F g-1).

  2. IONIZATION AND FRAGMENTATION OF ANTHRACENE UPON INTERACTION WITH keV PROTONS AND α PARTICLES

    International Nuclear Information System (INIS)

    The interaction of keV ions with polyaromatic hydrocarbons is dominated by charge exchange and electronic stopping. We have studied the response of the polyaromatic hydrocarbon anthracene (C14H10) upon keV H+ and He2+ impact using high-resolution time-of-flight mass spectrometry. Extensive fragmentation into small CnH q+m as well as formation of up to triply charged parent ions is observed. Ab initio electron densities are used to calculate the molecular excitation due to electronic stopping. Fragment yields increase with the increase of electronic stopping as a function of projectile velocity. For equal electronic stopping, He2+ is found to induce more fragmentation than H+. The difference in fragmentation is concluded to be due to two electron processes, which are relevant channels only for He2+.

  3. Growth of large naphthalene and anthracene single-crystal sheets at the liquid–air interface

    International Nuclear Information System (INIS)

    The growth of organic single crystals of naphthalene (C10H8) and anthracene (C14H10) at the liquid‒air interface from a mixture of solvents has been investigated. The growth technique used in the study makes it possible to obtain single-crystal sheets up to 10 mm in size for 24 h. The surface morphology and structure of the crystals have been analyzed by optical microscopy and X-ray diffraction. C10H8 and C14H10 single crystals grow coplanarly along the (001) plane. A thermodynamic model of the flat-crystal nucleus formation at the liquid‒air interface, based on the analysis of the change in the free Gibbs energy, is considered

  4. Size-dependent optical properties of 9,10-bis(phenylethynyl)anthracene crystals

    Energy Technology Data Exchange (ETDEWEB)

    Yagita, Yoshimi; Matsui, Kazunori, E-mail: matsui@kanto-gakuin.ac.jp

    2015-05-15

    The optical properties of 9,10-bis(phenylethynyl)anthracene (BPEA) were studied for various states: nanoparticles (~100 nm), microcrystals (~1 μm), bulk crystals (~1 mm), and vacuum-deposited film. The absorption spectra showed a red shift from ethanol solution to bulk crystals with an increase in crystal size. The vacuum-deposited film seemed to have mixed spectral characteristics of nanoparticles and bulk crystals. The fluorescence of BPEA showed two peaks for the various crystals. The fluorescence of the shorter wavelength peak was shifted toward the blue from 556 to 527 nm from the bulk to nanoparticles. On the other hand, the position of the longest wavelength peak changed little, staying around 596 nm. The relative intensity of the former and latter increased with a decrease in the crystal size. The time-resolved fluorescence spectra clearly confirmed the existence of two emissive sites in the bulk crystals. These sites are probably located at the peripheral and inner positions of the crystals. Change in the relative proportions of the two sites could be the main reason for the size-dependent fluorescence. - Highlights: ●The optical properties of 9,10-bis(phenylethynyl)anthracene crystals were studied. ●The absorption spectra showed a red-shift with an increase in crystal size. ●The fluorescence spectra showed size-dependent and size-independent peaks. ●A size-dependent peak with a shorter decay is attributed to the surface molecules. ●A size-independent peak with a longer decay is attributed to the bulk crystals.

  5. A multielectrochromic copolymer based on anthracene and thiophene via electrochemical copolymerization in boron trifluoride diethyl etherate

    International Nuclear Information System (INIS)

    Highlights: ► A copolymer film based on anthracene and thiophene has been successfully deposited on ITO electrode in boron trifluoride diethyl etherate. ► The formation of the copolymer has been confirmed by CVs, FT-IR and XPS. ► The copolymer film presents multicolor electrochromism (yellowish red, yellow, yellow green, blue green, light blue and dark blue). ► The film has good electrochromic properties such as fast switching rate, reasonable coloration efficiency and stability. - Abstract: A copolymer based on thiophene and anthracene was prepared on indium tin oxide (ITO) glass electrode via electrochemical copolymerization in boron trifluoride diethyl etherate (BFEE). The resultant copolymer is characterized by cyclic voltammetry, FT-IR, XPS, SEM and spectroelectrochemical analysis. The copolymer film presents multicolor electrochromism and can exhibit six colors (yellowish red, yellow, yellow green, blue green, light blue and dark blue) under various applied potentials. The optical contrasts of the copolymer film at 491, 767 and 1100 nm are 21%, 38% and 37%, respectively, and the corresponding switching rates are 1.9, 1.3 and 2.3 s. The film has superior coloration efficiency which is calculated to be 327 cm2 C−1 (491 nm), 240 cm2 C−1 (767 nm) and 296 cm2 C−1 (1100 nm). Furthermore, the film presents reasonable electrochemical and optical stability which retains 73% of its original electroactivity after 500 cycles and 73.6% of its optical contrast after 800 steps. All of these indicate the satisfactory electrochromic properties of the copolymer film.

  6. Fluorescence Quenching of Anthracene by N,N-Diethylaniline and Phenothiazine in Triton X-100/n-C10H21OH/H2O Microemulsion

    Institute of Scientific and Technical Information of China (English)

    GUO Xia; XU Hui; GUO Rong

    2003-01-01

    The photo-induced electron transfer reactions of anthracene with N,N-diethylaniline(DEA) and phenothiazine(PTZ) occur in the membrane phase of a Triton X-100/n-C10H21OH(1-decanol)/H2O microemulsion. DEA and PTZ exist in the membrane phase of the microemulsion. Anthracene exists in the oil continuous phase of the W/O microemulsion and in the oil core and membrane phase of the O/W microemulsion.

  7. Anthraphane: An Anthracene-Based, Propeller-Shaped D(3h)-Symmetric Hydrocarbon Cyclophane and Its Layered Single Crystal Structures.

    Science.gov (United States)

    Servalli, Marco; Trapp, Nils; Wörle, Michael; Klärner, Frank-Gerrit

    2016-03-18

    The novel hydrocarbon propeller-shaped D3h-symmetric cyclophane (3), "anthraphane", was prepared through a revisited and optimized gram-scale synthesis of the key building block anthracene-1,8-ditriflate 7. Anthraphane has a high tendency to crystallize and single crystals in size ranges of 100-200 μm are easily obtained from different solvents. The crystallization behavior of 3 was extensively studied to unravel packing motifs and determine whether the packing can be steered into a desired direction, so to allow topochemical photopolymerization. SC-XRD shows that anthraphane packs in layers irrespective of the solvent used for crystallization. However, within the layers, intermolecular arrangements and π-π interactions of the anthracene units vary strongly. Four interaction motifs for the anthracene moieties are observed and discussed in detail: two types of exclusively edge-to-face (etf), a mixture of edge-to-face and face-to-face (ftf), and no anthracene-anthracene interaction at all. To elucidate why an exclusive ftf stacking was not observed, electrostatic potential surface (EPS) calculations with the semiempirical PM3 method were performed. They show qualitatively that the anthracene faces bear a strong negative surface potential, which may be the cause for this cyclophane to avoid ftf interactions. This combined crystallographic and computational study provides valuable insights on how to create all-ftf packings. PMID:26919259

  8. 9,10-Bis{2-[1-(2-pyridylmethylimidazolium-3-yl]ethoxy}anthracene bis(hexafluoridophosphate

    Directory of Open Access Journals (Sweden)

    Li-Hui Guo

    2008-01-01

    Full Text Available The cation of the title compound, C36H34N6O22+·2PF6−, lies across a crystallographic inversion centre. The imidazole and pyridine rings form dihedral angles of 82.28 (5° and 11.87 (7°, respectively, with the anthracene ring system. The crystal packing is stabilized by π–π interactions between the pyridine ring and the central ring of anthracene, with a ring centroid–centroid distance of 3.684 (3 Å. The PF6− anion is disordered over three different positions with occupancies of 0.284 (6, 0.354 (8 and 0.362 (9.

  9. Anthracene and TCNQ doping of substituted nickel phthalocyanine: Effects on the electrical and optical properties of spin coated thin films

    Directory of Open Access Journals (Sweden)

    Hassan Aseel K.

    2013-08-01

    Full Text Available In this work, we study the controlled doping of thin films of substituted nickel phthalocyanine, NiPcR8, where R=-SC6H13, with anthracene and TCNQ and investigate the effects of the extent of this doping on the optical and electrical properties of NiPcR8 films. Optical constants, namely index of refraction (n and extinction coefficient (k have increased for both types of doping, as determined from spectroscopic ellipsometry measurements. Conductivity is shown to increase by about four orders of magnitudes compared to pure NiPcR8 films as a result of anthracene doping while TCNQ has resulted in almost six orders of magnitudes increase in the film’s conductivity.

  10. Tuning the properties of an anthracene-based PPE-PPV copolymer by fine variation of its macromolecular parameters

    Czech Academy of Sciences Publication Activity Database

    Tinti, F.; Sabir, F. K.; Gazzano, M.; Righi, S.; Ulbricht, C.; Usluer, Ö.; Pokorná, Veronika; Cimrová, Věra; Yohannes, T.; Egbe, D. A. M.; Camaioni, N.

    2013-01-01

    Roč. 3, č. 19 (2013), s. 6972-6980. ISSN 2046-2069 R&D Projects: GA ČR GAP106/12/0827; GA ČR(CZ) GA13-26542S Institutional support: RVO:61389013 Keywords : anthracene-containing PPE-PPV copolymer * macromolecular parameters * structural and transport properties Subject RIV: CD - Macromolecular Chemistry Impact factor: 3.708, year: 2013

  11. Effect of Indole-3-Acetic Acid-Producing Bacteria on Phytoremediation of Soil Contaminated with Phenanthrene and Anthracene by Mungbean

    OpenAIRE

    Waraporn Chouychai; Thidarat Paemsom; Chittra Pobsuwan; Khanitta Somtrakoon; Hung Lee

    2016-01-01

    The use of indole-3-acetic acid (IAA)-producing bacteria isolated from non-contaminated weed rhizosphere to enhance plant growth and PAH phytoremediation capacity was investigated. IAA-producing bacterial isolates, designated NSRU1, NSRU2, and NSRU3, were isolated from the rhizosphere of Eleusine indica (Poaceae) and Chromolaena odorata (Asteraceae). The isolates were able to produce IAA in nutrient broth. However, when grown in the presence of 100 mg/l of either phenanthrene or anthracene, t...

  12. On the spin distribution in bridged anthracene-viologen molecules : an electron-nuclear double resonance study

    OpenAIRE

    Sariciftci, Serdar; Werner, Andreas; Grupp, Arthur; Mehring, Michael; Götz, Günther; Bäuerle, Peter; Effenberger, Franz

    1992-01-01

    Studies on the spin distribution in the radical state of anthracene-σ bridge viologen supermolecules with different bridge units are reported. Electronnuclear double resonance experiments (ENDOR) were performed on electrochemically reduced molecules. Proton hyperfine coupling constants at different molecular sites were obtained and are discussed in detail. The experimentally determined values are compared with quantum chemical calculations of the INDO type. The observed spin distribution...

  13. Self-Assembly of Amphiphilic Anthracene-Functionalized β-Cyclodextrin (CD-AN) through Multi-Micelle Aggregation.

    Science.gov (United States)

    Zhang, Yuannan; Xu, Hongjie; Ma, Xiaodong; Shi, Zixing; Yin, Jie; Jiang, Xuesong

    2016-06-01

    Multi-micelle aggregation (MMA) mechanism is widely acknowledged to explicate large spherical micelles self-assembly, but the process of MMA during self-assembly is hard to observe. Herein, a novel kind of strong, regular microspheres fabricated from self-assembly of amphiphilic anthracene-functionalized β-cyclodextrin (CD-AN) via Cu(I)-catalyzed azide-alkyne click reactions is reported. The obtained CD-AN amphiphiles can self-assemble in water from primary core-shell micelles to secondary aggregates with the diameter changing from several tens nm to around 600-700 nm via MMA process according to the images of scanning electron microscopy, transmission electron microscopy, and atomic force microscopy as well as the dynamic light scattering measurements, followed by further crosslinking through photo-dimerization of anthracene. What merits special attention is that such photo-crosslinked self-assemblies are able to disaggregate reversibly into primary nanoparticles when changing the solution conditions, which is benefited from the designed regular structure of CD-AN and the rigid ranging of anthracene during assembly, thus confirming the process of MMA. PMID:27145434

  14. Vibrational properties of organic donor-acceptor molecular crystals: Anthracene-pyromellitic-dianhydride (PMDA) as a case study

    KAUST Repository

    Fonari, A.

    2015-12-10

    We establish a reliable quantum-mechanical approach to evaluate the vibrational properties of donor-acceptor molecular crystals. The anthracene-PMDA (PMDA = pyromellitic dianhydride) crystal, where anthracene acts as the electron donor and PMDA as the electron acceptor, is taken as a representative system for which experimental non-resonance Raman spectra are also reported. We first investigate the impact that the amount of nonlocal Hartree-Fock exchange (HFE) included in a hybrid density functional has on the geometry, normal vibrational modes, electronic coupling, and electron-vibrational (phonon) couplings. The comparison between experimental and theoreticalRaman spectra indicates that the results based on the αPBE functional with 25%-35% HFE are in better agreement with the experimental results compared to those obtained with the pure PBE functional. Then, taking αPBE with 25% HFE, we assign the vibrational modes and examine their contributions to the relaxation energy related to the nonlocal electron-vibration interactions. The results show that the largest contribution (about 90%) is due to electron interactions with low-frequency vibrational modes. The relaxation energy in anthracene-PMDA is found to be about five times smaller than the electronic coupling.

  15. Vibrational properties of organic donor-acceptor molecular crystals: Anthracene-pyromellitic-dianhydride (PMDA) as a case study

    International Nuclear Information System (INIS)

    We establish a reliable quantum-mechanical approach to evaluate the vibrational properties of donor-acceptor molecular crystals. The anthracene-PMDA (PMDA = pyromellitic dianhydride) crystal, where anthracene acts as the electron donor and PMDA as the electron acceptor, is taken as a representative system for which experimental non-resonance Raman spectra are also reported. We first investigate the impact that the amount of nonlocal Hartree-Fock exchange (HFE) included in a hybrid density functional has on the geometry, normal vibrational modes, electronic coupling, and electron-vibrational (phonon) couplings. The comparison between experimental and theoretical Raman spectra indicates that the results based on the αPBE functional with 25%-35% HFE are in better agreement with the experimental results compared to those obtained with the pure PBE functional. Then, taking αPBE with 25% HFE, we assign the vibrational modes and examine their contributions to the relaxation energy related to the nonlocal electron-vibration interactions. The results show that the largest contribution (about 90%) is due to electron interactions with low-frequency vibrational modes. The relaxation energy in anthracene-PMDA is found to be about five times smaller than the electronic coupling

  16. Reaction engineering studies on the biodegradation of anthracene on bioremediation of diesel contaminated soil using Acinetobacter sp. (ATCC no. 14293)

    Energy Technology Data Exchange (ETDEWEB)

    Roy, R.; Bhattacharya, P.; Chowdhury, R. [Jadavpur Univ., Kolkata, West Bengal (India). Dept. of Chemical Engineering

    2006-08-15

    Bioremediation is a simple and cost-effective means of cleaning up chemically contaminated soil. This study was conducted to better understand the complex reaction chemistry associated with the biodegradation of anthracene. Anthracene was selected as a model PAH because it represents a typical polyaromatic hydrocarbon found in diesel. This paper presented the results of a systematic bioprocess study of the monoculture system that can decompose anthracene from its simulated mixture in methanol using a pure bacterial strain, Acinetobacter sp. (ATCC no. 14293). In a separate attempt, bioremediation of diesel contaminated soil to reduce total aromatic content using the same bacterial strain was carried out. The kinetic parameters needed for bioreactor design were also evaluated. It was observed that Monod's classical substrate uninhibited model can predict cell growth rate and substrate depletion kinetics. When coupled with first order cell decay rate, it can also be used to express the reaction engineering behaviour of the bioremediation of diesel contaminated soil. It was shown that the maximum specific cell growth rate in soil depends on moisture content of the oil-contaminated soil. 20 refs., 1 tab., 7 figs.

  17. Enhanced bioremediation of anthracene contaminated soil by bioaugmentation and application of non-ionic surfactant -- Fuelbuster reg-sign

    International Nuclear Information System (INIS)

    Surfactants enable the mass transfer of hydrophobic compounds to more hydrophilic phases, thereby increasing bioavailability to microorganisms for degradation. Indigenous soil bacteria was enriched over three months to selectively degrade anthracene. Enhanced soil remediation was determined using radiolabeled anthracene and comparing the end product 14-CO2 from different treatment and control groups. Bioreactors were engineered, fitted with inflow of air and CO2 trapping devices. The two treatment groups included were, (1) sterile soil seeded with enriched microorganisms and (2) sterile soil seeded with microorganisms and Fuelbuster reg-sign at concentrations below its critical micellar concentrations (determined by surface tension method). The control group had only sterile soil to account for any abiotic degradation. Remediation was monitored over 91 days and the end product was analyzed by liquid scintillation counting. On day 50 of remediation the relative CO2 evolution was 0.086 : 0.22 : 0.69 for control: Treatment 1: Treatment 2. On day 50 additional Fuelbuster reg-sign was injected into Treatment 2, which resulted in a 30% increase in CO2 evolution when the study was terminated. Binding effect of soil on the bioavailability of anthracene is currently being studied using the same experimental setup, excluding soil from all treatment groups

  18. Vibrational properties of organic donor-acceptor molecular crystals: Anthracene-pyromellitic-dianhydride (PMDA) as a case study

    Energy Technology Data Exchange (ETDEWEB)

    Fonari, A.; Corbin, N. S.; Coropceanu, V., E-mail: jean-luc.bredas@kaust.edu.sa, E-mail: coropceanu@gatech.edu [School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400 (United States); Vermeulen, D.; McNeil, L. E. [Department of Physics and Astronomy, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3255 (United States); Goetz, K. P.; Jurchescu, O. D. [Department of Physics, Wake Forest University, Winston-Salem, North Carolina 27109-7507 (United States); Bredas, J. L., E-mail: jean-luc.bredas@kaust.edu.sa, E-mail: coropceanu@gatech.edu [School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400 (United States); Solar and Photovoltaics Engineering Research Center, Division of Physical Science and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900 (Saudi Arabia)

    2015-12-14

    We establish a reliable quantum-mechanical approach to evaluate the vibrational properties of donor-acceptor molecular crystals. The anthracene-PMDA (PMDA = pyromellitic dianhydride) crystal, where anthracene acts as the electron donor and PMDA as the electron acceptor, is taken as a representative system for which experimental non-resonance Raman spectra are also reported. We first investigate the impact that the amount of nonlocal Hartree-Fock exchange (HFE) included in a hybrid density functional has on the geometry, normal vibrational modes, electronic coupling, and electron-vibrational (phonon) couplings. The comparison between experimental and theoretical Raman spectra indicates that the results based on the αPBE functional with 25%-35% HFE are in better agreement with the experimental results compared to those obtained with the pure PBE functional. Then, taking αPBE with 25% HFE, we assign the vibrational modes and examine their contributions to the relaxation energy related to the nonlocal electron-vibration interactions. The results show that the largest contribution (about 90%) is due to electron interactions with low-frequency vibrational modes. The relaxation energy in anthracene-PMDA is found to be about five times smaller than the electronic coupling.

  19. Effect of Indole-3-Acetic Acid-Producing Bacteria on Phytoremediation of Soil Contaminated with Phenanthrene and Anthracene by Mungbean

    Directory of Open Access Journals (Sweden)

    Waraporn Chouychai

    2016-07-01

    Full Text Available The use of indole-3-acetic acid (IAA-producing bacteria isolated from non-contaminated weed rhizosphere to enhance plant growth and PAH phytoremediation capacity was investigated. IAA-producing bacterial isolates, designated NSRU1, NSRU2, and NSRU3, were isolated from the rhizosphere of Eleusine indica (Poaceae and Chromolaena odorata (Asteraceae. The isolates were able to produce IAA in nutrient broth. However, when grown in the presence of 100 mg/l of either phenanthrene or anthracene, the amount of IAA produced by each isolate was reduced significantly. Mungbean seedlings were planted in 100 mg/kg phenanthrene- or anthracene-contaminated soil without or with inoculation of ≈106 CFU/g dry soil with one of the bacterial isolates. Inoculation with either NSRU1 or NSRU2 was effective at enhancing shoot length of mungbean in phenanthrene-contaminated soil on day 16. Also, inoculation with isolate NSRU1 led to increased root dry weight of mungbean in phenanthrene-contaminated soil on day 30. Phenanthrene and anthracene degradation on day 16 and 30 in planted and inoculated soil ranged between 92 - 93.8% and 92.2 - 94.1%, respectively, which were not significantly different from planted and uninoculated soil (93.9 and 94.9%. These data showed that IAA-producing bacteria could enhance plant growth, but was unable to increase PAH biodegradation under the conditions tested.

  20. Discrimination of Primary Alkyl and Arylamines by a New Binaphthyl-Azacrown-Anthracene Fluorophore

    International Nuclear Information System (INIS)

    A new binaphthyl-azacrown-anthracene fluorophore (1) was prepared and utilized as a selective fluorescent chemosensor for the discrimination of primary alkyl and arylamine HCl salts in ethanol. Primary arylamine HCl salts were found to induce large CHEF effects with the excitation wavelength of 390 nm. On the other hand, primary alkylamine HCl salts were found not to induce any CHEF effect with the excitation wavelength of 390 nm. From the 1H NMR titration study, we found that primary arylamine HCl salts form complex effectively with compound 1 while primary alkylamine HCl salts do not. The development of highly sensitive and selective detection techniques for the discrimination of biologically toxic materials is of considerable importance in the fields of chemical, biological, and environmental sciences. Primary arylamines originated from occupational sources and/or tobacco smoking are known to be carcinogenic. For example, 4-aminobiphenyl, 2-naphthylamine and benzidine have been known to induce bladder cancer. In this instance, the methods for the detection of primary arylamines are quite important

  1. Crystal induced phosphorescence from Benz(a)anthracene microcrystals at room temperature.

    Science.gov (United States)

    Maity, Samir; Mazumdar, Prativa; Shyamal, Milan; Sahoo, Gobinda Prasad; Misra, Ajay

    2016-03-15

    Pure organic compounds that are also phosphorescent at room temperature are very rare in literature. Here, we report efficient phosphorescence emission from aggregated hydrosol of Benz(a)anthracene (BaA) at room temperature. Aggregated hydrosol of BaA has been synthesized by re-precipitation method and SDS is used as morphology directing agent. Morphology of the particles is characterized using optical and scanning electronic microcopy (SEM). Photophysical properties of the aggregated hydrosol are carried out using UV-vis, steady state and time resolved fluorescence study. The large stoke shifted structured emission from aggregated hydrosol of BaA has been explained due to phosphorescence emission of BaA at room temperature. In the crystalline state, the restricted intermolecular motions (RIM) such as rotations and vibrations are activated by crystal lattice. This rigidification effect makes the chromophore phosphorescent at room temperature. The possible stacking arrangement of the neighboring BaA within the aggregates has been substantiated by computing second order Fukui parameter as local reactivity descriptors. Computational study also reveals that the neighboring BaA molecules are present in parallel slipped conformation in its aggregated crystalline form. PMID:26720419

  2. Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals

    Science.gov (United States)

    Rudebusch, Gabriel E.; Zafra, José L.; Jorner, Kjell; Fukuda, Kotaro; Marshall, Jonathan L.; Arrechea-Marcos, Iratxe; Espejo, Guzmán L.; Ponce Ortiz, Rocío; Gómez-García, Carlos J.; Zakharov, Lev N.; Nakano, Masayoshi; Ottosson, Henrik; Casado, Juan; Haley, Michael M.

    2016-08-01

    The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air- and temperature-stable biradical compound.

  3. The anharmonic quartic force field infrared spectra of three polycyclic aromatic hydrocarbons: Naphthalene, anthracene, and tetracene

    Energy Technology Data Exchange (ETDEWEB)

    Mackie, Cameron J., E-mail: mackie@strw.leidenuniv.nl; Candian, Alessandra; Tielens, Alexander G. G. M. [Leiden Observatory, Leiden University, P.O. Box 9513, 2300 RA Leiden (Netherlands); Huang, Xinchuan [SETI Institute, 189 Bernardo Avenue, Suite 100, Mountain View, California 94043 (United States); Maltseva, Elena; Buma, Wybren Jan [University of Amsterdam, Science Park 904, 1098 XH Amsterdam (Netherlands); Petrignani, Annemieke [Leiden Observatory, Leiden University, P.O. Box 9513, 2300 RA Leiden (Netherlands); Radboud University, FELIX Laboratory, Toernooiveld 7, 6525 ED Nijmegen (Netherlands); Oomens, Jos [Radboud University, FELIX Laboratory, Toernooiveld 7, 6525 ED Nijmegen (Netherlands); Lee, Timothy J. [NASA Ames Research Center, Moffett Field, California 94035-1000 (United States)

    2015-12-14

    Current efforts to characterize and study interstellar polycyclic aromatic hydrocarbons (PAHs) rely heavily on theoretically predicted infrared (IR) spectra. Generally, such studies use the scaled harmonic frequencies for band positions and double harmonic approximation for intensities of species, and then compare these calculated spectra with experimental spectra obtained under matrix isolation conditions. High-resolution gas-phase experimental spectroscopic studies have recently revealed that the double harmonic approximation is not sufficient for reliable spectra prediction. In this paper, we present the anharmonic theoretical spectra of three PAHs: naphthalene, anthracene, and tetracene, computed with a locally modified version of the SPECTRO program using Cartesian derivatives transformed from Gaussian 09 normal coordinate force constants. Proper treatments of Fermi resonances lead to an impressive improvement on the agreement between the observed and theoretical spectra, especially in the C–H stretching region. All major IR absorption features in the full-scale matrix-isolated spectra, the high-temperature gas-phase spectra, and the most recent high-resolution gas-phase spectra obtained under supersonically cooled molecular beam conditions in the CH-stretching region are assigned.

  4. Helium induced fine structure in the electronic spectra of anthracene derivatives doped into superfluid helium nanodroplets

    Energy Technology Data Exchange (ETDEWEB)

    Pentlehner, D.; Slenczka, A., E-mail: alkwin.slenczka@chemie.uni-regensburg.de [Institut für Physikalische und Theoretische Chemie, Universität Regensburg, 93040 Regensburg (Germany)

    2015-01-07

    Electronic spectra of organic molecules doped into superfluid helium nanodroplets show characteristic features induced by the helium environment. Besides a solvent induced shift of the electronic transition frequency, in many cases, a spectral fine structure can be resolved for electronic and vibronic transitions which goes beyond the expected feature of a zero phonon line accompanied by a phonon wing as known from matrix isolation spectroscopy. The spectral shape of the zero phonon line and the helium induced phonon wing depends strongly on the dopant species. Phonon wings, for example, are reported ranging from single or multiple sharp transitions to broad (Δν > 100 cm{sup −1}) diffuse signals. Despite the large number of example spectra in the literature, a quantitative understanding of the helium induced fine structure of the zero phonon line and the phonon wing is missing. Our approach is a systematic investigation of related molecular compounds, which may help to shed light on this key feature of microsolvation in superfluid helium droplets. This paper is part of a comparative study of the helium induced fine structure observed in electronic spectra of anthracene derivatives with particular emphasis on a spectrally sharp multiplet splitting at the electronic origin. In addition to previously discussed species, 9-cyanoanthracene and 9-chloroanthracene will be presented in this study for the first time.

  5. Direct observation of the photodegradation of anthracene and pyrene adsorbed onto mangrove leaves.

    Directory of Open Access Journals (Sweden)

    Ping Wang

    Full Text Available An established synchronous fluorimetry method was used for in situ investigation of the photodegradation of pyrene (PYR and anthracene (ANT adsorbed onto fresh leaves of the seedlings of two mangrove species, Aegiceras corniculatum (L. Blanco (Ac and Kandelia obovata (Ko in multicomponent mixtures (mixture of the ANT and PYR. Experimental results indicated that photodegradation was the main transformation pathway for both ANT and PYR in multicomponent mixtures. The amount of the PAHs volatilizing from the leaf surfaces and entering the inner leaf tissues was negligible. Over a certain period of irradiation time, the photodegradation of both PYR and ANT adsorbed onto the leaves of Ac and Ko followed first-order kinetics, with faster rates being observed on Ac leaves. In addition, the photodegradation rate of PYR on the leaves of the mangrove species in multicomponent mixtures was much slower than that of adsorbed ANT. Compared with the PAHs adsorbed as single component, the photodegradation rate of ANT adsorbed in multicomponent mixtures was slower, while that of PYR was faster. Moreover, the photodegradation of PYR and ANT dissolved in water in multicomponent mixtures was investigated for comparison. The photodegradation rate on leaves was much slower than in water. Therefore, the physical-chemical properties of the substrate may strongly influence the photodegradation rate of adsorbed PAHs.

  6. The anharmonic quartic force field infrared spectra of three polycyclic aromatic hydrocarbons: Naphthalene, anthracene, and tetracene

    International Nuclear Information System (INIS)

    Current efforts to characterize and study interstellar polycyclic aromatic hydrocarbons (PAHs) rely heavily on theoretically predicted infrared (IR) spectra. Generally, such studies use the scaled harmonic frequencies for band positions and double harmonic approximation for intensities of species, and then compare these calculated spectra with experimental spectra obtained under matrix isolation conditions. High-resolution gas-phase experimental spectroscopic studies have recently revealed that the double harmonic approximation is not sufficient for reliable spectra prediction. In this paper, we present the anharmonic theoretical spectra of three PAHs: naphthalene, anthracene, and tetracene, computed with a locally modified version of the SPECTRO program using Cartesian derivatives transformed from Gaussian 09 normal coordinate force constants. Proper treatments of Fermi resonances lead to an impressive improvement on the agreement between the observed and theoretical spectra, especially in the C–H stretching region. All major IR absorption features in the full-scale matrix-isolated spectra, the high-temperature gas-phase spectra, and the most recent high-resolution gas-phase spectra obtained under supersonically cooled molecular beam conditions in the CH-stretching region are assigned

  7. Solubility of anthracene and pyrene in binary alcohol + alcohol solvent mixtures

    Energy Technology Data Exchange (ETDEWEB)

    Zvaigzne, A.I.; McHale, M.E.R.; Powell, J.R.; Kauppila, A.S.M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1995-11-01

    Solid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the petroleum industry, particularly in light of present trends toward heavier feedstocks and known carcinogenicity/mutagenicity of many of the larger polycyclic aromatic compounds. Experimental solubilities are reported for anthracene dissolved in binary 1-octanol + 2-propanol, 2-butanol + 1-butanol, 1-octanol + 1-butanol, 3-methyl-1-butanol + 1-propanol, and 2-methyl-1-propanol + 1-butanol mixtures at 25 C, and for pyrene dissolved in binary solvent mixtures containing 2-ethyl-1-hexanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-octanol, 2-methyl-1-propanol, and 3-methyl-1-butanol at 26 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the 12 systems studied, the combined NIBS/Redlich-Kister equation was found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being on the order of 0.4%. Slightly larger deviations were noted in the case of the modified Wilson equation.

  8. Helium induced fine structure in the electronic spectra of anthracene derivatives doped into superfluid helium nanodroplets

    International Nuclear Information System (INIS)

    Electronic spectra of organic molecules doped into superfluid helium nanodroplets show characteristic features induced by the helium environment. Besides a solvent induced shift of the electronic transition frequency, in many cases, a spectral fine structure can be resolved for electronic and vibronic transitions which goes beyond the expected feature of a zero phonon line accompanied by a phonon wing as known from matrix isolation spectroscopy. The spectral shape of the zero phonon line and the helium induced phonon wing depends strongly on the dopant species. Phonon wings, for example, are reported ranging from single or multiple sharp transitions to broad (Δν > 100 cm−1) diffuse signals. Despite the large number of example spectra in the literature, a quantitative understanding of the helium induced fine structure of the zero phonon line and the phonon wing is missing. Our approach is a systematic investigation of related molecular compounds, which may help to shed light on this key feature of microsolvation in superfluid helium droplets. This paper is part of a comparative study of the helium induced fine structure observed in electronic spectra of anthracene derivatives with particular emphasis on a spectrally sharp multiplet splitting at the electronic origin. In addition to previously discussed species, 9-cyanoanthracene and 9-chloroanthracene will be presented in this study for the first time

  9. Biodegradation of anthracene and fluoranthene by fungi isolated from an experimental constructed wetland for wastewater treatment.

    Science.gov (United States)

    Giraud, F; Guiraud, P; Kadri, M; Blake, G; Steiman, R

    2001-12-01

    Pilot-scale constructed wetlands were used to treat water contaminated by polycyclic aromatic hydrocarbons (PAHs), particularly fluoranthene, and the possible role of fungi present in these ecosystems was investigated. A total of 40 fungal species (24 genera) were isolated and identified from samples (gravel and sediments) from a contaminated wetland and a control wetland. All of them were assayed for their ability to remove anthracene (AC) and fluoranthene (FA) from liquid medium. FA was degraded efficiently by 33 species while only 2 species were able to remove AC over 70%. A selection of 10 strains of micromycetes belonging to various taxonomic groups was further investigated for FA and AC degradation, toxicity assays and phenoloxidases (POx) detection. Interesting and not previously reported species were revealed (Absidia cylindrospora, Cladosporium sphaerospermum, and Ulocladium chartarum). They were all able to highly degrade the PAH-model compounds chosen. An interesting inducibility was noted for Ulocladium chartarum. Degradative ability of fungi was not related to their extracellular POx activity. This study may contribute to the improvement of constructed wetlands for water treatment, which may be enriched in efficient fungi. PMID:11791842

  10. Crystal induced phosphorescence from Benz(a)anthracene microcrystals at room temperature

    Science.gov (United States)

    Maity, Samir; Mazumdar, Prativa; Shyamal, Milan; Sahoo, Gobinda Prasad; Misra, Ajay

    2016-03-01

    Pure organic compounds that are also phosphorescent at room temperature are very rare in literature. Here, we report efficient phosphorescence emission from aggregated hydrosol of Benz(a)anthracene (BaA) at room temperature. Aggregated hydrosol of BaA has been synthesized by re-precipitation method and SDS is used as morphology directing agent. Morphology of the particles is characterized using optical and scanning electronic microcopy (SEM). Photophysical properties of the aggregated hydrosol are carried out using UV-vis, steady state and time resolved fluorescence study. The large stoke shifted structured emission from aggregated hydrosol of BaA has been explained due to phosphorescence emission of BaA at room temperature. In the crystalline state, the restricted intermolecular motions (RIM) such as rotations and vibrations are activated by crystal lattice. This rigidification effect makes the chromophore phosphorescent at room temperature. The possible stacking arrangement of the neighboring BaA within the aggregates has been substantiated by computing second order Fukui parameter as local reactivity descriptors. Computational study also reveals that the neighboring BaA molecules are present in parallel slipped conformation in its aggregated crystalline form.

  11. Obtaining the lattice energy of the anthracene crystal by modern yet affordable first-principles methods

    Science.gov (United States)

    Sancho-García, J. C.; Aragó, J.; Ortí, E.; Olivier, Y.

    2013-05-01

    The non-covalent interactions in organic molecules are known to drive their self-assembly to form molecular crystals. We compare, in the case of anthracene and against experimental (electronic-only) sublimation energy, how modern quantum-chemical methods are able to calculate this cohesive energy taking into account all the interactions between occurring dimers in both first-and second-shells. These include both O(N6)- and O(N5)-scaling methods, Local Pair Natural Orbital-parameterized Coupled-Cluster Single and Double, and Spin-Component-Scaled-Møller-Plesset perturbation theory at second-order, respectively, as well as the most modern family of conceived density functionals: double-hybrid expressions in several variants (B2-PLYP, mPW2-PLYP, PWPB95) with customized dispersion corrections (-D3 and -NL). All-in-all, it is shown that these methods behave very accurately producing errors in the 1-2 kJ/mol range with respect to the experimental value taken into account the experimental uncertainty. These methods are thus confirmed as excellent tools for studying all kinds of interactions in chemical systems.

  12. Discrimination of Primary Alkyl and Arylamines by a New Binaphthyl-Azacrown-Anthracene Fluorophore

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Kyu Jung; Li, Yinan; Kim, Kwang Soo; Hyun, Myung Ho [Pusan National Univ., Busan (Korea, Republic of)

    2010-04-15

    A new binaphthyl-azacrown-anthracene fluorophore (1) was prepared and utilized as a selective fluorescent chemosensor for the discrimination of primary alkyl and arylamine HCl salts in ethanol. Primary arylamine HCl salts were found to induce large CHEF effects with the excitation wavelength of 390 nm. On the other hand, primary alkylamine HCl salts were found not to induce any CHEF effect with the excitation wavelength of 390 nm. From the {sup 1}H NMR titration study, we found that primary arylamine HCl salts form complex effectively with compound 1 while primary alkylamine HCl salts do not. The development of highly sensitive and selective detection techniques for the discrimination of biologically toxic materials is of considerable importance in the fields of chemical, biological, and environmental sciences. Primary arylamines originated from occupational sources and/or tobacco smoking are known to be carcinogenic. For example, 4-aminobiphenyl, 2-naphthylamine and benzidine have been known to induce bladder cancer. In this instance, the methods for the detection of primary arylamines are quite important.

  13. Facile and economical synthesis of high-contrast multielectrochromic copolymers based on anthracene and 3,4-ethylenedioxythiophene via electrocopolymerization in boron trifluoride diethyl etherate

    International Nuclear Information System (INIS)

    Highlights: ► We prepared copolymers based on anthracene and EDOT in BFEE solution. ► The copolymer film exhibits multicolor electrochromism and tunable color change with the feed ratio. ► The copolymer prepared with the feed ratio of anthracene/EDOT at 1/4 has a maximum optical contrast of 82% at 503 nm. ► The copolymer film presents reasonable switching response, good color retaining ability and electrochemical stability. - Abstract: Copolymers based on anthracene and 3,4-ethylenedioxythiophene (EDOT) are successfully electrodeposited on ITO electrodes in boron trifluoride diethyl etherate (BFEE). The resultant copolymers are characterized by cyclic voltammetry (CV), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and spectroelectrochemical analysis. The copolymer films can present multicolor electrochromism under various applied potentials and the color change can be tuned through controlling the feed ratio of anthracene/EDOT. With the feed ratio of anthracene/EDOT at 1/4, the prepared copolymer shows a maximum optical contrast of 82% at 503 nm which is much near to the highest optical contrast of electrochromic materials. The switching time and coloration efficiency at 507 nm are 2.3 s and 278 cm C−1, respectively. Furthermore, the copolymer exhibits excellent electrochemical stability which retains 89.8% of its original electroactivity after 2000 cycles.

  14. Organic light-emitting diodes based on 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit as the deep-blue emitting layer

    Energy Technology Data Exchange (ETDEWEB)

    Song, Ji Young; Lee, Seul Bee [Department of Chemistry, Sungkyunkwan University, Suwon 440-746 (Korea, Republic of); Lee, Seok Jae [Department of Information Display, Hongik University, Seoul 121-791 (Korea, Republic of); Kim, Young Kwan, E-mail: kimyk@wow.hongik.ac.kr [Department of Information Display, Hongik University, Seoul 121-791 (Korea, Republic of); Yoon, Seung Soo, E-mail: ssyoon@skku.edu [Department of Chemistry, Sungkyunkwan University, Suwon 440-746 (Korea, Republic of)

    2015-02-27

    A series of 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit, which prevented molecular aggregation and self-quenching effect, was designed and synthesized. By using various bridges between the 9-(2-naphthyl)anthracene group and the triphenylsilane unit, five deep-blue emitters were obtained and applied as non-doped emitting materials in organic light-emitting diodes (OLEDs) with a device structure of indium–tin-oxide (ITO) (180 nm)/4,4-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPB) (50 nm)/emitting materials (30 nm)/4,7-diphenyl-1,10-phenanthroline (Bphen) (30 nm)/lithium quinolate (Liq) (2 nm)/Aluminium (100 nm). All devices showed blue emissions and their electroluminescence efficiencies are sensitive to the structural changes of the emitting materials. In particular, a device using 9-(2-naphthalenyl)-10-[6-(triphenylsilyl)-2-naphthalenyl]-anthracene (4) exhibited high luminous, power and quantum efficiencies of 2.28 cd/A, 1.42 lm/W and 2.40% at 20 mA/cm{sup 2}, respectively, and this device showed the deep blue emission with the CIE coordinates of (0.16, 0.10) at 6.0 V. - Highlights: • We synthesized 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit. • We study the conjugation-length effect on the electroluminescence properties. • The bulky triphenylsilane-anthracene derivatives show resistance to self-aggregation.

  15. Organic light-emitting diodes based on 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit as the deep-blue emitting layer

    International Nuclear Information System (INIS)

    A series of 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit, which prevented molecular aggregation and self-quenching effect, was designed and synthesized. By using various bridges between the 9-(2-naphthyl)anthracene group and the triphenylsilane unit, five deep-blue emitters were obtained and applied as non-doped emitting materials in organic light-emitting diodes (OLEDs) with a device structure of indium–tin-oxide (ITO) (180 nm)/4,4-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPB) (50 nm)/emitting materials (30 nm)/4,7-diphenyl-1,10-phenanthroline (Bphen) (30 nm)/lithium quinolate (Liq) (2 nm)/Aluminium (100 nm). All devices showed blue emissions and their electroluminescence efficiencies are sensitive to the structural changes of the emitting materials. In particular, a device using 9-(2-naphthalenyl)-10-[6-(triphenylsilyl)-2-naphthalenyl]-anthracene (4) exhibited high luminous, power and quantum efficiencies of 2.28 cd/A, 1.42 lm/W and 2.40% at 20 mA/cm2, respectively, and this device showed the deep blue emission with the CIE coordinates of (0.16, 0.10) at 6.0 V. - Highlights: • We synthesized 9-(2-naphthyl)anthracene derivatives with a triphenylsilane unit. • We study the conjugation-length effect on the electroluminescence properties. • The bulky triphenylsilane-anthracene derivatives show resistance to self-aggregation

  16. Synthesis, characterization and properties of yellow-light-emitting polyethers containing bis(styryl)anthracene units

    Energy Technology Data Exchange (ETDEWEB)

    Gioti, M., E-mail: mgiot@physics.auth.gr; Pitsalidis, C., E-mail: mgiot@physics.auth.gr; Tzounis, L.; Logothetidis, S., E-mail: logot@auth.gr [Laboratory for Thin Films-Nanosystems and Nanometrology (LTFN), Physics Department, Aristotle University of Thessaloniki, GR-54124 Thessaloniki (Greece); Andreopoulou, A. K.; Kallitsis, J. K. [Department of Chemistry, University of Patras, University Campus, Rio-Patras GR26504, Greece and Foundation for Research and Technology Hellas, Institute of Chemical Engineering Sciences (FORTH/ICE-HT), Platani Str., Patras GR26504 (Greece); Mparmpoutsis, E. [Department of Chemistry, University of Patras, University Campus, Rio-Patras GR26504 (Greece)

    2015-02-17

    Aromatic aliphatic polyethers containing bis(styryl)anthracene units in the main chain separated by flexible spacer of 11 (AND52) or 12 (AND53) methylene units, were synthesized and characterized aiming to be applied as emitting materials in polymer light emitting diode (PLED) devices. The polymers are soluble in common organic solvents and have average molecular weight of about 15kDa. Differentiations owing to an odd-even number of methylene units (χ=11 vs χ=12) are observed in their optical properties in solid state. Thin films as well as PLED devices were fabricated via conventional spin-coating process. Initially, various parameters have been investigated concerning the solubility of the polymers, the effect of film thickness on the electrical properties, and their thermal stability. The optical properties of the two polymers were investigated by NIR-Vis-far UV spectroscopic ellipsometry (SE). The accurate determination of the thickness and the optical constants (refractive index and dielectric function as a function of wavelength) were derived. These provide substantial insights into the final design of the optimum final multi-layer structure of the PLEDs, if we take into account that the external quantum efficiency (EQE) of electroluminescence (EL) strongly depends on the optical interference of the beams of emitted light that have been multiply reflected from the layer interfaces. The morphological characterization of the AND52 and AND53 polymeric thin films was carried out using atomic force microscopy (AFM), while current density-voltage (J-V) characteristics of the devices were studied by electrical measurements. The single PLED devices were switched on at relatively low operation voltages, showing the potential as backplanes for active matrix PLED applications. In this perspective, it can be assumed that further studies of the presented materials will enable the development of flexible PLEDs with the possibility to scale up their dimensions for bigger

  17. Synthesis, characterization and properties of yellow-light-emitting polyethers containing bis(styryl)anthracene units

    International Nuclear Information System (INIS)

    Aromatic aliphatic polyethers containing bis(styryl)anthracene units in the main chain separated by flexible spacer of 11 (AND52) or 12 (AND53) methylene units, were synthesized and characterized aiming to be applied as emitting materials in polymer light emitting diode (PLED) devices. The polymers are soluble in common organic solvents and have average molecular weight of about 15kDa. Differentiations owing to an odd-even number of methylene units (χ=11 vs χ=12) are observed in their optical properties in solid state. Thin films as well as PLED devices were fabricated via conventional spin-coating process. Initially, various parameters have been investigated concerning the solubility of the polymers, the effect of film thickness on the electrical properties, and their thermal stability. The optical properties of the two polymers were investigated by NIR-Vis-far UV spectroscopic ellipsometry (SE). The accurate determination of the thickness and the optical constants (refractive index and dielectric function as a function of wavelength) were derived. These provide substantial insights into the final design of the optimum final multi-layer structure of the PLEDs, if we take into account that the external quantum efficiency (EQE) of electroluminescence (EL) strongly depends on the optical interference of the beams of emitted light that have been multiply reflected from the layer interfaces. The morphological characterization of the AND52 and AND53 polymeric thin films was carried out using atomic force microscopy (AFM), while current density-voltage (J-V) characteristics of the devices were studied by electrical measurements. The single PLED devices were switched on at relatively low operation voltages, showing the potential as backplanes for active matrix PLED applications. In this perspective, it can be assumed that further studies of the presented materials will enable the development of flexible PLEDs with the possibility to scale up their dimensions for bigger

  18. Determination of Anthracene on Ag-Au Alloy Nanoparticles/Overoxidized-Polypyrrole Composite Modified Glassy Carbon Electrodes

    Directory of Open Access Journals (Sweden)

    Emmanuel I. Iwuoha

    2010-10-01

    Full Text Available A novel electrochemical sensor for the detection of anthracene was prepared by modifying a glassy carbon electrode (GCE with over-oxidized polypyrrole (PPyox and Ag-Au (1:3 bimetallic nanoparticles (Ag-AuNPs. The composite electrode (PPyox/Ag-AuNPs/GCE was prepared by potentiodynamic polymerization of pyrrole on GCE followed by its overoxidation in 0.1 M NaOH. Ag-Au bimetallic nanoparticles were chemically prepared by the reduction of AgNO3 and HAuCl4 using C6H5O7Na3 as the reducing agent as well as the capping agent and then immobilized on the surface of the PPyox/GCE. The nanoparticles were characterized by UV-visible spectroscopy technique which confirmed the homogeneous formation of the bimetallic alloy nanoparticles. Transmission electron microscopy showed that the synthesized bimetallic nanoparticles were in the range of 20–50 nm. The electrochemical behaviour of anthracene at the PPyox/Ag-AuNPs/GCE with Ag: Au atomic ratio 25:75 (1:3 exhibited a higher electrocatalytic effect compared to that observed when GCE was modified with each constituent of the composite (i.e., PPyox, Ag-AuNPs and bare GCE. A linear relationship between anodic current and anthracene concentration was attained over the range of 3.0 × 10−6 to 3.56 × 10−4 M with a detection limit of 1.69 × 10−7 M. The proposed method was simple, less time consuming and showed a high sensitivity.

  19. 5-(Anthracen-9-yl-3-(4-nitrophenyl-1-phenyl-4,5-dihydro-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Bao-Li Dong

    2010-11-01

    Full Text Available In the title compound, C29H21N3O2, the five-membered pyrazoline ring is nearly planar, the maximum deviation being 0.037 (3 Å. The anthracene ring system is approximately perpendicular to the central pyrazoline ring, making a dihedral angle of 86.55 (16°, whereas the two attached benzene rings are oriented at smaller dihedral angles of 12.9 (2 and 14.7 (2°with respect to the pyrazoline ring. An intramolecular C—H...N hydrogen bond is observed.

  20. Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

    OpenAIRE

    Kumaresh Ghosh; Tanmay Sarkar; Chattopadhyay, Asoke P

    2010-01-01

    A new anthracene labeled pyridinium amide–urea conjugate 1 has been designed and synthesized. The receptor shows a different fluorometric response with L-N-acetylvaline and L-N-acetylalanine salts in CH3CN in contrast to the other salts of L-N-acetyl α-amino acids and (S)-α-hydroxy acids studied. Upon complexation of the tetrabutylammonium salt of L-N-acetylvaline, the emission of 1 increases accompanied by the formation of a new band at higher wavelength and this characterist...

  1. Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

    OpenAIRE

    Ghosh, Kumaresh; Sarkar, Tanmay; Chattopadhyay, Asoke P

    2010-01-01

    A new anthracene labeled pyridinium amide–urea conjugate 1 has been designed and synthesized. The receptor shows a different fluorometric response with L-N-acetylvaline and L-N-acetylalanine salts in CH3CN in contrast to the other salts of L-N-acetyl α-amino acids and (S)-α-hydroxy acids studied. Upon complexation of the tetrabutylammonium salt of L-N-acetylvaline, the emission of 1 increases accompanied by the formation of a new band at higher wavelength and this characteristic change distin...

  2. Stereoselective metabolism of dibenz(a,h)anthracene to trans-dihydrodiols and their activation to bacterial mutagens.

    OpenAIRE

    Platt, K L; Schollmeier, M.; Frank, H; Oesch, F

    1990-01-01

    Dibenz(a,h)anthracene (DBA), a carcinogenic, polycyclic aromatic hydrocarbon ubiquitous in the environment, is metabolized by the hepatic microsomal fraction of immature Sprague-Dawley rats pretreated with Aroclor 1254 to 27 ethyl acetate-extractable metabolites. More than half of these metabolites (51%) consisted of trans-1,2-; -3,4-; and -5,6-dihydrodiols including their identified secondary metabolites. The three trans-dihydrodiols (4.9, 15.8, and 0.6% of total metabolic conversion) were h...

  3. Mono- and Dinuclear Manganese Carbonyls Supported by 1,8-Disubstituted (L = Py, SMe, SH) Anthracene Ligand Scaffolds.

    Science.gov (United States)

    Manes, Taylor A; Rose, Michael J

    2016-06-01

    Presented herein is a synthetic scheme to generate symmetric and asymmetric ligands based on a 1,8-disubstituted anthracene scaffold. The metal-binding scaffolds were prepared by aryl chloride activation of 1,8-dichloroanthracene using Suzuki-type couplings facilitated by [Pd(dba)2] as a Pd source; the choice of cocatalyst (XPhos or SPhos) yielded symmetrically or asymmetrically substituted scaffolds (respectively): namely, Anth-SMe2 (3), Anth-N2 (4), and Anth-NSMe (6). The ligands exhibit a nonplanar geometry in the solid state (X-ray), owing to steric hindrance between the anthracene scaffold and the coupled aryl units. To determine the flexibility and binding characteristics of the anthracene-based ligands, the symmetric scaffolds were complexed with [Mn(CO)5Br] to afford the mononuclear species [(Anth-SMe2)Mn(CO)3Br] (8) and [(Anth-N2)Mn(CO)3Br] (9), in which the donor moieties chelate the Mn center in a cis fashion. The asymmetric ligand Anth-NSMe (6) binds preferentially through the py moieties, affording the bis-ligated complex [(Anth-NSMe)2Mn(CO)3Br] (10), wherein the thioether-S donors remain unbound. Alternatively, deprotection of the thioether in 6 affords the free thiol ligand Anth-NSH (7), which more readily binds the Mn center. Complexation of 7 ultimately affords the mixed-valence Mn(I)/Mn(II) dimer of formula [(Anth-NS)3Mn2(CO)3] (11), which exhibits a fac-{Mn(CO)3} unit supported by a triad of bridging thiolates, which are in turn ligated to a supporting Mn(II) center (EPR: |D| = 0.053 cm(-1), E/|D| = 0.3, Aiso = -150 MHz). All of the metal complexes have been characterized by single-crystal X-ray diffraction, IR spectroscopy and NMR/EPR measurements-all of which demonstrate that the meta-linked, anthracene-based ligand scaffold is a viable approach for the coordination of metal carbonyls. PMID:27195661

  4. Anthracene and TCNQ doping of substituted nickel phthalocyanine: Effects on the electrical and optical properties of spin coated thin films

    OpenAIRE

    Hassan Aseel K.; Basova Tamara; Gürek Ayse Gül; Ahsen Vefa

    2013-01-01

    In this work, we study the controlled doping of thin films of substituted nickel phthalocyanine, NiPcR8, where R=-SC6H13, with anthracene and TCNQ and investigate the effects of the extent of this doping on the optical and electrical properties of NiPcR8 films. Optical constants, namely index of refraction (n) and extinction coefficient (k) have increased for both types of doping, as determined from spectroscopic ellipsometry measurements. Conductivity is shown to increase by about four order...

  5. Toxicity of benz(a)anthracene and fluoranthene to marine phytoplankton in culture: Does cell size really matter?

    Energy Technology Data Exchange (ETDEWEB)

    Othman, Hiba Ben [UMR 5119 ECOSYM, CNRS-IRD-Universite Montpellier II-Ifremer-Universite Montpellier I, SMEL 2 rue des Chantiers, F-34200 Sete (France); Laboratoire de Cytologie Vegetale et Phytoplanctonologie, Faculte des Sciences de Bizerte, Universite de Carthage, Zarzouna 7021, Bizerte (Tunisia); Leboulanger, Christophe, E-mail: christophe.leboulanger@ird.fr [UMR 5119 ECOSYM, CNRS-IRD-Universite Montpellier II-Ifremer-Universite Montpellier I, SMEL 2 rue des Chantiers, F-34200 Sete (France); Le Floc' h, Emilie [UMS MEDIMEER, CNRS-Universite Montpellier II, SMEL 2 rue des Chantiers F-34200 Sete (France); Hadj Mabrouk, Hassine; Sakka Hlaili, Asma [Laboratoire de Cytologie Vegetale et Phytoplanctonologie, Faculte des Sciences de Bizerte, Universite de Carthage, Zarzouna 7021, Bizerte (Tunisia)

    2012-12-15

    Highlights: Black-Right-Pointing-Pointer Polycyclic aromatic hydrocarbons (PAHs) in the marine environment are a hazardous chemical legacy. Black-Right-Pointing-Pointer Benz(a)anthracene and fluoranthene are toxic to phytoplankton photosynthesis and growth in culture. Black-Right-Pointing-Pointer Acute (photosynthesis) and chronic (population growth) effects have different thresholds. Black-Right-Pointing-Pointer Toxicity depends on both the species selected as a model and the compound considered. Black-Right-Pointing-Pointer Further study of the size/sensitivity relationship is required to draw more general conclusions. - Abstract: The toxicity of benz(a)anthracene and fluoranthene (polycyclic aromatic hydrocarbons, PAHs) was evaluated on seven species of marine algae in culture belonging to pico-, nano-, and microphytoplankton, exposed to increasing concentrations of up to 2 mg L{sup -1}. The short-term (24 h) toxicity was assessed using chlorophyll a fluorescence transients, linked to photosynthetic parameters. The maximum quantum yield Fv/Fm was lower at the highest concentrations tested and the toxicity thresholds were species-dependent. For acute effects, fluoranthene was more toxic than benz(a)anthracene, with LOECs of 50.6 and 186 {mu}g L{sup -1}, respectively. After 72 h exposure, there was a dose-dependent decrease in cell density, fluoranthene being more toxic than benz(a)anthracene. The population endpoint at 72 h was affected to a greater extent than the photosynthetic endpoint at 24 h. EC50 was evaluated using the Hill model, and species sensitivity was negatively correlated to cell biovolume. The largest species tested, the dinoflagellate Alexandrium catenella, was almost insensitive to either PAH. The population endpoint EC50s for fluoranthene varied from 54 {mu}g L{sup -1} for the picophytoplankton Picochlorum sp. to 418 {mu}g L{sup -1} for the larger diatom Chaetoceros muelleri. The size/sensitivity relationship is proposed as a useful model when

  6. Chemical insight from density functional modeling of molecular adsorption: Tracking the bonding and diffusion of anthracene derivatives on Cu(111) with molecular orbitals

    Energy Technology Data Exchange (ETDEWEB)

    Wyrick, Jonathan; Bartels, Ludwig, E-mail: ludwig.bartels@ucr.edu [Pierce Hall, University of California-Riverside, Riverside, California 92521 (United States); Einstein, T. L. [Department of Physics and Condensed Matter Theory Center, University of Maryland, College Park, Maryland 20742-4111 (United States)

    2015-03-14

    We present a method of analyzing the results of density functional modeling of molecular adsorption in terms of an analogue of molecular orbitals. This approach permits intuitive chemical insight into the adsorption process. Applied to a set of anthracene derivates (anthracene, 9,10-anthraquinone, 9,10-dithioanthracene, and 9,10-diselenonanthracene), we follow the electronic states of the molecules that are involved in the bonding process and correlate them to both the molecular adsorption geometry and the species’ diffusive behavior. We additionally provide computational code to easily repeat this analysis on any system.

  7. Chemical insight from density functional modeling of molecular adsorption: Tracking the bonding and diffusion of anthracene derivatives on Cu(111) with molecular orbitals

    International Nuclear Information System (INIS)

    We present a method of analyzing the results of density functional modeling of molecular adsorption in terms of an analogue of molecular orbitals. This approach permits intuitive chemical insight into the adsorption process. Applied to a set of anthracene derivates (anthracene, 9,10-anthraquinone, 9,10-dithioanthracene, and 9,10-diselenonanthracene), we follow the electronic states of the molecules that are involved in the bonding process and correlate them to both the molecular adsorption geometry and the species’ diffusive behavior. We additionally provide computational code to easily repeat this analysis on any system

  8. Excellent deep-blue emitting materials based on anthracene derivatives for non-doped organic light-emitting diodes

    Science.gov (United States)

    Wang, Zhiqiang; Liu, Wei; Xu, Chen; Ji, Baoming; Zheng, Caijun; Zhang, Xiaohong

    2016-08-01

    Two deep-blue emitting materials 2-tert-butyl-9,10-bis(3,5-diphenylphenyl)anthracene (An-1) and 2-tert-butyl-9,10-bis(3,5-diphenylbiphenyl-4‧-yl)anthracene (An-2) were successfully synthesized by the Pd-catalyzed Suzuki coupling reaction. Both of these compounds have high thermal stabilities and show strong deep-blue emission as solid-state film as well as in n-hexane solution. Two non-doped electroluminescent devices employing An-1 and An-2 as emitting layers were fabricated by vacuum vapor deposition. These devices exhibited highly efficient and stable deep-blue emission with high color purity. The CIE coordinate and maximum EQE of An-1 based device are 4.2% and (0.16, 0.06), respectively. Device based on An-2 achieved a maximum EQE of 4.0% and a CIE coordinate of (0.16, 0.10).

  9. Effects of anthracene on filtration rates, antioxidant defense system, and redox proteomics in the Mediterranean clam Ruditapes decussatus (Mollusca: Bivalvia).

    Science.gov (United States)

    Sellami, Badreddine; Khazri, Abdelhafidh; Louati, Héla; Dellali, Mohamed; Driss, Mouhamed Ridha; Aïssa, Patricia; Mahmoudi, Ezzeddine; Hamouda, Beyrem; Coelho, Ana Varela; Sheehan, David

    2015-07-01

    This study aimed at analyzing the impact of a toxic polyaromatic hydrocarbon (PAH), anthracene (ANT), on Ruditapes decussatus collected from a Tunisian coastal lagoon (Bizerte Lagoon). Filtration rates, several antioxidant enzymes--superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), glutathione reductase (GR), and glutathione transferase (GST)--as well as indices of protein oxidation status were determined in various tissues of this bivalve. Specimens were exposed to 100 μg/L of ANT for 2 days. ANT levels were evaluated using HPLC and were detected in the gill and digestive gland at different amounts. ANT exposure altered the behavior of bivalves by changing the siphon movement and decreasing filtration rate significantly. The enzymatic results indicated that ANT exposure affected the oxidative stress status of the gills of R. decussatus. In addition, modification of proteins was detected in the gills using redox proteomics after ANT treatment. Three protein spots were successfully identified by matrix-assisted laser desorption/ionization tandem time-of-flight mass spectrometry (MALDI-TOF-MS). These proteins can be roughly related to muscle contraction function. In contrast, no significant modification of enzymatic and protein responses was detected in the digestive gland after ANT treatment. These data demonstrate that combined behavioral and biochemical analyses are a powerful tool to provide valuable insights into possible mechanisms of toxicity of anthracene in R. decussatus. Additionally, the results highlight the potential of the gill as a valuable candidate for investigating PAH toxicity. PMID:25779113

  10. Impact of obesity on ovotoxicity induced by 7,12-dimethylbenz[a]anthracene in mice.

    Science.gov (United States)

    Nteeba, Jackson; Ganesan, Shanthi; Keating, Aileen F

    2014-03-01

    Insulin, elevated during obesity, regulates xenobiotic biotransformation enzymes, potentially through phosphatidylinositol 3-kinase (PI3K) signaling, in extraovarian tissues. PI3K regulates oocyte viability, follicular activation, and ovarian chemical biotransformation. 7,12-Dimethylbenz[a]anthracene (DMBA), a carcinogen and ovotoxicant, destroys all stages of follicles, leading to premature ovarian failure. Obesity has been reported to promote DMBA-induced tumors, but it remains unknown whether obesity affects ovarian xenobiotic metabolism. Therefore, we investigated ovarian expression of xenobiotic metabolism genes-microsomal epoxide hydrolase (Ephx1), glutathione S-transferase (GST) class Pi (Gstp1) and class mu 1 (Gstm1), and PI3K-signaling members (protein kinase B [AKT] alpha [Akt1], beta [Akt2], and the forkhead transcription factor subfamily 3 [Foxo3])-in lean and obese female mice after DMBA exposure (1 mg/kg; intraperitoneal injection for 14 days). Relative to lean, obese mice had decreased (P < 0.05) healthy primordial and primary follicle numbers but increased (P < 0.05) secondary and preovulatory follicles numbers. Obesity increased (P < 0.05) Akt1, Akt2, Gstm1, and Ephx1 mRNA and pAKT(Ser473/Thr308), GSTM1, GSTP1, and EPHX1 protein levels. DMBA decreased (P < 0.05) ovarian weight in lean and obese mice, however, obese DMBA-treated females had a greater reduction (P < 0.05) in ovarian weight. In both lean and obese mice, DMBA decreased (P < 0.05) all stages of healthy follicle numbers, increased Gstp1 and Ephx1 mRNA as well as GSTM1, GSTP1, and EPHX1 protein levels, and decreased Akt1 and Akt2 mRNA as well as pAKT(Ser473) or pAKT(Thr308), FOXO3, and pFOXO3(Ser253) protein expression. There was an additive effect between obesity and DMBA exposure for increased Gstm1 and Ephx1 mRNA as well as GSTM1 and EPHX1 protein expression. PMID:24501177

  11. Bacteria capable of degrading anthracene, phenanthrene, and fluoranthene as revealed by DNA based stable-isotope probing in a forest soil.

    Science.gov (United States)

    Song, Mengke; Jiang, Longfei; Zhang, Dayi; Luo, Chunling; Wang, Yan; Yu, Zhiqiang; Yin, Hua; Zhang, Gan

    2016-05-01

    Information on microorganisms possessing the ability to metabolize different polycyclic aromatic hydrocarbons (PAHs) in complex environments helps in understanding PAHs behavior in natural environment and developing bioremediation strategies. In the present study, stable-isotope probing (SIP) was applied to investigate degraders of PAHs in a forest soil with the addition of individually (13)C-labeled phenanthrene, anthracene, and fluoranthene. Three distinct phylotypes were identified as the active phenanthrene-, anthracene- and fluoranthene-degrading bacteria. The putative phenanthrene degraders were classified as belonging to the genus Sphingomona. For anthracene, bacteria of the genus Rhodanobacter were the putative degraders, and in the microcosm amended with fluoranthene, the putative degraders were identified as belonging to the phylum Acidobacteria. Our results from DNA-SIP are the first to directly link Rhodanobacter- and Acidobacteria-related bacteria with anthracene and fluoranthene degradation, respectively. The results also illustrate the specificity and diversity of three- and four-ring PAHs degraders in forest soil, contributes to our understanding on natural PAHs biodegradation processes, and also proves the feasibility and practicality of DNA-based SIP for linking functions with identity especially uncultured microorganisms in complex microbial biota. PMID:26808242

  12. Mass spectrometric analysis of 7-sulfoxymethyl-12-methylbenz[a]anthracene and related electrophilic polycyclic aromatic hydrocarbon metabolites.

    Science.gov (United States)

    Lehner, Andreas F; Horn, Jamie; Flesher, James W

    2004-11-01

    The Meso-region theory of polycyclic aromatic hydrocarbon (PAH) carcinogenesis predicts that the development of pronounced carcinogenicity depends on the introduction of a good leaving group on alkyl side-chains attached to the exceptionally reactive meso-anthracenic or L-region positions of PAHs. Thus, the first step in carcinogenesis by methylated PAHs such as 7,12-dimethylbenz[a]anthracene (DMBA) would be the hydroxylation of the L-region methyl groups, particularly the 7-methyl group. The second would be the formation of a metabolite, e.g. a sulfate ester, which is expected to be a good leaving group capable of generating a highly reactive benzylic carbocation. 7-Hydroxymethyl-12-methylbenz[a]anthracene (7-HMBA) is a metabolite of DMBA, and sulfation of 7-HMBA to a 7-sulfoxymethyl metabolite (7-SMBA) is a known Phase II metabolic process designed to facilitate excretion, but actually enabling more destructive side-reactions. These side-reactions occur with generation of an electrophilic 7-methylene carbonium ion, and/or by in vivo halide exchange to provide neutral side-products more capable of entering cells, especially those of DMBA target tissues. Electrospray ionization mass spectrometry (MS) enabled us to visualize 7-SMBA as an intact m/z 351 conjugate anion by negative mode, and as a released m/z 255 carbonium ion by positive mode. Upon prolonged refrigeration, 7-SMBA accumulated an m/z 383 photooxide, which appeared capable of re-evolving the starting material as visualized by tandem quadrupole MS, or MS/MS. The 7-SMBA carbonium ion provided interpretable fragments when studied by fragment ion MS/MS, including those representing the loss of up to several protons. Subtle differences in this property were encountered upon perturbing 7-SMBA, either by warming it at 37 degrees C for 2 h or by substituting the initial sulfoxy group with an iodo group. Side-reactions accounting for such proton losses are proposed, and are of interest whether they occur in the

  13. Chemistry of anthracene-acetylene oligomers XXV: on-surface chirality of a self-assembled molecular network of a fan-blade-shaped anthracene-acetylene macrocycle with a long alkyl chain.

    Science.gov (United States)

    Tsuya, Takuya; Iritani, Kohei; Tahara, Kazukuni; Tobe, Yoshito; Iwanaga, Tetsuo; Toyota, Shinji

    2015-03-27

    An anthracene cyclic dimer with two different linkers and a dodecyl group was synthesized by means of coupling reactions. The calculated structure had a planar macrocyclic π core and a linear alkyl chain. Scanning tunneling microscopy observations at the 1-phenyloctane/graphite interface revealed that the molecules formed a self-assembled monolayer that consisted of linear striped bright and dark bands. In each domain, the molecular network consisted of either Re or Si molecules that differed in the two-dimensional chirality about the macrocyclic faces, which led to a unique conglomerate-type self-assembly. The molecular packing mode and the conformation of the alkyl chains are discussed in terms of the intermolecular interactions and the interactions between the molecules and the graphite surface with the aid of MM3 simulations of a model system. PMID:25688524

  14. Enhanced photostability of the anthracene chromophore in aqueous medium upon protein encapsulation.

    Science.gov (United States)

    Alonso, Rafael; Yamaji, Minoru; Jiménez, M Consuelo; Miranda, Miguel A

    2010-09-01

    In the present work, 9-anthraceneacetic acid (1) has been selected as a simple, water-compatible derivative of the anthracene chromophore to investigate the photophysical and photochemical behavior upon binding to human and bovine serum albumins (HSA and BSA) and alpha-acid glycoproteins (HAAG and BAAG). The UV-vis absorption spectrum of 1 exhibited the typical four maxima between 320 and 400 nm, which were slightly red-shifted in the presence of proteins. These minor changes suggested the formation of 1@protein complexes; their stoichiometry (1:1) was determined by means of the corresponding Job plots. As expected, the fluorescence spectrum of 1 in phosphate-buffered saline (PBS) consisted of a structured emission with maxima between 390 and 470 nm. The addition of increasing amounts of HSA resulted in a decrease in the emission intensity. In the presence of BSA, HAAG, or BAAG, the same trend was observed, although the changes were less pronounced. The determination of binding constants was achieved from fluorescence titration, considering one (AAGs) or two (SAs) binding sites. The binding constants (K(B)) were found to be 2.3 x 10(6) M(-1) (HAAG), 2.4 x 10(6) M(-1) (BAAG), 4.57 x 10(4)/1.45 x 10(6) M(-1) (HSA), and 1.44 x 10(4)/1.20 x 10(6) M(-1) (BSA). Binding within two different sites of SAs was confirmed by displacement experiments using warfarin and ibuprofen as site I and site II probes, respectively. Laser flash photolysis of 1 at lambda(exc) = 355 nm in PBS/air gave rise to several transient species; by contrast, in the presence of 1 equiv of proteins, only the triplet excited state was detected. Moreover, the triplet lifetime (tau(T)) monitored at 420 nm lengthened considerably (up to 50-fold) in the protein media. This can be attributed to a slower deactivation of the species inside the protein binding pockets, where an exceptional microenvironment provides protection from attack by a second molecule of 1, oxygen, or other reagents. In agreement with

  15. Effect of Rosmarinus officinalis in modulating 7,12-dimethylbenz(a)anthracene induced skin tumorigenesis in mice.

    Science.gov (United States)

    Sancheti, Garima; Goyal, P K

    2006-11-01

    The chemopreventive potential of rosemary (Rosmarinus officinalis) on 7,12-dimethlybenz(a)anthracene (DMBA) initiated and croton oil promoted mouse skin tumorigenesis was assessed. The modulatory effects of R. officinalis was monitored on the basis of the average latency period, tumor incidence, tumor burden, tumor yield, tumor weight and diameter as well as lipid peroxidation and glutathione level. The results indicate that R. officinalis leaves extract could prolong the latency period of tumor occurrence, decrease the tumor incidence, tumor burden and tumor yield. The average weight and diameter of tumors recorded were comparatively lower in the rosemary extract treated mouse groups. The level of lipid peroxidation was significantly reduced in blood serum and liver. Furthermore, depleted levels of glutathione were restored in RE-administered animal groups. Thus, at a dose rate of 500 mg/kg body wt/mouse, the oral administration of rosemary extract was found to be significantly protective against two-stage skin tumorigenesis. PMID:16927448

  16. Chemopreventive potential of Tribulus terrestris against 7,12- dimethylbenz (a) anthracene induced skin papillomagenesis in mice.

    Science.gov (United States)

    Kumar, Manish; Soni, Anil Kumar; Shukla, Shalini; Kumar, Ashok

    2006-01-01

    In the present investigation, the chemopreventive potential of aqueous extracts of the root and fruit of Tribulus terrestris (an Ayurvedic medicinal plant) on 7, 12 - dimethylbenz (a) anthracene (DMBA) induced papillomagenesis in male Swiss albino mice was studied. A significant reduction in tumor incidence, tumor burden and cumulative number of papillomas was observed, along with a significant increase in average latent period in mice treated orally with Tribulus terrestris suspension continuously at pre, peri and post-initiation stages of papillomagenesis as compared to the control group treated with DMBA and croton oil alone. Treatment with Tribulus terrestris suspension by oral gavage for 7 days resulted in a significant increase in the reduced glutathione content in the liver (P< 0.001 for both root and fruit extracts). Conversely, lipid peroxidation levels were significantly decreased (P< 0.001). PMID:16839225

  17. Solubility of anthracene in binary alkane + methyl tert-butyl ether solvent mixtures at 298.15 K

    Energy Technology Data Exchange (ETDEWEB)

    McHale, M.E.R.; Kauppila, A.S.M.; Acree, W.E. Jr. [Univ. of North Texas, Denton, TX (United States). Dept. of Chemistry

    1996-09-01

    Experimental solubilities are reported for anthracene dissolved in seven binary mixtures containing methyl tert-butyl ether (also called 2-methoxy-2-methylpropane) with hexane, heptane, octane, cyclohexane, methylcyclohexane, 2,2,4-trimethylpentane, and tert-butylcyclohexane (also called (1,1-dimethylethyl)-cyclohexane) at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the seven systems studied, both equations were found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being on the order of 0.5%.

  18. Diagnostics for specific PAHs in the far-IR: searching neutral naphthalene and anthracene in the Red Rectangle

    CERN Document Server

    Mulas, G; Joblin, C; Toublanc, D

    2006-01-01

    Context. In the framework of the interstellar polycyclic aromatic hydrocarbons (PAHs) hypothesis, far-IR skeletal bands are expected to be a fingerprint of single species in this class. Aims. We address the question of detectability of low energy PAH vibrational bands, with respect to spectral contrast and intensity ratio with ``classical'' Aromatic Infrared Bands (AIBs). Methods. We extend our extablished Monte-Carlo model of the photophysics of specific PAHs in astronomical environments, to include rotational and anharmonic band structure. The required molecular parameters were calculated in the framework of the Density Functional Theory. Results. We calculate the detailed spectral profiles of three low-energy vibrational bands of neutral naphthalene, and four low-energy vibrational bands of neutral anthracene. They are used to establish detectability constraints based on intensity ratios with ``classical'' AIBs. A general procedure is suggested to select promising diagnostics, and tested on available Infra...

  19. Pattern of distribution of dimethylbenz(a)anthracene in the Amazon molly, Poecilia formosa (Girard), after intraperitoneal injection

    Energy Technology Data Exchange (ETDEWEB)

    Woodhead, A.D.; Bornbusch, A.

    1983-01-01

    The present paper describes the distribution and accumulation labelled dimethylbenz(a)anthracene (DMBA) in the Amazon molly after intraperitoneal injection. The study was made to see whether there was preferential accumulation of the compound in the spleen; the findings showed that this was not the case. Two hours after injection, DMBA was present throughout the body, except in the brain and the ovary. There was enhanced deposition at four sites, in the macrophages of the atrium of the heart and the peritoneum, the liver and the exocrine pancreas. DMBA was taken up by reticuloendothelial macrophages for 78 h after injection, then it was lost. The accumulation and disappearance of radioactive label seen in the liver and pancreatic cells probably represented the pattern of metabolism of the compound. By 400 h after injection there was little DMBA remaining. Label accumulated in the ameloblasts, which secrete the enamel capping of the teeth. 12 references, 3 figures, 1 table.

  20. Unique anisotropic optical properties of a highly stable metal-organic framework based on trinuclear iron(iii) secondary building units linked by tetracarboxylic linkers with an anthracene core.

    Science.gov (United States)

    Vinogradov, A V; Milichko, V A; Zaake-Hertling, H; Aleksovska, A; Gruschinski, S; Schmorl, S; Kersting, B; Zolnhofer, E M; Sutter, J; Meyer, K; Lönnecke, P; Hey-Hawkins, E

    2016-05-01

    A highly stable metal-organic framework, [{Fe3(ACTBA)2}X·6DEF]n (1; X = monoanion), based on trinuclear iron(iii) secondary building units connected by tetracarboxylates with an anthracene core, 2,6,9,10-tetrakis(p-carboxylatophenyl)anthracene (ACTBA), is reported. Depending on the direction of light polarisation, crystals of 1 exhibit anisotropic optical properties with birefringence Δn = 0.3 (λ = 590 nm). PMID:26906040

  1. Novel “turn on” fluorescent sensors based on anthracene and carbazone units for Cu (II) ion in CH{sub 3}CN–H{sub 2}O

    Energy Technology Data Exchange (ETDEWEB)

    Erdemir, Serkan, E-mail: serdemir82@gmail.com; Malkondu, Sait

    2015-02-15

    Two novel anthracene-based receptors containing Schiff base and urea groups (AOC and ATC) were synthesized in one step and full characterized. The optical properties of receptors AOC and ATC towards metal ions were investigated by UV–visible and fluorescence spectroscopy. It was found that both receptors AOC and ATC show highly selectivity towards Cu{sup 2+} over other 17 metal ions in CH{sub 3}CN–H{sub 2}O (9/1, v/v). - Highlights: • Novel fluorescent sensors based on anthracene and carbazide AOC and ATC were synthesized. • The optical properties of AOC and ATC were observed by UV–visible and fluorescence spectroscopy. • AOC and ATC showed highly selective and sensitive to Cu{sup 2+} over other 17 metal ions.

  2. Mass Spectrometric Fragmentation of 1,8-Bis[4-substituted-(oxazolin-2-yl)] anthracenes: Ring-contraction Rearrangement of Oxazoline Ring under Electron-Impact Ionization Conditions

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    The mass spectrometric fragmentation of 1,8-bis[4-substituted(oxazolin-2-yl)] anthracenes(AnBOXes) was investigated by using mass-analyzed ion kinetic energy spectrometry under electron-impact ionization conditions. All the compounds could undergo a ring contraction by the loss of an RCH=CH2 molecule to form 1-oxazirinyl-8-(oxazolin-2-yl) anthracene ions, which could further lose an R radical, followed by the loss of oxazoline. These ions could also eliminate an R radical and subsequently undergo ring-contraction rearrangements to lose a CHCH2O fragment and an epoxide molecule, respectively. The ions that are formed could further lose CHCH2O and CH2=CH fragments. Several ring-contraction rearrangements of the oxazoline ring were observed under electron-impact ionization conditions.

  3. Quantitative structure–activity relationships for chronic toxicity of alkyl-chrysenes and alkyl-benz[a]anthracenes to Japanese medaka embryos (Oryzias latipes)

    International Nuclear Information System (INIS)

    Highlights: • Medaka embryos were exposed to alkyl chrysenes and benzo[a]anthracenes (BAA). • Concentrations were kept constant by partition controlled delivery. • Chrysene was not toxic within solubility limits, in contrast to BAA. • Alkylation increased the toxicity of chrysene and BAA. • Toxicity was related to hydrophobicity and to specific modes of action. - Abstract: Alkylated polycyclic aromatic hydrocarbons (alkyl-PAHs) are a class of compounds found at significant concentrations in crude oils, and likely the main constituents responsible for the chronic toxicity of oil to fish. Alkyl substituents at different locations on the aromatic rings change the size and shape of PAH molecules, which results in different interactions with tissue receptors and different severities of toxicity. The present study is the first to report the toxicity of several alkylated derivatives of chrysene and benz[a]anthracene to the embryos of Japanese medaka (Oryzias latipes) using the partition controlled delivery (PCD) method of exposure. The PCD method maintained the desired exposure concentrations by equilibrium partitioning of hydrophobic test compounds from polydimethylsiloxane (PDMS) films. Test concentrations declined by only 13% over a period of 17 days. Based on the prevalence of signs of blue sac disease (BSD), as expressed by median effective concentrations (EC50s), benz[a]anthracene (B[a]A) was more toxic than chrysene. Alkylation generally increased toxicity, except at position 2 of B[a]A. Alkyl-PAHs substituted in the middle region had a lower EC50 than those substituted at the distal region. Except for B[a]A and 7-methylbenz[a]anthracene (7-MB), estimated EC50 values were higher than their solubility limits, which resulted in limited toxicity within the range of test concentrations. The regression between log EC50s and log Kow values provided a rough estimation of structure–activity relationships for alkyl-PAHs, but Kow alone did not provide a complete

  4. Reduced energy intake and moderate exercise reduce mammary tumor incidence in virgin female BALB/c mice treated with 7,12-dimethylbenz(a)anthracene

    Science.gov (United States)

    Lane, Helen W.; Teer, Patricia; Keith, Robert E.; White, Marguerite T.; Strahan, Susan

    1991-01-01

    The concurrent effects of diet (standard AIN-76A, restricted AIN-76A and high-fat diet) and moderate rotating-drum treadmill exercise on the incidence of 7,12-dimethylbenz(a)anthracene-induced mammary carcinomas in virgin female BALB/cMed mice free of murine mammary tumor virus are evaluated. Analyses show that, although energy intake was related to mammary tumor incidence, neither body weight nor dietary fat predicted tumor incidence.

  5. Pro-apoptotic and anti-inflammatory potential of andrographolide during 7,12-dimethylbenz[a]anthracene induced hamster buccal pouch carcinogenesis

    OpenAIRE

    Karthikeyan Sekar; Baskaran Nagarethinam; Arjun Kumar Singh; Manoharan Shanmugam

    2012-01-01

    Objective: Aim of the present study was to investigate the modulating effect of andrographolide on apoptotic and inflammatory markers during 7,12-dimethyl-benz[a]anthracene (DMBA) induced hamster buccal pouch carcinogenesis. Methods: Oral tumors were developed in the buccal pouch of golden Syrian hamsters by painting with 0.5% DMBA in liquid paraffin three times a week for 14 weeks. The expression pattern of molecular markers were assayed using immunohistochemistry (p53, Bcl-2 and Bax), ELISA...

  6. 7,12-Dimethylbenz[A]Anthracene Induces Sertoli–Leydig-Cell Tumors in the Follicle-Depleted Ovaries of Mice Treated with 4-Vinylcyclohexene Diepoxide

    OpenAIRE

    Craig, Zelieann R.; Davis, John R; Marion, Samuel L.; Barton, Jennifer K.; Hoyer, Patricia B.

    2010-01-01

    Ovarian cancer is associated with high mortality due to its late onset of symptoms and lack of reliable screening methods for early detection. Furthermore, the incidence of ovarian cancer is higher in postmenopausal women. Mice rendered follicle-depleted through treatment with 4-vinylcyclohexene diepoxide (VCD) are a model of ovary-intact menopause. The present study was designed to induce ovarian neoplasia in this model by treating mice with 7,12-dimethylbenz[a]anthracene (DMBA). Female B6C3...

  7. Covalent functionalization of single-walled carbon nanotubes with anthracene by green chemical approach and their temperature dependent magnetic and electrical conductivity studies

    Energy Technology Data Exchange (ETDEWEB)

    Hariharasubramanian, A. [Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamilnadu (India); Dominic Ravichandran, Y., E-mail: ydominic64@yahoo.co.in [Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamilnadu (India); Rajesh, R.; Rajendra Kumar, K. [Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamilnadu (India); Kanagaraj, M.; Arumugam, S. [Centre for High Pressure Research, School of Physics, Bharathidasan University, Thiruchirapalli 620024 (India)

    2014-01-15

    Single-walled carbon nanotubes (SWCNTs) were covalently functionalized with anthracene in molten urea by a green chemical approach. The anthracene functionalized single-walled carbon nanotubes (Ant-f-SWCNTs) were examined along with SWCNTs, using Fourier transform infrared spectroscopy (FTIR), Raman spectroscopy, powder X-Ray diffraction (XRD), and scanning, and transmission electron microscopy. The observations revealed the functionalization of SWCNTs by anthracene. The temperature dependent magnetization (300–5 K) and electrical resistivity were also measured for both SWCNTs and Ant-f-SWCNTs. The electrical resistivity of Ant-f-SWCNTs at 300 K was found to be 1.27 KΩm, which is much lower than 388.55 KΩm for pristine. This indicated a 300 fold increase in conductivity at room temperature for Ant-f-SWCNTs when compared to SWCNTs. The temperature dependence of the conductivity provided an indication of the semiconducting behaviour. - Highlights: • SWCNTs were functionalized using 2-aminoanthracene by green chemistry. • Characterized by FTIR, Raman, XRD, SEM and TEM. • Temperature dependent magnetization and conductivity were investigated. • 300 fold increase in conductivity was observed for Ant-f-SWCNTs. • Semiconductor behaviour was observed in the case of Ant-f-SWCNTs.

  8. Covalent functionalization of single-walled carbon nanotubes with anthracene by green chemical approach and their temperature dependent magnetic and electrical conductivity studies

    International Nuclear Information System (INIS)

    Single-walled carbon nanotubes (SWCNTs) were covalently functionalized with anthracene in molten urea by a green chemical approach. The anthracene functionalized single-walled carbon nanotubes (Ant-f-SWCNTs) were examined along with SWCNTs, using Fourier transform infrared spectroscopy (FTIR), Raman spectroscopy, powder X-Ray diffraction (XRD), and scanning, and transmission electron microscopy. The observations revealed the functionalization of SWCNTs by anthracene. The temperature dependent magnetization (300–5 K) and electrical resistivity were also measured for both SWCNTs and Ant-f-SWCNTs. The electrical resistivity of Ant-f-SWCNTs at 300 K was found to be 1.27 KΩm, which is much lower than 388.55 KΩm for pristine. This indicated a 300 fold increase in conductivity at room temperature for Ant-f-SWCNTs when compared to SWCNTs. The temperature dependence of the conductivity provided an indication of the semiconducting behaviour. - Highlights: • SWCNTs were functionalized using 2-aminoanthracene by green chemistry. • Characterized by FTIR, Raman, XRD, SEM and TEM. • Temperature dependent magnetization and conductivity were investigated. • 300 fold increase in conductivity was observed for Ant-f-SWCNTs. • Semiconductor behaviour was observed in the case of Ant-f-SWCNTs

  9. Effect of anthracene on the interaction between Platymonas helgolandica var. tsingtaoensis and Heterosigma akashiwo in laboratory cultures

    Science.gov (United States)

    Bi, Rong; Wang, You; Wang, Renjun; Li, Wei; Tang, Xuexi

    2015-02-01

    Two species of marine phytoplankton, Platymonas helgolandica var. tsingtaoensis and Heterosigma akashiwo, were cultivated in bi-algal cultures to investigate the effect of anthracene (ANT) on the interaction between them. Without ANT, H. akashiwo out-competed P. helgolandica at low initial biomass ratios ( P. helgolandica ( P): H. akashiwo ( H) = 1:4 and 1:1), but not at the highest ( P: H = 4:1). This observation was consistent with the description in Lotka-Volterra two species competition model. It was found that P. helgolandica was excluded at low initial biomass ratios, while the unstable equilibrium between two species was predicted at the highest. For both species, carrying capacity and maximal specific growth rate decreased in bi-algal cultures compared to those in monocultures. H. akashiwo exhibited a higher sensitivity to ANT than P. helgolandica. This resulted markedly in a reduced cell density of H. akashiwo but an increased cell density of P. helgolandica. Carrying capacity of P. helgolandica was consistently higher in bi-algal cultures with ANT than those without ANT, suggesting that ANT, through the elimination of H. akashiwo, generated the dominance of P. helgolandica independently of initial biomass ratios. This study showed a density-dependent effect of harmful alga ( H. akashiwo) on dietary alga ( P. helgolandica), and indicated that ocean pollutant ANT could induce the succession of marine phytoplankton.

  10. Anthracene excimer-based "turn on" fluorescent sensor for Cr(3+) and Fe(3+) ions: Its application to living cells.

    Science.gov (United States)

    Erdemir, Serkan; Kocyigit, Ozcan

    2016-09-01

    A novel anthracene based fluorescent probe containing benzothiazole group (BFA) was designed and synthesized. The cation binding properties of BFA were studied in the presence of various cations. Both UV-vis and fluorescence spectroscopic studies indicated that BFA was highly sensitive and selective toward trivalent cations (Cr(3+) and Fe(3+)), while there was no response to monovalent, divalent cations and also Al(3+) ion. The interaction of BFA with Cr(3+) and Fe(3+) caused a significant enhancement in emission intensity due to the combination of a unique anthracenyl static excimer formation, the restricted C=N isomerization and the suppression of highly efficient photoinduced electron transfer (PET) process. The detection limits of BFA for Cr(3+) and Fe(3+) were 0.46 and 0.45µM, which presented a pronounced sensitivity toward Cr(3+) and Fe(3+), respectively. Also, possible utilization of BFA as bio-imaging fluorescent probe to detect Cr(3+) and Fe(3+) in human prostate cancer cell lines was observed by confocal fluorescence microscopy. PMID:27343579

  11. Soil sterilization affects aging-related sequestration and bioavailability of p,p'-DDE and anthracene to earthworms

    International Nuclear Information System (INIS)

    Laboratory experiments investigated the effects of soil sterilization and compound aging on the bioaccumulation of spiked p,p'-DDE and anthracene by Eisenia fetida and Lumbricus terrestris. Declines in bioavailability occurred as pollutant residence time in both sterile and non-sterile soils increased from 3 to 203 d. Accumulation was generally higher in sterile soils during initial periods of aging (from 3-103 d). By 203 d, however, bioavailability of the compounds was unaffected by sterilization. Gamma irradiation and autoclaving may have altered bioavailability by inducing changes in the chemistry of soil organic matter (SOM). The results support a dual-mode partitioning sorption model in which the SOM components associated with short-term sorption (the 'soft' or 'rubbery' phases) are more affected than are the components associated with long-term sorption (the 'glassy' or microcrystalline phases). Risk assessments based on data from experiments in which sterile soil was used could overestimate exposure and bioaccumulation of pollutants. - Soil sterilization affects aging-related sequestration of organic contaminants.

  12. Crystal structure of the 4 + 2 cycloadduct of photooxidized anthracene and C60 fullerene

    Directory of Open Access Journals (Sweden)

    Gábor Bortel

    2014-11-01

    Full Text Available The structure of the title compound, 5,6-[(1R,10S-2,9-dioxatricyclo[8.6.03,8.011,16]hexadecane-1,10-diyl]-(C60–Ih[5,6]fullerene methanedithione 0.1-solvate, C74H10O2·0.1CS2, has tetragonal (P42/n symmetry at 100 K. It has a unique eight-membered ring, with two incorporated O atoms in place of the original central ring of the anthracene. The distortion of the molecular geometry around the cycloadduct bonds corresponds to that seen in related fullerene derivatives. Close packing of the adduct forms cavities partially filled with disordered carbon disulfide solvent molecule. The 41% occupancy of the cavities yields an overall 1:0.103 adduct–solvent ratio. Reaction steps are described as light-assisted singlet-oxygen generation, peroxide, epoxide and dioxocin derivative formation and the final step of thermally activated cycloaddition.

  13. Effect of Anthracene on the Interaction BetweenPlatymonas helgolandicavar. tsingtaoensis andHeterosigma akashiwo in Laboratory Cultures

    Institute of Scientific and Technical Information of China (English)

    BI Rong; WANG You; WANG Renjun; LI Wei; TANG Xuexi

    2015-01-01

    Two species of marine phytoplankton,Platymonas helgolandicavar. tsingtaoensis andHeterosigma akashiwo, were cul-tivated in bi-algal cultures to investigate the effect of anthracene (ANT) on the interaction between them. Without ANT,H. akashiwo out-competedP. helgolandica at low initial biomass ratios (P. helgolandica (P): H. akashiwo (H)=1:4 and 1:1), but not at the highest (P:H=4:1). This observation was consistent with the description in Lotka-Volterra two species competition model. It was found that P. helgolandica was excluded at low initial biomass ratios, while the unstable equilibrium between two species was predicted at the highest. For both species, carrying capacity and maximal specific growth rate decreased in bi-algal cultures compared to those in monocultures.H. akashiwo exhibited a higher sensitivity to ANT thanP. helgolandica. This resulted markedly in a reduced cell den-sity ofH. akashiwo but an increased cell density ofP. helgolandica. Carrying capacity ofP. helgolandica was consistently higher in bi-algal cultures with ANT than those without ANT, suggesting that ANT, through the elimination ofH. akashiwo, generated the dominance ofP. helgolandica independently of initial biomass ratios. This study showed a density-dependent effect of harmful alga (H. akashiwo) on dietary alga (P. helgolandica), and indicated that ocean pollutant ANT could induce the succession of marine phytoplankton.

  14. Microemulsions of N-alkylimidazolium ionic liquid and their performance as microreactors for the photocycloaddition of 9-substituted anthracenes.

    Science.gov (United States)

    Li, Xin-Wei; Zhang, Jin; Zheng, Li-Qiang; Chen, Bin; Wu, Li-Zhu; Lv, Feng-Feng; Dong, Bin; Tung, Chen-Ho

    2009-05-19

    The phase behavior of the ternary system consisting of an ionic liquid (1-tetradecyl-3-methylimidazolium bromide [C14mim]Br), p-xylene, and water were investigated. Depending on the composition of the ternary system, formation of hexagonal and lamellar liquid crystals as well as microemulsions was observed. 1H NMR spectroscopy study, 2D ROESY spectroscopic analysis, and rheological measurements of the microemulsions indicated that p-xylene is preferably located in the hydrophobic core and the palisade shells of the microemulsions. The sizes of the microemulsion droplets for the samples with water/[C14mim]Br ratio of 78:22 are measured by both dynamic light scattering (DLS) and transmission electron microscopy with the freeze-fracture technique (FF-TEM). Upon change of the mole ratio of the solubilized xylene to [C14mim]Br from 0 to 2.4, the diameters of the microemulsion droplets increase from ca. 20 to 90 nm and size distribution gets broad. These microemulsions can solubilize and preorientate anthracene derivatives with a polar 9-substituent, and thus may enhance the head-to-head cyclomers in the photocyclization of these substrates. PMID:19432490

  15. Terahertz spectroscopy and solid-state density functional theory calculation of anthracene: Effect of dispersion force on the vibrational modes

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Feng; Tominaga, Keisuke, E-mail: atmyh@ntu.edu.tw, E-mail: tominaga@kobe-u.ca.jp, E-mail: junichi.nishizawa@hanken.jp [Molecular Photoscience Research Center, Kobe University, Nada, Kobe 657-0013 (Japan); Hayashi, Michitoshi, E-mail: atmyh@ntu.edu.tw, E-mail: tominaga@kobe-u.ca.jp, E-mail: junichi.nishizawa@hanken.jp; Wang, Houng-Wei [Center for Condensed Matter Sciences, National Taiwan University, 1 Roosevelt Rd., Sec. 4, Taipei 10617, Taiwan (China); Kambara, Ohki; Sasaki, Tetsuo [Research Institute of Electronics, Shizuoka University, 3-5-1 Jyohoku, Naka-ku, Hamamatsu, Shizuoka 432-8561 (Japan); Nishizawa, Jun-ichi, E-mail: atmyh@ntu.edu.tw, E-mail: tominaga@kobe-u.ca.jp, E-mail: junichi.nishizawa@hanken.jp [Jun-ichi Nishizawa Memorial Research Center, Tohoku University, 519-1176 Aoba, Aramaki, Aoba-ku, Sendai 980-0845 (Japan)

    2014-05-07

    The phonon modes of molecular crystals in the terahertz frequency region often feature delicately coupled inter- and intra-molecular vibrations. Recent advances in density functional theory such as DFT-D{sup *} have enabled accurate frequency calculation. However, the nature of normal modes has not been quantitatively discussed against experimental criteria such as isotope shift (IS) and correlation field splitting (CFS). Here, we report an analytical mode-decoupling method that allows for the decomposition of a normal mode of interest into intermolecular translation, libration, and intramolecular vibrational motions. We show an application of this method using the crystalline anthracene system as an example. The relationship between the experimentally obtained IS and the IS obtained by PBE-D{sup *} simulation indicates that two distinctive regions exist. Region I is associated with a pure intermolecular translation, whereas region II features coupled intramolecular vibrations that are further coupled by a weak intermolecular translation. We find that the PBE-D{sup *} data show excellent agreement with the experimental data in terms of IS and CFS in region II; however, PBE-D{sup *} produces significant deviations in IS in region I where strong coupling between inter- and intra-molecular vibrations contributes to normal modes. The result of this analysis is expected to facilitate future improvement of DFT-D{sup *}.

  16. LUPEOL PROTECTS ABNORMALITIES IN CELL SURFACE MOITIES DURING 7, 12-DIMETHYLBENZ[A]ANTHRACENE INDUCED HAMSTER BUCCAL POUCH CARCINOGENESIS

    Directory of Open Access Journals (Sweden)

    D. Palanimuthu and S. Manoharan*

    2012-05-01

    Full Text Available Lupeol, a pentacyclic triterpene, possesses diverse pharmacological and biochemical activities including anticancer and antioxidant effects. Abnormalities in the status of glycoconjugates and lipids in the cell results in malignant transformation. The aim of the present study was to investigate the protective effect of lupeol on cell surface glycoconjugates and lipids abnormalities during 7,12-dimethylbenz[a]anthracene (DMBA-induced hamster buccal pouch carcinogenesis. Oral squamous cell carcinoma was developed in the buccal pouches of golden Syrian hamsters by treating with 0.5% DMBA in liquid paraffin, three times a week, for 14 weeks. The status of glycoconjugates and lipids were measured using specific colorimetric methods. We observed 100% tumor formation with marked abnormalities in the status of glycoconjugates and lipids in hamsters treated with DMBA alone. Oral administration of lupeol at a dose of 50mg/kg bw, completely prevented the formation of tumors and restored the status of glycoconjugates and lipids in hamsters treated with DMBA. The results of the present study thus suggest that lupeol has the potential to protect cell surface abnormalities during DMBA-induced hamster buccal pouch carcinogenesis.

  17. Unexpected formation of π-expanded isoquinoline from anthracene possessing four electron-donating groups via the Duff reaction.

    Science.gov (United States)

    Węcławski, Marek K; Deperasińska, Irena; Leniak, Arkadiusz; Banasiewicz, Marzena; Kozankiewicz, Bolesław; Gryko, Daniel T

    2016-08-01

    New synthetic methods leading towards π-expanded heterocycles are sought after mainly due to their promising opto-electronic properties. Subjecting 1,5,9,10-tetramethoxyanthracene to the modern Duff reaction conditions led to the formation of a compound possessing the 2-azabenzoanthrone (dibenzo[de,h]isoquinolin-7-on) skeleton instead of the expected dialdehyde. This non-typical course of reaction can be rationalized by the double electrophilic aromatic substitution at two neighboring electron-rich positions of anthracene followed by oxidation of the resulting intermediate to form a pyridine ring. Optical studies supported by the quantum chemistry calculations indicated the lack of excited-state intramolecular proton transfer (ESIPT); for energy reasons, only one tautomeric form, with a hydrogen atom bonded to one of the two nearby oxygen atoms, was populated in the electronic ground S0 and in the excited S1 states. Nonradiative depopulation of the S1 state proceeded via internal conversion stimulated by the presence of the low frequency vibrational modes. Our serendipitous discovery represents the most complex case of rearrangement of aromatic compounds under Duff reaction conditions and could help to design analogous processes. At the same time this is the simplest method for the synthesis of derivatives of 2-azabenzoanthrone. PMID:27367169

  18. Estrogenic status modulates the effect of soy on hepatic responses to 7,12-dimethylbenz(a)anthracene (DMBA)

    International Nuclear Information System (INIS)

    We examined the influence of estradiol (E2) status and soy protein isolate (SPI) intake on the hepatic responses altered by 7,12-dimethylbenz(a)anthracene (DMBA, a polycyclic aromatic hydrocarbon [PAH]). Sprague-Dawley rats were ovariectomized (OVX) at PND50 and infused with E2 or vehicle for 14 d and gavaged with 50 mg/kg DMBA or vehicle 24 h before sacrifice at PND64. Rats were fed an AIN-93G diet made with SPI or casein as sole protein source throughout the study. Basal AhR protein levels were reduced (P TM) revealed 231 genes common to SPI + DMBA and SPI + E2 + DMBA (normalized to E2) treatments. AhR-activated genes (CYP1A1, CYP1A2, and NQO1) were down-regulated by SPI + E2 + DMBA compared to SPI + DMBA. Unique interactions among SPI, DMBA and E2 altered the expression profile of 316 genes, not observed by either treatment alone. Our data suggest that although E2 status does not effect soy-mediated AhR degradation, it modulates the effects of soy on many genes, including CYP1A1

  19. Polyvinyl pyrrolidone capped fluorescent anthracene nanoparticles for sensing fluorescein sodium in aqueous solution and analytical application for ophthalmic samples.

    Science.gov (United States)

    Bhopate, Dhanaji P; Mahajan, Prasad G; Garadkar, Kalyanrao M; Kolekar, Govind B; Patil, Shivajirao R

    2015-11-01

    Based on the known complexation ability between polyvinyl pyrrolidone (PVP) and fluorescein sodium (FL Na(+)), fluorescent PVP capped anthracene nanoparticles (PVP-ANPs) were prepared using a reprecipitation method for detection of fluorescein in aqueous solution using the fluorescence resonance energy transfer (FRET) approach. A dynamic light scattering histogram of PVP-ANPs showed narrower particle size distribution and the average particle size was 15 nm. The aggregation-induced enhanced emission (AIEE) of PVP-ANPs was red shifted from its monomer by 1087.22 cm(-1). The maximum emission was seen to occur at 420 nm. The presence of FL Na(+) in the vicinity of PVP-ANPs quenched the fluorescence of PVP-ANPs because of its adsorption on the surface of PVP-ANPs in aqueous suspension. The FL Na(+) and PVP-ANPs were brought close enough, typically to 7.89 nm, which was less than the distance of 10 nm that is required between the energy donor-acceptor molecule for efficient FRET. The quenching results fit into the Stern-Volmer relationship even at temperatures greater than ambient temperatures. The thermodynamic parameters determined from FRET results helped to propose binding mechanisms involving hydrophobic and electrostatic molecular interaction. The fluorescence quenching results were used further to develop an analytical method for estimation of fluorescein sodium from ophthalmic samples available commercially in the market. PMID:25736374

  20. CO-induction of rat intestinal cancers with 7,12-dimethylbenz(a)anthracene and medroxyprogesterone acetate

    Energy Technology Data Exchange (ETDEWEB)

    Hass, G.; Galt, R.; Coogan, P.; Friese, J.

    1986-03-01

    Medroxy progesterone acetate (P) is a progestin used for treatment of sex hormone-dependent human cancers. In a study of its action, 7,12-dimethyl-benz(a)anthracene (DMBA) was given, i.g., to 50-52 day old intact or gonadectomized Sprague-Dawley rats of both sexes. Groups were given 0, 5, 25 or 100 mg of P +/- 2, .5, .1, .01 or .001 mg of 17 beta estradiol (E2), s.c., each week for 12-36 weeks. Those given P often developed, independent of sex or gonadectomy, multiple intestinal adenomas and carcinomas, especially in the jejunum. At doses of P tumor incidence was as follows: 0 mg, 2/63; 5 mg, 18/96; 25 mg, 35/57; 100 mg, 72/155. Combinations of P with doses of E2 at 2, .5 or .1 mg reduced tumor incidence 65%. At 25 or 100 mg doses of P, DMBA induction of mammary tumors was inhibited, while atrophy of ovaries and adrenal cortex was impressive. Hence, this is the only progestin, which favors DMBA induction of tumors of the rat intestine, while extinguishing mammary tumors. This matter may bear on presence of hormone receptors in human colo-rectal cancers.

  1. Monolayers and Langmuir-Blodgett films of luminescent 1,3,5-triazine derivatives containing naphthalene or anthracene chromophores

    Science.gov (United States)

    Cai, Ya-Qi; Wu, Wei; Wang, Hua; Miyake, Jun; Qian, Dong-Jin

    2011-02-01

    Monolayer behaviors and Langmuir-Blodgett (LB) films of three luminescent aryl triazines, 2,4,6-tri(naphthalen-1-yl)-1,3,5-triazine (TN 1Ta), 2,4,6-tri(naphthalen-2-yl)-1,3,5-triazine (TN 2Ta), and 2,4,6-tri(anthracen-9-yl)-1,3,5-triazine (TATa) have been investigated. Surface pressure-area isotherms indicated that pure aryl triazines were difficult to form stable monolayers, while their mixtures with arachidic acid (AA) could be stabilized at the air-water interface. The mixed LB films of triazine-AA were deposited on substrate surfaces and analyzed by using UV-vis and infrared absorption spectra, X-ray photoelectron spectra, as well as scanning electron microscopy. Morphologies of the LB films and molecular aggregates were closely dependent on the structure of triazines and the surface pressures of deposition. Under UV radiation, TN 1Ta and TN 2Ta emitted at 410-460 nm while TATa emitted at 500-510 nm, with the emission lifetime falling into the range of 0.29 to 10.8 ns. Compared with those in solutions, the emissions of aryl triazines were red shifted in the LB films, especially for the TN 1Ta-AA and TN 2Ta-AA, which was attributed to the closely packed arrangement for the molecules in the LB films.

  2. Tomato and garlic by gavage modulate 7,12-dimethylbenz[a]anthracene-induced genotoxicity and oxidative stress in mice

    Directory of Open Access Journals (Sweden)

    V. Bhuvaneswari

    2004-07-01

    Full Text Available Chemoprotection by dietary agents is a promising strategy for cancer prevention. The aim of the present study was to evaluate the combined effect of tomato and garlic against 7,12-dimethylbenz- [a]anthracene (DMBA-induced genetic damage and oxidative stress in 12-14-week-old male Swiss albino mice. The animals were randomized into experimental and control groups and divided into eight groups of five animals each. Group 1 animals were injected intraperitoneally with 35 mg/kg body weight DMBA suspended in peanut oil as a single dose. Groups 2-4 animals received tomato (500 mg/kg body weight, garlic (125 mg/kg body weight and a combination of tomato and garlic for 5 days by gavage, respectively, followed by DMBA 1.5 h after the final feeding. The doses of tomato and garlic correspond to the average human daily consumption. Animals in groups 5, 6 and 7 received tomato alone, garlic alone and tomato + garlic combination, respectively, for 5 days. Group 8 animals received the same volume of water and served as control. The incidence of bone marrow micronuclei and the extent of lipid peroxidation and the concentrations of antioxidants glutathione, glutathione peroxidase and glutathione-S-transferase were measured in the liver, 48 h after DMBA exposure. Increased frequency of micronuclei and enhanced lipid peroxidation accompanied by compromised antioxidant defenses were observed in DMBA-treated animals. Although pretreatment with tomato or garlic significantly reduced the frequency of DMBA-induced bone marrow micronuclei, the combination of tomato and garlic exhibited more profound effect in inhibiting DMBA-induced genotoxicity and oxidative stress. We suggest that a broad spectrum of antimutagenic and anticlastogenic effects can be achieved through an effective combination of functional foods such as tomato and garlic.

  3. Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene

    International Nuclear Information System (INIS)

    Activation of nuclear factor erythroid 2-related factor (Nrf2), which belongs to the basic leucine zipper transcription factor family, is a strategy for cancer chemopreventive phytochemicals. It is an important regulator of genes induced by oxidative stress, such as glutathione S-transferases, heme oxygenase-1 and peroxiredoxin 1, by activating the antioxidant response element (ARE). We hypothesized that (1) the citrus coumarin auraptene may suppress premalignant mammary lesions via activation of Nrf2/ARE, and (2) that Nrf2 knockout (KO) mice would be more susceptible to mammary carcinogenesis. Premalignant lesions and mammary carcinomas were induced by medroxyprogesterone acetate and 7,12-dimethylbenz[a]anthracene treatment. The 10-week pre-malignant study was performed in which 8 groups of 10 each female wild-type (WT) and KO mice were fed either control diet or diets containing auraptene (500 ppm). A carcinogenesis study was also conducted in KO vs. WT mice (n = 30-34). Comparisons between groups were evaluated using ANOVA and Kaplan-Meier Survival statistics, and the Mann-Whitney U-test. All mice treated with carcinogen exhibited premalignant lesions but there were no differences by genotype or diet. In the KO mice, there was a dramatic increase in mammary carcinoma growth rate, size, and weight. Although there was no difference in overall survival, the KO mice had significantly lower mammary tumor-free survival. Also, in the KO mammary carcinomas, the active forms of NF-κB and β-catenin were increased ~2-fold whereas no differences in oxidized proteins were observed. Many other tumors were observed, including lymphomas. Interestingly, the incidences of lung adenomas in the KO mice were significantly higher than in the WT mice. We report, for the first time, that there was no apparent difference in the formation of premalignant lesions, but rather, the KO mice exhibited rapid, aggressive mammary carcinoma progression

  4. Enhanced susceptibility of ovaries from obese mice to 7,12-dimethylbenz[a]anthracene-induced DNA damage

    International Nuclear Information System (INIS)

    7,12-Dimethylbenz[a]anthracene (DMBA) depletes ovarian follicles and induces DNA damage in extra-ovarian tissues, thus, we investigated ovarian DMBA-induced DNA damage. Additionally, since obesity is associated with increased offspring birth defect incidence, we hypothesized that a DMBA-induced DNA damage response (DDR) is compromised in ovaries from obese females. Wild type (lean) non agouti (a/a) and KK.Cg-Ay/J heterozygote (obese) mice were dosed with sesame oil or DMBA (1 mg/kg; intraperitoneal injection) at 18 weeks of age, for 14 days. Total ovarian RNA and protein were isolated and abundance of Ataxia telangiectasia mutated (Atm), X-ray repair complementing defective repair in Chinese hamster cells 6 (Xrcc6), breast cancer type 1 (Brca1), Rad 51 homolog (Rad51), poly [ADP-ribose] polymerase 1 (Parp1) and protein kinase, DNA-activated, catalytic polypeptide (Prkdc) were quantified by RT-PCR or Western blot. Phosphorylated histone H2AX (γH2AX) level was determined by Western blotting. Obesity decreased (P < 0.05) basal protein abundance of PRKDC and BRCA1 proteins but increased (P < 0.05) γH2AX and PARP1 proteins. Ovarian ATM, XRCC6, PRKDC, RAD51 and PARP1 proteins were increased (P < 0.05) by DMBA exposure in lean mice. A blunted DMBA-induced increase (P < 0.05) in XRCC6, PRKDC, RAD51 and BRCA1 was observed in ovaries from obese mice, relative to lean counterparts. Taken together, DMBA exposure induced γH2AX as well as the ovarian DDR, supporting that DMBA causes ovarian DNA damage. Additionally, ovarian DDR was partially attenuated in obese females raising concern that obesity may be an additive factor during chemical-induced ovotoxicity. - Highlights: • DMBA induces markers of ovarian DNA damage. • Obesity induces low level ovarian DNA damage. • DMBA-induced DNA repair response is altered by obesity

  5. Enhanced susceptibility of ovaries from obese mice to 7,12-dimethylbenz[a]anthracene-induced DNA damage

    Energy Technology Data Exchange (ETDEWEB)

    Ganesan, Shanthi, E-mail: shanthig@iastate.edu; Nteeba, Jackson, E-mail: nteeba@iastate.edu; Keating, Aileen F., E-mail: akeating@iastate.edu

    2014-12-01

    7,12-Dimethylbenz[a]anthracene (DMBA) depletes ovarian follicles and induces DNA damage in extra-ovarian tissues, thus, we investigated ovarian DMBA-induced DNA damage. Additionally, since obesity is associated with increased offspring birth defect incidence, we hypothesized that a DMBA-induced DNA damage response (DDR) is compromised in ovaries from obese females. Wild type (lean) non agouti (a/a) and KK.Cg-Ay/J heterozygote (obese) mice were dosed with sesame oil or DMBA (1 mg/kg; intraperitoneal injection) at 18 weeks of age, for 14 days. Total ovarian RNA and protein were isolated and abundance of Ataxia telangiectasia mutated (Atm), X-ray repair complementing defective repair in Chinese hamster cells 6 (Xrcc6), breast cancer type 1 (Brca1), Rad 51 homolog (Rad51), poly [ADP-ribose] polymerase 1 (Parp1) and protein kinase, DNA-activated, catalytic polypeptide (Prkdc) were quantified by RT-PCR or Western blot. Phosphorylated histone H2AX (γH2AX) level was determined by Western blotting. Obesity decreased (P < 0.05) basal protein abundance of PRKDC and BRCA1 proteins but increased (P < 0.05) γH2AX and PARP1 proteins. Ovarian ATM, XRCC6, PRKDC, RAD51 and PARP1 proteins were increased (P < 0.05) by DMBA exposure in lean mice. A blunted DMBA-induced increase (P < 0.05) in XRCC6, PRKDC, RAD51 and BRCA1 was observed in ovaries from obese mice, relative to lean counterparts. Taken together, DMBA exposure induced γH2AX as well as the ovarian DDR, supporting that DMBA causes ovarian DNA damage. Additionally, ovarian DDR was partially attenuated in obese females raising concern that obesity may be an additive factor during chemical-induced ovotoxicity. - Highlights: • DMBA induces markers of ovarian DNA damage. • Obesity induces low level ovarian DNA damage. • DMBA-induced DNA repair response is altered by obesity.

  6. Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene

    Directory of Open Access Journals (Sweden)

    Yamamoto Masayuki

    2010-10-01

    Full Text Available Abstract Background Activation of nuclear factor erythroid 2-related factor (Nrf2, which belongs to the basic leucine zipper transcription factor family, is a strategy for cancer chemopreventive phytochemicals. It is an important regulator of genes induced by oxidative stress, such as glutathione S-transferases, heme oxygenase-1 and peroxiredoxin 1, by activating the antioxidant response element (ARE. We hypothesized that (1 the citrus coumarin auraptene may suppress premalignant mammary lesions via activation of Nrf2/ARE, and (2 that Nrf2 knockout (KO mice would be more susceptible to mammary carcinogenesis. Methods Premalignant lesions and mammary carcinomas were induced by medroxyprogesterone acetate and 7,12-dimethylbenz[a]anthracene treatment. The 10-week pre-malignant study was performed in which 8 groups of 10 each female wild-type (WT and KO mice were fed either control diet or diets containing auraptene (500 ppm. A carcinogenesis study was also conducted in KO vs. WT mice (n = 30-34. Comparisons between groups were evaluated using ANOVA and Kaplan-Meier Survival statistics, and the Mann-Whitney U-test. Results All mice treated with carcinogen exhibited premalignant lesions but there were no differences by genotype or diet. In the KO mice, there was a dramatic increase in mammary carcinoma growth rate, size, and weight. Although there was no difference in overall survival, the KO mice had significantly lower mammary tumor-free survival. Also, in the KO mammary carcinomas, the active forms of NF-κB and β-catenin were increased ~2-fold whereas no differences in oxidized proteins were observed. Many other tumors were observed, including lymphomas. Interestingly, the incidences of lung adenomas in the KO mice were significantly higher than in the WT mice. Conclusions We report, for the first time, that there was no apparent difference in the formation of premalignant lesions, but rather, the KO mice exhibited rapid, aggressive mammary

  7. Caribbean yellow band disease compromises the activity of catalase and glutathione S-transferase in the reef-building coral Orbicella faveolata exposed to anthracene.

    Science.gov (United States)

    Montilla, Luis Miguel; Ramos, Ruth; García, Elia; Cróquer, Aldo

    2016-05-01

    Healthy and diseased corals are threatened by different anthropogenic sources, such as pollution, a problem expected to become more severe in the near future. Despite the fact that coastal pollution and coral diseases might represent a serious threat to coral reef health, there is a paucity of controlled experiments showing whether the response of diseased and healthy corals to xenobiotics differs. In this study, we exposed healthy and Caribbean yellow band disease (CYBD)-affected Orbicella faveolata colonies to 3 sublethal concentrations of anthracene to test if enzymatic responses to this hydrocarbon were compromised in CYBD-affected tissues. For this, a 2-factorial fully orthogonal design was used in a controlled laboratory bioassay, using tissue condition (2 levels: apparently healthy and diseased) and pollutant concentration (4 levels: experimental control, 10, 30 and 100 ppb concentration) as fixed factors. A permutation-based ANOVA (PERMANOVA) was used to test the effects of condition and concentration on the specific activity of 3 enzymatic biomarkers: catalase, glutathione S-transferase, and glutathione peroxidase. We found a significant interaction between the concentration of anthracene and the colony condition for catalase (Pseudo-F = 3.84, df = 3, p < 0.05) and glutathione S-transferase (Pseudo-F = 3.29, df = 3, p < 0.05). Moreover, our results indicated that the enzymatic response to anthracene in CYBD-affected tissues was compromised, as the activity of these enzymes decreased 3- to 4-fold compared to healthy tissues. These results suggest that under a potential scenario of increasing hydrocarbon coastal pollution, colonies of O. faveolata affected with CYBD might become more vulnerable to the deleterious effects of chemical pollution. PMID:27137073

  8. Effects of UVB and 7, 12, dimethylbenz(alpha)anthracene (DMBA) on epidermal melanocytes of the tail in C57BL mice

    Energy Technology Data Exchange (ETDEWEB)

    Blog, F.B.; Szabo, G.

    1979-12-01

    The morphological and numerical changes in the epidermal melanocyte system of the tail of C57BL mice were studied after exposure to 7, 12, dimethylbenz(alpha)anthracene(DMBA) followed by UVB irradiation. Biopsies were studied by the combined skin-splitting DOPA and electron microscopic techniques. After 10 weeks of DMBA treatment the following changes were observed: the original brick-like arrangement of melanocytes became confluent, melanocytes were irregularly shaped, dendrites shortened and clumped together, and the outer root sheaths of the hair follicles became covered with melanocytes. Damage of melanocytes by the DMBA treatment was seen, but no inflammation or tumor formation was observed.

  9. 1-[3-(Anthracen-9-yl-5-(pyridin-2-yl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

    Directory of Open Access Journals (Sweden)

    Kun Huang

    2012-05-01

    Full Text Available In the title compound, C24H19N3O, the pyrazoline ring adopts an envelope conformation with the C atom linking to the pyridine ring as the flap. The mean plane of the pyrazoline ring makes dihedral angles of 85.54 (4 and 81.66 (3° with the pyridine ring and the anthracene ring system, respectively. In the crystal, molecules are linked by C—H...O hydrogen bonds. In addition, weak π–π interactions [centroid–centroid distances = 3.695 (3–3.850 (7 Å] are observed.

  10. Supramolecular Self-Assembly of Histidine-Capped-Dialkoxy-Anthracene: A Visible Light Triggered Platform for facile siRNA Delivery

    KAUST Repository

    Patil, Sachin

    2016-06-29

    Supramolecular self-assembly of histidine-capped-dialkoxy-anthracene (HDA) results in the formation of light responsive nanostructures.Single-crystal X-ray diffraction analysis of HDA shows two types of hydrogen bonding. The first hydrogen bond is established between the imidazole moieties while the second involves the oxygen atom of one amide group and the hydrogen atom of a second amide group. When protonated in acidic aqueous media, HDA successfully complexes siRNA yielding spherical nanostructures. This biocompatible platform controllably delivers siRNA with high efficacy upon visible light irradiation leading up to 90% of gene silencing in live cells.

  11. Miscibility of Two Components in a Binary Mixture of 9-Phenyl Anthracene Mixed with Stearic Acid or Polymethyl Methacrylate at Air-Water Interface

    Institute of Scientific and Technical Information of China (English)

    P. K. Paul; Md. N. Islam; D. Bhattacharjee; S. A. Hussain

    2007-01-01

    We report the miscibility characteristics of two components in a binary mixture of 9-phenyl anthracene (PA) mixed with stearic acid (SA) or polymethyl methacrylate (PMMA). The behaviour of surface pressure versus area per molecule isotherms reveal that the area per molecule decreases systematically with increasing molefractions of PA. The characteristics of areas per molecule versus molefractions and collapse pressure vs molefraction indicate that various interactions involved among the sample and matrix molecules. The interaction scheme is found to change with the change in surface pressure and molefraction of mixing. Scanning electron microscopic study confirms the aggregation of PA molecules in the mixed films.

  12. Quantitative structure–activity relationships for chronic toxicity of alkyl-chrysenes and alkyl-benz[a]anthracenes to Japanese medaka embryos (Oryzias latipes)

    Energy Technology Data Exchange (ETDEWEB)

    Lin, Hongkang [Department of Biology, Queen' s University, Kingston, Ontario K7L3N6 (Canada); Morandi, Garrett D. [School of Environmental Studies, Queen' s University, Kingston, Ontario K7L3N6 (Canada); Brown, R. Stephen [School of Environmental Studies, Queen' s University, Kingston, Ontario K7L3N6 (Canada); Department of Chemistry, Queen' s University, Kingston, Ontario K7L3N6 (Canada); Snieckus, Victor; Rantanen, Toni [Department of Chemistry, Queen' s University, Kingston, Ontario K7L3N6 (Canada); Jørgensen, Kåre B. [Department of Mathematics and Natural Sciences, University of Stavanger, 4036 Stavanger (Norway); Hodson, Peter V., E-mail: peter.hodson@queensu.ca [Department of Biology, Queen' s University, Kingston, Ontario K7L3N6 (Canada); School of Environmental Studies, Queen' s University, Kingston, Ontario K7L3N6 (Canada)

    2015-02-15

    Highlights: • Medaka embryos were exposed to alkyl chrysenes and benzo[a]anthracenes (BAA). • Concentrations were kept constant by partition controlled delivery. • Chrysene was not toxic within solubility limits, in contrast to BAA. • Alkylation increased the toxicity of chrysene and BAA. • Toxicity was related to hydrophobicity and to specific modes of action. - Abstract: Alkylated polycyclic aromatic hydrocarbons (alkyl-PAHs) are a class of compounds found at significant concentrations in crude oils, and likely the main constituents responsible for the chronic toxicity of oil to fish. Alkyl substituents at different locations on the aromatic rings change the size and shape of PAH molecules, which results in different interactions with tissue receptors and different severities of toxicity. The present study is the first to report the toxicity of several alkylated derivatives of chrysene and benz[a]anthracene to the embryos of Japanese medaka (Oryzias latipes) using the partition controlled delivery (PCD) method of exposure. The PCD method maintained the desired exposure concentrations by equilibrium partitioning of hydrophobic test compounds from polydimethylsiloxane (PDMS) films. Test concentrations declined by only 13% over a period of 17 days. Based on the prevalence of signs of blue sac disease (BSD), as expressed by median effective concentrations (EC50s), benz[a]anthracene (B[a]A) was more toxic than chrysene. Alkylation generally increased toxicity, except at position 2 of B[a]A. Alkyl-PAHs substituted in the middle region had a lower EC50 than those substituted at the distal region. Except for B[a]A and 7-methylbenz[a]anthracene (7-MB), estimated EC50 values were higher than their solubility limits, which resulted in limited toxicity within the range of test concentrations. The regression between log EC50s and log K{sub ow} values provided a rough estimation of structure–activity relationships for alkyl-PAHs, but K{sub ow} alone did not provide

  13. Effect of phosphatidylinositol-3 kinase inhibition on ovotoxicity caused by 4-vinylcyclohexene diepoxide and 7, 12-dimethylbenz[a]anthracene in neonatal rat ovaries

    OpenAIRE

    Keating, Aileen F.; Mark, Connie J.; Sen, Nivedita; Sipes, I. Glenn; Hoyer, Patricia B.

    2009-01-01

    4-vinylcyclohexene diepoxide (VCD) is an ovotoxicant that specifically destroys primordial and small primary follicles in the ovaries of mice and rats. In contrast, 7,12-dimethylbenz[a]anthracene (DMBA) is ovotoxic to all ovarian follicle classes. This study investigated phosphatidylinositol-3 kinase signaling involvement in VCD- and DMBA-induced ovotoxicity. Postnatal day (PND) 4 Fischer 344 (F344) rat whole ovaries were cultured for 2–12d in vehicle control, VCD (30 μM), or DMBA (1 μM), ± P...

  14. Mutagenicity and tumorigenicity of the four enantiopure bay-region 3,4-diol-1,2-epoxide isomers of dibenz[a,h]anthracene

    OpenAIRE

    Chang, Richard L.; Wood, Alexander W.; Huang, Mou Tuan; Xie, Jian Guo; Cui, Xiao Xing; Reuhl, Kenneth R.; Boyd, D. R.; Lin, Yong; Shih, Weichung Joe; Balani, Suresh K.; Yagi, Haruhiko; Jerina, Donald M.; Conney, Allan H.

    2013-01-01

    Each enantiomer of the diastereomeric pair of bay-region dibenz[a,h]anthracene 3,4-diol-1,2-epoxides in which the benzylic 4-hydroxyl group and epoxide oxygen are either cis (isomer 1) or trans (isomer 2) were evaluated for mutagenic activity. In strains TA 98 and TA 100 of Salmonella typhimurium, the diol epoxide with (1S,2R,3S,4R) absolute configuration [(–)-diol epoxide-1] had the highest mutagenic activity. In Chinese hamster V-79 cells, the diol epoxide with (1R,2S,3S,4R) absolute con...

  15. Characterization and determination of the thermodynamic and kinetic properties of the adsorption of molybdenum (VI) onto microcrystalline anthracene modified with 8-hydroxyquinoline

    International Nuclear Information System (INIS)

    A reliable and effective method for the determination of trace molybdenum in effluents is proposed. Molybdenum (VI) is analyzed by Microwave Plasma Torch Optical Emission Spectrometry (MPT-OES) based on the adsorption collection onto microcrystalline anthracene modified with 8-hydroxyquinoline. The possible reaction mechanism was discussed in detail and the optimum conditions for adsorption of Mo (VI) were confirmed. The experimental data were fitted well with the pseudo-second-order kinetic model and Langmuir model at all studied temperatures. The calculated thermodynamic parameters (ΔGT, ΔHT and ΔST) showed that the adsorption of molybdenum onto microcrystalline anthracene was feasible, spontaneous and endothermic at 280-320 K. The recovery of this method is in the range of 96.5%-103.3% with preconcentration factor of 100 and the limit detection after preconcentration is 0.078 μg L-1. The proposed method has been successfully applied to the determination of trace Mo (VI) in environmental water samples with satisfactory results. Highlights: → The preparation of the sorbent, MICRO-AN-8-hydroxyquinoline, is relatively simple. → Excellent properties of the sorbent have been illustrated in detail. → Exhaustive data concerning Mo(VI) adsorption behavior are provided. → Adsorption mechanism is firstly discussed from the view of ion-exchange reaction. → Offer reference for the studies on other metal ions adsorption onto the sorbent.

  16. Anthracene coupled thiourea as a colorimetric sensor for F{sup −}/Cu{sup 2+} and fluorescent sensor for Hg{sup 2+}/picric acid

    Energy Technology Data Exchange (ETDEWEB)

    Udhayakumari, Duraisamy [Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli-620 015 (India); Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC (China); Velmathi, Sivan, E-mail: velmathis@nitt.edu [Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli-620 015 (India); Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC (China); Venkatesan, Parthiban; Wu, Shu-Pao [Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC (China)

    2015-05-15

    A new dual chemosensor (Z)-2-(anthracen-9-ylmethylene)-N-phenylhydrazinecarbothioamide R1 was synthesized by incorporating a thiourea derivative as a binding unit and an anthracene group as a fluorescence signalling unit. R1 selectively binds with Cu{sup 2+} and Hg{sup 2+} ions in aqueous medium. R1 exhibits highly selective recognition towards F{sup −} ion and picric acid in organic medium. Fluorescence quenching was observed in case of R1 with Cu{sup 2+} and Hg{sup 2+} ions over commonly coexistent metal ions. Furthermore, fluorescence imaging experiments of Cu{sup 2+} and Hg{sup 2+} ions in living RAW 264.7 cells demonstrate its value of practical applications in biological systems. - Highlights: • R1 exhibited highly selective recognition towards Cu{sup 2+}, Hg{sup 2+} and F{sup −} ions. • The anion detection by R1 is further confirmed by {sup 1}H NMR titration method. • Detection of Cu{sup 2+} and Hg{sup 2+} ion in the living cell was achieved using fluorescence microscope. • R1 selectively sense picric acid over other nitroaromatics.

  17. Characterization and determination of the thermodynamic and kinetic properties of the adsorption of molybdenum (VI) onto microcrystalline anthracene modified with 8-hydroxyquinoline

    Energy Technology Data Exchange (ETDEWEB)

    Wang Xu [College of Chemistry and Environmental Science, Henan Normal University, Henan Key Laboratory for Environmental Pollution Control, Xinxiang, Henan 453007 (China); Zhang Yan [College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang, Henan 453003 (China); Li Quanmin, E-mail: mercury6068@hotmail.com [College of Chemistry and Environmental Science, Henan Normal University, Henan Key Laboratory for Environmental Pollution Control, Xinxiang, Henan 453007 (China)

    2011-12-01

    A reliable and effective method for the determination of trace molybdenum in effluents is proposed. Molybdenum (VI) is analyzed by Microwave Plasma Torch Optical Emission Spectrometry (MPT-OES) based on the adsorption collection onto microcrystalline anthracene modified with 8-hydroxyquinoline. The possible reaction mechanism was discussed in detail and the optimum conditions for adsorption of Mo (VI) were confirmed. The experimental data were fitted well with the pseudo-second-order kinetic model and Langmuir model at all studied temperatures. The calculated thermodynamic parameters ({Delta}G{sup T}, {Delta}H{sup T} and {Delta}S{sup T}) showed that the adsorption of molybdenum onto microcrystalline anthracene was feasible, spontaneous and endothermic at 280-320 K. The recovery of this method is in the range of 96.5%-103.3% with preconcentration factor of 100 and the limit detection after preconcentration is 0.078 {mu}g L{sup -1}. The proposed method has been successfully applied to the determination of trace Mo (VI) in environmental water samples with satisfactory results. Highlights: {yields} The preparation of the sorbent, MICRO-AN-8-hydroxyquinoline, is relatively simple. {yields} Excellent properties of the sorbent have been illustrated in detail. {yields} Exhaustive data concerning Mo(VI) adsorption behavior are provided. {yields} Adsorption mechanism is firstly discussed from the view of ion-exchange reaction. {yields} Offer reference for the studies on other metal ions adsorption onto the sorbent.

  18. Full-dimensional multilayer multiconfigurational time-dependent Hartree study of electron transfer dynamics in the anthracene/C60 complex

    Energy Technology Data Exchange (ETDEWEB)

    Xie, Yu; Zheng, Jie; Lan, Zhenggang, E-mail: lanzg@qibebt.ac.cn [CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101 (China); University of Chinese Academy of Sciences, Beijing 100049 (China)

    2015-02-28

    Electron transfer at the donor-acceptor heterojunctions plays a critical role in the photoinduced process during the solar energy conversion in organic photovoltaic materials. We theoretically investigate the electron transfer process in the anthracene/C60 donor-acceptor complex by using quantum dynamics calculations. The electron-transfer model Hamiltonian with full dimensionality was built by quantum-chemical calculations. The quantum dynamics calculations were performed using the multiconfigurational time-dependent Hartree (MCTDH) theory and multilayer (ML) MCTDH methods. The latter approach (ML-MCTDH) allows us to conduct the comprehensive study on the quantum evolution of the full-dimensional electron-transfer model including 4 electronic states and 246 vibrational degrees of freedom. Our quantum dynamics calculations exhibit the ultrafast anthracene → C60 charge transfer process because of the strong coupling between excitonic and charge transfer states. This work demonstrates that the ML-MCTDH is a very powerful method to treat the quantum evolution of complex systems.

  19. Determination of the Residual Anthracene Concentration in Cultures of Haloalkalitolerant Actinomycetes by Excitation Fluorescence, Emission Fluorescence, and Synchronous Fluorescence: Comparative Study

    Directory of Open Access Journals (Sweden)

    Reyna del Carmen Lara-Severino

    2016-01-01

    Full Text Available Polycyclic aromatic hydrocarbons (PAHs are compounds that can be quantified by fluorescence due to their high quantum yield. Haloalkalitolerant bacteria tolerate wide concentration ranges of NaCl and pH. They are potentially useful in the PAHs bioremediation of saline environments. However, it is known that salinity of the sample affects fluorescence signal regardless of the method. The objective of this work was to carry out a comparative study based on the sensitivity, linearity, and detection limits of the excitation, emission, and synchronous fluorescence methods, during the quantification of the residual anthracene concentration from the following haloalkalitolerant actinomycetes cultures Kocuria rosea, Kocuria palustris, Microbacterium testaceum, and 4 strains of Nocardia farcinica, in order to establish the proper fluorescence method to study the PAHs biodegrading capacity of haloalkalitolerant actinobacteria. The study demonstrated statistical differences among the strains and among the fluorescence methods regarding the anthracene residual concentration. The results showed that excitation and emission fluorescence methods performed very similarly but sensitivity in excitation fluorescence is slightly higher. Synchronous fluorescence using Δλ=150 nm is not the most convenient method. Therefore we propose the excitation fluorescence as the fluorescence method to be used in the study of the PAHs biodegrading capacity of haloalkalitolerant actinomycetes.

  20. Impact of 7,12-dimethylbenz[a]anthracene exposure on connexin gap junction proteins in cultured rat ovaries

    International Nuclear Information System (INIS)

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles in a concentration-dependent manner. The impact of DMBA on connexin (CX) proteins that mediate communication between follicular cell types along with pro-apoptotic factors p53 and Bax were investigated. Postnatal day (PND) 4 Fisher 344 rat ovaries were cultured for 4 days in vehicle medium (1% DMSO) followed by a single exposure to vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and cultured for 4 or 8 days. RT-PCR was performed to quantify Cx37, Cx43, p53 and Bax mRNA level. Western blotting and immunofluorescence staining were performed to determine CX37 or CX43 level and/or localization. Cx37 mRNA and protein increased (P < 0.05) at 4 days of 12.5 nM DMBA exposure. Relative to vehicle control-treated ovaries, mRNA encoding Cx43 decreased (P < 0.05) but CX43 protein increased (P < 0.05) at 4 days by both DMBA exposures. mRNA expression of pro-apoptotic p53 was decreased (P < 0.05) but no changes in Bax expression were observed after 4 days of DMBA exposures. In contrast, after 8 days, DMBA decreased Cx37 and Cx43 mRNA and protein but increased both p53 and Bax mRNA levels. CX43 protein was located between granulosa cells, while CX37 was located at the oocyte cell surface of all follicle stages. These findings support that DMBA exposure impacts ovarian Cx37 and Cx43 mRNA and protein prior to both observed changes in pro-apoptotic p53 and Bax and follicle loss. It is possible that such interference in follicular cell communication is detrimental to follicle viability, and may play a role in DMBA-induced follicular atresia. - Highlights: • DMBA increases Cx37 and Cx43 expression prior to follicle loss. • During follicle loss both Cx37 and Cx43 expressions are reduced. • CX43 protein is absent in follicle remnants lacking an oocyte

  1. UVA Photoirradiation of Oxygenated Benz[a]anthracene and 3-Methylcholanthene - Generation of Singlet Oxygen and Induction of Lipid Peroxidation

    Directory of Open Access Journals (Sweden)

    Diógenes Herreño Sáenz

    2008-03-01

    Full Text Available Polycyclic aromatic hydrocarbons (PAHs are widespread genotoxic environmental pollutants and potentially pose a health risk to humans. Although the biological and toxicological activities, including metabolism, mutagenicity, and carcinogenicity, of PAHs have been thoroughly studied, their phototoxicity and photo-induced biological activity have not been well examined. We have long been interested in phototoxicity of PAHs and their derivatives induced by irradiation with UV light. In this paper we report the photoirradiation of a series of oxygenated benz[a]anthracene (BA and 3-methylcholanthene (3-MC by UVA light in the presence of a lipid, methyl linoleate. The studied PAHs include 2-hydroxy-BA (2-OH-BA, 3-hydroxy-BA (3-OH-BA, 5-hydroxymethyl-BA (5-CH2OH-BA, 7-hydroxymethyl-BA (7-CH2OH-BA, 12-hydroxymethyl-BA (12-CH2OH-BA, 7-hydroxymethyl-12-methyl-BA (7-CH2OH-12-MBA, 5-formyl-BA (5-CHO-BA, BA 5,6-cis-dihydrodiol (BA 5,6-cis-diol, 1-hydroxy-3- methylcholanthene (1-OH-3-MC, 1-keto-3-methylcholanthene (1-keto-3-MC, and 3-MC 1,2-diol. The results indicate that upon photoirradiation by UVA at 7 and 21 J/cm2, respectively all these compounds induced lipid peroxidation and exhibited a relationship between the dose of the light and the level of lipid peroxidation induced. To determine whether or not photoirradiation of these compounds by UVA light produces ROS, an ESR spin-trap technique was employed to provide direct evidence. Photoirradiation of 3-keto-3-MC by UVA (at 389 nm in the presence of 2,2,6,6-tetramethylpiperidine (TEMP, a specific probe for singlet oxygen, resulted in the formation of TEMPO, indicating that singlet oxygen was generated. These overall results suggest that UVA photoirradiation of oxygenated BA and 3-methylcholanthrene generates singlet oxygen, one of the reactive oxygen species (ROS, which induce lipid peroxidation.

  2. Trianthema portulacastrum Linn. exerts chemoprevention of 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis in rats

    International Nuclear Information System (INIS)

    Highlights: • Dietary administration of an ethanolic extract of aerial parts of T. portulacastrum (TPE) exhibits a striking chemopreventive effect in an experimentally induced classical animal model of breast cancer. • The mammary tumor-inhibitory effect of TPE could be achieved, at least in part, though intervention of key hallmark capabilities of tumor cells, such as abnormal cell proliferation and evasion of apoptosis. • TPE is capable of diminishing activated canonical Wnt/β-catenin signaling to exhibit antiproliferative, proapoptotic and oncostatic effects during this early-stage mammary carcinoma. • These results coupled with a safety profile of T. portulacastrum may encourage further studies to understand the full potential of this dietary plant for chemoprevention of breast cancer. - Abstract: Due to limited treatment options for advanced-stage metastatic breast cancer, a high priority should be given to develop non-toxic chemopreventive drugs. The value of various natural and dietary agents to reduce the risk of developing breast cancer is well established. Trianthema portulacastrum Linn. (Aizoaceae), a dietary and medicinal plant, has been found to exert antihepatotoxic and antihepatocarcinogenic properties in rodents. This study was initiated to investigate mechanism-based chemopreventive potential of an ethanolic extract of T. portulacastrum (TPE) against 7,12-dimethylbenz(a)anthracene (DMBA)-initiated rat mammary gland carcinogenesis, an experimental tumor model that closely resembles human breast cancer. Rats had access to a basal diet supplemented with TPE to yield three dietary doses of the extract, i.e., 50, 100 and 200 mg/kg body weight. Following two weeks of TPE treatment, mammary tumorigenesis was initiated by oral administration of DMBA (50 mg/kg body weight). At the end of the study (16 weeks after DMBA exposure), TPE exhibited a striking reduction of DMBA-induced mammary tumor incidence, total tumor burden and average tumor weight

  3. Protective role for ovarian glutathione S-transferase isoform pi during 7,12-dimethylbenz[a]anthracene-induced ovotoxicity

    Energy Technology Data Exchange (ETDEWEB)

    Bhattacharya, Poulomi, E-mail: poulomib@iastate.edu; Keating, Aileen F., E-mail: akeating@iastate.edu

    2012-04-15

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all developmental stages. This study investigated a role for the glutathione S-transferase (Gst) isoforms alpha (a), mu (m) and pi (p) and the transcription factors, Ahr and Nrf2, during DMBA-induced ovotoxicity, and their regulation by phosphatidylinositol-3 kinase (PI3K) signaling. Negative regulation of JNK by GSTP during DMBA exposure was also studied. Post-natal day (PND) 4 Fischer 344 rat ovaries were exposed to vehicle control (1% DMSO) ± DMBA (1 μM) or vehicle control (1% DMSO) ± LY294002 (PI3K inhibitor; 20 μM) for 1, 2, 4, or 6 days. Total RNA or protein was isolated, followed by RT-PCR or Western blotting to determine mRNA or protein level, respectively. Immunoprecipitation using an anti-GSTP antibody was performed to determine interaction between GSTP and JNK, followed by Western blotting to determine JNK and p-c-Jun protein level. DMBA had no impact on Gsta, Gstm or Nrf2 mRNA level, but increased Gstp mRNA and protein after 2 days. Ahr mRNA and protein increased after 2 and 4 days of DMBA exposure, respectively and DMBA increased NRF2 protein level after 4 days. JNK bound to GSTP was increased during DMBA exposure, with a concomitant decrease in unbound JNK and p-c-Jun. Ahr and Gstp mRNA were decreased (2 days) and increased (4 days) by PI3K inhibition, while Gstm mRNA increased (P < 0.05) after both time points, and there was no effect on Nrf2 mRNA. PI3K inhibition increased AHR, NRF2 and GSTP protein level. These findings support involvement of ovarian GSTP during DMBA exposure, and indicate a regulatory role for the PI3K signaling pathway on ovarian xenobiotic metabolism gene expression. -- Highlights: ► Ovarian GSTP is activated in response to DMBA exposure. ► AhR and Nrf2 transcription factors are up-regulated by DMBA. ► PI3K signaling regulates Ahr, Nrf2 and Gstp expression. ► GSTP negatively regulates ovarian JNK in response to DMBA exposure.

  4. Protective role for ovarian glutathione S-transferase isoform pi during 7,12-dimethylbenz[a]anthracene-induced ovotoxicity

    International Nuclear Information System (INIS)

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all developmental stages. This study investigated a role for the glutathione S-transferase (Gst) isoforms alpha (a), mu (m) and pi (p) and the transcription factors, Ahr and Nrf2, during DMBA-induced ovotoxicity, and their regulation by phosphatidylinositol-3 kinase (PI3K) signaling. Negative regulation of JNK by GSTP during DMBA exposure was also studied. Post-natal day (PND) 4 Fischer 344 rat ovaries were exposed to vehicle control (1% DMSO) ± DMBA (1 μM) or vehicle control (1% DMSO) ± LY294002 (PI3K inhibitor; 20 μM) for 1, 2, 4, or 6 days. Total RNA or protein was isolated, followed by RT-PCR or Western blotting to determine mRNA or protein level, respectively. Immunoprecipitation using an anti-GSTP antibody was performed to determine interaction between GSTP and JNK, followed by Western blotting to determine JNK and p-c-Jun protein level. DMBA had no impact on Gsta, Gstm or Nrf2 mRNA level, but increased Gstp mRNA and protein after 2 days. Ahr mRNA and protein increased after 2 and 4 days of DMBA exposure, respectively and DMBA increased NRF2 protein level after 4 days. JNK bound to GSTP was increased during DMBA exposure, with a concomitant decrease in unbound JNK and p-c-Jun. Ahr and Gstp mRNA were decreased (2 days) and increased (4 days) by PI3K inhibition, while Gstm mRNA increased (P < 0.05) after both time points, and there was no effect on Nrf2 mRNA. PI3K inhibition increased AHR, NRF2 and GSTP protein level. These findings support involvement of ovarian GSTP during DMBA exposure, and indicate a regulatory role for the PI3K signaling pathway on ovarian xenobiotic metabolism gene expression. -- Highlights: ► Ovarian GSTP is activated in response to DMBA exposure. ► AhR and Nrf2 transcription factors are up-regulated by DMBA. ► PI3K signaling regulates Ahr, Nrf2 and Gstp expression. ► GSTP negatively regulates ovarian JNK in response to DMBA exposure.

  5. Trianthema portulacastrum Linn. exerts chemoprevention of 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis in rats

    Energy Technology Data Exchange (ETDEWEB)

    Bishayee, Anupam, E-mail: abishayee@auhs.edu [Department of Pharmaceutical Sciences, School of Pharmacy, American University of Health Sciences, Signal Hill, CA 90755 (United States); Mandal, Animesh [Cancer Therapeutics and Chemoprevention Group, Department of Pharmaceutical Sciences, College of Pharmacy, Northeast Ohio Medical University, Rootstown, OH 44272 (United States)

    2014-10-15

    Highlights: • Dietary administration of an ethanolic extract of aerial parts of T. portulacastrum (TPE) exhibits a striking chemopreventive effect in an experimentally induced classical animal model of breast cancer. • The mammary tumor-inhibitory effect of TPE could be achieved, at least in part, though intervention of key hallmark capabilities of tumor cells, such as abnormal cell proliferation and evasion of apoptosis. • TPE is capable of diminishing activated canonical Wnt/β-catenin signaling to exhibit antiproliferative, proapoptotic and oncostatic effects during this early-stage mammary carcinoma. • These results coupled with a safety profile of T. portulacastrum may encourage further studies to understand the full potential of this dietary plant for chemoprevention of breast cancer. - Abstract: Due to limited treatment options for advanced-stage metastatic breast cancer, a high priority should be given to develop non-toxic chemopreventive drugs. The value of various natural and dietary agents to reduce the risk of developing breast cancer is well established. Trianthema portulacastrum Linn. (Aizoaceae), a dietary and medicinal plant, has been found to exert antihepatotoxic and antihepatocarcinogenic properties in rodents. This study was initiated to investigate mechanism-based chemopreventive potential of an ethanolic extract of T. portulacastrum (TPE) against 7,12-dimethylbenz(a)anthracene (DMBA)-initiated rat mammary gland carcinogenesis, an experimental tumor model that closely resembles human breast cancer. Rats had access to a basal diet supplemented with TPE to yield three dietary doses of the extract, i.e., 50, 100 and 200 mg/kg body weight. Following two weeks of TPE treatment, mammary tumorigenesis was initiated by oral administration of DMBA (50 mg/kg body weight). At the end of the study (16 weeks after DMBA exposure), TPE exhibited a striking reduction of DMBA-induced mammary tumor incidence, total tumor burden and average tumor weight

  6. Impact of 7,12-dimethylbenz[a]anthracene exposure on connexin gap junction proteins in cultured rat ovaries

    Energy Technology Data Exchange (ETDEWEB)

    Ganesan, Shanthi, E-mail: shanthig@iastate.edu; Keating, Aileen F., E-mail: akeating@iastate.edu

    2014-01-15

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles in a concentration-dependent manner. The impact of DMBA on connexin (CX) proteins that mediate communication between follicular cell types along with pro-apoptotic factors p53 and Bax were investigated. Postnatal day (PND) 4 Fisher 344 rat ovaries were cultured for 4 days in vehicle medium (1% DMSO) followed by a single exposure to vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and cultured for 4 or 8 days. RT-PCR was performed to quantify Cx37, Cx43, p53 and Bax mRNA level. Western blotting and immunofluorescence staining were performed to determine CX37 or CX43 level and/or localization. Cx37 mRNA and protein increased (P < 0.05) at 4 days of 12.5 nM DMBA exposure. Relative to vehicle control-treated ovaries, mRNA encoding Cx43 decreased (P < 0.05) but CX43 protein increased (P < 0.05) at 4 days by both DMBA exposures. mRNA expression of pro-apoptotic p53 was decreased (P < 0.05) but no changes in Bax expression were observed after 4 days of DMBA exposures. In contrast, after 8 days, DMBA decreased Cx37 and Cx43 mRNA and protein but increased both p53 and Bax mRNA levels. CX43 protein was located between granulosa cells, while CX37 was located at the oocyte cell surface of all follicle stages. These findings support that DMBA exposure impacts ovarian Cx37 and Cx43 mRNA and protein prior to both observed changes in pro-apoptotic p53 and Bax and follicle loss. It is possible that such interference in follicular cell communication is detrimental to follicle viability, and may play a role in DMBA-induced follicular atresia. - Highlights: • DMBA increases Cx37 and Cx43 expression prior to follicle loss. • During follicle loss both Cx37 and Cx43 expressions are reduced. • CX43 protein is absent in follicle remnants lacking an oocyte.

  7. 7,12-Dimethylbenz[a]anthracene exposure induces the DNA repair response in neonatal rat ovaries

    Energy Technology Data Exchange (ETDEWEB)

    Ganesan, Shanthi, E-mail: shanthig@iastate.edu; Bhattacharya, Poulomi, E-mail: poulomib@iastate.edu; Keating, Aileen F., E-mail: akeating@iastate.edu

    2013-11-01

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all stages of development. This study investigated DMBA-induced DNA double strand break (DSB) formation with subsequent activation of the ovarian DNA repair response in models of pre-antral or pre-ovulatory follicle loss. Postnatal day (PND) 4 Fisher 344 (F344) rat ovaries were cultured for 4 days followed by single exposures of vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and maintained in culture for 4 or 8 days. Alternately, PND4 F344 rat ovaries were exposed to 1 μM DMBA at the start of culture for 2 days. Total RNA or protein was isolated, followed by qPCR or Western blotting to quantify mRNA or protein level, respectively. γH2AX and phosphorylated ATM were localized and quantified using immunofluorescence staining. DMBA exposure increased caspase 3 and γH2AX protein. Additionally, DMBA (12.5 nM and 1 μM) increased levels of mRNA encoding Atm, Xrcc6, Brca1 and Rad51. In contrast, Parp1 mRNA was decreased on d4 and increased on d8 of DMBA exposure, while PARP1 protein increased after 8 days of DMBA exposure. Total ATM increased in a concentration-dependent temporal pattern (75 nM d4; 12.5 nM d8), while pATM was localized in large primary and secondary follicles and increased after 8 days of 75 nM DMBA exposure compared to both control and 12.5 nM DMBA. These findings support that, despite some concentration effects, DMBA induces ovarian DNA damage and that DNA repair mechanisms are induced as a potential mechanism to prevent follicle loss. - Highlights: • DMBA exposure increases ovarian caspase-3 protein expression. • DMBA exposure increases the γH2AX protein in oocytes. • DMBA exposure activates a DNA repair response in the ovary.

  8. 7,12-Dimethylbenz[a]anthracene exposure induces the DNA repair response in neonatal rat ovaries

    International Nuclear Information System (INIS)

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all stages of development. This study investigated DMBA-induced DNA double strand break (DSB) formation with subsequent activation of the ovarian DNA repair response in models of pre-antral or pre-ovulatory follicle loss. Postnatal day (PND) 4 Fisher 344 (F344) rat ovaries were cultured for 4 days followed by single exposures of vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and maintained in culture for 4 or 8 days. Alternately, PND4 F344 rat ovaries were exposed to 1 μM DMBA at the start of culture for 2 days. Total RNA or protein was isolated, followed by qPCR or Western blotting to quantify mRNA or protein level, respectively. γH2AX and phosphorylated ATM were localized and quantified using immunofluorescence staining. DMBA exposure increased caspase 3 and γH2AX protein. Additionally, DMBA (12.5 nM and 1 μM) increased levels of mRNA encoding Atm, Xrcc6, Brca1 and Rad51. In contrast, Parp1 mRNA was decreased on d4 and increased on d8 of DMBA exposure, while PARP1 protein increased after 8 days of DMBA exposure. Total ATM increased in a concentration-dependent temporal pattern (75 nM d4; 12.5 nM d8), while pATM was localized in large primary and secondary follicles and increased after 8 days of 75 nM DMBA exposure compared to both control and 12.5 nM DMBA. These findings support that, despite some concentration effects, DMBA induces ovarian DNA damage and that DNA repair mechanisms are induced as a potential mechanism to prevent follicle loss. - Highlights: • DMBA exposure increases ovarian caspase-3 protein expression. • DMBA exposure increases the γH2AX protein in oocytes. • DMBA exposure activates a DNA repair response in the ovary

  9. 1,2-Bis{4-[1-(anthracen-9-ylmethyl-1H-1,2,3-triazol-4-yl]phenyl}-1,2-bis[4,5-bis(methylsulfanyl-1,3-dithiol-2-ylidene]ethane

    Directory of Open Access Journals (Sweden)

    Karimulla Mulla

    2012-12-01

    Full Text Available The title molecule, C58H44N6S8, has point symmetry 2 (in the Schönfliess notation C2. The related crystallographic twofold axis bisects the central ethane bond while it is parallel to the monoclinic unique axis of the unit cell. The dithiole=C—C=dithiole torsion angle is 103.7 (4° and the triazole–anthracene moieties adopt a pincer-like conformation. The crystal structure features C—H...S and C—H...N contacts. The distance between the stacked anthracene fragments [centroid—centroid separations of 3.6871 (19 Å, off-set by 1.516 (3 Å and mean anthracene plane-plane separations of 3.361 (2 Å], which are parallel to (101 and (-101, indicates intermolecular anthracene–anthracene π–π contacts. One of the terminal methylsulfanyl groups was modelled as being disordered with two refined orientations that converged to occupancies of 0.809 (5 and 0.191 (5.

  10. Trace Copper Determination in Environmental Samples via Separation and Preconcentration on Microcrystalline Anthracene%微晶蒽分离富集测定痕量铜(Ⅱ)

    Institute of Scientific and Technical Information of China (English)

    王旭; 郑立庆; 李全民

    2011-01-01

    建立了一种利用微晶蒽吸附分离富集环境水样中痕量Cu(Ⅱ)的新方法.研究表明,pH =3.0时,Cu(Ⅱ)与1-(2-吡啶偶氮)-2-萘酚形成红棕色螯合物被微晶蒽定量吸附,而Pb(Ⅱ)、in(Ⅱ)、Co(Ⅱ)、Ni(Ⅱ)、Cd(Ⅱ)、Zn(Ⅱ)、Fe(Ⅲ)和Al(Ⅲ)等完全留在溶液中,从而实现Cu(Ⅱ)与它们的分离.该方法可直接用于1L水样中痕量Cu(Ⅱ)的分离与富集,富集倍数达200倍,回收率91.0%~104.0%,最低检出限为0.026 μg/L;应用于不同水样中Cu(Ⅱ)的测定,结果令人满意.%A new method using microcrystalline anthracene as an adsorbent to separate and preconcentrate trace copper in environmental water samples has been developed. Effects of different parameters, such as the acidity, types of salt, amounts of l-(2-pyridylazo)-2-naphthol( PAN) and anthracene, preconcentration time, etc. On the enrichment yield of Cu(II) have been investigated. The results indicate that at pH =3. 00, a red chelate complex generated by the reaction between Cu( II ) and PAN can be quantitatively adsorbed on the surface of microcrystalline anthracene, whereas Pb(II) , Mn( D), Co(E), Ni(II), Cd(II), Zn(fl), Fe(Ⅲ), Al(Ⅲ) etc. Completely remain in the solution. Therefore, the aim of separation and preconcentration of trace copper could be achieved. The possible reaction mechanism of the enrichment of copper is discussed in detail in this paper. The recovery is in the range of 91. 0% ~ 104. 0% with the enrichment factor of 200. The limit of detection after preconcentration is 0. 026 μg/L. The proposed method could be directly applied to the determination of trace copper in different environmental water samples of large volume( 1 L) with satisfactory results.

  11. Entropy Variation in the Two-dimensional Phase Transition of Anthracene Adsorbed at the Hg Electrode/Ethylene Glycol Solution Interface

    Directory of Open Access Journals (Sweden)

    Claudio Fontanesi

    2010-03-01

    Full Text Available The adsorption of anthracene (C14H10, at the mercury electrode/ethylene glycol (EG solution interface, is characterized by a low and almost constant capacity (about 8 μF cm−2 region (capacitive “pit” or “plateau” in capacity vs. potential curves, upon selection of suitable values of temperature, bulk concentration and applied potential values. This result is rationalized assuming the occurrence of a 2D phase transition between two distinct adsorbed phases: (i a “disordered” phase, characterized by a flat “parallel” disposition of the aromatic moiety on the electrode surface (ii an “ordered” phase, characterized by a “perpendicular” disposition of the aromatic moiety on the electrode surface. The experimental evidence is rationalized by considering the chemical potential as an explicit function of the “electric field/adsorbed molecule” interaction. Such a modelistic approach enables the determination of the relevant standard entropy variation.

  12. A new fluorescent enhanced probe based on (E)-9-(2-nitrovinyl)-anthracene for the detection of bisulfite anions and its practical application

    Science.gov (United States)

    Chao, Jianbin; Liu, Yuhong; Zhang, Yan; Zhang, Yongbin; Huo, Fangjun; Yin, Caixia; Wang, Yu; Qin, Liping

    2015-07-01

    A new fluorescent enhanced probe based on (E)-9-(2-nitrovinyl)-anthracene is developed, which shows high selectivity and sensitivity for the detection of bisulfite anions at Na2HPO4 citric acid buffer solutions (pH 5.0). When addition of HSO3-, the fluorescence intensity is significantly enhanced and the probe displays apparent fluorescence color changes from non-fluorescence to blue under a UV lamp illumination, the solution color also changes from yellow to colorless. The detection limit is determined to be as low as 6.30 μM. This offers another specific colorimetric and fluorescent probe for bisulfite anions detection, furthermore it is applied in detecting the level of bisulfite in sugar samples.

  13. Evolution of energy deposition processes in anthracene single crystal from photochemistry to radiation chemistry under excitation with synchrotron radiation from 3 to 700 eV

    International Nuclear Information System (INIS)

    Absolute values of quantum yield Φ(hν) of singlet exciton formation in anthracene single crystals were measured as a function of photon energy hν, with the usage of synchrotron radiation (SR) in 3-700 eV region. Values of Φ(hν) were found to increase linearly for hν≥75 eV. For hν≤40 eV, values of Φ(hν) gave a wealth of structures and are not linear to hν. Because number of secondary electrons produced by radiation is thought to increase in proportional to the incident photon energy, it is natural to conclude that the radiation chemistry effect becomes dominant above 75 eV. On the other hand, values of Φ(hν) showed response due to resonance rather than linear dependence with hν, which implies that the photochemical effect is dominant below 40 eV

  14. Improved efficiency in organic light-emitting devices with tris-(8-hydroxyquinoline) aluminium doped 9,10-di(2-naphthyl) anthracene emission layer

    International Nuclear Information System (INIS)

    Organic light-emitting devices with tris-(8-hydroxyquinoline) aluminium (Alq3) doped 9,10-di(2-naphthyl) anthracene (ADN) as the emission layer (EML) have been fabricated. These devices exhibit efficient electroluminescence (EL) originated from the Alq3 as the mass ratio of Alq3 to ADN was varied from 1 to 50%. The devices with an optimal Alq3 mass ratio of 10 wt% showed a peak EL efficiency and an external quantum efficiency of 9.1 cd A-1 and 2.7% at a luminance of 1371 cd m-2, which is improved by a factor of 2.2 compared with 4.1 cd A-1 and 1.2% at a luminance of 3267 cd m-2 for conventional devices with the neat Alq3 as the EML.

  15. Effect of permethrin, anthracene and mixture exposure on shell components, enzymatic activities and proteins status in the Mediterranean clam Venerupis decussata

    International Nuclear Information System (INIS)

    Highlights: • We assessed toxicity of anthracene, permethrin and their mixture on clams. • Tissue and stressor-dependent changes were observed in biochemical responses. • Permethrin induces phase transition from aragonite to calcite in shell structure. • Interactive effects were observed on digestive gland and gill biomarkers. • Both approaches give new vision to risk assessment of organic pollution. - Abstract: Anthracene (ANT) and permethrin (PER) are two of the more toxic compounds reaching the marine environment. This study aimed to determine the impact of these molecules on Venerupis decussata, an economically important species cultured on the Tunisian coast. Shell structure and its possible transformation upon exposure to the two contaminants were studied by X-ray diffraction and gravimetric analyses. Results revealed a phase transition in shell composition from aragonite to calcite after PER exposure, to a mixture of PER and ANT (Mix) but not for ANT alone. Catalase (CAT), superoxide dismutase (SOD) and glutathione transferase (GST) activities were determined in digestive gland and gills after exposure to ANT, PER and Mix to assess the impact of the contamination on the oxidative status of V. decussata. Enzyme activities increased in the digestive gland after PER treatment and in the gills after ANT treatment. PER exposure significantly reduced the levels of free thiols and increased levels of carbonylated proteins in the digestive gland, as compared to controls. In contrast, ANT exposure significantly reduced free thiols and increased the number of carbonylated proteins in the gills. Mix induced additive effects as measured by both enzymatic and proteomic approaches. The present study suggests that PER has a strong effect on shell structure; that PER and ANT exposure generate compound-dependent oxidative stress in the tissues of V. decussata and that a mixture of the two compounds has synergistic effects on biochemical response

  16. Vertical and adiabatic excitations in anthracene from quantum Monte Carlo: Constrained energy minimization for structural and electronic excited-state properties in the JAGP ansatz

    Energy Technology Data Exchange (ETDEWEB)

    Dupuy, Nicolas, E-mail: nicolas.dupuy@impmc.upmc.fr [Institut de Minéralogie, de Physique des Matériaux et de Cosmochimie, Université Pierre et Marie Curie, case 115, 4 place Jussieu, 75252 Paris Cedex 05 (France); Bouaouli, Samira, E-mail: samira.bouaouli@lct.jussieu.fr [Laboratoire de Chimie Théorique, Université Pierre et Marie Curie, case 115, 4 place Jussieu, 75252 Paris Cedex 05 (France); Mauri, Francesco, E-mail: francesco.mauri@impmc.upmc.fr; Casula, Michele, E-mail: michele.casula@impmc.upmc.fr [CNRS and Institut de Minéralogie, de Physique des Matériaux et de Cosmochimie, Université Pierre et Marie Curie, case 115, 4 place Jussieu, 75252 Paris Cedex 05 (France); Sorella, Sandro, E-mail: sorella@sissa.it [International School for Advanced Studies (SISSA), Via Beirut 2-4, 34014 Trieste, Italy and INFM Democritos National Simulation Center, Trieste (Italy)

    2015-06-07

    We study the ionization energy, electron affinity, and the π → π{sup ∗} ({sup 1}L{sub a}) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed on molecular orbitals (MOs). The MO-based JAGP ansatz allows one to rigorously treat electron transitions, such as the HOMO → LUMO one, which underlies the {sup 1}L{sub a} excited state. We present a QMC optimization scheme able to preserve the rank of the antisymmetrized geminal power matrix, thanks to a constrained minimization with projectors built upon symmetry selected MOs. We show that this approach leads to stable energy minimization and geometry relaxation of both ground and excited states, performed consistently within the correlated QMC framework. Geometry optimization of excited states is needed to make a reliable and direct comparison with experimental adiabatic excitation energies. This is particularly important in π-conjugated and polycyclic aromatic hydrocarbons, where there is a strong interplay between low-lying energy excitations and structural modifications, playing a functional role in many photochemical processes. Anthracene is an ideal benchmark to test these effects. Its geometry relaxation energies upon electron excitation are of up to 0.3 eV in the neutral {sup 1}L{sub a} excited state, while they are of the order of 0.1 eV in electron addition and removal processes. Significant modifications of the ground state bond length alternation are revealed in the QMC excited state geometry optimizations. Our QMC study yields benchmark results for both geometries and energies, with values below chemical accuracy if compared to experiments, once zero point energy effects are taken into account.

  17. Effect of permethrin, anthracene and mixture exposure on shell components, enzymatic activities and proteins status in the Mediterranean clam Venerupis decussata

    Energy Technology Data Exchange (ETDEWEB)

    Sellami, Badreddine, E-mail: sellamibadreddine@gmail.com [Laboratory of Environment Biomonitoring, Coastal Ecology Unit, Faculty of Sciences of Bizerta, University of Carthage, 7021 Zarzouna (Tunisia); Khazri, Abdelhafidh [Laboratory of Environment Biomonitoring, Coastal Ecology Unit, Faculty of Sciences of Bizerta, University of Carthage, 7021 Zarzouna (Tunisia); Mezni, Amine [Unit of Research 99/UR12-30, Department of Chemistry, Faculty of Sciences of Bizerte, 7021 Jarzouna (Tunisia); Louati, Héla; Dellali, Mohamed; Aissa, Patricia; Mahmoudi, Ezzeddine; Beyrem, Hamouda [Laboratory of Environment Biomonitoring, Coastal Ecology Unit, Faculty of Sciences of Bizerta, University of Carthage, 7021 Zarzouna (Tunisia); Sheehan, David, E-mail: d.sheehan@ucc.ie [Environmental Research Institute and Department of Biochemistry, University College Cork, Western Gateway Building, Western Road, Cork (Ireland)

    2015-01-15

    Highlights: • We assessed toxicity of anthracene, permethrin and their mixture on clams. • Tissue and stressor-dependent changes were observed in biochemical responses. • Permethrin induces phase transition from aragonite to calcite in shell structure. • Interactive effects were observed on digestive gland and gill biomarkers. • Both approaches give new vision to risk assessment of organic pollution. - Abstract: Anthracene (ANT) and permethrin (PER) are two of the more toxic compounds reaching the marine environment. This study aimed to determine the impact of these molecules on Venerupis decussata, an economically important species cultured on the Tunisian coast. Shell structure and its possible transformation upon exposure to the two contaminants were studied by X-ray diffraction and gravimetric analyses. Results revealed a phase transition in shell composition from aragonite to calcite after PER exposure, to a mixture of PER and ANT (Mix) but not for ANT alone. Catalase (CAT), superoxide dismutase (SOD) and glutathione transferase (GST) activities were determined in digestive gland and gills after exposure to ANT, PER and Mix to assess the impact of the contamination on the oxidative status of V. decussata. Enzyme activities increased in the digestive gland after PER treatment and in the gills after ANT treatment. PER exposure significantly reduced the levels of free thiols and increased levels of carbonylated proteins in the digestive gland, as compared to controls. In contrast, ANT exposure significantly reduced free thiols and increased the number of carbonylated proteins in the gills. Mix induced additive effects as measured by both enzymatic and proteomic approaches. The present study suggests that PER has a strong effect on shell structure; that PER and ANT exposure generate compound-dependent oxidative stress in the tissues of V. decussata and that a mixture of the two compounds has synergistic effects on biochemical response.

  18. Ameliorative effect of Ananus comosus peel on 7, 12 dimethylbenz(α)anthracene induced mammary carcinogenesis with reference to oxidative stresss

    Institute of Scientific and Technical Information of China (English)

    M Kalaiselvi; D Gomathi; G Ravikumar; K Devaki; C Uma

    2013-01-01

    Objective: To Ananus comosus (A. comosus), has demonstrated a wide variety of biological activities which make it a good plant source for the treatment of many oxidative stress mediated diseases. The present study was aimed to evaluate therapeutic potential by assaying the activities of oxidative stress parameters in 7, 12 dimethylbenz(α)anthracene induced breast cancer rats. Methods: Animals were divided into five groups of six animals. Group I served as control, group II induced mammary carcinogenesis by 7, 12 dimethylbenz(α)anthracene, group III and IV are treatment groups (plant extract 250 mg/kg body weight and standard drug 10 mg/kg body weight) and group V served as animals treated with plant extract alone. All the animals were sacrificed after 30 days treatment and breast tissues are used for the analysis of protein content, enzymic and non-enzymic antioxidants using standard protocols. Results: The oral administrations of ethanolic peel extract of A. comosus (250 mg/kg body weight) to breast cancer bearing rats for 30 days demonstrated a significant (P<0.05) increased in body weight, tissue weight, protein content, enzymatic and non enzymatic levels. The altered activities of lipid peroxidation and tumor weight in breast tissue of control and experimental cancer bearing rats were significantly (P<0.05) were reverted to near normal levels by the administration of ethanolic extract suggesting that the extract have quenching capacity against free radicals thereby exhibiting anticancer potential of A. comosus in breast cancer bearing rats. Conclusions: Thus, modulatory effects of A. comosus on attenuating the lipid peroxidation and upregulation of oxidative stress key enzymes like enzymatic and non-enzymatic antioxidants, protein content afford a pledge for widespread use for the treatment of breast cancer in the future.

  19. Vertical and adiabatic excitations in anthracene from quantum Monte Carlo: Constrained energy minimization for structural and electronic excited-state properties in the JAGP ansatz.

    Science.gov (United States)

    Dupuy, Nicolas; Bouaouli, Samira; Mauri, Francesco; Sorella, Sandro; Casula, Michele

    2015-06-01

    We study the ionization energy, electron affinity, and the π → π(∗) ((1)La) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed on molecular orbitals (MOs). The MO-based JAGP ansatz allows one to rigorously treat electron transitions, such as the HOMO → LUMO one, which underlies the (1)La excited state. We present a QMC optimization scheme able to preserve the rank of the antisymmetrized geminal power matrix, thanks to a constrained minimization with projectors built upon symmetry selected MOs. We show that this approach leads to stable energy minimization and geometry relaxation of both ground and excited states, performed consistently within the correlated QMC framework. Geometry optimization of excited states is needed to make a reliable and direct comparison with experimental adiabatic excitation energies. This is particularly important in π-conjugated and polycyclic aromatic hydrocarbons, where there is a strong interplay between low-lying energy excitations and structural modifications, playing a functional role in many photochemical processes. Anthracene is an ideal benchmark to test these effects. Its geometry relaxation energies upon electron excitation are of up to 0.3 eV in the neutral (1)La excited state, while they are of the order of 0.1 eV in electron addition and removal processes. Significant modifications of the ground state bond length alternation are revealed in the QMC excited state geometry optimizations. Our QMC study yields benchmark results for both geometries and energies, with values below chemical accuracy if compared to experiments, once zero point energy effects are taken into account. PMID:26049481

  20. Vertical and adiabatic excitations in anthracene from quantum Monte Carlo: Constrained energy minimization for structural and electronic excited-state properties in the JAGP ansatz

    International Nuclear Information System (INIS)

    We study the ionization energy, electron affinity, and the π → π∗ (1La) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed on molecular orbitals (MOs). The MO-based JAGP ansatz allows one to rigorously treat electron transitions, such as the HOMO → LUMO one, which underlies the 1La excited state. We present a QMC optimization scheme able to preserve the rank of the antisymmetrized geminal power matrix, thanks to a constrained minimization with projectors built upon symmetry selected MOs. We show that this approach leads to stable energy minimization and geometry relaxation of both ground and excited states, performed consistently within the correlated QMC framework. Geometry optimization of excited states is needed to make a reliable and direct comparison with experimental adiabatic excitation energies. This is particularly important in π-conjugated and polycyclic aromatic hydrocarbons, where there is a strong interplay between low-lying energy excitations and structural modifications, playing a functional role in many photochemical processes. Anthracene is an ideal benchmark to test these effects. Its geometry relaxation energies upon electron excitation are of up to 0.3 eV in the neutral 1La excited state, while they are of the order of 0.1 eV in electron addition and removal processes. Significant modifications of the ground state bond length alternation are revealed in the QMC excited state geometry optimizations. Our QMC study yields benchmark results for both geometries and energies, with values below chemical accuracy if compared to experiments, once zero point energy effects are taken into account

  1. The effect of diet, exercise, and 7,12-dimethylbenz(a)anthracene on food intake, body composition, and carcass energy levels in virgin female BALB/c mice

    Science.gov (United States)

    Lane, Helen W.; Keith, Robert E.; Strahan, Susan; White, Marguerite T.

    1991-01-01

    The effects of diet, exercise, and 7,12-dimethylbenz(a)anthracene (DMBA), a mammary-tumor carcinogen, on food intake, energy consumption, body weight, and body composition in virgin female BALB/c mice are investigated. Diet, exercise, and DMBA all had pronounced effects on energy consumption, which in turn affected body composition. These treatments may influence manifestations of breast cancer via their effects on body composition.

  2. Effects of anthracene and UV-B radiation on larvae of Argopecten irradians%蒽和UV-B辐射增强对海湾扇贝早期发育的影响

    Institute of Scientific and Technical Information of China (English)

    谭海丽; 王玉堃; 唐学玺; 周斌; 王其翔; 王悠

    2013-01-01

    The effects of anthracene and UV-B radiation on the early stage embryos development of benthos, and the single and joint a-cute toxicological effects of anthracene and UV-B radiation on the trochophore and D larvae of Argopecten irradians under the controlled laboratory conditions were studied. The results showed that with the increase of time and the anthracenes concentration or the increase of days and radiation does, the liabilities of the trochophore and D larvae declined. With the combination of anthracene and UV-B radiation , the liabilities of trochophore and D larvae were lower than those in the single action. Compared to D larvae, the trochophore was more sensitive to anthracene and UV-B radiation.%为了探讨蒽和UV-B辐射对底栖生物早期发育的影响,在实验生态学的条件下,选择海湾扇贝(Argopecten irradians)担轮幼虫和D型幼虫作为受试生物进行单一和联合急性毒性试验.结果表明:在实验的蒽浓度和UV-B辐射剂量下,随着蒽浓度和作用时间的增加,海湾扇贝担轮幼虫和D型幼虫的存活率逐渐降低;随着UV-B辐射剂量和辐射天数的增加,海湾扇贝担轮幼虫和D型幼虫存活率下降;在蒽和UV-B辐射共同作用对担轮幼虫和D型幼虫处理时,其两个发育阶段的存活率较两者单独作用的存活率均低很多;担轮幼虫较D型幼虫对蒽和UV-B辐射更敏感.

  3. Influence of mode of exposure and the presence of a tubiculous polychaete on the fate of benz[a]anthracene in the benthos

    International Nuclear Information System (INIS)

    The distribution and metabolism of [14C-12]benz[a]-anthracene (BA) was followed in benthic microcosms in the presence and absence of the polychaete Nereis virens for periods of 4-25 days to simultaneously assess the effects of mode of introduction and the presence of large burrowing organisms on the fate of polycyclic aromatic hydrocarbons (PAH) and their metabolites in the benthos. Radiolabeled BA was added to the chambers in three ways: already sorbed to the entire sediment reservoir, directly into the water column, or incorporated into food for the worms. BA added to the water column was more available for uptake and metabolism by worms and microbial mineralization to CO2 than BA previously sorbed to the entire sediment reservoir. In experiments with the sediment reservoir uniformly labeled with BA, worms increased flux of BA from the sediment, and with time, their presence led to increased rates of microbial mineralization of BA to CO2. Dietary BA was most rapidly metabolized by Nereis

  4. The mechanism of anthracene interaction with photosynthetic apparatus: A study using intact cells, thylakoid membranes and PS II complexes isolated from Chlamydomonas reinhardtii

    Energy Technology Data Exchange (ETDEWEB)

    Aksmann, Anna, E-mail: bioaak@ug.edu.pl [Department of Plant Physiology, University of Gdansk, Al. Marszalka Pilsudskiego 46, 81-378 Gdynia (Poland); Shutova, Tatiana; Samuelsson, Goeran [Umea Plant Science Centre, Department of Plant Physiology, Umea University, SE 90187 Umea (Sweden); Tukaj, Zbigniew [Department of Plant Physiology, University of Gdansk, Al. Marszalka Pilsudskiego 46, 81-378 Gdynia (Poland)

    2011-08-15

    Intact cells of Chlamydomonas reinhardtii as well as isolated thylakoid membranes and photosystem II complexes were used to examine a possible mechanism of anthracene (ANT) interaction with the photosynthetic apparatus. Since ANT concentrations above 1 mM were required to significantly inhibit the rate of oxygen evolution in PS II membrane fragments it may indicate that the toxicant did not directly interact with this photosystem. On the other hand, stimulation of oxygen uptake by ANT-treated thylakoids suggested that ANT could either act as an artificial electron acceptor in the photosynthetic electron transport chain or function as an uncoupler. Electron transfer from excited chlorophyll to ANT is impossible due to the very low reduction potential of ANT and therefore we propose that toxic concentrations of ANT increase the thylakoid membrane permeability and thereby function as an uncoupler, enhancing electron transport in vitro. Hence, its unspecific interference with photosynthetic membranes in vitro suggests that the inhibitory effect observed on intact cell photosynthesis is caused by uncoupling of phosphorylation.

  5. The mechanism of anthracene interaction with photosynthetic apparatus: A study using intact cells, thylakoid membranes and PS II complexes isolated from Chlamydomonas reinhardtii

    International Nuclear Information System (INIS)

    Intact cells of Chlamydomonas reinhardtii as well as isolated thylakoid membranes and photosystem II complexes were used to examine a possible mechanism of anthracene (ANT) interaction with the photosynthetic apparatus. Since ANT concentrations above 1 mM were required to significantly inhibit the rate of oxygen evolution in PS II membrane fragments it may indicate that the toxicant did not directly interact with this photosystem. On the other hand, stimulation of oxygen uptake by ANT-treated thylakoids suggested that ANT could either act as an artificial electron acceptor in the photosynthetic electron transport chain or function as an uncoupler. Electron transfer from excited chlorophyll to ANT is impossible due to the very low reduction potential of ANT and therefore we propose that toxic concentrations of ANT increase the thylakoid membrane permeability and thereby function as an uncoupler, enhancing electron transport in vitro. Hence, its unspecific interference with photosynthetic membranes in vitro suggests that the inhibitory effect observed on intact cell photosynthesis is caused by uncoupling of phosphorylation.

  6. Red Mold Rice Mitigates Oral Carcinogenesis in 7,12-Dimethyl-1,2-Benz[a]anthracene-Induced Oral Carcinogenesis in Hamster

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    Ruei-Lan Tsai

    2011-01-01

    Full Text Available The prevalence of oral tumor has exponentially increased in recent years; however, the effective therapies or prevention strategies are not sufficient. Red mold rice is a traditional Chinese food, and several reports have demonstrated that red mold rice had an anti-tumor effect. However, the possible anti-tumor mechanisms of the red mold rice are unclear. In this study, we examined the anti-tumor effect of red mold rice on 7,12-dimethyl-1,2-benz[a]anthracene (DMBA-induced oral tumor in hamster. The ethanol extract of red mold rice (RMRE treatment significantly decreases the levels of DMBA-induced reactive oxygen species, nitro oxide and prostaglandin E2 than those of the lovastatin-treated group (P < .001. Moreover, RMRE decreases the formation of oral tumor induced by DMBA. Monacolin K, monascin, ankaflavin or other red mold rice metabolites had been reported to decrease inflammation and oxidative stress and exerted anti-tumor effects. Therefore, we evaluated the anti-inflammation and anti-oxidative stress effects of monacolin K, monascin, ankaflavin and citrinin in lipopolysaccharide-treated RAW264.7 cells. We found that RMRE reduced the LPS-induced nitrite levels in RAW264.7 cells better than monacolin K, monascin, ankaflavin or citrinin (P < .05.

  7. Time-dependent density functional study on the electronic excitation energies of polycyclic aromatic hydrocarbon radical cations of naphthalene, anthracene, pyrene, and perylene

    International Nuclear Information System (INIS)

    Time-dependent density functional theory (TDDFT) and its modification, the Tamm - Dancoff approximation to TDDFT, are employed to calculate the electronic excitation energies and oscillator strengths for a series of polycyclic aromatic hydrocarbon radical cations. For the radical cations of naphthalene and anthracene, TDDFT using the Becke - Lee - Yang - Parr functional and the 6-31G** basis set provides the excitation energies that are roughly within 0.3 eV of the experimental data. The assignments of the electron transitions proposed by TDDFT accord with the previous assignments made by accurate ab initio calculations, except that TDDFT indicates the existence of a few additional transitions of π*left-arrow σ character among the several low-lying transitions. The calculated energies for these π*left-arrow σ transitions are found to be consistent with the onset of a σ electron ionization manifold in the photoelectron spectra. For the pyrene radical cation, TDDFT supports the previous assignments made by semiempirical calculations, whereas for the perylene radical cation, TDDFT suggests the energy ordering of the three lowest-lying excited states be changed from those of the semiempirical results. copyright 1999 American Institute of Physics

  8. The anharmonic quartic force field infrared spectra of five non-linear polycyclic aromatic hydrocarbons: Benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene.

    Science.gov (United States)

    Mackie, Cameron J; Candian, Alessandra; Huang, Xinchuan; Maltseva, Elena; Petrignani, Annemieke; Oomens, Jos; Mattioda, Andrew L; Buma, Wybren Jan; Lee, Timothy J; Tielens, Alexander G G M

    2016-08-28

    The study of interstellar polycyclic aromatic hydrocarbons (PAHs) relies heavily on theoretically predicted infrared spectra. Most earlier studies use scaled harmonic frequencies for band positions and the double harmonic approximation for intensities. However, recent high-resolution gas-phase experimental spectroscopic studies have shown that the harmonic approximation is not sufficient to reproduce experimental results. In our previous work, we presented the anharmonic theoretical spectra of three linear PAHs, showing the importance of including anharmonicities into the theoretical calculations. In this paper, we continue this work by extending the study to include five non-linear PAHs (benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene), thereby allowing us to make a full assessment of how edge structure, symmetry, and size influence the effects of anharmonicities. The theoretical anharmonic spectra are compared to spectra obtained under matrix isolation low-temperature conditions, low-resolution, high-temperature gas-phase conditions, and high-resolution, low-temperature gas-phase conditions. Overall, excellent agreement is observed between the theoretical and experimental spectra although the experimental spectra show subtle but significant differences. PMID:27586928

  9. Use of the Integrated Biomarker Response to Measure the Effect of Short-term Exposure to Dibenz[a,h]anthracene in Common carp (Cyprinus carpio).

    Science.gov (United States)

    Kim, Ja-Hyun; Kim, Woo-Keun

    2016-04-01

    Dibenz[a,h]anthracene (DbA) is a polycyclic aromatic hydrocarbon that is released into the environment through incomplete combustion of gasoline, cigarettes, and coal tar. The effects of short-term (10 days) exposure of common carp (Cyprinus carpio) to DbA (0-50 µg L(-1)) were evaluated using the following four biomarkers: DNA damage, 7-ethoxyresorufin-O-deethylase (EROD) activity, acetylcholinesterase (AChE) activity, and vitellogenin (VTG) levels. An integrated biomarker response (IBR) was calculated for exposure to DbA, and the results were compared with those in our previous study of two other PAHs, benzo[k]fluoranthene (BkF) and benzo[a]pyrene (BaP). DbA exposure resulted in a significant (p IBR increased as the concentration of DbA increased. Based on the IBR values, the order of toxicity for the PAHs was BkF > BaP > DbA. Our results suggest that the IBR can be used as a quantitative tool for evaluating the responses of multiple biomarkers to PAH exposure. PMID:26744022

  10. Aggregation-enhanced emission and piezochromic luminescence of 9,10-bis(p-dibutylaminostyryl)-2,6-bis(p-t-butylstyryl)anthracene

    Energy Technology Data Exchange (ETDEWEB)

    Sun, Mingxiao; Zhang, Deteng; Li, Yiping; Wang, Jianfeng; Gao, Yangyang; Yang, Wenjun, E-mail: ywjph2004@qust.edu.cn

    2014-04-15

    A cruciform 9,10-distyrylanthracene-containing luminogen, 9,10-bis(p-dibutylaminostyryl)-2,6-bis(p-t-butylstyryl)anthracene (DDC), has been synthesized and the optical properties investigated. The results show that DDC is an aggregation-induced enhanced emission (AIEE) and piezofluorochromic (PFC) dye. The fluorescence quantum yield in THF/water=1/9 (18.1%) is about 12-fold over that in THF (1.53%). PFC experiment shows that the fluorescence colors (emission spectra) of DDC solid change reversibly between orange-red (602 nm) and red (632 nm) emissions upon pressing and annealing. Wide-angle X-ray diffraction and differential scanning calorimetric analyses reveal that the grinding has induced the phase transition of DDC solid from pristine crystalline to ground amorphous states, and annealing could cause the re-crystallization of amorphized DDC solid. This transformation between crystalline and amorphous states is responsible for the reversible PFC behavior upon external stimuli. Highlights: • A two-dimensional cross-conjugated luminogen (DDC) was synthesized. • DDC exhibits aggregation-enhanced emission and piezofluorochromic behaviors. • DDC emits bluer light in the crystalline phase than in the amorphous phase. • The PFC mechanism is ascribed to grinding-induced amorphization.

  11. Effect of permethrin, anthracene and mixture exposure on shell components, enzymatic activities and proteins status in the Mediterranean clam Venerupis decussata.

    Science.gov (United States)

    Sellami, Badreddine; Khazri, Abdelhafidh; Mezni, Amine; Louati, Héla; Dellali, Mohamed; Aissa, Patricia; Mahmoudi, Ezzeddine; Beyrem, Hamouda; Sheehan, David

    2015-01-01

    Anthracene (ANT) and permethrin (PER) are two of the more toxic compounds reaching the marine environment. This study aimed to determine the impact of these molecules on Venerupis decussata, an economically important species cultured on the Tunisian coast. Shell structure and its possible transformation upon exposure to the two contaminants were studied by X-ray diffraction and gravimetric analyses. Results revealed a phase transition in shell composition from aragonite to calcite after PER exposure, to a mixture of PER and ANT (Mix) but not for ANT alone. Catalase (CAT), superoxide dismutase (SOD) and glutathione transferase (GST) activities were determined in digestive gland and gills after exposure to ANT, PER and Mix to assess the impact of the contamination on the oxidative status of V. decussata. Enzyme activities increased in the digestive gland after PER treatment and in the gills after ANT treatment. PER exposure significantly reduced the levels of free thiols and increased levels of carbonylated proteins in the digestive gland, as compared to controls. In contrast, ANT exposure significantly reduced free thiols and increased the number of carbonylated proteins in the gills. Mix induced additive effects as measured by both enzymatic and proteomic approaches. The present study suggests that PER has a strong effect on shell structure; that PER and ANT exposure generate compound-dependent oxidative stress in the tissues of V. decussata and that a mixture of the two compounds has synergistic effects on biochemical response. PMID:25461742

  12. The effect of plant phenolics on the formation of 7,12-dimethylbenz[a]anthracene-DNA adducts and TPA-stimulated polymorphonuclear neutrophils chemiluminescence in vitro

    International Nuclear Information System (INIS)

    Phenolics, common plant constituents, form up an important part of human diet and are considered potential chemopreventive agents. In the present study, structurally diverse phenolics, such as tannic acid, protocatechuic acid, chlorogenic acid and resveratrol, were investigated for their inhibitory effects on covalent binding of 7,12-dimethylbenz[a]anthracene (DMBA) to DNA in vitro and the suppression of oxidative burst in 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated human polymorphonuclear neutrophils (PMNs). 32P-postlabeling analysis of DNA incubated with DMBA in the presence of 3-methylcholanthrene (3-MC)-induced microsomes produced three major adducts derived from anti-, syn- and anti-dihydrodiol epoxides through reactions with dGuo and dAdo, respectively. Phenolic compounds at the concentration of 150 μM reduced the levels of all DMBA-DNA adducts by 55-98%. The most dramatic effect was observed in case of tannic acid, which completely inhibited the formation of DMBA-dAdo adducts. Chlorogenic acid was the least effective inhibitor of DMBA-DNA adducts formation particularly syn-DMBADE-dAdo (20%). Human neutrophils showed a significant dose-related decrease of TPA-induced chemiluminescence after pretreatment with phenolic compounds. The most effective inhibitors were tannic acid and resveratrol with IC50=5.19 and 5.76 μM, respectively. These results suggest that the suppression of reactive oxygen species (ROS) and carcinogen-DNA adducts formation may be important for anticarcinogenic activity of the examined phenolics

  13. DNA excision repair in human cells treated with ultraviolet radiation and 7,12-dimethylbenz[a]anthracene 5,6-oxide

    International Nuclear Information System (INIS)

    Excision repair was measured in normal human and xeroderma pigmentosum group C cells treated with 7,12-dimethylbenz[a]anthracene 5,6-oxide and with ultraviolet radiation by the techniques of unscheduled DNA synthesis, repair replication, a modification of bromodeoxyuridine photolysis employing the dye Hoechst 33258 and 365 nm radiation, and endonuclease-sensitive sites assay. Radioautography and repair replication showed that in normal cells the magnitude of repair after a saturation dose of the epoxide (approx. 10 μM) to be 0.1-0.2 that after a saturating ultraviolet dose (20 J/m2 at 254), though survival data showed that both doses gave nearly similar killings. Repair was of the long-patch type and repair kinetics after the epoxide treatment were similar to ultraviolet. After a combined treatment with both agents, unscheduled synthesis in normal cells was more than additive, although, considering the experimental errors, these data and those of repair replication are consistent with additivity. The epoxide did not inhibit loss of sites sensitive to the ultraviolet endonuclease. However, after a combined treatment to xeroderma pigmentosum cells there was appreciably less unscheduled synthesis than for the sum of both treatments and the epoxide inhibited the loss of nuclease-sensitive sites. (Auth.)

  14. Chemopreventive and Antilipidperoxidative Efficacy of Piper longum (Linn.) on 7,12-dimethylbenz (a) anthracene (DMBA) Induced Hamster Buccal Pouch Carcinogenesis

    Science.gov (United States)

    Senthil, Namasivayam; Manoharan, Shanmugam; Balakrishnan, Subramanian; Rajmani Ramachandran, Cinnamanoor; Muralinaidu, Radhakrishnan

    Aim of the present study was to find out the chemopreventive efficacy of Piper longum, a plant having diverse medicinal properties, in 7,12-dimethyl benz (a) anthracene (DMBA) induced oral carcinogenesis. The mechanistic pathway for its chemopreventive potential was analysed by measuring lipid peroxidation and antioxidants status in DMBA induced oral cancer. DMBA painting in hamster buccal pouch three times per week for 14 weeks resulted in well developed, well differentiated squamous cell carcinoma. Elevated lipid peroxidation and decline in antioxidants were noticed in tumor bearing hamsters as compared to control animals. Oral administration of ethanolic extract of Piper longum dried fruits (PLEFet) on alternate days to DMBA painting significantly prevented the tumor incidence, volume and burden and restored the status of lipid peroxidation and antioxidants in DMBA painted hamsters. Our results indicate that the dried fruits of P. longum has suppressing effects on cell proliferation, which is probably due to its antilipid peroxidative and antioxidative potential during DMBA induced oral carcinogenesis.

  15. Chemoprevention of 7,12-dimethylbenz[a]anthracene (DMBA)-induced hamster cheek pouch carcinogenesis by a 5-lipoxygenase inhibitor, garcinol.

    Science.gov (United States)

    Chen, Xin; Zhang, Xinyan; Lu, Ye; Shim, Joong-Youn; Sang, Shengmin; Sun, Zheng; Chen, Xiaoxin

    2012-01-01

    Our previous studies have shown that aberrant arachidonic acid metabolism, especially the 5-lipoxygenase (5-Lox) pathway, is involved in oral carcinogenesis and can be targeted for cancer prevention. To develop potent topical agents for oral cancer chemoprevention, 5 known 5-Lox inhibitors from dietary and synthetic sources (Zileuton, ABT-761, licofelone, curcumin, and garcinol) were evaluated in silico for their potential efficacy. Garcinol, a polyisoprenylated benzophenone from the fruit rind of Garcinia spp., was found to be a promising agent based on the calculation of a theoretical activity index. Computer modeling showed that garcinol well fit the active site of 5-Lox, and potentially inhibited enzyme activity through interactions between the phenolic hydroxyl groups and the non-heme catalytic iron. In a short-term study on 7,12-dimethylbenz[a]anthracene (DMBA)-treated hamster cheek pouch, topical garcinol suppressed leukotriene B4 (LTB4) biosynthesis and inhibited inflammation and cell proliferation in the oral epithelium. In a long-term carcinogenesis study, topical garcinol significantly reduced the size of visible tumors, the number of cancer lesions, cell proliferation, and LTB4 biosynthesis. These results demonstrated that topical application of a 5-Lox inhibitor, garcinol, had chemopreventive effect on DMBA-induced hamster cheek pouch carcinogenesis. PMID:23137051

  16. Quercetin attenuates the development of 7, 12-dimethyl benz (a) anthracene (DMBA) and croton oil-induced skin cancer in mice

    Institute of Scientific and Technical Information of China (English)

    Huma Ali; Savita Dixit

    2015-01-01

    To evaluate the chemopreventive potential of quercetin in an experimental skin carcinogenesis mouse model.Skin tumor was induced by topical application of 7,12-dimethyl Benz (a) anthracene (DMBA) and Croton oil in Swiss albino mouse.Quercetin was orally administered at a concentration of 200 mg/kg and 400 mg/kg body weight daily for 16 weeks in mouse to evaluate chemopreventive potential.Skin cancer was assessed by histopathological analysis.We found that quercetin reduced the tumor size and the cumulative number of papillomas.The mean latent period was significantly increased as compared to carcinogen treated controls.Quercetin significantly decreased the serum levds of glutamate oxalate transaminase,glutamate pyruvate transaminase,alkaline phosphatase and bilirubin.It significantly increased the levels of glutathione,superoxide dismutase and catalase.The elevated level of lipid peroxides in the control group was significantly inhibited by quercetin.Futhermore,DNA damage was significantly decreased in quercetin treated mice as compared to DMBA and croton oil treated mice.The results suggest that quercetin exerts chemopreventive effect on DMBA and croton oil induced skin cancer in mice by increasing antioxidant activities.

  17. Synthesis, crystal structure, spectroscopic and density functional theory (DFT) study of N-[3-anthracen-9-yl-1-(4-bromo-phenyl)-allylidene]-N-benzenesulfonohydrazine

    Science.gov (United States)

    Arshad, Muhammad Nadeem; Asiri, Abdullah M.; Alamry, Khalid A.; Mahmood, Tariq; Gilani, Mazhar Amjad; Ayub, Khurshid; Birinji, Abdulhadi Salih

    2015-05-01

    N-[3-anthracen-9-yl-1-(4-bromo-phenyl)-allylidene]-N-benzenesulfonohydrazine has been synthesized and characterized by various spectroscopic techniques including FT-IR, UV-vis, 1H-NMR, 13C-NMR spectroscopy, and the structure was unequivocally confirmed by single crystal X-ray diffraction studies. The compound crystallized in monoclinic system with P21/n space group, and adopted cis-geometry around the azomethine Cdbnd N double bond. The X-ray crystal structure revealed that the intermolecular packing was stabilized by C-H⋯O type hydrogen bonding interaction, whereas NH was not involved in hydrogen bonding due to steric hindrance. Absorption wavelength was studied by scanning UV-vis. absorption spectrum in different solvents to explore excited state stability of the molecule in polar solvent. Density functional theory calculations were performed at B3LYP/6-31G (d, p) level in order to compare the experimental results with the theoretical results. The simulated molecular electrostatic potential (MEP), Mulliken charges and NPA (natural population analysis) also confirmed the presence of specific intermolecular hydrogen bonding (C-H⋯O). In addition natural bond orbital (NBO) analysis (intra and inter molecular bonding and interaction among bonds), frontier molecular orbital analysis (electronic properties) and first hyperpolarizability analysis (nonlinear optical response) were simulated at B3LYP/6-31G (d, p) level of theory.

  18. Modulation of lipid peroxidation and antioxidant status upon administration of 'Shemamruthaa' in 7,12-dimethylbenz[a]anthracene induced mammary carcinoma bearing rats

    Institute of Scientific and Technical Information of China (English)

    Ayyakkannu Purushothaman; Elumalai Nandhakumar; Panchanatham Sachdanandam

    2012-01-01

    Objective: To investigate the therapeutic efficacy of a Shemamruthaa (SM), (combination of Hibiscus rosasinensis (H. rosasinensis) flowers, fruits of Phyllanthus emblica (P. emblica) and pure honey in definite ratio), against lipid peroxidation (LPO) and antioxidant status in experimentally induced mammary carcinoma rats. Methods: Adult female Sprague-Dawley rats were used for the study and were divided into four groups. Group I control animals received standard pellet diet and water ad libitum. Group II rats were induced with 7,12-dimethyl benz[a]anthracene (DMBA) (25 mg in 1 mL olive oil) by gastric intubation, whereas another set of DMBA-induced rats were treated with SM (400 mg/kg body weight/d) in olive oil orally by gastric intubation for 14 d after 3 months of induction period (group III). Group IV rats served as SM-treated control animals. At the end of the experimental period, the rats were anaesthetised and sacrificed and used for biochemical measures and histology studies. Results: The LPO was increased and antioxidant levels were decreased in the serum, liver and mammary tissues of cancer-induced rats. The administration of SM drug significantly (P<0.05) decreased LPO and reversed the status of antioxidants to near normal level in cancer-bearing animals. Conclusions: The results obtained indicate the additive and synergistic action of constituents’ plants in the SM drug against oxidative damage and its protective role in DMBA induced mammary cancer.

  19. Promoting Effects of Milk on the Development of 7,12-dimethylbenz(a)anthracene (DMBA)-induced Mammary Tumors in Rats

    International Nuclear Information System (INIS)

    To assess the effect of milk on the development of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary tumors, 48 female Sprague-Dawley rats treated with DMBA were divided into 3 groups and given 1 of 3 test solutions for 20 weeks as their drinking liquid: milk, estrone sulfate solution or tap water. The milk group showed a significantly great incidence (75%) in tumor development compared with the water group (38%) and was comparable to the estrone sulfate group (69%). Mean tumor number per rat in the milk group was significantly higher than that in the water group (p=0.009). We classified the mammary tumors into three histological types: intraductal papilloma, fibroadenoma, and adenocarcinoma. Although the percent of intraductal papilloma and fibroadenoma was almost same among the three groups, malignant tumor was found only in the milk and estrone sulfate groups. In conclusion, our results indicate that milk as well as estrone sulfate promotes the development of DMBA-induced mammary tumors in rat and could be associated with the occurrence of adenocarcinoma

  20. Aggregation-enhanced emission and piezochromic luminescence of 9,10-bis(p-dibutylaminostyryl)-2,6-bis(p-t-butylstyryl)anthracene

    International Nuclear Information System (INIS)

    A cruciform 9,10-distyrylanthracene-containing luminogen, 9,10-bis(p-dibutylaminostyryl)-2,6-bis(p-t-butylstyryl)anthracene (DDC), has been synthesized and the optical properties investigated. The results show that DDC is an aggregation-induced enhanced emission (AIEE) and piezofluorochromic (PFC) dye. The fluorescence quantum yield in THF/water=1/9 (18.1%) is about 12-fold over that in THF (1.53%). PFC experiment shows that the fluorescence colors (emission spectra) of DDC solid change reversibly between orange-red (602 nm) and red (632 nm) emissions upon pressing and annealing. Wide-angle X-ray diffraction and differential scanning calorimetric analyses reveal that the grinding has induced the phase transition of DDC solid from pristine crystalline to ground amorphous states, and annealing could cause the re-crystallization of amorphized DDC solid. This transformation between crystalline and amorphous states is responsible for the reversible PFC behavior upon external stimuli. Highlights: • A two-dimensional cross-conjugated luminogen (DDC) was synthesized. • DDC exhibits aggregation-enhanced emission and piezofluorochromic behaviors. • DDC emits bluer light in the crystalline phase than in the amorphous phase. • The PFC mechanism is ascribed to grinding-induced amorphization

  1. Paternal selenium deficiency but not supplementation during preconception alters mammary gland development and 7,12-dimethylbenz[a]anthracene-induced mammary carcinogenesis in female rat offspring.

    Science.gov (United States)

    Guido, Luiza N; Fontelles, Camile C; Rosim, Mariana P; Pires, Vanessa C; Cozzolino, Silvia M F; Castro, Inar A; Bolaños-Jiménez, Francisco; Barbisan, Luis F; Ong, Thomas P

    2016-10-15

    Breast cancer is a global public health problem and accumulating evidence indicates early-life exposures as relevant factors in the disease risk determination. Recent studies have shown that paternal nutrition can influence offspring health including breast cancer risk. Selenium is a micronutrient with essential role in central aspects of embryogenesis, male fertility and cancer and that has been extensively studied as a chemopreventive agent in several breast cancer experimental models. Thus, we designed an animal study to evaluate whether paternal selenium deficiency or supplementation during preconception could affect the female offspring mammary gland development and breast cancer susceptibility. Male Sprague-Dawley rats were fed AIN93-G diet containing 0.15 ppm (control diet), 0.05 ppm (deficient diet) or 1 ppm (supplemented diet) of selenium for 9 weeks and mated with control female rats. Mammary carcinogenesis was induced with 7,12-dimethylbenz[a]anthracene (DMBA) in their female offspring. Paternal selenium deficiency increased the number of terminal end buds, epithelial elongation and cell proliferation in the mammary gland of the female rat offspring and these effects were associated with higher susceptibility to DMBA-induced mammary tumors (increased incidence and higher grade tumors). On the other hand, paternal selenium supplementation did not influence any of these parameters. These results highlight the importance of father's nutrition including selenium status as a relevant factor affecting daughter's breast cancer risk and paternal preconception as a potential developmental stage to start disease preventive strategies. PMID:27270969

  2. Eu3+/Sm3+ hybrids based with 8-hydroxybenz[de]anthracen-7-one organically modified mesoporous silica SBA-15/16

    Science.gov (United States)

    Gu, Yan-Jing; Yan, Bing

    2015-12-01

    A series of organic-inorganic hybrid materials were prepared by linking lanthanide (Eu3+, Sm3+) complexes to mesoporous SBA-15/SBA-16 through 8-hydroxybenz[de]anthracen-7-one modified silane (HBA-Si) as linker. The physical characterizations of these hybrids revealed that they all have high surface area, uniformity in mesostructure. The luminescence properties of these covalently bonded materials (denoted as Ln(HBA-SBA-15)3phen and Ln(HBA-SBA-16)3phen) were compared with ternary complexes (Ln(HBA)3phen) (Ln = Eu, Sm). Eu(HBA-SBA-15(16))3phen hybrids display better thermal stability, whose luminescent lifetimes and quantum efficiencies were matchable with those of Eu(HBA)3phen complex in spite of its much lower effective condensation of Eu3+ species. In addition, the luminescent performance of functionalized SBA-15 hybrids was more favorable than that of functionalized SBA-16 hybrids, revealing that SBA-15 was a better host material for lanthanide complex than mesoporous silica SBA-16.

  3. 7,12-dimethylbenz[a]anthracene plus near-u.v. light initiates DNA damage and repair in Chinese hamster cells

    International Nuclear Information System (INIS)

    Earlier results on the photodynamic action of several carcinogenic polycyclic aromatic hydrocarbons, and particularly 7,12-dimethylbenz[a]anthracene (DMBA), have been extended to determine if DMBA + near-u.v. light produces damage to DNA. DMBA by itself introduces relatively few breaks into genomic DNA. The addition of near-u.v. light, however, inserts large numbers of single-strand breaks in a dose-dependent way. Incubation following exposure initially results in the rapid repair of these breaks. A primary role for DNA damage in photodynamic cell killing is not supported by other observations, however. Thus, a starting point for mutagenic and carcinogenic action in the absence of light is suggested although activation of DMBA by a P-450 system does not appear to be a prerequisite of DMBA - DNA association. Still, DNA as such may not be the initial or the primary target for light-induced cell killing. In addition to interacting with DNA, DMBA is sequestered by membranes, suggesting that killing results from an oxygen-dependent release of catabolic enzymes. These enzymes, which may come from lysosomes, degrade DNA but concomitantly release surface-attached cells into the medium. (author)

  4. Photodynamic cytotoxicity of mammalian cells exposed to sunlight-simulating near ultraviolet light in the presence of the carcinogen 7, 12-dimethylbenz(a)anthracene

    International Nuclear Information System (INIS)

    The coal-derived carcinogen 7,12-dimethylbenz(a)anthracene (DMBA), added to cultures of V79 Chinese Hamster, C3H mouse 10T1/2, and human HeLa cells enhanced photolethality induced by the sunlight-simulating emission from Westinghouse Sun Lamps (approximately 290-400 nm) but only in the presence of 02. Treatment of cells with DMBA after irradiation was without lethal effect; the endoperoxide of DMBA was ineffective both before as well as after irradiation, and DMBA incubation before far-UV exposure (254 nm) was protective. Cells rendered photosensitive by incubation with DMBA rapidly lost their sensitivity (in 0C) if incubation in a DMBA-free solution containing serum, but maintained their sensitivity at least for several hours if a serum-free solution was used. Although DMBA enhanced light-induced killing of cells in all phases of the cycle, those undergoing DNA syntheses were preferentially sensitized. The data supported photodynamic lethality due to one or both of the following: (1) the reaction with DNA of either DMBA radicals followed by oxidation, or DMBA-produced single oxygen; or (2) the peroxidation of lysosomal membranes followed by the release of hydrolases including DNAses. As a model system of the combined effects of a fossil-fuel derived polycyclic aromatic hydrocarbon and sunlight, the results with DMBA + near-UV are discussed in the context of altered cell properties (e.g. neoplastic transformation) in sublethally affected cells. (author)

  5. Pro-apoptotic and anti-inflammatory potential of andrographolide during 7,12-dimethylbenz[a]anthracene induced hamster buccal pouch carcinogenesis

    Directory of Open Access Journals (Sweden)

    Karthikeyan Sekar

    2012-08-01

    Full Text Available Objective: Aim of the present study was to investigate the modulating effect of andrographolide on apoptotic and inflammatory markers during 7,12-dimethyl-benz[a]anthracene (DMBA induced hamster buccal pouch carcinogenesis. Methods: Oral tumors were developed in the buccal pouch of golden Syrian hamsters by painting with 0.5% DMBA in liquid paraffin three times a week for 14 weeks. The expression pattern of molecular markers were assayed using immunohistochemistry (p53, Bcl-2 and Bax, ELISA (COX-2 and real-time PCR (NFκB. Results: We noticed 100% tumor formation accompanied by deregulation in the apoptotic and inflammatory markers in the buccal mucosa of hamsters treated with DMBA alone. Oral administration of andrographolide at a dose of 50 mg/kg b.w to hamsters treated with DMBA, not only completely prevented the tumor formation but also modulated the status of above mentioned molecular markers in favor of inhibiting cell proliferation as evidenced by no tumor formation. Conclusion: The present study suggests that the anti-tumor effect of andrographolide could partly be attributed to its apoptotic and anti-inflammatory potential during DMBA-induced hamster buccal pouch carcinogenesis. [J Exp Integr Med 2012; 2(4: 313-319

  6. Effect of phosphatidylinositol-3 kinase inhibition on ovotoxicity caused by 4-vinylcyclohexene diepoxide and 7, 12-dimethylbenz[a]anthracene in neonatal rat ovaries

    International Nuclear Information System (INIS)

    4-vinylcyclohexene diepoxide (VCD) is an ovotoxicant that specifically destroys primordial and small primary follicles in the ovaries of mice and rats. In contrast, 7,12-dimethylbenz[a]anthracene (DMBA) is ovotoxic to all ovarian follicle classes. This study investigated phosphatidylinositol-3 kinase signaling involvement in VCD- and DMBA-induced ovotoxicity. Postnatal day (PND) 4 Fischer 344 (F344) rat whole ovaries were cultured for 2-12 days in vehicle control, VCD (30 μM), or DMBA (1 μM), ± PI3 kinase inhibitor LY294002 (20 μM) or its inactive analog LY303511 (20 μM). Following culture, ovaries were histologically evaluated, and healthy follicles were classified and counted. PI3 kinase inhibition had no effect on primordial follicle number, but reduced (P 0.05) at any time, but did cause loss (P < 0.05) of small primary follicles. DMBA exposure caused primordial and small primary follicle loss (P < 0.05) on day 6. Further, DMBA-induced primordial and small primary follicle loss was greater with PI3 kinase inhibition (P < 0.05) than with DMBA alone. These results support that (1) PI3 kinase mediates primordial to small primary follicle recruitment, (2) VCD, but not DMBA, enhances ovotoxicity by increasing primordial to small primary follicle recruitment, and (3) in addition to xenobiotic-induced ovotoxicity, VCD is also a useful model chemical with which to elucidate signaling mechanisms involved in primordial follicle recruitment.

  7. Influence of mode of exposure and the presence of a tubiculous polychaete on the fate of benz(a)anthracene in the benthos

    Energy Technology Data Exchange (ETDEWEB)

    McElroy, A.E.; Farrington, J.W.; Teal, J.M. (Woods Hole Oceanographic Institution, MA (USA))

    1990-11-01

    The distribution and metabolism of ({sup 14}C-12)benz(a)-anthracene (BA) was followed in benthic microcosms in the presence and absence of the polychaete Nereis virens for periods of 4-25 days to simultaneously assess the effects of mode of introduction and the presence of large burrowing organisms on the fate of polycyclic aromatic hydrocarbons (PAH) and their metabolites in the benthos. Radiolabeled BA was added to the chambers in three ways: already sorbed to the entire sediment reservoir, directly into the water column, or incorporated into food for the worms. BA added to the water column was more available for uptake and metabolism by worms and microbial mineralization to CO{sub 2} than BA previously sorbed to the entire sediment reservoir. In experiments with the sediment reservoir uniformly labeled with BA, worms increased flux of BA from the sediment, and with time, their presence led to increased rates of microbial mineralization of BA to CO{sub 2}. Dietary BA was most rapidly metabolized by Nereis.

  8. Isolation of an Anthracene-Degrading Strain Aspergillus fumigatus A10 and Its Degradation Characteristics%蒽降解菌烟曲霉A10的分离及降解性能研究

    Institute of Scientific and Technical Information of China (English)

    强婧; 尹华; 彭辉; 叶锦韶; 秦华明; 何宝燕; 张娜

    2009-01-01

    从污染环境中筛选出1株蒽降解菌A10,经鉴定为烟曲霉(Aspergillus fumigatus),其对蒽的降解率随时间的延长逐渐升高,在12~84 h,蒽降解率增长速率较快;此后降解率的增加趋于平缓,最终(168 h)能够达到83%左右.当无机盐培养液中蒽初始浓度为10 mg/L,A10投菌量为50 g/L(以湿重计),菌龄为36 h时, 5 d内蒽降解率为79.37%.蒽浓度对菌发挥降解作用有较大影响,浓度为5 mg/L时,降解率最高,达92.17%.培养液初始pH为5.0~7.5时,降解率维持在60%左右;温度为30℃、氧气量为4.30 mg/L时蒽降解效果较好.一定量的营养盐的添加能在一定程度上促进蒽的降解.共代谢底物乳糖的添加,能使蒽的降解率提高37.15%.对蒽降解过程的初步研究表明,菌株A10对蒽的降解是一个胞外吸附/胞内降解的动态变化过程.红外光谱分析显示,在微生物作用下,蒽的结构发生改变,生成了含有1~2个苯环的芳香酸、芳香酮、芳香醛和饱和碳氢化合物等一系列降解产物.%An anthracene-degrading strain (A10) was isolated from contaminated environment and identified as Aspergillus fumigatus.The experimental results showed that the biodegradation rate of anthracene increased with the increasing time.Between 12-84 h interval, the biodegradation performed rapidly, while after this, the increase of biodegradation rate tended to become slow, and ultimately the biodegradation rate could achieve approximately 83%.The degradation rate of anthracene reached 79.37% within 5 days when the initial concentration of anthracene in mineral salts medium (MSM) was 10 mg/L, the inoculum dosage was 50 g/L (wet weight) and the cell age was 36 h.The concentration of anthracene had notable influence on degradation function of strain A10 and the highest degradation rate (92.17%) was achieved when anthracene concentration was 5 mg/L.The degradation rate could maintain about 60% with initial pH of MSM in the range of 5

  9. The influence of melatonin on metabolic changes in female rats induced by continuous irradiation and/or administration of 7,12-dimethylbenz/a/anthracene

    International Nuclear Information System (INIS)

    Metabolic profile is an important biological marker of neoplastic processes not only in the tumor itself but also in the host organism. The neuro-hormone melatonin has been implicated in the experiments as an oncostatic agent. Female Wistar:Han SPF rats (Velaz, Prague, Czech Republic) were irradiated continuously for 15 days using a daily gamma rays dose of 96 mGy. At the end of exposure one group of rats was administered 5 mg/kg b.w. of dimethylbenz/a/anthracene (DMBA) intragastrically. During the period of exposure to ionizing radiation a part of the animals was supplied with melatonin (M) at a concentration of 20 μl/ml in drinking water. Selected parameters of lipid and carbohydrate metabolism and levels of selected hormones were determined 2, 30 and 100 days post-irradiation. The irradiation itself caused only small changes in tissue lipids. The application of a single low dose (subthreshold from the point of view of induction of mammary tumors) of DMBA caused more pronounced changes in nonirradiated animals; of the changes observed an increase in lipids in the liver, triacylglycerol (TG) in the thymus and decrease in myocardial glycogen predominated. The intake (by drinking) of exogenous M prevented the biochemical pattern of fatty liver in animals administered DMBA in both groups, irradiated an nonirradiated. A Prolonged effect of exogenous M, demonstrated by prevention of increase in TG in the thymus and of irradiated animals caused by administration of DMBA, was observed. The mechanism of metabolic effect of M is not known. Additional experiments are needed to explain the relationship between the beneficial effect of M on metabolic changes and its presumable oncostatic effect in rats. (author)

  10. 9D nonadiabatic quantum dynamics through a four-state conical intersection: Investigating the homolysis of the O-O bond in anthracene-9,10-endoperoxide

    Science.gov (United States)

    Assmann, Mariana; Worth, Graham A.; González, Leticia

    2012-12-01

    The excited state dynamics of anthracene-9,10-endoperoxide is investigated using quantum wavepacket dynamics. APO is an aromatic endoperoxide which, upon excitation to S1, shows a cleavage of the oxygen-oxygen bond, leading to rearrangement products. It was shown that the dynamics of the O-O cleavage is modulated by a four-state degeneracy [D. Mollenhauer, I. Corral, and L. González, J. Phys. Chem. Lett. 1, 1036 (2010)], 10.1021/jz100196q. The most important mode to describe the O-O cleavage is the opening of the O-O bond. Excitation to higher excited states Sn (n ⩾ 2) leads to the release of singlet molecular oxygen. For this release, the twist of the oxygen atoms around the molecular axis is an important mode. These two degrees of freedom were employed to calculate two-dimensional potential energy surfaces for the four singlet states which become degenerate. Further modes were included in terms of harmonic oscillators. Using the multiconfigurational time-dependent Hartree method, quantum dynamic simulations were performed in up to nine degrees of freedom. Moreover, the nine branching space vectors, which prove the degeneracy to be a four-state conical intersection (4CI), were calculated and included in the wavepacket propagations. The resulting dynamics show that the 4CI is reached very fast (in less than 30 fs after excitation) and the wavepacket distributes over all states. The degree of distribution into the states is very much dependent on which modes are included in the simulation.

  11. Anticancer and antimutagenic properties of Acacia nilotica (Linn.) on 7,12-dimethylbenz(a)anthracene-induced skin papillomagenesis in Swiss albino mice.

    Science.gov (United States)

    Meena, Punar Dutt; Kaushik, Pallavi; Shukla, Shalini; Soni, Anil Kumar; Kumar, Manish; Kumar, Ashok

    2006-01-01

    We report the chemopreventive activity of Acacia nilotica (Linn.) gum, flower and leaf aqueous extracts, on 7,12-dimethylbenz(a)anthracene (DMBA) induced skin papillomagenesis in male Swiss albino mice. Animals were divided into following groups: Group I (Controls) given DMBA and croton oil, with no extract ; Group II (treatment) animals treated with Acacia nilotica gum (Group II-a) (800 mg/kg body weight), flowers (Group II-b) (800 mg/kg body weight), or leaves (Group II-c) (800 mg/kg body weight) during the peri- and post initiation periods of DMBA and croton oil application. A significant reduction in the values of tumor burden, tumor incidence and cumulative number of papillomas was observed in mice treated by oral gavage with the Acacia nilotica gum, flower and leaf extracts as compared with the control group. The latency period in treatment Group-II (b) and Group-II (c) was significantly increased as compared with the control group. A significant reduction in the frequency of micronuclei was also observed in mice treated by oral gavage with the aqueous extracts, along with significant decrease in total chromosomal aberrations in the form of chromatid breaks, chromosome breaks, centric rings, dicentrics, acentric fragments and exchange. Treatment with Acacia nilotica flower (Group II-B) and leaf (Group II-C) aqueous extracts by oral gavage for 15 days resulted in a highly significant decrease in the lipid peroxidation (LPO) level in the liver, but this was less evident with the gum (Group II-A) . Conversely, reduced glutathione (GSH) content was observed to be significantly elevated as compared with the control group with leaves (Group II-C) and flowers (Group II-B). The chemopreventive and antimutagenic activity of the leaf extract of Acacia nilotica was most significant followed by the flower extract and then by gum. PMID:17250441

  12. Impact of obesity on 7,12-dimethylbenz[a]anthracene-induced altered ovarian connexin gap junction proteins in female mice

    International Nuclear Information System (INIS)

    The ovarian gap junction proteins alpha 4 (GJA4 or connexin 37; CX37), alpha 1 (GJA1 or connexin 43; CX43) and gamma 1 (GJC1 or connexin 45; CX45) are involved in cell communication and folliculogenesis. 7,12-dimethylbenz[a]anthracene (DMBA) alters Cx37 and Cx43 expression in cultured neonatal rat ovaries. Additionally, obesity has an additive effect on DMBA-induced ovarian cell death and follicle depletion, thus, we investigated in vivo impacts of obesity and DMBA on CX protein levels. Ovaries were collected from lean and obese mice aged 6, 12, 18, or 24 wks. A subset of 18 wk old mice (lean and obese) were dosed with sesame oil or DMBA (1 mg/kg; ip) for 14 days and ovaries collected 3 days thereafter. Cx43 and Cx45 mRNA and protein levels decreased (P < 0.05) after 18 wks while Cx37 mRNA and protein levels decreased (P < 0.05) after 24 wks in obese ovaries. Cx37 mRNA and antral follicle protein staining intensity were reduced (P < 0.05) by obesity while total CX37 protein was reduced (P < 0.05) in DMBA exposed obese ovaries. Cx43 mRNA and total protein levels were decreased (P < 0.05) by DMBA in both lean and obese ovaries while basal protein staining intensity was reduced (P < 0.05) in obese controls. Cx45 mRNA, total protein and protein staining intensity level were decreased (P < 0.05) by obesity. These data support that obesity temporally alters gap junction protein expression and that DMBA-induced ovotoxicity may involve reduced gap junction protein function. - Highlights: • Ovarian gap junction proteins are affected by ovarian aging and obesity. • DMBA exposure negatively impacts gap junction proteins. • Altered gap junction proteins may contribute to infertility

  13. Impact of obesity on 7,12-dimethylbenz[a]anthracene-induced altered ovarian connexin gap junction proteins in female mice

    Energy Technology Data Exchange (ETDEWEB)

    Ganesan, Shanthi, E-mail: shanthig@iastate.edu; Nteeba, Jackson, E-mail: nteeba@iastate.edu; Keating, Aileen F., E-mail: akeating@iastate.edu

    2015-01-01

    The ovarian gap junction proteins alpha 4 (GJA4 or connexin 37; CX37), alpha 1 (GJA1 or connexin 43; CX43) and gamma 1 (GJC1 or connexin 45; CX45) are involved in cell communication and folliculogenesis. 7,12-dimethylbenz[a]anthracene (DMBA) alters Cx37 and Cx43 expression in cultured neonatal rat ovaries. Additionally, obesity has an additive effect on DMBA-induced ovarian cell death and follicle depletion, thus, we investigated in vivo impacts of obesity and DMBA on CX protein levels. Ovaries were collected from lean and obese mice aged 6, 12, 18, or 24 wks. A subset of 18 wk old mice (lean and obese) were dosed with sesame oil or DMBA (1 mg/kg; ip) for 14 days and ovaries collected 3 days thereafter. Cx43 and Cx45 mRNA and protein levels decreased (P < 0.05) after 18 wks while Cx37 mRNA and protein levels decreased (P < 0.05) after 24 wks in obese ovaries. Cx37 mRNA and antral follicle protein staining intensity were reduced (P < 0.05) by obesity while total CX37 protein was reduced (P < 0.05) in DMBA exposed obese ovaries. Cx43 mRNA and total protein levels were decreased (P < 0.05) by DMBA in both lean and obese ovaries while basal protein staining intensity was reduced (P < 0.05) in obese controls. Cx45 mRNA, total protein and protein staining intensity level were decreased (P < 0.05) by obesity. These data support that obesity temporally alters gap junction protein expression and that DMBA-induced ovotoxicity may involve reduced gap junction protein function. - Highlights: • Ovarian gap junction proteins are affected by ovarian aging and obesity. • DMBA exposure negatively impacts gap junction proteins. • Altered gap junction proteins may contribute to infertility.

  14. Daphnetin ameliorates 7,12-dimethylbenz[a]anthracene-induced mammary carcinogenesis through Nrf-2-Keap1 and NF-κB pathways.

    Science.gov (United States)

    Kumar, Abhishek; Jha, S; Pattanayak, Shakti P

    2016-08-01

    Cancer is a faction of disorders that conjugated primarily with oxidative imbalance. In mammary carcinoma, oxidative stress secondarily changes various gene expressions and signalling pathways that bring genomic instability and mutagenic alterations that fascinating carcinogenesis. Several coumarin compounds are active against various malignancies. Among them, daphnetin (DAP) exhibits valuable safety and bioactivity profile that contributes towards its efficacy against cancer. In this study, the antioxidative and chemotherapeutic potential of DAP against 7,12-dimethylbenz(a)anthracene (DMBA)- induced mammary carcinogenesis was evaluated in female Sprague-Dawley rats. Besides this, we have determined the effect of DAP on Keap1-Nrf-2, associated HO-1 and NF-κB expressions behind the antioxidative and anti-proliferating activity. In our findings, a protective effect of DAP was established against lipid peroxidation, enzymic (Total SOD, MnSOD, CuZnSOD, CAT, GPx) and non-enzymic (GSH) antioxidative markers in serum, liver, kidney and breast tissue of both control and experimental groups. An up-regulation of protective Nrf-2 & HO-1 with a synchronized suppression in Keap1 & NF-κB mRNA and protein expressions were observed. DAP revealed the inhibition of p-AKT which accountable for decrease in NF-κB expressions but shown to be ineffective on p-ERK1/2. This study revealed that DAP inhibits mammary carcinogenesis through multiple mechanisms. Dual efficacy of DAP on Nrf-2-Keap1 pathway and NF-κB expressions propose it as a potential chemotherapeutic agent in mammary cancer management. PMID:27470383

  15. Chronic unpredictable stress (CUS) enhances the carcinogenic potential of 7,12-dimethylbenz(a)anthracene (DMBA) and accelerates the onset of tumor development in Swiss albino mice.

    Science.gov (United States)

    Suhail, Nida; Bilal, Nayeem; Hasan, Shirin; Ahmad, Ausaf; Ashraf, Ghulam Md; Banu, Naheed

    2015-11-01

    Social stressors evolving from individual and population interactions produce stress reactions in many organisms (including humans), influencing homeostasis, altering the activity of the immunological system, and thus leading to various pathological states including cancer and their progression. The present study sought to validate the effectiveness of chronic unpredictable stress (CUS) in cancer promotion and to assess oxidative stress outcomes in terms of various in vivo biochemical parameters, oxidative stress markers, DNA damage, and the development of skin tumors in Swiss albino mice. Animals were randomized into different groups based on their exposure to CUS alone, 7,12-dimethylbenz(a)anthracene (DMBA) alone (topical), and DMBA-12-O-tetradecanoylphorbol-13-acetate (TPA) (topical) and exposure to CUS prior to DMBA or DMBA-TPA treatments and sacrificed after 16 weeks of treatment. Prior exposure to CUS significantly increased the pro-oxidant effect of carcinogen, depicted by compromised levels of antioxidants in the circulation and skin, accompanied by enhanced lipid peroxidation, plasma corticosterone, and marker enzymes as compared to DMBA-alone or DMBA-TPA treatments. DNA damage results corroborated the above biochemical outcomes. Also, the development of skin tumors (in terms of their incidence, tumor yield, and tumor burden) in mice in the presence and absence of stress further strongly supported our above biochemical measurements. CUS may work as a promoter of carcinogenesis by enhancing the pro-oxidant potential of carcinogens. Further studies may be aimed at the development of interventions for disease prevention by identifying the relations between psychological factors and DNA damage. PMID:26272695

  16. Hepatic dysfunction induced by 7, 12-dimethylbenz(αanthracene and its obviation with erucin using enzymatic and histological changes as indicators.

    Directory of Open Access Journals (Sweden)

    Rohit Arora

    Full Text Available The toxicity induced by 7, 12-dimethylbenz(αanthracene (DMBA has been widely delineated by a number of researchers. This potent chemical damages many internal organs including liver, by inducing the production of reactive oxygen species, DNA-adduct formation and affecting the activities of phase I, II, antioxidant and serum enzymes. Glucosinolate hydrolytic products like isothiocyanates (ITCs are well known for inhibiting the DNA-adduct formation and modulating phase I, II enzymes. Sulforaphane is ITC, currently under phase trials, is readily metabolized and inter-converted into erucin upon ingestion. We isolated erucin from Eruca sativa (Mill. Thell. evaluated its hepatoprotective role in DMBA induced toxicity in male wistar rats. The rats were subjected to hepatic damage by five day regular intraperitoneal doses of DMBA. At the end of the protocol, the rats were euthanized, their blood was collected and livers were processed. The liver homogenate was analyzed for phase I (NADPH-cytochrome P450 reductase, NADH-cytochrome b5 reductase, cytochrome P450, cytochrome P420 and cytochrome b5, phase II (DT diaphorase, glutathione-S-transferase and γ-glutamyl transpeptidase and antioxidant enzymes (superoxide dismutase, catalase, guaiacol peroxidise, ascorbate peroxidise, glutathione reductase and lactate dehydrogenase. The level of thiobarbituric acid reactive substances, lipid hydroperoxides, conjugated dienes and reduced glutathione in the liver homogenate was also analyzed. The serum was also analyzed for markers indicating hepatic damage (alkaline phosphatase, serum glutamic oxaloacetic transaminase, serum glutamic pyruvic transaminase, direct bilirubin and total bilirubin. Erucin provided significant protection against DMBA induced damage by modulating the phase I, II and antioxidant enzymes. The histological evaluation of liver tissue was also conducted, which showed the hepatoprotective role of erucin.

  17. Derivation of transplantable 7,12-dimethylbenz[a]anthracene-induced chicken fibrosarcoma lines: differences in metastasizing properties and organ specificity

    International Nuclear Information System (INIS)

    Transplantable 7,12-dimethylbenz[a]anthracene-induced SC chicken fibrosarcoma (CHCT-NYU) lines were studied for their ability to grow in internal organs after iv injection (artificial metastases) into 1- to 3-week-old chickens. Some tumor lines were recently derived, whereas others were studied after many serial subcutaneous transplantations. Artificial metastases were seen in the stomach, pancreas, lungs, heart, and muscle, and occasionally in the kidneys and liver. Agammaglobulinemic recipients showed more extensive organ involvement than normal recipients of the same age. Whole-body ν-irradiation enhanced the incidence of artificial metastases, particularly in lungs. Antibody from the serum of a primary tumor-bearing host reduced the growth of the corresponding tumor in many organs. The metastatic pattern of line CHCT-NYU4 was a relatively stable property. However, intravenous transplantation of tumor cells from line CHCT-NYU4 taken from the liver, lungs, and pancreas of a single recipient established sublines with changes in organ specificity. After a few such serial transplants of liver-derived tumor, a line was derived that grew virtually in the liver alone. A subline with preference for growth in lungs was also obtained, but its ability to grow in the pancreas persisted. A pancreas-derived tumor line also grew in the liver and lungs. Subcutaneous transplants of tissue fragments of the lung-derived tumor line caused the appearance of spontaneous metastases in lungs. The incidence of spontaneous metastases with the lung-derived line was much greater than that with the liver-derived line or with the original CHCT-NYU4 line

  18. Controlled release low dose medroxyprogesterone acetate (MPA) inhibits the development of mammary tumors induced by dimethyl-benz(a) anthracene in the rat.

    Science.gov (United States)

    Labrie, F; Li, S; Bélanger, A; Côté, J; Mérand, Y; Lepage, M

    1993-01-01

    Medroxyprogesterone acetate (MPA) is well recognized to have beneficial effects for the treatment of advanced breast cancer which are comparable to those achieved with other forms of endocrine therapy. Using mammary tumors induced in the rat by dimethylbenz(a)anthracene (DMBA) as a model, we have studied the possibility that low dose MPA could prevent the development of these tumors. Single subcutaneous injection of Depo-Provera (crystalline suspension of MPA) or MPA encapsulated in biodegradable microspheres of 50:50 poly[DL-lactide-co-glycolide] was given 7 days before oral DMBA. While 63% of intact animals developed palpable mammary tumors within 85 days after DMBA administration, tumor incidence decreased to 28% and 23% in animals who had received 30 mg and 100 mg of Depo-Provera, respectively. The same amounts of MPA delivered in microspheres caused a further decrease in tumor incidence to respective values of 7% and 6%. Average tumor area, on the other hand, decreased from 4.89 cm2 in intact rats to about 0.75 (0.57-0.88) cm2 and approximately 0.20 (0.14-0.22) cm2 in the Depo-Provera and microsphere-treated groups, respectively. Using the 50:50 formulation of poly[DL-lactide-co-glycolide] designed to release MPA at a constant rate for a 4-month period, the serum MPA concentration at 3 months was measured at 4.99 +/- 0.43 ng/ml. Such data suggest that administration of a low dose controlled-release formulation of MPA in 50:50 poly[DL-lactide-co-glycolide] microspheres could well be an efficient and well tolerated approach for the prevention of breast cancer in women. PMID:8251650

  19. Chemopreventive effects of Furan-2-yl-3-pyridin-2-yl-propenone against 7,12-dimethylbenz[a]anthracene-inducible genotoxicity

    International Nuclear Information System (INIS)

    1-Furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) is an anti-inflammatory agent with a propenone moiety and chemically synthesized recently. In this study, we examined the chemopreventive effect of FPP-3 on 7,12-dimethylbenz[a]anthracene (DMBA)-induced genotoxicity in MCF-7 cells. FPP-3 reduced the formation of the DMBA-DNA adduct. DMBA-induced CYP1A1 and CYP1B1 gene expression and enzyme activity were inhibited by FPP-3. It inhibited DMBA-induced aryl hydrocarbon receptor (AhR) transactivation and DMBA-inducible nuclear localization of the AhR. Induction of detoxifying phase II genes by chemopreventive agents represents a coordinated protective response against oxidative stress and neoplastic effects of carcinogens. Transcription factor NF-E2 related factor 2 (Nrf2) regulates antioxidant response element (ARE) of phase II detoxifying and antioxidant enzymes, such as glutathione S-transferase (GST) and NAD(P)H:quinone oxidoreductase (QR). FPP-3 increased the expression and enzymatic activity of GST and QR. Moreover, FPP-3 increased transcriptional activity of GST and QR. GST and QR induction and Nrf2 translocation by FPP-3 were blocked by the PKC inhibitor Goe6983, and the p38 inhibitor SB203580. These results reflected a partial role of PKCδ and p38 signaling in FPP-3-mediated GSTA and QR induction through nuclear translocation of Nrf2. Classically, chemopreventive agents either inhibit CYP metabolizing enzyme or induce phase II detoxifying enzymes. These results suggest that FPP-3 has a potent protective effect against DMBA-induced genotoxicity through modulating phase I and II enzymes and that it has potential as a chemopreventive agent

  20. (Z-3-(Anthracen-9-yl-1-(2-ethoxyphenylprop-2-en-1-oneThis paper is dedicated to the late His Royal Highness Prince Mahidol of Songkla for his contributions to the development of medical education in Thailand on the occasion of Mahidol Day which falls on the 24th September.

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2010-10-01

    Full Text Available The molecule of the title chalcone, C25H20O2, consisting of 2-ethoxyphenyl and anthracene rings bridged by a prop-2-en-1-one unit, is twisted and exists in the Z configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 78.17 (9°. The propene unit makes dihedral angles of 44.5 (2 and 81.1 (2° with the benzene and anthracene rings, respectively. The ethoxy substituent is almost coplanar with the attached benzene ring [C—O—C—C torsion angle = 178.57 (19°]. In the crystal, molecules are linked into chains along the a axis by weak C—H...O interactions. The crystal structure is further stabilized by C—H...π interactions.

  1. Chemoprevention of 7, 12-dimethylbenz[a]anthracene (DMBA)-induced oral carcinogenesis in hamster cheek pouch by topical application of a dual inhibitor of epidermal growth factor receptor (EGFR) and ErbB2 tyrosine kinases

    OpenAIRE

    Sun, Zheng; Sood, Sandeep; Li, Ning; Yang, Peiying; Newman, Robert A.; Yang, Chung S.; Chen, Xiaoxin

    2007-01-01

    Oral cancer is a common neoplasm worldwide with tobacco and alcohol being the major etiological factors contributing to its pathogenesis. Epidermal growth factor receptor (EGFR) and ErbB2 are known to be involved in the development of oral cancer with the former up-regulated in up to 90% human cases. The goal of this study was to evaluate the chemopreventive effects of a dual inhibitor of EGFR and ErbB2 tyrosine kinases, GW2974, in the 7, 12-dimethylbenz[a]anthracene (DMBA)-induced hamster ch...

  2. (E-3-(Anthracen-9-yl-1-(furan-2-ylprop-2-en-1-oneThis paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand (King Rama IX for his sustainable development of the country.

    Directory of Open Access Journals (Sweden)

    Jirapa Horkaew

    2010-04-01

    Full Text Available In the molecule of the title heteroaryl chalcone derivative, C21H14O2, the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087 (1 Å] forms dihedral angles of 5.81 (7 and 49.85 (6°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the molecules are linked into a two-dimensional network parallel to (100 by C—H...O hydrogen bonds and π...π interactions involving the furan rings [centroid–centroid distance = 3.7205 (6 Å].

  3. Repair of DNA treated with. gamma. -irradiation and chemical carcinogens. Progress report, June 1, 1975--January 31, 1976. [MMS, methylnitrosourea, 7-bromomethyl-12-methylbenz(a)-anthracene, Escherichia coli

    Energy Technology Data Exchange (ETDEWEB)

    Goldthwait, D.A.

    1976-02-01

    Enzymatic mechanisms of DNA repair are under investigation. From E. coli an endonuclease active on apurinic acid has been separated from endonuclease II active on DNA treated with methylmethane sulfonate, methylnitrosourea, 7-bromomethyl-12-methylbenz(a)anthracene and ..gamma..-irradiation. Mutants have been identified for each enzyme. The purification of both enzymes is proceeding and the mechanism of action of endonuclease II which has both an N-glycosidase and a phosphodiester hydrolase activity is under investigation. Evidence demonstrating exonuclease III is an enzyme separate from the apurinic acid endonuclease and endonuclease II has been accumulated but this is still under investigation. Work has been completed on 7-bromomethyl-12-methylbenz(a)anthracene treated DNA as a substrate and is being continued on the inhibitory effects of phorbol ester on endonuclease II. Finally, the properties of an enzyme from calf liver active on depurinated DNA have been compared with those of a comparable enzyme from calf thymus. Evidence that they are isozymes has been found.

  4. Vitamin D postpones the progression of epithelial ovarian cancer induced by 7, 12-dimethylbenz [a] anthracene both in vitro and in vivo

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    Liu LZ

    2016-04-01

    Full Text Available Lizhi Liu,1,* Zhiyong Hu,2,* Hemei Zhang,3 Yongfeng Hou,1 Zengli Zhang,4 Guangming Zhou,5 Bingyan Li1,5 1School of Public Health, Medical College of Soochow University, Suzhou, 2Department of Chronic Disease Management, Lishui Center for Disease Control and Prevention, Lishui, 3Department of Chronic Disease Management, Wenzhou Center for Disease Control and Prevention, Wenzhou, 4Department of Labor Hygiene and Environmental Health, School of Public Health, Soochow University, Suzhou, 5School of Radiation Medicine and Protection, Soochow University, Suzhou, People’s Republic of China *These authors contributed equally to this work Purpose: Ovarian cancer is the most lethal malignancy of the female reproductive system, and the prevention and treatment of ovarian carcinoma are still far from optimal. Epidemiological studies reported that ovarian cancer risk was inversely associated with low level of 25-hydroxy vitamin D [25(OH]. Therefore, this study focuses on exploring the chemoprevention of vitamin D on epithelial ovarian cancer induced by 7, 12-dimethylbenz [a] anthracene (DMBA.Methods: The mouse ovarian surface epithelial cells were isolated from estrus mice by mild trypsinization and maintained in completed culture medium by repeated passaging. The malignant transformation of mouse ovarian surface epithelial cells was induced by DMBA in vitro. DMBA was directly injected into the bursa of mouse ovary to produce optimized in vivo ovarian cancer model.Results: The results indicate that 1α,25 dihydroxyvitamin D3 may delay malignant transformation of mouse ovarian surface epithelial cells induced by DMBA and significantly decreased the colony formation rate from 18.4% to 3.2% (P<0.05. There was a negative correlation between incidence of DMBA-induced tumor and 25-hydroxy vitamin D level (R2=0.978, P<0.05. Vitamin D3 can delay the progression of ovarian cancer induced by DMBA, and the administration of vitamin D3 during the whole process worked

  5. Acute 7,12-dimethylbenz[a]anthracene exposure causes differential concentration-dependent follicle depletion and gene expression in neonatal rat ovaries

    Energy Technology Data Exchange (ETDEWEB)

    Madden, Jill A. [Department of Animal Science, Iowa State University, Ames, IA 50011 (United States); Hoyer, Patricia B. [Department of Physiology, University of Arizona, Tucson, AZ 85724 (United States); Devine, Patrick J. [INRS—Institut Armand-Frappier Research Centre, University of Quebec, Laval, QC H7V 1B7 (Canada); Keating, Aileen F., E-mail: akeating@iastate.edu [Department of Animal Science, Iowa State University, Ames, IA 50011 (United States); Department of Physiology, University of Arizona, Tucson, AZ 85724 (United States)

    2014-05-01

    Chronic exposure to the polycyclic aromatic hydrocarbon 7,12-dimethylbenz[a]anthracene (DMBA), generated during combustion of organic matter including cigarette smoke, depletes all ovarian follicle types in the mouse and rat, and in vitro models mimic this effect. To investigate the mechanisms involved in follicular depletion during acute DMBA exposure, two concentrations of DMBA at which follicle depletion has (75 nM) and has not (12.5 nM) been observed were investigated. Postnatal day four F344 rat ovaries were maintained in culture for four days before a single exposure to vehicle control (1% DMSO; CT) or DMBA (12 nM; low-concentration or 75 nM; high-concentration). After four or eight additional days of culture, DMBA-induced follicle depletion was evaluated via follicle enumeration. Relative to control, DMBA did not affect follicle numbers after 4 days of exposure, but induced large primary follicle loss at both concentrations after 8 days; while, the low-concentration DMBA also caused secondary follicle depletion. Neither concentration affected primordial or small primary follicle number. RNA was isolated and quantitative RT-PCR performed prior to follicle loss to measure mRNA levels of genes involved in xenobiotic metabolism (Cyp2e1, Gstmu, Gstpi, Ephx1), autophagy (Atg7, Becn1), oxidative stress response (Sod1, Sod2) and the phosphatidylinositol 3-kinase (PI3K) pathway (Kitlg, cKit, Akt1) 1, 2 and 4 days after exposure. With the exception of Atg7 and cKit, DMBA increased (P < 0.05) expression of all genes investigated. Also, BECN1 and pAKT{sup Thr308} protein levels were increased while cKIT was decreased by DMBA exposure. Taken together, these results suggest an increase in DMBA bioactivation, add to the mechanistic understanding of DMBA-induced ovotoxicity and raise concern regarding female low concentration DMBA exposures. - Highlights: • Acute DMBA exposures induce large primary and/or secondary follicle loss. • Acute DMBA exposure did not impact

  6. 7,12-Dimethylbenz(a)anthracene-induced genotoxicity on bone marrow cells from mice phenotypically selected for low acute inflammatory response.

    Science.gov (United States)

    Katz, Iana Suly Santos; Albuquerque, Layra Lucy; Suppa, Alessandra Paes; da Silva, Graziela Batista; Jensen, José Ricardo; Borrego, Andrea; Massa, Solange; Starobinas, Nancy; Cabrera, Wafa Hanna Koury; De Franco, Marcelo; Borelli, Primavera; Ibañez, Olga Martinez; Ribeiro, Orlando Garcia

    2016-01-01

    Exposure to polycyclic aromatic hydrocarbon (PAH) environmental contaminants has been associated with the development of mutations and cancer. 7,12-Dimethylbenz(a)anthracene ( DMBA), a genotoxic agent, reacts with DNA directly, inducing p53-dependent cytotoxicity resulting in cell death by apoptosis or giving rise to cancer. DMBA metabolism largely depends on activation of the aryl hydrocarbon receptor (AhR). Mice phenotypically selected for high (AIRmax) or low (AIRmin) acute inflammatory response present a complete segregation of Ahr alleles endowed with low (Ahr(d)) or high (Ahr(b1)) affinity to PAHs, respectively. To evaluate the role of AhR genetic polymorphism on the bone marrow susceptibility to DMBA, AIRmax and AIRmin mice were treated with a single intraperitoneal injection of DMBA (50mg/kg b.w.) in olive oil. Bone marrow cells (BMCs) were phenotyped by both flow cytometry and cytoslide preparations. Despite a significant decrease in total cell count in BM from AIRmin mice, there was an increase of blast cells and immature neutrophils at 1 and 50 days after DMBA treatment, probably due to a cell-cycle blockade at the G1/S transition leading to immature stage cell production. A panel of proteins related to cell cycle regulation was evaluated in immature BM cells (Lin(-)) by Western Blot, and DNA damage and repair were measured using an alkaline version of the Comet assay. In Lin(-) cells isolated from AIRmin mice, high levels were found in both p53 and p21 protein contents in contrast with the low levels of CDK4 and Ciclin D1. Evaluation of DNA repair in DMBA-treated BMCs, indicated long-lasting genotoxicity and cytotoxicity in BMC from AIRmin mice and a blockade of cell cycle progression. On the other hand, AIRmax mice have a high capacity of DNA damage repair and protection. These mechanisms can be associated with the differential susceptibility to the toxic and carcinogenic effects of DMBA observed in these mice. PMID:26687588

  7. Acute 7,12-dimethylbenz[a]anthracene exposure causes differential concentration-dependent follicle depletion and gene expression in neonatal rat ovaries

    International Nuclear Information System (INIS)

    Chronic exposure to the polycyclic aromatic hydrocarbon 7,12-dimethylbenz[a]anthracene (DMBA), generated during combustion of organic matter including cigarette smoke, depletes all ovarian follicle types in the mouse and rat, and in vitro models mimic this effect. To investigate the mechanisms involved in follicular depletion during acute DMBA exposure, two concentrations of DMBA at which follicle depletion has (75 nM) and has not (12.5 nM) been observed were investigated. Postnatal day four F344 rat ovaries were maintained in culture for four days before a single exposure to vehicle control (1% DMSO; CT) or DMBA (12 nM; low-concentration or 75 nM; high-concentration). After four or eight additional days of culture, DMBA-induced follicle depletion was evaluated via follicle enumeration. Relative to control, DMBA did not affect follicle numbers after 4 days of exposure, but induced large primary follicle loss at both concentrations after 8 days; while, the low-concentration DMBA also caused secondary follicle depletion. Neither concentration affected primordial or small primary follicle number. RNA was isolated and quantitative RT-PCR performed prior to follicle loss to measure mRNA levels of genes involved in xenobiotic metabolism (Cyp2e1, Gstmu, Gstpi, Ephx1), autophagy (Atg7, Becn1), oxidative stress response (Sod1, Sod2) and the phosphatidylinositol 3-kinase (PI3K) pathway (Kitlg, cKit, Akt1) 1, 2 and 4 days after exposure. With the exception of Atg7 and cKit, DMBA increased (P < 0.05) expression of all genes investigated. Also, BECN1 and pAKTThr308 protein levels were increased while cKIT was decreased by DMBA exposure. Taken together, these results suggest an increase in DMBA bioactivation, add to the mechanistic understanding of DMBA-induced ovotoxicity and raise concern regarding female low concentration DMBA exposures. - Highlights: • Acute DMBA exposures induce large primary and/or secondary follicle loss. • Acute DMBA exposure did not impact

  8. (1,4,7,10,13,16-Hexaoxacyclooctadecane-κ6Obis(tetrahydrofuran-κOpotassium bis[(1,2,3,4-η-anthracene]cobalt(−I tetrahydrofuran monosolvate

    Directory of Open Access Journals (Sweden)

    Haiyan He

    2014-01-01

    Full Text Available The asymmetric unit of the title compound, [K(C12H24O6(C4H8O2][Co(C14H102]·C4H8O, consists of one cationic potassium complex, one anionic cobalt dianthracene complex and one tetrahydrofuran solvent molecule. The potassium cation is situated at the centre of an 18-crown-6 molecule and between two tetrahydrofuran molecules, the latter coordinating above and below the mean plane formed by the O atoms of the crown ether molecule. The Co atom is coordinated by eight C atoms of two anthracene molecules in an η4 manner. The third free tetrahydrofuran molecule shows orientational disorder on two partially occupied positions [occupancy ratio 0.561 (8:0.439 (8].

  9. Crystal structure of 2-[(3S,4S-4-(anthracen-9-yl-1-(4-methoxyphenyl-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione unknown solvate

    Directory of Open Access Journals (Sweden)

    Ísmail Çelik

    2015-03-01

    Full Text Available The central β-lactam ring of the title compound, C36H24N2O4, is almost planar (r.m.s. deviation = 0.003 Å and makes dihedral angles of 17.17 (19, 89.76 (17 and 78.44 (17° with the benzene ring, the anthracene ring (r.m.s. deviation = 0.003 Å and the 1H-benzo[de]isoquinoline-1,3(2H-dione moiety, which is nearly planar [maximum deviation = 0.098 (2 Å], respectively. The molecular structure is stabilized by an intramolecular C—H...N hydrogen bond. In the crystal, molecules are linked via C—H...π and π–π stacking interactions [centroid–centroid distances = 3.5270 (19 and 3.779 (2 Å], forming a three-dimensional structure. A region of disordered electron density, probably disordered solvent molecules, was treated with the SQUEEZE procedure in PLATON [Spek (2015. Acta Cryst. C71, 9–18], which indicated a solvent cavity of 322 Å3 containing approximately 91 electrons. Their formula mass and unit-cell characteristics were not taken into account during the refinement.

  10. Modulatory Effect of Taurine on 7,12-Dimethylbenz(a)Anthracene-Induced Alterations in Detoxification Enzyme System, Membrane Bound Enzymes, Glycoprotein Profile and Proliferative Cell Nuclear Antigen in Rat Breast Tissue.

    Science.gov (United States)

    Vanitha, Manickam Kalappan; Baskaran, Kuppusamy; Periyasamy, Kuppusamy; Selvaraj, Sundaramoorthy; Ilakkia, Aruldoss; Saravanan, Dhiravidamani; Venkateswari, Ramachandran; Revathi Mani, Balasundaram; Anandakumar, Pandi; Sakthisekaran, Dhanapal

    2016-08-01

    The modulatory effect of taurine on 7,12-dimethylbenz(a)anthracene (DMBA)-induced breast cancer in rats was studied. DMBA (25 mg/kg body weight) was administered to induce breast cancer in rats. Protein carbonyl levels, activities of membrane bound enzymes (Na(+) /K(+) ATPase, Ca(2+) ATPase, and Mg(2+) ATPase), phase I drug metabolizing enzymes (cytochrome P450, cytochrome b5, NADPH cytochrome c reductase), phase II drug metabolizing enzymes (glutathione-S-transferase and UDP-glucuronyl transferase), glycoprotein levels, and proliferative cell nuclear antigen (PCNA) were studied. DMBA-induced breast tumor bearing rats showed abnormal alterations in the levels of protein carbonyls, activities of membrane bound enzymes, drug metabolizing enzymes, glycoprotein levels, and PCNA protein expression levels. Taurine treatment (100 mg/kg body weight) appreciably counteracted all the above changes induced by DMBA. Histological examination of breast tissue further supported our biochemical findings. The results of the present study clearly demonstrated the chemotherapeutic effect of taurine in DMBA-induced breast cancer. PMID:27091720

  11. Evaluation of 3-(4'-(4″-fluorophenyl)-6'-phenylpyrimidin-2'-yl)-2-phenylthiazolidin-4-one for in vivo modulation of biomarkers of chemoprevention in the 7,12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis.

    Science.gov (United States)

    Thanusu, J; Kanagarajan, V; Nagini, S; Gopalakrishnan, M

    2011-06-01

    A new bis heterocycle comprising both bioactive 2-aminopyrimidine and thiazolidin-4-one nuclei namely 3-(4'-(4″-fluorophenyl)-6'-phenylpyrimidin-2'-yl)-2-phenylthiazolidin-4-one 3 was synthesized, characterized with the help of melting point, elemental analysis, FT-IR, MS, one-dimensional NMR ((1)H, (13)C) spectra and we evaluated the chemopreventive potential of 3-(4'-(4″-fluorophenyl)-6'-phenylpyrimidin-2'-yl)-2-phenylthiazolidin-4-one based on in vivo inhibitory effects on 7,12-dimethylbenz[a]anthracene (DMBA)-induced hamster buccal pouch carcinogenesis. Administration of 3 effectively suppressed oral carcinogenesis initiated with DMBA as revealed by the reduced incidence of neoplasms. Lipid peroxidation, glutathione (GSH) content, and the activities of glutathione peroxidase (GPx), glutathione S-transferase (GST) were used to biomonitor the chemopreventive potential of 3. Lipid peroxidation was found to be significantly decreased, whereas GSH, GPx, GST, and GGT were elevated in the oral mucosa of tumor-bearing animals. Our data suggest that 3 may exert its chemopreventive effects in the oral mucosa by modulation of lipid peroxidation and enhancing the levels of GSH, GPx, and GST. PMID:21028942

  12. Combinatorial chemopreventive effect of butyric acid, nicotinamide and calcium glucarate against the 7,12-dimethylbenz(a)anthracene induced mouse skin tumorigenesis attained by enhancing the induction of intrinsic apoptotic events.

    Science.gov (United States)

    Tiwari, Prakash; Sahay, Satya; Pandey, Manuraj; Qadri, Syed S Y H; Gupta, Krishna P

    2015-01-25

    We explored the basis of the combinatorial chemopreventive effect of butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) on mouse skin exposed to 7,12-dimethylbenz(a)anthracene (DMBA). We studied the effects of topical application of DMBA in the presence or absence of BA, NA and CAG on the regulators of apoptosis. DMBA treatment suppressed Bax, Bax/Bcl-2 ratio, release of cyt c, Apaf1, caspase-9, -3 mediated apoptosis. Downregulation of p21 and upregulation of Bcl-2, mut p53 were also observed in only DMBA treated mice. Simultaneous application of BA, NA and CAG induced a mitochondria-mediated apoptosis, characterized by a rise in the Bax, Bax/Bcl-2 ratio, release of cyt c, upregulation of Apaf1 with down-stream activation of caspase-9, -3. Furthermore treatment with BA, NA and CAG demonstrated an upregulation of p21 and downregulation of Bcl-2, mut p53. But this effect was enhanced in the presence of all the three compounds together in combination. Chemoprevention by a combination of BA, NA and CAG by inducing the apoptosis, the natural cell death, suggest the importance of the potential combinational strategies capable of preventing skin tumor development. PMID:25478867

  13. Modulation of miR-203 and its regulators as a function of time during the development of 7, 12 dimethylbenz [a] anthracene induced mouse skin tumors in presence or absence of the antitumor agents.

    Science.gov (United States)

    Tiwari, Prakash; Gupta, Krishna P

    2014-07-15

    We investigated the chemopreventive effects of naturally occurring compounds like butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) individually or in combination in 7, 12-dimethylbenz [a] anthracene (DMBA) treated mouse skin at 4 and 16 weeks, the time before and after the tumor development. DMBA application did not show any skin tumors at 4 weeks but well defined tumors appeared at 16 weeks. BA, NA or CAG prevented the tumor development significantly but the protection was highly enhanced when all these compounds were given together. In order to see the molecular changes progressing with tumors, we showed the downregulation of tumor suppressor miR-203 at 16 weeks and upregulation of histone deacetylases (HDAC), DNA methyltransferase, promoter methylation of miR-203 at 4 or 16 weeks. Regulators of micro RNA biogenesis such as DICER1 and Ago2 were also deregulated by DMBA. Proto-oncogene c-myc and BMI1 were upregulated and tumor suppressor gene p16 was downregulated by DMBA as a function of time. Effects of BA, NA or CAG were more pronounced after 16 weeks as compared to 4 weeks in preventing the tumor development and altered gene expression. Concomitant administration of BA, NA and CAG tried to prevent these alterations more effectively than that of individual compound possibly by regulating miR-203 status through epigenetic or biogenetic modulations before and after the tumor development. Study provides a rationale for chemoprevention by combination of different compounds targeting miR-203. PMID:24792773

  14. Modulation of miR-203 and its regulators as a function of time during the development of 7, 12 dimethylbenz [a] anthracene induced mouse skin tumors in presence or absence of the antitumor agents

    International Nuclear Information System (INIS)

    We investigated the chemopreventive effects of naturally occurring compounds like butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) individually or in combination in 7, 12-dimethylbenz [a] anthracene (DMBA) treated mouse skin at 4 and 16 weeks, the time before and after the tumor development. DMBA application did not show any skin tumors at 4 weeks but well defined tumors appeared at 16 weeks. BA, NA or CAG prevented the tumor development significantly but the protection was highly enhanced when all these compounds were given together. In order to see the molecular changes progressing with tumors, we showed the downregulation of tumor suppressor miR-203 at 16 weeks and upregulation of histone deacetylases (HDAC), DNA methyltransferase, promoter methylation of miR-203 at 4 or 16 weeks. Regulators of micro RNA biogenesis such as DICER1 and Ago2 were also deregulated by DMBA. Proto-oncogene c-myc and BMI1 were upregulated and tumor suppressor gene p16 was downregulated by DMBA as a function of time. Effects of BA, NA or CAG were more pronounced after 16 weeks as compared to 4 weeks in preventing the tumor development and altered gene expression. Concomitant administration of BA, NA and CAG tried to prevent these alterations more effectively than that of individual compound possibly by regulating miR-203 status through epigenetic or biogenetic modulations before and after the tumor development. Study provides a rationale for chemoprevention by combination of different compounds targeting miR-203. - Highlights: • DMBA modulates miR-203 and its regulator before and after the onset of tumors. • Suppression of miR-203 and p16 could be the result of gene promoter methylation. • BA, NA or CAG prevents the effects of DMBA. • Combination of BA, NA or CAG is more effective in preventing the DMBA modulations

  15. A Comparative Account of the Kinetics of Light-Induced E-Z Isomerization of an Anthracene-Based Organogelator in Sol, Gel, Xerogel, and Powder States: Fiber to Crystal Transformation.

    Science.gov (United States)

    Mondal, Sanjoy; Chakraborty, Priyadarshi; Das, Sujoy; Bairi, Partha; Nandi, Arun K

    2016-05-31

    The organogel of (E)-N'-(anthracene-10-ylmethylene)-3,4,5-tris(dodecyloxy)benzohydrazide (I) in methyl cyclohexane having a fibrillar network structure exhibits excellent fluorescence, which decreases sharply with time upon photoirradiation at λ = 365 nm. It has been attributed to the transformation of the E isomer of I to the Z isomer, and the kinetics of E-Z isomerization are compared for the sol, gel, xerogel, and powder states. The rate constants at different temperatures are measured from Avrami plots and its increase with an increase in temperature, indicating temperature acts as a promoter for photoirradiated E-Z isomeization along the imine (C═N) bond. In the powder form, the rate constant values are the lowest compared to those of other states for all temperatures and the xerogels exhibit the highest rate of E-Z isomerization. The rate constants of sol and gel states mostly lie between the two. The wide-angle X-ray scattering pattern changes after ultraviolet (UV) irradiation with the generation of new sharp peaks whose intensities increase with an increase in irradiation time. A polarized optical microscopic study indicates formation of small crystalline dots on the fibers in the gels, dendritic morphology on the xerogel fibers, and large needlelike morphology at the surface boundary of the solid. The dried I gel exhibits a melting peak at 96.7 °C, but upon irradiation, two peaks are observed at 98.5 and 152.7 °C; the latter has been attributed to the melting of crystals of Z isomers. Similar higher melting peaks are observed both for the xerogel and for powders after UV irradiation; the powders exhibit the highest meting peak at 159.4 °C. Possible reasons for the variation of rate constant values in the four different states and the difference in morphology and melting points of crystals of Z isomers of I are discussed. PMID:27159227

  16. UV-B辐射和蒽共同作用对三叶浮萍的毒性效应%Joint Toxic Effects of UV-B Radiation and Anthracene on Lemna Minor

    Institute of Scientific and Technical Information of China (English)

    张攀; 王仁君; 周晶; 沙未来

    2012-01-01

    本实验采用常见的三叶浮萍作为实验材料,研究了多环芳烃( PAHs)蒽(Anthracene)与UV-B辐射单独胁迫和共同作用对浮萍(Lemna minor)的毒性效应.浮萍的初始个数为45个,蒽的质量浓度分别设为0、0.5、2.5、5、10、20mg·L-1,设计三个个平行组,每组辐射剂量均是810 J·m-2.结果表明,蒽、紫外线单独胁迫都会对浮萍产生损害,使其生长量有下降趋势.当辐射剂量达到810 J·m-2时,叶绿素含量达到最大,随着辐射剂量的增加,叶绿素含量减少.且随着蒽浓度的不断增大,对浮萍生长的其抑制作用更加明显,存在着明显的剂量-效应关系.蒽和UV-B辐射共同作用对浮萍产生抑制作用,并且随着蒽浓度的增加,抑制作用逐渐增强.

  17. Modulation of miR-203 and its regulators as a function of time during the development of 7, 12 dimethylbenz [a] anthracene induced mouse skin tumors in presence or absence of the antitumor agents

    Energy Technology Data Exchange (ETDEWEB)

    Tiwari, Prakash; Gupta, Krishna P., E-mail: krishnag522@yahoo.co.in

    2014-07-15

    We investigated the chemopreventive effects of naturally occurring compounds like butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) individually or in combination in 7, 12-dimethylbenz [a] anthracene (DMBA) treated mouse skin at 4 and 16 weeks, the time before and after the tumor development. DMBA application did not show any skin tumors at 4 weeks but well defined tumors appeared at 16 weeks. BA, NA or CAG prevented the tumor development significantly but the protection was highly enhanced when all these compounds were given together. In order to see the molecular changes progressing with tumors, we showed the downregulation of tumor suppressor miR-203 at 16 weeks and upregulation of histone deacetylases (HDAC), DNA methyltransferase, promoter methylation of miR-203 at 4 or 16 weeks. Regulators of micro RNA biogenesis such as DICER1 and Ago2 were also deregulated by DMBA. Proto-oncogene c-myc and BMI1 were upregulated and tumor suppressor gene p16 was downregulated by DMBA as a function of time. Effects of BA, NA or CAG were more pronounced after 16 weeks as compared to 4 weeks in preventing the tumor development and altered gene expression. Concomitant administration of BA, NA and CAG tried to prevent these alterations more effectively than that of individual compound possibly by regulating miR-203 status through epigenetic or biogenetic modulations before and after the tumor development. Study provides a rationale for chemoprevention by combination of different compounds targeting miR-203. - Highlights: • DMBA modulates miR-203 and its regulator before and after the onset of tumors. • Suppression of miR-203 and p16 could be the result of gene promoter methylation. • BA, NA or CAG prevents the effects of DMBA. • Combination of BA, NA or CAG is more effective in preventing the DMBA modulations.

  18. Preventive effects of butyric acid, nicotinamide, calcium glucarate alone or in combination during the 7, 12-dimethylbenz (a) anthracene induced mouse skin tumorigenesis via modulation of K-Ras-PI3K-AKTpathway and associated micro RNAs.

    Science.gov (United States)

    Tiwari, Prakash; Sahay, Satya; Pandey, Manuraj; Qadri, Syed S Y H; Gupta, Krishna P

    2016-02-01

    Skin cancer is among the most common cancers worldwide and identifiable molecular changes for early and late stage of skin tumorigenesis can suggest the better targets for its control. In this study, we investigated the status of K-Ras-PI3K-AKTpathway followed by NF-κB, cyclin D1, MMP-9 and regulatory micro RNA during 7, 12-dimethylbenz[a]anthracene (DMBA) induced mouse skin tumorigenesis and its prevention by butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG), individually or in combination with respect to time. DMBA upregulated the K-Ras, PI3K, Akt, NF-κB, cyclin D1 and MMP-9, but downregulated the PTEN in a time dependent manner. DMBA also reduced the levels of micoRNA let-7a but induced the levels of miR-21 and miR-20a as a function of time. BA, NA and CAG were found to prevent DMBA induced changes, but they were most effective when used together in a combination. Reduced let-7a and miR-211 were correlated with the overexpression of K-Ras and MMP-9. Overexpression of miR-21 and miR-20a was correlated with the down regulation of PTEN and overexpression of Cyclin D1. Collectively, the enhanced chemopreventive potential of natural compound in combination via regulation of K-Ras-PI3K-AKTpathway along with regulatory micro RNAs provide a newer and effective mean for cancer management. PMID:26655363

  19. The relationship between sirtuin 1 (SIRT1 expression and tumor size, Proliferating Cell Nuclear Antigen (PCNA expression and histological grading in rat breast carcinoma induced by dimethylbenz(anthracene (DMBA

    Directory of Open Access Journals (Sweden)

    Novrita Padauleng Dewajani Purnomosari, Sri Herwiyanti Harjadi, Irianiwati, Sitarina Widyarini

    2014-08-01

    Full Text Available Controversy regarding the role of SIRT1 in pathology of cancers exists and is still under debate.SIRT1 could act as either a tumor supressor or tumor promotor. This study was conducted toevaluate the relationship between SIRT1 expression and tumor size, Proliferating Cell NuclearAntigen (PCNA expression and histological grading in rat breast carcinoma induced bydimethylbenz(áanthracene (DMBA. Thirty female Sprague Dawley rats were randomly allocatedinto three groups with 10 rats in each group. Group 1 as negative control was just fed thestandard food. Group 2 as vehicle control was fed the standard food and corn oil. Group 3 asinduction group was fed the standard food and induced with DMBA at dose of 20 mg/kg bodyweight (BW in corn oil twice a week for five weeks. All rats were palpated weekly to determinethe appearance, size and location of tumors. Sixteen weeks after DMBA induction rats weresacrified and histological preparations of the breast carcinoma tissue were then processed forSIRT1 and PCNA expression examination as well as histological grading. The result showed thatSIRT1 expression was significantly higher in breast carcinoma tissue compared to normal gland(26.12 vs 0.05; p = 0.004. SIRT1-positive was observed mostly in poor histological gradecarcinomas (56.2%, and it was not observed in good histological grade carcinomas. However,there was no significantly difference between SIRT1 and histological grading (p = 0.097; r =0.285. A significant correlation between SIRT1 expression and the tumor size (p =0.009; r=0.877, as well as PCNA expression (p =0.000; r =0.790 was observed. In conclusion, thereis relationship between SIRT1 expression and tumor size as well as PCNA expression in rat breastcarcinoma induced by DMBA.

  20. CYP1 and AhR expression in 7,12-dimethylbenz[a]anthracene-induced mammary carcinoma of rats prenatally exposed to 3,3',4,4',5-pentachlorobiphenyl

    International Nuclear Information System (INIS)

    We previously reported the finding that prenatal exposure to a relatively low dose of 3,3',4,4',5-pentachlorobiphenyl (PCB126) acted as an enhancing agent for 17-beta-estradiol (E2)-dependent 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary carcinoma, while a high dose decreased it. E2 is a known risk factor for mammary carcinoma, and CYP1A1 and 1B1 (CYP1) are the major enzymes catalyzing 2- and 4-hydroxylation of E2, respectively. We investigated the induction of CYP1 and aryl hydrocarbon receptor (AhR) in DMBA-induced mammary carcinoma using female Sprague-Dawley rats whose dams had been treated (i.g.) with 2.5 ng, 250 ng, 7.5 μg of PCB126/kg or the vehicle on days 13-19 post-conception. Immunohistochemical analysis revealed that the mammary carcinoma of the 250 ng group showed a significantly higher number of nuclei expressing estrogen receptor α (ER) and proliferating cell nuclear antigen (PCNA) compared to those of the other groups. Quantitative real-time RT-PCR analysis revealed that the 7.5 μg group showed a significantly higher level of CYP1A1 mRNA, and that the 250 ng group showed significantly higher levels of CYP1B1 mRNA. The level of AhR mRNA was significantly higher in both the 7.5 μg and 250 ng groups. Western blotting analysis was consistent with mRNA changes. It has been revealed that CYP1B1 catalyzes a step in the formation of 4-hydroxylated E2 metabolites, which show quite high mammary carcinogenicity. This study indicates that the enhancement of DMBA-induced mammary carcinogenicity in a relatively low PCB126 dose group might partially involve the higher expression of CYP1B1 and AhR in these carcinomas

  1. Metformin inhibits 7,12-dimethylbenz[a]anthracene-induced breast carcinogenesis and adduct formation in human breast cells by inhibiting the cytochrome P4501A1/aryl hydrocarbon receptor signaling pathway

    International Nuclear Information System (INIS)

    Recent studies have established that metformin (MET), an oral anti-diabetic drug, possesses antioxidant activity and is effective against different types of cancer in several carcinogen-induced animal models and cell lines. However, whether MET can protect against breast cancer has not been reported before. Therefore, the overall objectives of the present study are to elucidate the potential chemopreventive effect of MET in non-cancerous human breast MCF10A cells and explore the underlying mechanism involved, specifically the role of cytochrome P4501A1 (CYP1A1)/aryl hydrocarbon receptor (AhR) pathway. Transformation of the MCF10A cells into initiated breast cancer cells with DNA adduct formation was conducted using 7,12-dimethylbenz[a]anthracene (DMBA), an AhR ligand. The chemopreventive effect of MET against DMBA-induced breast carcinogenesis was evidenced by the capability of MET to restore the induction of the mRNA levels of basic excision repair genes, 8-oxoguanine DNA glycosylase (OGG1) and apurinic/apyrimidinic endonuclease1 (APE1), and the level of 8-hydroxy-2-deoxyguanosine (8-OHdG). Interestingly, the inhibition of DMBA-induced DNA adduct formation was associated with proportional decrease in CYP1A1 and in NAD(P)H:quinone oxidoreductase 1 (NQO1) gene expression. Mechanistically, the involvements of AhR and nuclear factor erythroid 2-related factor-2 (Nrf2) in the MET-mediated inhibition of DMBA-induced CYP1A1 and NQO1 gene expression were evidenced by the ability of MET to inhibit DMBA-induced xenobiotic responsive element and antioxidant responsive element luciferase reporter gene expression which suggests an AhR- and Nrf2-dependent transcriptional control. However, the inability of MET to bind to AhR suggests that MET is not an AhR ligand. In conclusion, the present work shows a strong evidence that MET inhibits the DMBA-mediated carcinogenicity and adduct formation by inhibiting the expression of CYP1A1 through an AhR ligand-independent mechanism

  2. Metformin inhibits 7,12-dimethylbenz[a]anthracene-induced breast carcinogenesis and adduct formation in human breast cells by inhibiting the cytochrome P4501A1/aryl hydrocarbon receptor signaling pathway

    Energy Technology Data Exchange (ETDEWEB)

    Maayah, Zaid H. [Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh 11451 (Saudi Arabia); Ghebeh, Hazem [Stem Cell & Tissue Re-Engineering, King Faisal Specialist Hospital and Research Center, Riyadh 11211 (Saudi Arabia); Alhaider, Abdulqader A. [Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh 11451 (Saudi Arabia); Camel Biomedical Research Unit, College of Pharmacy and Medicine, King Saud University, Riyadh 11451 (Saudi Arabia); El-Kadi, Ayman O.S. [Faculty of Pharmacy & Pharmaceutical Sciences, University of Alberta, Edmonton (Canada); Soshilov, Anatoly A.; Denison, Michael S. [Department of Environmental Toxicology, University of California at Davis, Davis, CA 95616 (United States); Ansari, Mushtaq Ahmad [Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh 11451 (Saudi Arabia); Korashy, Hesham M., E-mail: hkorashy@ksu.edu.sa [Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh 11451 (Saudi Arabia)

    2015-04-15

    Recent studies have established that metformin (MET), an oral anti-diabetic drug, possesses antioxidant activity and is effective against different types of cancer in several carcinogen-induced animal models and cell lines. However, whether MET can protect against breast cancer has not been reported before. Therefore, the overall objectives of the present study are to elucidate the potential chemopreventive effect of MET in non-cancerous human breast MCF10A cells and explore the underlying mechanism involved, specifically the role of cytochrome P4501A1 (CYP1A1)/aryl hydrocarbon receptor (AhR) pathway. Transformation of the MCF10A cells into initiated breast cancer cells with DNA adduct formation was conducted using 7,12-dimethylbenz[a]anthracene (DMBA), an AhR ligand. The chemopreventive effect of MET against DMBA-induced breast carcinogenesis was evidenced by the capability of MET to restore the induction of the mRNA levels of basic excision repair genes, 8-oxoguanine DNA glycosylase (OGG1) and apurinic/apyrimidinic endonuclease1 (APE1), and the level of 8-hydroxy-2-deoxyguanosine (8-OHdG). Interestingly, the inhibition of DMBA-induced DNA adduct formation was associated with proportional decrease in CYP1A1 and in NAD(P)H:quinone oxidoreductase 1 (NQO1) gene expression. Mechanistically, the involvements of AhR and nuclear factor erythroid 2-related factor-2 (Nrf2) in the MET-mediated inhibition of DMBA-induced CYP1A1 and NQO1 gene expression were evidenced by the ability of MET to inhibit DMBA-induced xenobiotic responsive element and antioxidant responsive element luciferase reporter gene expression which suggests an AhR- and Nrf2-dependent transcriptional control. However, the inability of MET to bind to AhR suggests that MET is not an AhR ligand. In conclusion, the present work shows a strong evidence that MET inhibits the DMBA-mediated carcinogenicity and adduct formation by inhibiting the expression of CYP1A1 through an AhR ligand-independent mechanism

  3. Cytochrome P450-dependent binding of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[a]pyrene (B[a]P) in murine heart, lung, and liver endothelial cells

    Energy Technology Data Exchange (ETDEWEB)

    Lizette Granberg, A.; Brunstroem, B.; Brandt, I. [Uppsala Univ. (Sweden). Dept. of Environmental Toxicology

    2000-12-01

    Autoradiography was used to investigate the cellular sites of irreversible binding of {sup 3}H-labelled 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[a]pyrene (B[a]P) in mice. Autoradiograms obtained from solvent-extracted tape-sections revealed an even distribution of DMBA- and B[a]P-derived radioactivity in control mice lacking sites of selective binding in the tissues. In mice pretreated with a cytochrome P4501A (CYPIA) inducer, {beta}-naphthoflavone (BNF) or 3,3',4,4', 5-pentachlorobiphenyl (PCB 126), a noticeable accumulation of bound radioactivity was observed in the pulmonary alveolar region. Increased labelling was also observed in heart tissue of induced mice. As demonstrated by microautoradiography of tissues from CYP1A-induced mice treated with {sup 3}H-DMBA or {sup 3}H-B[a]P in vivo, irreversible binding in lung tissue was present in endothelial cells of arteries and veins, in the alveolar septal walls, and in type 2 pneumocytes. In heart tissue, binding was confined to endothelial cells of arteries, capillaries and veins. In liver, binding was found in the hepatocytes as well as in endothelial cells of the portal veins, whereas no binding was seen in endothelial cells of the sinusoids, central veins, or arteries. These findings were confirmed in vitro using {sup 3}H-DMBA-exposed precision-cut slices, indicating that reactive intermediates of DMBA and B(a)P were formed in situ. The addition of the CYP1A inhibitor ellipticine abolished binding in the target endothelial cells. Increased endothelial binding in the lungs and liver of CYP1A-induced mice was concomitant with increased 7-ethoxyresorufin O-deethylase (EROD) and DMBA hydroxylase activity. In heart, endothelial binding was positively correlated with EROD, but not with DMBA hydroxylase. The results suggest that endothelial cells may be targets for CYP-dependent activation of such toxicants as polycyclic aromatic hydrocarbons. Consequently, the possibility that chemically induced

  4. RING FISSION OF ANTHRACENE BY A EUKARYOTE

    Science.gov (United States)

    Ligninolytic fungi are unique among eukaryotes in their ability to degrade polycyclic aromatic hydrocarbons (PAHs), but the mechanism for this process is unknown. lthough certain PAHs are oxidized in vitro by the fungal lignin peroxidases (LiPs) that catalyze ligninolysis, it has...

  5. (6aS,11aR,11cS-8-Sulfanylidene-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate

    Directory of Open Access Journals (Sweden)

    Liang Wang

    2011-07-01

    Full Text Available The title compound, C15H23N2S+·Cl−·0.5H2O, was prepared from (6aS,11aR,11cS-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracene-8-one (sophocarpine and Lawesson's reagent. The thione-substituted ring is in an envelope conformation and the three other six-membered rings are in chair conformations. In the crystal, anions and cations are linked by N—H...Cl and weak C—H...Cl hydrogen bonds. One 0.5-occupancy solvent water molecule lies on a twofold rotation axis and another 0.25-occupancy solvent water molecule is in a general position. The H atoms of these water molecules were not located or included in the refinement.

  6. Redetermination of (E-3-(anthracen-9-yl-1-(2-hydroxyphenylprop-2-en-1-oneThis paper is dedicated to Her Royal Highness Princess Chulabhorn Walailak of Thailand for her contributions to science on the occasion of her 54th birthday, which fell on July 4th, 2011.

    Directory of Open Access Journals (Sweden)

    Jaruwan Joothamongkhon

    2011-10-01

    Full Text Available The redetermined structure of title chalcone derivative, C23H16O2, corrects errors in the title, scheme and synthesis in the previous report of the same structure [Jasinski et al. (2011. Acta Cryst. E67, o795]. There are two independent molecules in the asymmetric unit with slight differences in bond lengths and angles. The dihedral angle between the benzene ring and the anthracene ring system is 73.30 (4° in one molecule and 73.18 (4° in the other. Both molecules feature an intramolecular O—H...O hydrogen bond, which generates an S(6 ring. In the crystal, molecules are arranged into sheets lying parallel to the ac plane and further stacked along the b axis by π–π interactions with centroid–centroid distances in the range 3.6421 (6–3.7607 (6 Å. The crystal structure is further stabilized by C—H...π interactions. There are also C...O [3.2159 (15 Å] short contacts.

  7. Contaminação do solo com antraceno e creosoto e o crescimento vegetal e a colonização micorrízica pelo Glomus etunicatum Soil contamination with anthracene and creosote: impact on plant growth and mycorrhizal colonization by Glomus etunicatum

    Directory of Open Access Journals (Sweden)

    Alessandra Monteiro de Paula

    2007-08-01

    -derived, polycyclic aromatic hydrocarbons (PAHs, is a growing problem with serious environmental consequences. To evaluate the environmental impact of these products it is important to understand their effects on plants and the associated microbiota. The effects of PAHs on growth and mycorrhizal colonization of Brachiaria brizantha and Pueraria phaseoloides were evaluated here. Two PAHs, anthracene and creosote, were applied to a soil infested with the mycorrhizal fungus Glomus etunicatum at varied concentrations: anthracene (0; 0.25; 0.5; 0.75 and 1 g kg-1 soil and creosote (0; 0.5; 1; 2 and 3 g kg-1 soil. This soil was packed into plastic tubes (290 cm³ where test plants were sown and grown for six weeks. It was found that anthracene did not affect pueraria growth and had a slight stimulus on brachiaria growth at the lowest concentration, whereas creosote had no effect on pueraria either, but inhibited brachiaria growth. Both contaminants inhibited mycorrhizal colonization in pueraria by about 90 %, compared to the control. At concentrations below those found in contaminated soils, AM colonization was inhibited by 50 %. The potential impact of these products on plant-AM fungus relationships is quite evident here. No colonization was found in brachiaria, regardless of the presence of PAHs. The results showed a differentiated sensitivity of the plants to the contaminants and their marked negative effect on G. etunicatum root colonization. In the evaluated concentration range, pueraria was insensitive to both compounds, which indicates the species for further studies on phytoremediation of areas under the impact of these contaminants.

  8. Renoprotective effects of Moringa oleifera pods in 7,12-dimethylbenz[a]anthracene-exposed mice%油椒木豆荚提取物对二甲基苯蒽诱导小鼠肾组织损伤的保护作用

    Institute of Scientific and Technical Information of China (English)

    Veena Sharma; Ritu Paliwal; Pracheta Janmeda; Shatruhan Sharma

    2012-01-01

    目的:通过二甲基苯蒽(7,12-dimethylbenz[a]anthracene,DMBA)诱导雄性白化小鼠肾组织损伤来研究油椒木豆荚的水乙醇提取物对肾脏的保护作用.方法:予实验小鼠口服15 mg/kg DMBA两周前,分别予200和400 mg/kg的油椒木豆荚的水乙醇提取物以及浓度为0.5%和1%的叔丁基对羟基茴香醚灌胃.测定各组小鼠细胞色素(cytochrome,Cyt)P450及Cytb5、还原型谷光甘肽(reduced glutathione,GSH)、谷胱甘肽转移酶(glutathione-S-transferase,GST)以及肾组织天冬氨酸氨基转移酶( aspartate transaminase,AST)、丙氨酸氨基转移酶(alanine transaminase,ALT)、碱性磷酸酶(alkaline phosphatase,ALP)活性及总胆固醇和蛋白质含量.结果:口服15 mg/kg的DMBA可显著增加小鼠Cyt P450和Cyt b5的浓度(P<0.01).小鼠肾组织GSH、GST活性显著降低(P<0.01,P<0.05).实验小鼠在口服DMBA后,肾组织AST、ALT、ALP活性和蛋白质含量也显著降低,总胆固醇含量则显著增加(P<0.01).但是经200和400 mg/kg油椒木豆荚提取物预处理14 d的实验小鼠,其由DMBA诱发的各项组织生化指标变化发生显著逆转(P<0.01).结论:油椒木豆荚的提取物可通过提高细胞抗氧化活性、减少自由基的生成来减少DMBA的毒副作用,起到保护肾组织的作用.%OBJECTIVE:To investigate the potential of hydroethanolic extract of Moringa oleifera (MOHE) against 7,12-dimethylbenz[a]anthracene (DMBA)-induced toxicity in male Swiss albino mice.METHODS:Experimental mice were respectively pretreated with 200 and 400 mg/kg of MOHE,and 0.5% and 1% of butylated hydroxyanisole (BHA) for two weeks prior to the administration of 15 mg/kg of DMBA,respectively.Levels of xenobiotic metabolizing enzymes such as cytochrome (Cyt) P450 and Cyt b5,activities of reduced glutathione (GSH) and glutathione-S-transferase (GST) and renal aspartate aminotransaminase (AST),alanine aminotransaminase (ALT) and alkaline phosphatase (ALP),and content of

  9. Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate

    Science.gov (United States)

    Bugenhagen, Bernhard; Al Jasem, Yosef; Hindawi, Bassam al; Al Rawashdeh, Nathir; Thiemann, Thies

    2013-01-01

    In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent mol­ecules (A and B) that differ in the conformation of the ester eth­oxy group. In the crystal, the mol­ecules form inversion dimers via pairs of C—H⋯O inter­actions. Within the dimers, the anthracenyl units have inter­planar distances of 0.528 (2) and 0.479 (2) Å for dimers of mol­ecules A and B, respectively. Another short C—H⋯O contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111) layers and there are π–π stacking inter­actions [centroid–centroid distances = 3.6446 (15) and 3.6531 (15) Å] between the anthracenyl units from the neighbouring columns. In addition, there are C—H⋯π inter­actions between the anthracenyl unit of dimers A and dimers B within the same column. PMID:23476390

  10. Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate

    OpenAIRE

    Nathir Al Rawashdeh; Bassam al Hindawi; Yosef Al Jasem; Bernhard Bugenhagen; Thies Thiemann

    2012-01-01

    In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent molecules (A and B) that differ in the conformation of the ester ethoxy group. In the crystal, the molecules form inversion dimers via pairs of C—H...O interactions. Within the dimers, the anthracenyl units have interplanar distances of 0.528 (2) and 0.479 (2) Å for dimers of molecules A and B, respectively. Another short C—H...O contact between symmetry-independent di...

  11. Ethyl (E-3-(anthracen-9-ylprop-2-enoate

    Directory of Open Access Journals (Sweden)

    Nathir Al Rawashdeh

    2013-01-01

    Full Text Available In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent molecules (A and B that differ in the conformation of the ester ethoxy group. In the crystal, the molecules form inversion dimers via pairs of C—H...O interactions. Within the dimers, the anthracenyl units have interplanar distances of 0.528 (2 and 0.479 (2 Å for dimers of molecules A and B, respectively. Another short C—H...O contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111 layers and there are π–π stacking interactions [centroid–centroid distances = 3.6446 (15 and 3.6531 (15 Å] between the anthracenyl units from the neighbouring columns. In addition, there are C—H...π interactions between the anthracenyl unit of dimers A and dimers B within the same column.

  12. Neue Fluoreszenzfarbstoffe mit Anthracen- und Fluoranthengrundgerüst

    OpenAIRE

    Kunze, Markus

    2004-01-01

    1. Anthracenderivate Durch Suzuki-Kupplung gelingt es, ausgehend von 9,10-Dibrom-2,6-di-tert-butylanthracen 9,10-diarylsubstituierte Anthracenderivate mit Ausbeuten von 22 - 82 % herzustellen. Die Kupplung von halogensubstituerten Arylen erfolgt durch nucleophile Addition einer Arylgrignardverbindung an 2,6-Di-tert-butylanthrachinon mit anschließender wässriger Aufarbeitung und Reduktion. Eine zweite Gruppe von Anthracenderivaten wird durch Pyrimidin-Kondensation aus Amidinen und Vinamid...

  13. Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives

    Directory of Open Access Journals (Sweden)

    2008-12-01

    Full Text Available When 9,10-dibromoanthracene was treated with bromine in CCl4 without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene (3 was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide 3 under various conditions. Pyridine-induced elimination of hexabromide 3 afforded 2,9,10-tribromoanthracene (12 in 75% yield, and tribromide 12 was transformed to trimethoxy compound 13 and trinitrile 14 by copper-assisted nucleophilic substitution reactions.

  14. Tumor initiating activities of various derivatives of benz(a)anthracene and 7, 12-dimethyl-benz(a)anthracene in mouse skin

    Energy Technology Data Exchange (ETDEWEB)

    Slaga, T.J.; Gleason, G.L.; DiGiovanni, J.; Berry, D.L.; Juchau, M.R.; Harvey, R.G.

    1978-01-01

    Current information indicates that polycyclic aromatic hydrocarbons (PAH) exert their toxic, mutagenic, and carcinogenic activities after they have been metabolically activated by target cells to reactive epoxides. The results obtained from IN VIVO and IN VITRO binding, mutagenicity, metabolism, and carcinogenicity studies have led to the conclusion that BP-7, 8-diol is a proximate carcinogenic metabolite of BP, and the BP-diol-epoxide is an ultimate carcinogenic metabolite of BP. Recent results concerning the strong carcinogenicity of BP-7..beta.., 8..cap alpha..-diol-9..cap alpha..,10..cap alpha..-epoxide in newborn mice and in mouse skin strongly indicate that it is the ultimate carcinogenic metabolite of BP. Since diol-epoxides may be responsible for the carcinogenicity of PAH other than BP, diols and diol-epoxides as well as other derivatives of PAH were tested for skin tumor-initiation in a two-stage system of tumorigenesis. In addition, since activation of methylated PAH may involve the side-chain methyl group, the skin tumor-initiating activity of various side-chain derivatives of methylated PA were determined. In this report, the skin tumor initiation of various derivatives of a nonmethylated PAH, BA as well as a methylated PAH, DMBA are compared. The data suggest that bay region diol-epoxides may be important in BA and DMBA carcinogenicity in mice which is supportive of the theory proposed by Jerina and co-workers which predicts that diol-epoxides in the bay region are the major determinants of PAH carcinogenicity.

  15. Highly conductive single naphthalene and anthracene molecular junction with well-defined conductance

    Energy Technology Data Exchange (ETDEWEB)

    Liu, Chenyang [Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 W4-10, Ookayama, Meguro-ku, Tokyo 152-8551 (Japan); School of Materials Science and Engineering, Tsinghua University, Beijing 100084 (China); Kaneko, Satoshi; Komoto, Yuki; Fujii, Shintaro, E-mail: fujii.s.af@m.titech.ac.jp; Kiguchi, Manabu, E-mail: kiguti@chem.titech.ac.jp [Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 W4-10, Ookayama, Meguro-ku, Tokyo 152-8551 (Japan)

    2015-03-09

    We performed electronic investigation on single acene molecular junctions bridging Au-electrodes in ultra-high vacuum conditions using mechanically controllable break junction technique. While the molecular junctions displayed various conductance values at 100 K, they exhibited well-defined high conductance values (∼0.3 G{sub 0}) at 300 K, which is close to that of metal atomic contact. Direct π-binding of the molecules to the Au-electrodes leads to the high conductivities at the metal-molecule interface. At the elevated temperature, single molecular junctions trapped in local metastable structures can be fallen into energetically preferential more stable state and thus we fabricated structurally well-defined molecular junctions.

  16. TELOMERASE ACTIVITY DURING 7, 12-DIMETHYLBENZ [a] ANTHRACENE-INDUCED HAMSTER BUCCAL POUCH CARCINOGENESIS

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Objective: To investigate the roles of telomerase activity (TA) in relation to hamster buccal pouch tumor progression. Methods: male hamster were treated three times weekly with 0.5% of 7, 12-dimethyl- benzanthracene (DMBA) over a 15 weeks experimental period. Hamsters were sacrificed at 3, 6, 9, 12 and 15 weeks after treatment. Telomerase activity of hamster buccal pouch tissue were measured along with the analyses of the formation of DMBA-induced hamster buccal pouch tumors. Results: DMBA-induced squamous cell carcinomas were found at the 6th week after dosing. Telomerase activity elevation began at the 3rd week and was increasing to a plateau at the 12th week. Conclusion: Our results show that telomerase activity in the target tissue may be detected at the early stage of the DMBA-induced hamster buccal pouch tumor formation and suggests that telomerase activity may be used as a biomarker for an early clinical detection of buccal pouch cancer.

  17. Hexamolybdenum cluster complexes with pyrene and anthracene carboxylates: Ultrabright red emitters with the antenna effect

    Czech Academy of Sciences Publication Activity Database

    Kirakci, Kaplan; Fejfarová, Karla; Kučeráková, Monika; Lang, Kamil

    2014-01-01

    Roč. 2014, č. 14 (2014), s. 2331-2336. ISSN 1434-1948 R&D Projects: GA ČR GA13-05114S Institutional support: RVO:61388980 ; RVO:68378271 Keywords : cluster compounds * energy transfer * luminescence * sensors * singlet oxygen Subject RIV: CA - Inorganic Chemistry Impact factor: 2.942, year: 2014

  18. Studying the effect of high pressure on the cycloaddition reactions of maleic anhydride and substituted anthracenes

    Science.gov (United States)

    Kiselev, V. D.; Shakirova, I. I.; Kornilov, D. A.; Kashaeva, E. A.; Potapova, L. N.; Konovalov, A. I.

    2013-01-01

    The kinetics (rate, activation, and volume) of the high-pressure (up to 2500 bar) Diels-Alder reactions of maleic anhydride with 9-phenylanthracene and 9,10-dimethylanthracene in toluene is investigated.

  19. Interlayer Energy Transfer from Naphthalene to Anthracene Chromophores Organized in Langmuir—Blodgett Films

    Institute of Scientific and Technical Information of China (English)

    LiQianLI; ChiMingCHE; 等

    2002-01-01

    Interlayer energy transfer between 2,3-naphthol-10-hexadecylaza-15-crown-5(NC16) and N-[1-(9-methoxyanthryl)] decylaza-15-crown-5(A10C) within multilayer Langmuir-Blodgett films has been studied by steady-state fluorescence spectra. The donor and acceptor could be separated precisely by inserting stearic acid (SA) spacers. The efficiency of the energy transfer increases with the decrease in the donor-acceptor distance by a quadratic manner, suggesting the donor excitations are delocalized in the layer.

  20. Interlayer Energy Transfer from Naphthalene to Anthracene Chromophores Organized in Langmuir-Blodgett Films

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    Interlayer energy transfer between 2, 3-naphtho-10-hexadecylaza-15-crown-5 (NC16) and N-[1-(9-methoxyanthryl)]decylaza-15-crown-5 (A10C) within multilayer Langmuir-Blodgett films has been studied by steady-state fluorescence spectra. The donor and acceptor could be separated precisely by inserting stearic acid (SA) spacers. The efficiency of the energy transfer increases with the decrease in the donor-acceptor distance by a quadratic manner, suggesting the donor excitations are delocalized in the layer.

  1. Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

    OpenAIRE

    Kiymet Berkil Akar; Osman Cakmak; Orhan Büyükgüngör; Ertan Sahin

    2011-01-01

    Efficient and stereoselective syntheses are described for the preparation of 2,3,9,10-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydroanthracenes 7, 8 and the corresponding 1,4-diol 17 by silver ion-assisted solvolysis of hexabromotetrahydroanthracene 6. Base-promoted aromatization of 7 and 8 afforded synthetically valuable tribromo-1-methoxyanthracenes 10 and 11. The reaction of 17 with sodium methoxide generated tribromodihydroanthracene-1,4-diol 27, whose oxidation with PCC gave 2,9,10-tribromo...

  2. Preparation, characterization, physical properties, and photoconducting behaviour of anthracene derivative nanowires

    Science.gov (United States)

    Xiao, Jinchong; Yin, Zongyou; Yang, Bo; Liu, Yi; Ji, Li; Guo, Jun; Huang, Ling; Liu, Xuewei; Yan, Qingyu; Zhang, Hua; Zhang, Qichun

    2011-11-01

    Organic nanowires of 9,10-dibromoanthracene (DBA) and 9,10-dicyanoanthracene (DCNA) were obtained by adding the THF solution of DBA/DCNA into water containing P123 surfactants. The as-prepared nanowires were characterized by UV-vis, fluorescence spectra, Field Emission Scanning Electron Microscopy (FESEM), and Transmission Electron Microscopy (TEM). We found that DBA and DCNA nanowires emitted green light rather than blue light for molecules in THF solution. The red-shift UV and fluorescent spectra of DBA and DCNA nanowires implied that these nanowires were formed through J-aggregation. The photoconducting study of DBA/DCNA nanowire-based network on rGO/SiO2/Si shows different photocurrent behaviors upon irradiation, which displayed that electron transfer from DCNA nanowire to rGO was stronger than that of DBA nanowires to rGO.Organic nanowires of 9,10-dibromoanthracene (DBA) and 9,10-dicyanoanthracene (DCNA) were obtained by adding the THF solution of DBA/DCNA into water containing P123 surfactants. The as-prepared nanowires were characterized by UV-vis, fluorescence spectra, Field Emission Scanning Electron Microscopy (FESEM), and Transmission Electron Microscopy (TEM). We found that DBA and DCNA nanowires emitted green light rather than blue light for molecules in THF solution. The red-shift UV and fluorescent spectra of DBA and DCNA nanowires implied that these nanowires were formed through J-aggregation. The photoconducting study of DBA/DCNA nanowire-based network on rGO/SiO2/Si shows different photocurrent behaviors upon irradiation, which displayed that electron transfer from DCNA nanowire to rGO was stronger than that of DBA nanowires to rGO. Electronic supplementary information (ESI) available: XRD patterns and simulations, and FT-IR spectra. CCDC reference numbers 840471. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1nr10655d

  3. 7,12-Dimethylbenz[a]anthracene-Induced Malignancies in a Mouse Model of Menopause

    OpenAIRE

    Marion, Samuel L.; Watson, Jennifer; Sen, Nivedita; Brewer, Molly A; Barton, Jennifer K.; Hoyer, Patricia B.

    2013-01-01

    Ovarian cancer has a high mortality rate because there are few symptoms in early disease development. The incidence of ovarian cancer increases in women after menopause. Understanding early events in this disease can best be achieved by using animal models. Therefore, the objective of this study was to develop and track the onset of ovarian tumorigenesis in mice mimicking characteristics of postmenopausal epithelial cancer in women. Female B6C3F1 mice (age, 28 d) received 4-vinylcyclohexene d...

  4. erbB expression changes in ethanol and 7, 12- dimethylbenz (a) anthracene-induced oral carcinogenesis

    OpenAIRE

    Jacinto Alemán, Luís Fernando; García Carrancá, Alejandro; Leyba Huerta, Elba Rosa; Zenteno Galindo, Edgar; Jiménez Farfán Farfán, María Dolores; Hernández Guerrero, Juan Carlos

    2013-01-01

    Objetive: The aim of this study was to determine erbB expression in normal mucosa, oral dysplasia, and invasive carcinomas developed in the hamster’s buccal pouch chemical carcinogenesis model. Study design: Fifty Syrian golden hamsters were equally divided in five groups (A-E); two controls and three experimental group exposed to alcohol, DMBA, or both for 14 weeks. Number of tumors per cheek, volume, histological condition, erbB expression were determined and results were analyzed by the Ma...

  5. Molecule-solid interaction: Electronic states of anthracene-9-carboxylic acid adsorbed on the surface of TiO2

    International Nuclear Information System (INIS)

    Electronic excited states of athracene-9-carboxylic acid chemisorbed on the surface of TiO2 nanoparticles were investigated by means of the electroabsorption (Stark effect) spectroscopy at low temperature. In addition to a fraction of molecules adsorbed with no significant spectral changes, two forms absorbing at lowered energy (25,600 cm-1 and 24,900 cm-1) were observed, that exhibit a large increase in the excited-minus-ground state dipole moments, 2.7 D and 9.5 D, respectively, as well as changed molecular polarizabilities. The dipole moments are interpreted as indicators of partial charge-transfer character of the excited state, corresponding to the optical electron transfer from the adsorbate onto TiO2 concomitantly with the photon absorption. Consequences of these observations are shortly discussed in the context of the electron transfer process in dye-sensitized solar cells.

  6. Charge carrier mobility, photovoltaic, and electroluminescent properties of anthracene-based conjugated polymers bearing randomly distributed side chains

    Czech Academy of Sciences Publication Activity Database

    Usluer, Ö.; Kästner, C.; Abbas, M.; Ulbricht, C.; Cimrová, Věra; Wild, A.; Birckner, E.; Tekin, N.; Sariciftci, N. S.; Hoppe, H.; Rathgeber, S.; Egbe, D. A. M.

    2012-01-01

    Roč. 50, č. 16 (2012), s. 3425-3436. ISSN 0887-624X R&D Projects: GA MŠk(CZ) 1M06031 Institutional research plan: CEZ:AV0Z40500505 Keywords : conjugated polymers * organic field-effect transistors * organic solar cells Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 3.543, year: 2012

  7. Inclusion of an Anthracene-based Fluorophore within Molecular Containers: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families.

    Science.gov (United States)

    Ganguly, Aniruddha; Ghosh, Soumen; Guchhait, Nikhil

    2016-05-19

    In this paper, the binding interaction of a promising chloride channel blocker, 9-methyl anthroate (9-MA), with two different classes of molecular containers, β-cyclodextrins (β-CD and methyl-β-CD) and cucurbit[7]uril, having comparable cavity dimensions, has been thoroughly demonstrated via inspection of the modulation of the excited-state properties of the emissive molecule. Spectral data suggest that CB7 encapsulates the probe more efficiently in a 1:2 fashion, whereas the efficacies of β-CDs are relatively less and the corresponding stoichiometry is 1:1. Interestingly, despite being thermodynamically much more favorable than the probe-β-CD complexation equilibria, the fraction of probe-CB7 complex formed is appreciably smaller with respect to that of probe-β-CD complexes. This apparent inconsistency has been addressed via the proposition that since the formation of a 1:2 complex is entropically disadvantageous, it is anticipated that the activation barrier of the corresponding reaction is reasonably high, and thus only a small fraction of the reactants are able to surpass the energy barrier to form the products. This proposition has been thoroughly corroborated by fluorescence lifetime measurements at different temperatures. PMID:27119387

  8. Bromelain nanoparticles protect against 7,12-dimethylbenz[a]anthracene induced skin carcinogenesis in mouse model.

    Science.gov (United States)

    Bhatnagar, Priyanka; Pant, Aditya B; Shukla, Yogeshwer; Chaudhari, Bhushan; Kumar, Pradeep; Gupta, Kailash C

    2015-04-01

    Conventional cancer chemotherapy leads to severe side effects, which limits its use. Nanoparticles (NPs) based delivery systems offer an effective alternative. Several evidences highlight the importance of Bromelain (BL), a proteolytic enzyme, as an anti-tumor agent which however has been limited due to the requirement of high doses at the tumor site. Therefore, we illustrate the development of BL loaded poly (lactic-co-glycolic acid) NPs that show enhanced anti-tumor effects compared to free BL. The formulated NPs with a mean particle size of 130.4 ± 8.81 nm exhibited sustained release of BL. Subsequent investigation revealed enhanced anti-tumor ability of NPs in 2-stage skin tumorigenesis mice model. Reduction in average number of tumors (∼ 2.3 folds), delay in tumorigenesis (∼ 2 weeks), percent tumorigenesis (∼ 4 folds), and percent mortality rate as well as a reduction in the average tumor volume (∼ 2.5 folds) in mice as compared to free BL were observed. The NPs were found to be superior in exerting chemopreventive effects over chemotherapeutic effects at 10 fold reduced dose than free BL, validated by the enhanced ability of NPs (∼ 1.8 folds) to protect the DNA from induced damage. The effects were also supported by histopathological evaluations. NPs were also capable of modulating the expression of pro-apoptotic (P53, Bax) and anti-apoptotic (Bcl2) proteins. Therefore, our findings demonstrate that developed NPs formulation could be used to improve the efficacy of chemotherapy by exerting chemo-preventive effects against induced carcinogenesis at lower dosages. PMID:25619920

  9. Aqueous solubility data for pressurized hot water extraction for solid heterocyclic analogs of anthracene, phenanthrene and fluorene

    Czech Academy of Sciences Publication Activity Database

    Karásek, Pavel; Planeta, Josef; Roth, Michal

    2007-01-01

    Roč. 1140, 1-2 (2007), s. 195-204. ISSN 0021-9673 R&D Projects: GA ČR GA203/05/2106; GA ČR GA203/07/0886; GA AV ČR IAA4031301; GA AV ČR KJB400310504 Institutional research plan: CEZ:AV0Z40310501 Keywords : aqueous solubility * pressurized hot water * aromatic heterocycle Subject RIV: CB - Analytical Chemistry, Separation Impact factor: 3.641, year: 2007

  10. Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence

    OpenAIRE

    Mase, Nobuyuki; Takabe, Kunihiko; Tanaka, Fujie

    2013-01-01

    NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters.Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document.Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in PUBLICATION, Volume 54, Issue 32, 7 August 2013. DOI10.1016/j.tetlet.2013....

  11. JWA deficiency suppresses dimethylbenz[a]anthracene-phorbol ester induced skin papillomas via inactivation of MAPK pathway in mice.

    Directory of Open Access Journals (Sweden)

    Zhenghua Gong

    Full Text Available Our previous studies indicated that JWA plays an important role in DNA damage repair, cell migration, and regulation of MAPKs. In this study, we investigated the role of JWA in chemical carcinogenesis using conditional JWA knockout (JWA(Δ2/Δ2 mice and two-stage model of skin carcinogenesis. Our results indicated that JWA(Δ2/Δ2 mice were resistant to the development of skin papillomas initiated by 7, 12-dimethylbenz(aanthracene (DMBA followed by promotion with 12-O-tetradecanoylphorbol-13-acetate (TPA. In JWA(Δ2/Δ2 mice, the induction of papilloma was delayed, and the tumor number and size were reduced. In primary keratinocytes from JWA(Δ2/Δ2 mice, DMBA exposure induced more intensive DNA damage, while TPA-promoted cell proliferation was reduced. The further mechanistic studies showed that JWA deficiency blocked TPA-induced activation of MAPKs and its downstream transcription factor Elk1 both in vitro and in vivo. JWA(Δ2/Δ2 mice are resistance to tumorigenesis induced by DMBA/TPA probably through inhibition of transcription factor Elk1 via MAPKs. These results highlight the importance of JWA in skin homeostasis and in the process of skin tumor development.

  12. Decreased adrenal medullary tyrosine hydroxylase mRNA in DMBA (7,12-dimethylbenz(a)anthracene)-induced mammary carcinoma

    Energy Technology Data Exchange (ETDEWEB)

    Bunce, O.R.; Badary, O.A.; Abou El-Ela, S.; Hartle, D.K. (Univ. of Georgia, Athens (United States))

    1991-03-15

    Adrenal cortical hormones suppress initiation and promotion of DMBA-induced mammary tumorigenesis. The authors found a positive correlation between presence of DMBA-induced adrenal cortical necrosis and mammary tumor incidence. Because they find adrenal medullary as well as cortical lesions in tumor bearing (TB) DMBA-treated rats, they evaluated medullary function by quantitating hybridized cDNA- TH-S{sup 35} with in situ TH-mRNA u sing computer assisted quantitative autoradiographic technique. Virgin female Sprague-Dawley rats were given a 10 mg i.g. dose of DMBA. Three wks later, rats were placed on 20% polyunsaturated (PUFA) fat diets containing omega-6 and omega-3 fatty acids. All were killed 15 wks post-DMBA. TH-mRNA levels in adrenal medullae of TB animals were decreased compared to non-TB rats. Histopathology indicated a high incidence of medullary necrosis in TB rats, whereas, adrenal necrosis did not occur in non-TB animals. Adrenal necrosis correlated positively with tumor burden, but no correlation was found between incidence of adrenal lesions and type of PUFA in the diet. The authors suggest that DMBA adrenal necrosis may reduce TH-mRNA in the medulla, compromise its catecholamine synthetic capability, and thereby contribute to the overall metabolic stress condition of TB rats.

  13. Inhibition of murine splenic B lymphocyte activation following oral exposure to 7,12-dimethylbenz(a)anthracene (DMBA)

    International Nuclear Information System (INIS)

    Previous results from this laboratory have demonstrated that oral exposure of B6C3F1 mice to DMBA inhibited mitogen-stimulated lymphocyte activation in cells recovered from several lymphoid organs. These studies showed that both LPS and PHA-stimulated lymphocyte proliferation and PHA-induced Ca+2 mobilization were significantly inhibited by DMBA exposure, supporting the hypothesis that DMBA inhibits early events associated with lymphocyte activation. The purpose of the current studies was to test this hypothesis directly for B cell activation. B6C3F1 mice were treated with 0, 1.0, or 10 mg/kg/day doses of DMBA for 14 days (total cumulative doses of 0, 14, or 140 mg/kg). B lymphocyte populations were then selected on the flow cytometer by direct positive staining of spleen cells with phycoerythrin-labeled anti-Ly5 (B lymphocyte marker) antibodies. Ca+2 mobilization studies were performed using affinity-purified goat anti-mouse IgD antibodies as the stimulant and Indo-1 as the intracellular Ca+2 indicator. Cell proliferation studies were also performed using 3H-thymidine and insoluble anti-IgD antibodies. Anti-IgD stimulated Ca+2 mobilization was significantly reduced at the 140 mg/kg dose of DMBA. A statistically significant decrease in anti-IgD stimulated B lymphocyte proliferation at the 14 mg/kg and 140 mg/kg doses of DMBA was found. These results suggest that B lymphocytes may be important targets for DMBA-mediated immunosuppression

  14. A Systematic Study of the Effects of Naphthalene and Anthracene Substitution on the Properties of PPV Derivative Conjugated Systems

    OpenAIRE

    Lynch, Patrick; O'Neill, Luke; Bradley, David; Byrne, Hugh; McNamara, Mary

    2007-01-01

    The systematic synthesis of poly(phenylvinylene) (PPV) derivatives by the Wittig-Horner reaction is reported. The phenyl units of the PPV structure are methodically substituted by naphthyl and anthryl units to form a homologous series of structures. The 2,6 attachment of the vinylene linkage on the anthryl ring provides novel structures that have not been reported before due to their synthetic inaccessibility. The introduction of naphthyl units results in a hypsochromatic shift in the absorpt...

  15. 低浓度蒽对两种海洋微藻生长的兴奋效应%Stimulation effect of anthracene on marine microalgae growth

    Institute of Scientific and Technical Information of China (English)

    王悠; 唐学玺; 李永祺; 刘泳

    2002-01-01

    以两种海洋微藻金藻8701(Isochrysis galbana 8701)和骨条藻(Skeletonema costatum)为材料,研究了低浓度蒽(1.5~6μg*L-1)对两种海洋微藻生长的影响.结果表明,在一定浓度蒽作用下,两种微藻的生长均呈现出较明显的"兴奋效应",细胞密度有所增加,但达到最佳刺激作用的浓度与时间有所不同.在刺激浓度作用下,两种微藻体内的蛋白质、叶绿素a(chla.)、类胡萝卜素(car.)含量都有所增加,其变化趋势与细胞密度的变化类似.在整个实验过程中,微藻体内清除活性氧的关键性酶超氧化物歧化酶(SOD)始终处于较高水平,其变化趋势类似于细胞密度的变化.

  16. Concentrations of methylated naphthalenes, anthracenes, and phenanthrenes occurring in Czech river sediments and their effects on toxic events associated with carcinogenesis in rat liver cell lines

    Czech Academy of Sciences Publication Activity Database

    Vondráček, Jan; Šindlerová, Lenka; Pěnčíková, K.; Marvanová, S.; Krčmář, P.; Ciganek, M.; Neča, J.; Trosko, J.E.; Upham, B.; Kozubík, Alois; Machala, M.

    2007-01-01

    Roč. 26, č. 11 (2007), s. 2308-2316. ISSN 0730-7268 R&D Projects: GA ČR(CZ) GA524/05/0595 Institutional research plan: CEZ:AV0Z50040507; CEZ:AV0Z50040702 Keywords : monomethylated polycyclic aromatic hydrocarbons * aryl hydrocarbon receptor * cytochrome P4501A1 Subject RIV: BO - Biophysics Impact factor: 2.309, year: 2007

  17. 1,3-Dihydr­oxy-9,10-dioxo-9,10-di­hydro­anthracene-2-carbaldehyde

    OpenAIRE

    Awang, Khalijah; Ismail, Nor Hadiani; Ahmad, Rohaya; Saidan, Nor Hafizoh; Retailleau, Pascal

    2008-01-01

    The title compound, C15H8O5, also known as nordamnacanthal, was isolated from the Malaysian Morinda citrifolia L. The 20 non-H atoms are coplanar. The structure is stabilized by intra­molecular O—H⋯O hydrogen bonds and inter­molecular O—H⋯O and C—H⋯O hydrogen bonds, forming bilayers of mol­ecular tapes with alternating stacking directions along the a axis.

  18. Metabolism of benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene in cultured human bronchus and pancreatic duct

    DEFF Research Database (Denmark)

    1977-01-01

    patients with lung cancer were also compared with those from patients without lung cancer. The profiles were similar except for an observed higher percentage of organic solvent-extractable metabolites formed by bronchi from the noncancer patients that eluted from the column as a single peak. This peak...

  19. Chemopreventive and Antilipidperoxidative Potential of Clerodendron inerme (L) Gaertn in 7,12-dimethylbenz(a)anthracene Indcued Skin Carcinogenesis in Swiss Albino Mic

    OpenAIRE

    Gopi Lilly Renju; Shanmugam Manoharan; Subramanian Balakrishnan; Namasivayam Senthil

    2007-01-01

    The present study has investigated the chemopreventive and antilipidperoxidative effects of the ethanolic extract of Clerodendron inerme leaves (CiELet) in DMBA induced skin carcinogenesis in Swiss albino mice. The skin squamous cell carcinoma was induced in the shaved back of mice, by painting with DMBA (25 μg 0.1 mL-1 acetone) twice weekly for 8 weeks. We have observed 100% tumor formation in the fifteenth week of experimental period. Elevated lipid peroxidation and decline in enzymatic and...

  20. Dietary effects of soy isoflavones daidzein and genistein on 7,12-dimethylbenz[a]anthracene-induced mammary mutagenesis and carcinogenesis in ovariectomized Big Blue transgenic rats.

    OpenAIRE

    Manjanatha, Mugimane; Shelton, Sharon; Bishop, Michelle; Lyn-Cook, Lascelles; Aidoo, Anane

    2006-01-01

    Dietary modulation of cancer & cancer biomarkers. Dietary item or component studied: the isoflavones daidzein (DZ) and genistein (GE)Outcome studied: Mammary gland hyperplasia; DNA damage. Study type: Big Blue transgenic rats Tissue/biological material/sample size: mammary glands; lymphocytes isolated from the spleen. Mode of exposure: dietary. Impact on outcome (including dose-response): The isoflavones or E(2) supplementation alone resulted in the lac I MFs that were not significantly diff...

  1. Protective effect of Ocimum sanctum on 3-methylcholanthrene, 7,12-dimethylbenz(a)anthracene and aflatoxin B1 induced skin tumorigenesis in mice

    International Nuclear Information System (INIS)

    A study on the protective effect of alcoholic extract of the leaves of Ocimum sanctum on 3-mthylcholanthrene (MCA), 7,12-dimethylbenzanthracene (DMBA) and aflatoxin B1 (AFB1) induced skin tumorigenesis in a mouse model has been investigated. The study involved pretreatment of mice with the leaf extract prior to either MCA application or tetradecanoyl phorbol acetate (TPA) treatment in a two-stage tumor protocol viz a viz, DMBA/TPA and AFB1/TPA. The results of the present study indicate that the pretreatment with alcoholic extract of the leaves of O. sanctum decreased the number of tumors in MCA, DMBA/TPA and AFB1/TPA treated mice. The skin tumor induced animals pretreated with alcoholic extract led to a decrease in the expression of cutaneous γ-glutamyl transpeptidase (GGT) and glutathione-S-transferase-P (GST-P) protein. The histopathological examination of skin tumors treated with leaf extract showed increased infiltration of polymorphonuclear, mononuclear and lymphocytic cells, decreased ornithine decarboxylase activity with concomitant enhancement of interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) in the serum, implying the in vivo antiproliferative and immunomodulatory activity of leaf extract. The decrease in cutaneous phase I enzymes and elevation of phase II enzymes in response to topical application of leaf extract prior to MCA, AFB1, DMBA/TPA and AFB1/TPA treatment indicate the possibility of impairment in reactive metabolite(s) formation and thereby reducing skin carcinogenicity. Furthermore, pretreatment of leaf extract in the carcinogen induced animals resulted in elevation of glutathione levels and decrease in lipid peroxidation along with heat shock protein expression, indicating a scavenging or antioxidant potential of the extract during chemical carcinogenesis. Thus it can be concluded that leaf extract of O. sanctum provides protection against chemical carcinogenesis in one or more of the following mechanisms: (i) by acting as an antioxidant; (ii) by modulating phase I and II enzymes; (iii) by exhibiting antiproliferative activity

  2. Chemoprevention of 7,12-dimethylbenz[a]anthracene (DMBA)-induced Hamster Cheek Pouch Carcinogenesis by a 5-Lipoxygenase Inhibitor, Garcinol

    OpenAIRE

    Chen, Xin; Zhang, Xinyan; Lu, Ye; Shim, Joong-Youn; Sang, Shengmin; Sun, Zheng; Chen, Xiaoxin

    2012-01-01

    Our previous studies have shown that aberrant arachidonic acid metabolism, especially the 5-lipoxygenase (5-Lox) pathway, is involved in oral carcinogenesis, and can be targeted for cancer prevention. In order to develop potent topical agents for oral cancer chemoprevention, five known 5-Lox inhibitors from dietary and synthetic sources, Zileuton, ABT-761, Licofelone, Curcumin and Garcinol, were evaluated in silico for their potential efficacy. Garcinol, a polyisoprenylated benzophenone from ...

  3. Determination of the Residual Anthracene Concentration in Cultures of Haloalkalitolerant Actinomycetes by Excitation Fluorescence, Emission Fluorescence, and Synchronous Fluorescence: Comparative Study

    OpenAIRE

    Reyna del Carmen Lara-Severino; Miguel Ángel Camacho-López; Jessica Marlene García-Macedo; Gómez-Oliván, Leobardo M.; Sandoval-Trujillo, Ángel H.; Keila Isaac-Olive; Ninfa Ramírez-Durán

    2016-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are compounds that can be quantified by fluorescence due to their high quantum yield. Haloalkalitolerant bacteria tolerate wide concentration ranges of NaCl and pH. They are potentially useful in the PAHs bioremediation of saline environments. However, it is known that salinity of the sample affects fluorescence signal regardless of the method. The objective of this work was to carry out a comparative study based on the sensitivity, linearity, and detec...

  4. Pineal gland in rats with 7,12-dimethylbenz (a) anthracene-induced mammary tumors subjected to manipulations known as enhancers of pineal actions

    OpenAIRE

    Cos, S.; Bardasano, J. L.; Mediavilla, M D; Sánchez Barceló, E. J.

    1989-01-01

    The ultrastructure of pinealocytes was studied in rats with 7,17-dimethylbenz (a) anthraceneinduced manimary tumors which were subjected to experimental manipulations known as enhancers of pineal actions (anosmia, underfeeding or cold exposure). In these aniinals we found: (1) - more nuclei with deep nuclear invaginations; (11) - a large number of cytoplasmic organelles, including lipid droplets. myeloid bodies, synaptic ribbons and lysosomes; (111) - numer...

  5. Luteolin suppresses development of medroxyprogesterone acetate-accelerated 7,12-dimethylbenz(a)anthracene-induced mammary tumors in Sprague-Dawley rats.

    Science.gov (United States)

    Cook, Matthew T; Mafuvadze, Benford; Besch-Williford, Cynthia; Ellersieck, Mark R; Goyette, Sandy; Hyder, Salman M

    2016-02-01

    Postmenopausal women undergoing hormone-replacement therapy containing both progestins and estrogens are at an increased risk of developing breast cancer compared with women taking estrogen alone. We recently demonstrated that medroxyprogesterone acetate, a progestin commonly used for hormone-replacement therapy, accelerates development of mammary carcinogenesis in 7,12-dimethylbenz(a)anthracene‑treated Sprague-Dawley rats. Synthetic antiprogestins used to block the deleterious effects of progestins, are themselves associated with toxic side-effects. In order to circumvent this, we used the aforementioned model to identify less toxic natural compounds that may prevent the development of progestin-accelerated tumors. Luteolin, a naturally-occurring flavonoid commonly found in fruits and vegetables, has previously been shown to possess anticancer properties. In our studies, both low (1 mg/kg) and high (25 mg/kg) doses of luteolin significantly suppressed progestin-dependent increases in tumor incidence, while increasing tumor latency and reducing the occurrence of large (>300 mm3) mammary tumors. However, an intermediate dose of luteolin (10 mg/kg), while suppressing the development of large tumors, did not affect either tumor incidence or latency. Immunohistochemical analysis of tumor tissues revealed that all concentrations of luteolin (1, 10, and 25 mg/kg) significantly reduced levels of VEGF within tumors. The suppressive effects of luteolin on tumor incidence and volume, together with its ability to reduce VEGF and blood vessels, persisted even after treatment was terminated. This suggests that luteolin possesses anti‑angiogenic properties which could mechanistically explain its capacity to control tumor progression. Thus luteolin may be a valuable, non-toxic, naturally-occurring anticancer compound which may potentially be used to combat progestin-accelerated mammary tumors. PMID:26719029

  6. Evaluation of Serum Testosterone and Prostate Specific Antigen Levels in Sprague-Dawley Female Rats Bearing Mammary Tumours Induced by Dimethylbenz (A) Anthracene

    International Nuclear Information System (INIS)

    Breast Cancer is one of the most common malignancies among women in the world and is a leading cause of morbidity and mortality in females of both developed and developing countries. The present work aimed to study the diagnostic value of prostate specific antigen (PSA) for breast cancer and the importance of treatment by blue green algae Spirulina platensis supplementation on PSA and testosterone levels. Two different analytical techniques based on micro particle enzyme immunoassay (MPIA) and enzyme linked fluorescent assay (ILFA) for quantitative determination of total PSA (free PSA and PSA complexed to alpha-1-antichymptrypsin) were studied in the diagnosis of breast cancer before and after Spirulina platensis supplementation. Female rats secret PSA from female prostate gland, serum testosterone and PSA concentrations were not detected in control and rats supplemented by Spirulina platensis groups. Serum testosterone and PSA concentration were significantly higher (P< 0.05) in rats bearing mammary tumours than rats bearing mammary tumours supplemented with Spirulina platensis. These results suggest that the clinical applicability of total PSA for breast cancer diagnosis and the biological mechanism behind its increase should be further investigated. Finally, the physiological mechanism behind the total PSA increase in breast cancer and its ramifications with respect to tumour progression should be further investigated.

  7. Dietary vitamin B6 supplementation promotes the growth of 7,12-dimethylbenz(a)anthracene-induced mammary carcinoma in Sprague Dawley rats.

    OpenAIRE

    Hobbs, Lisa M

    2001-01-01

    In vitro data from our laboratory demonstrate that vitamin B6 (B6) supplementation of estrogen receptor - positive and - negative breast cancer cells is growth inhibitory. Others have reported that dietary B6 supplementation resulted in increased fibrosarcoma pyridoxal phosphate (PLP) concentrations and a significant inverse relationship between tumor PLP concentration and tumor volume in mice. This suggests that, in contrast to data reported for normal cells, tumor cells are capable of acc...

  8. Synthesis and Crystal Structure of Calix[4]arene Bearing a 1,8-Bis(propoxy)anthracene-9,10-dione

    Institute of Scientific and Technical Information of China (English)

    GU Shao-Jin; QIN Da-Bin; JIN Lin-Hai

    2008-01-01

    The title complex (C50 H44Cl4O8) was synthesized and structurally determined by single-crystal X-ray diffraction method.It crystallizes in monoclinic, space group P21/n with a = 19.7768(4), b =10.2085(2), c = 21.2721(4) A, β = 97.153(1)°, V = 4261.23(14) A3, Z = 4, Mr = 914.65, F(000) = 1904, Dc = 1.426 g/cm3, μ = 0.336, the final R = 0.0550 and wR = 0.1647.The compound was structurally characterized by IR and 1H NMR.The molecules are stacked through C-H…π interactions and intermolecular C-H…O hydrogen bonds.

  9. 40 CFR Appendix II to Part 258 - List of Hazardous Inorganic and Organic Constituents

    Science.gov (United States)

    2010-07-01

    ... Barium (Total) Barium Benzene 71-43-2 Benzene Benzo anthracene; Benzanthracene 56-55-3 Benz anthracene...-Dichloropropane 78-87-5 Propane, 1,2-dichloro- 1,3-Dichloropropane; Trimethylene dichloride 142-28-9 Propane,...

  10. 7, 12 dimethylbenz(a)anthracene(DMBA)-induced "early" Squamous Cell carcinoma in the Golden Syrian hamster: evaluation of an animal model and comparison with "early" forms of human Squamous Cell car

    Science.gov (United States)

    Andrejevic-Blant, Snezana; Savary, Jean-Francois; Fontolliet, Charlotte; Monnier, Philippe

    1995-03-01

    To improve our knowledge on PDT of human early squamous cell carcinomas of the upper aero-digestive tract and to evaluate new photosensitizers, we have set up the Syrian hamster as an animal model. A 0.5% oily solution of DMBA was applied topically to the left buccal pouch mucosa 3 times weekly. The contralateral buccal pouch served as control. Groups of 5 animals were sacrificed at 6, 8, 10 and 12 weeks from the first applications. Tissue samples of the buccal mucosa were analyzed by histopathologic and immunohistochemical techniques and compared with preneoplastic and neoplastic changes which are seen in the human carcinogenesis of the upper aero-digestive tract. After 6 to 9 weeks from the beginning of the application, we observed different degrees of epithelial dysplasia and after 10 weeks microinvasive carcinomas. The sequence of dysplastic changes to early carcinoma was reproducible in different groups of animals, and they were closely comparable with the human forms of `early' squamous cell cancer. Hyper- and dyskeratosis were present at all stages of tumor development. We are particularly interested in (mu) -invasive tumor forms appearing 10 weeks after the first application because they are potentially amenable to photodynamic therapy.

  11. In vivo DNA/RNA adduction of 7,12-dimethylbenz(a)anthracene (DMBA) and benzo(a)pyrene (BaP) in the liver of rainbow trout (Oncorhynchus mykiss)

    Energy Technology Data Exchange (ETDEWEB)

    Schnitz, A.R.; O' Connor, J.M. (New York University Medical Center, NY (United States))

    1992-07-01

    Juvenile rainbow trout were exposed via two intramuscular injections to either 14C-DMBA for 24 hr or 14C-BaP for 48 hr, after which the livers were removed for DNA extraction and analysis. In the fish exposed to 14C-BaP, 0.2 ng was bound to the DNA, representing 0.5% of the total liver PAH-derived radioactivity and 2.38% of the administered dose. Liver DNA and RNA were found to contain 0.5% of the administered dose, respectively. Liver analysis of rainbow trout exposed to 14C-DMBA demonstrated that 0.4 ng and 0.3 ng were bound to the DNA and RNA, respectively. This represents 1.0% and 0.6% of the liver DMBA burden, respectively. The DNA adduct concentrations formed were comparable to both in vitro and in vivo experiments with both mammals and fishes, indicating that relatively small, environmentally realistic' doses of PAH have the ability to bind significantly to critical cellular macromolecules of young fish in vivo.

  12. Modulatory effect of Ganoderma lucidum on expression of xenobiotic enzymes, oxidant-antioxidant and hormonal status in 7,12-dimethylbenz(a)anthracene-induced mammary carcinoma in rats

    OpenAIRE

    Krishnamoorthy Deepalakshmi; Sankaran Mirunalini

    2013-01-01

    Background: Mushrooms are an important natural source represents a major and untapped potent pharmaceutical product. Ganoderma lucidum (G. lucidum) an important medicinal mushroom has been shown to contain high amount of antioxidant. However, in vivo studies on G. lucidum fruiting bodies are lacking. Objectives: To determine the effects of G. lucidum fruiting bodies ethanolic extract (GLEet) on expression of xenobiotic enzymes, oxidant-antioxidant and hormonal status on 7,12-dimethyl benz[a]a...

  13. Poly[tetra­aqua­(μ6-9,10-dioxo-9,10-dihydro­anthracene-1,4,5,8-tetra­carboxyl­ato)dimanganese(II)

    OpenAIRE

    Rui Xu; Jian-Lan Liu

    2012-01-01

    The title complex, [Mn2(C18H4O10)(H2O)4]n, was synthesized from manganese(II) chloride tetrahydrate and 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid (H4AQTC) in water. The anthraquinone unit is located about a crystallographic center of inversion. Each asymmetric unit therefore contains one MnII atom, two water ligands and one half AQTC4− anion. The MnII atom is coordinated in a distorted octahedral geometry by four O atoms from three AQTC4− ligands and t...

  14. Prenatal 3,3',4,4',5-pentachlorobiphenyl exposure modulates induction of rat hepatic CYP 1A1, 1B1, and AhR by 7,12-dimethylbenz[a]anthracene

    International Nuclear Information System (INIS)

    We previously reported the finding that prenatal exposure to a relatively low dose of PCB126 increases the rate of DMBA-induced rat mammary carcinoma, while a high dose decreased it. One of the most important factors determining the sensitivity to mammary carcinogenesis is the metabolic stage at administration of the carcinogenic agent. DMBA is a procarcinogen that recruits the host metabolism to yield its ultimate carcinogenic form, and CYP1A1 and CYP1B1 (CYP1) conduct this metabolism. We investigated the hepatic expression of CYP1 and AhR following oral administration of DMBA (100 mg/kg b.w.) (i.g.) to 50-day-old female Sprague-Dawley rats whose dams had been treated (i.g.) with 2.5 ng, 250 ng, 7.5 μg of PCB126/kg or the vehicle on days 13 to 19 post-conception. Real-time quantitative RT-PCR analysis revealed that the prenatal exposure to a relatively low dose of PCB126 (the 250 ng group) prolonged the higher expression of CYP1A1, CYP1B1, and AhR mRNA, while prenatal exposure to a high dose of PCB126 (the 7.5 μg group) prolonged the higher expression of CYP1A1 and AhR mRNA. Western blotting and immunohistochemical analyses were consistent with mRNAs changes. Because DMBA oxidation produces a highly mutagenic metabolite and is finally catalyzed by CYP1B1, a relatively low PCB126 dose might produce the biological character to potentially increase the risk of DMBA-induced mammary carcinoma

  15. 40 CFR Appendix - Tables to Part 132

    Science.gov (United States)

    2010-07-01

    ... Acenaphthylene Acrolein; 2-propenal Acrylonitrile Aldrin Aluminum Anthracene Antimony Arsenic Asbestos 1,2... Endrin aldehyde Ethylbenzene Fluoranthene Fluorene; 9H-fluorene Fluoride Guthion Heptachlor...

  16. 40 CFR 132.6 - Application of part 132 requirements in Great Lakes States and Tribes.

    Science.gov (United States)

    2010-07-01

    ... Acenaphthylene Acrolein; 2-propenal Acrylonitrile Aldrin Aluminum Anthracene Antimony Arsenic Asbestos 1,2... Endrin aldehyde Ethylbenzene Fluoranthene Fluorene; 9H-fluorene Fluoride Guthion Heptachlor...

  17. Aggregation enhanced emission (AEE) in organic salt: A structure-property correlation based on single crystal studies

    Indian Academy of Sciences (India)

    Uttam Kumar Das; Parthasarathi Dastidar

    2014-09-01

    Salt formation has been shown as a simple strategy to induce aggregated induced emission or aggregated enhanced emission in primary ammonium salts derived from 9-anthracene carboxylic acid, 1-pyrene carboxylic acid, 3-coumarin carboxylic acid and histamine. All the salts displayed enhanced fluorescence in their solid state compared to that in their solution state. Single crystal structure of the salt of 9-anthracene carboxylic acid i.e., His-anthracene revealed that restricted intramolecular rotation of the fluorphoric moiety (anthracene) was responsible for such radiative pathway leading to enhanced emission.

  18. Determination of tritium concentration in aqua solutions by measuring photostimulated exoemission from the surface of organic materials

    International Nuclear Information System (INIS)

    Results re presented of measuring the photostimulated exoelectron response of anthracene, polystytene and stilbene after their irradiation by beta particles of tritium in aqua solutions with different concentration of tritium

  19. Downscaling the in vitro test of fungal bioremediation of polycyclic aromatic hydrocarbons: methodological approach.

    Science.gov (United States)

    Drevinskas, Tomas; Mickienė, Rūta; Maruška, Audrius; Stankevičius, Mantas; Tiso, Nicola; Mikašauskaitė, Jurgita; Ragažinskienė, Ona; Levišauskas, Donatas; Bartkuvienė, Violeta; Snieškienė, Vilija; Stankevičienė, Antanina; Polcaro, Chiara; Galli, Emanuela; Donati, Enrica; Tekorius, Tomas; Kornyšova, Olga; Kaškonienė, Vilma

    2016-02-01

    The miniaturization and optimization of a white rot fungal bioremediation experiment is described in this paper. The optimized procedure allows determination of the degradation kinetics of anthracene. The miniaturized procedure requires only 2.5 ml of culture medium. The experiment is more precise, robust, and better controlled comparing it to classical tests in flasks. Using this technique, different parts, i.e., the culture medium, the fungi, and the cotton seal, can be analyzed. A simple sample preparation speeds up the analytical process. Experiments performed show degradation of anthracene up to approximately 60% by Irpex lacteus and up to approximately 40% by Pleurotus ostreatus in 25 days. Bioremediation of anthracene by the consortium of I. lacteus and P. ostreatus shows the biodegradation of anthracene up to approximately 56% in 23 days. At the end of the experiment, the surface tension of culture medium decreased comparing it to the blank, indicating generation of surfactant compounds. PMID:26660875

  20. Use of antioxidant enzymes of clam Ruditapes philippinarum as biomarker to polycyclic aromatic hydrocarbon pollution

    Science.gov (United States)

    Zhu, Lin; Tang, Xuexi; Wang, Ying; Sui, Yadong; Xiao, Hui

    2016-03-01

    The typical organic pollutant polycyclic aromatic hydrocarbon (PAH) anthracene was selected as a contaminant to investigate its effects on the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px) in the clam Ruditapes philippinarum. The results show that SOD, CAT and GSH-Px had diff erent induction and inhibition reactions to anthracene stress, and that three diff erent organs in R. philippinarum (visceral mass, muscle tissue and mantle) had diff erent sensitivities to anthracene stress. This study suggest that SOD activities of the visceral mass, CAT activitities of the mantle and the visceral mass, and GSH-Px activity of the muscle tissue could be used as sensitive indicators of anthracene stress in R. philippinarum.

  1. Interplay between singlet and triplet excited states in a conformationally locked donor–acceptor dyad

    KAUST Repository

    Filatov, Mikhail A.

    2015-10-13

    The synthesis and photophysical characterization of a palladium(II) porphyrin – anthracene dyad bridged via short and conformationally rigid bicyclo[2.2.2]octadiene spacer were achieved. A spectroscopic investigation of the prepared molecule in solution has been undertaken to study electronic energy transfer in excited singlet and triplet states between the anthracene and porphyrin units. By using steady-state and time-resolved photoluminescence spectroscopy it was shown that excitation of the singlet excited state of the anthracene leads to energy transfer to the lower-lying singlet state of porphyrin. Alternatively, excitation of the porphyrin followed by intersystem crossing to the triplet state leads to very fast energy transfer to the triplet state of anthracene. The rate of this energy transfer has been determined by transient absorption spectroscopy. Comparative studies of the dynamics of triplet excited states of the dyad and reference palladium octaethylporphyrin (PdOEP) have been performed.

  2. Sources of polycyclic aromatic hydrocarbons (PAHs) pollution in marine sediment from Tuanku Abdul Rahman National Park, Sabah

    International Nuclear Information System (INIS)

    The concentrations of parent and alkyl Polycyclic Aromatic Hydrocarbons (PAHs) in marine sediment samples collected from Tuanku Abdul Rahman National Park, Sabah were determined by using GC-MS. The ratio of anthracene to anthracene plus phenanthrene, fluoranthene to fluoranthene plus pyrene, benz[a]anthracene to benz[a]anthracene plus chrysene and indeno[1,2,3-cd]pyrene to indeno[1,2,3-cd]pyrene plus benzo[g,h,i]perylene, compounds were used to identify the sources of PAHs pollution. The total concentration of parent and alkyl PAHs are ranged from 121.7 to 191.5 ng/ g dry weight. The concentrations of PAHs pollution in sediments were categorised as a moderate polluted. The ratio values of PAHs compound indicate the origin source of PAHs pollutions in marine sediment sample of Tuanku Abdul Rahman National Park were originated from fossil fuel combustion (pyrolytic). (author)

  3. A molecular-sized tunnel-porous crystal with a ratchet gear structure and its one-way guest-molecule transportation property

    Science.gov (United States)

    Kataoka, Keisuke; Yasumoto, Tetsuaki; Manabe, Yousuke; Sato, Hiroyasu; Yamano, Akihito; Katagiri, Toshimasa

    2013-01-01

    An anisotropic tunnel microporous crystal was prepared. Active transportation of anthracene as a guest molecule in the anisotropic tunnels was observed. The direction of anthracene movement implies that the anisotropic tunnel did not work as a flap-check valve. The direction of the movement was consistent with that caused by a Brownian ratchet.An anisotropic tunnel microporous crystal was prepared. Active transportation of anthracene as a guest molecule in the anisotropic tunnels was observed. The direction of anthracene movement implies that the anisotropic tunnel did not work as a flap-check valve. The direction of the movement was consistent with that caused by a Brownian ratchet. Electronic supplementary information (ESI) available. CCDC reference numbers 837539 and 837540. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2nr30880k

  4. Comments on Coulomb pairing in aromatic hydrocarbons

    CERN Document Server

    Huber, D L

    2013-01-01

    Recently reported anomalies in the double-photonionization spectra of aromatic molecules such as benzene, naphthalene, anthracene and coronene are attributed to Coulomb-pair resonances of pi electrons.

  5. EXCITON DYNAMICS IN ORGANIC MOLECULAR CRYSTALS

    OpenAIRE

    A. Matsui; Mizuno, K.; Kobayashi, M.

    1985-01-01

    Dynamical behavior of Frenkel excitons in aromatic hydrocarbon crystals, pyrene, α-perylene, β-perylene, and tetracene are overviewed based on the published references and in terms of the self-trap depth. Then pressure-induced instability in exciton states (the change in the self-trap depth) in α-perylene and anthracene is demonstrated and discussed. Finally a quasi-free exciton state is suggested to be the origin of the luminescence in anthracene at room temperature.

  6. 1,4,5,8-Tetraisopropylanthracene

    Directory of Open Access Journals (Sweden)

    Chitoshi Kitamura

    2010-09-01

    Full Text Available The molecules of the title compound, C26H34, possess crystallographically imposed inversion symmetry. The anthracene ring system is planar within 0.038 (1 Å. The two methyl groups in each independent isopropyl group are oriented on either side of the anthracene plane. In the crystal structure, the molecules adopt a herringbone-like arrangement without π–π stacking.

  7. Chemo Protective role of Moringa oleifera and its isolated Saponin against DMBA induced Tissue Damage in male mice: A Histopathological analysis

    OpenAIRE

    Veena Sharma; Ritu Paliwal

    2012-01-01

    Moringa oleifera, a well known traditional medicinal plant from Moringaceae family has a remarkable reputation among the indigenous medical practitioners. The chemo protective role of hydroethanolic extract of Moringa oleifera and its isolated saponin against 7, 12- dimethyl-benz[a]anthracene (DMBA) intoxicated mice was investigated in the present study with the help of histopathological analysis of soft tissues (liver and kidney). The PAH 7, 12-dimethyl-benz[a]anthracene (DMBA) acts as a pot...

  8. EFFECT OF HUMIC COMPOUNDS ON BACTERIAL GROWTH IN BIOREMEDIATION OF PAHS

    Directory of Open Access Journals (Sweden)

    R. Rezaei Kalantary, A. Badkoubi

    2006-01-01

    Full Text Available Polycyclic Aromatic Hydrocarbons (PAHs which are introduced into environment are potentially carcinogenic, mutagenic and toxic contaminants. The effect of extractable humic substances (EHS on bacterial density in bioremediation of anthracene in liquid systems was investigated. The ratio of EHS to anthracene were in two concentrations of 0.35 and 1.05 g dry EHS (with 30% organic matter per one mg anthracene. In the tests with EHS, an increase in bacterial density even by 8 fold of magnitude was seen in 12-15 days. Then a fast decrease was occurred and prolonged till the end of the test time for the tests that had EHS without anthracene. In the tests which anthracene was the only substrate increasing in bacterial population was not seen. The results showed that up to 21 days the system was free from degradation. So the first increasing in bacterial population showed that EHS might be used as a readily substrate for PAH degraders. The presence of EHS (fulvic and humic acid can stimulate bacterial community and activity that caused enhancement in anthracene bioremediation.

  9. The Synthesis and Anion Recognition Property of Symmetrical Chemosensors Involving Thiourea Groups: Theory and Experiments

    Directory of Open Access Journals (Sweden)

    Xuefang Shang

    2015-11-01

    Full Text Available The synthesis of four symmetrical compounds containing urea/thiourea and anthracene/nitrobenzene groups was optimized. N,N’-Di((anthracen-9-yl-methylene thio-carbonohydrazide showed sensitive and selective binding ability for acetate ion among the studied anions. The presence of other competitive anions including F−, H2PO4−, Cl−, Br− and I− did not interfere with the strong binding ability. The mechanism of the host-guest interaction was through multiple hydrogen bonds due to the conformational complementarity and higher basicity. A theoretical investigation explained that intra-molecular hydrogen bonds existed in the compound which could strengthen the anion binding ability. In addition, molecular frontier orbitals in molecular interplay were introduced in order to explain the red-shift phenomenon in the host-guest interaction process. Compounds based on thiourea and anthracene derivatives can thus be used as a chemosensor for detecting acetate ion in environmental and pharmaceutical samples.

  10. (E-Methyl 3-(10-bromoanthracen-9-ylacrylate

    Directory of Open Access Journals (Sweden)

    Bernhard Bugenhagen

    2013-07-01

    Full Text Available In the title molecule, C18H13BrO2, the anthracene unit forms an angle of 46.91 (2° with the mean plane of the methyl acrylate moiety. In the crystal, the molecules arrange themselves into strands parallel to [010] and, due to the crystal symmetry, there are eight strands crossing the unit cell. In each strand, molecules form short C—H...O and C—H...π contacts and have their anthracene groups parallel to each other. Neighboring strands, related by a c-glide operation, are connected via C—H...O interactions and form a layer parallel to (100. The arrangement of the acrylate and anthracene groups in the crystal do not allow for [2 + 2] or [4 + 4] cycloaddition.

  11. A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons.

    Science.gov (United States)

    Zhang, Rui-Feng; Hu, Wen-Jing; Liu, Yahu A; Zhao, Xiao-Li; Li, Jiu-Sheng; Jiang, Biao; Wen, Ke

    2016-07-01

    A shape-persistent cryptand 1, containing two face-to-face oriented electron-deficient 2,4,6-triphenyl-1,3,5-triazine units separated by approximately 7 Å, and bridged by two rigid 1,8-naphthyridine linkers and a pentaethylene oxide loop, is created for capturing polycyclic aromatic hydrocarbons. Cryptand 1 formed 1:1 complexes with PAH guest molecules, such as phenanthrene (6), anthracene (7), pyrene (8), triphenylene (9), and tetraphene (10). The single-crystal structure of complex 6⊂1 revealed that 6 was included in the cavity of 1 via face-to-face π···π stacking interactions. Soaking crystalline 1 in a toluene solution of anthracene resulted in anthracene from the toluene solution being picked up by the crystalline solid of 1. PMID:27258531

  12. Neutron imaging using the anisotropic response of crystalline organic scintillators

    International Nuclear Information System (INIS)

    An anisotropy in a scintillator's response to neutron elastic scattering interactions can in principle be used to gather directional information about a neutron source using interactions in a single detector. In crystalline organic scintillators, such as anthracene, both the amplitude and the time structure of the scintillation light pulse vary with the direction of the proton recoil with respect to the crystalline axes. Therefore, we have investigated the exploitation of this effect to enable compact, high-efficiency fast neutron detectors that have directional sensitivity via a precise measurement of the pulse shape. We report measurements of the pulse height and shape dependence on proton recoil angle in anthracene, stilbene, p-terphenyl, diphenyl anthracene (DPA), and tetraphenyl butadiene (TPB). Image reconstruction for simulated neutron sources is demonstrated using maximum likelihood methods for optimal directional sensitivity.

  13. Metabolism of polycyclic aromatic hydrocarbons in benthic microcosms

    International Nuclear Information System (INIS)

    [12-14C]Benz(a)anthracene was used as a tracer to follow the metabolism of polycyclic aromatic hydrocarbons in benthic microcosms containing fine sediment and polychaetes. Experiments were conducted using both large (230 L) and small (2 L) microcosms where the fate of the radiolabel was followed for up to 42 days in the water column, in the sediment reservoir, and in two species of polychaetes (Nereis virens and Nephtys incisa). Benz(a)anthracene was extensively metabolized in these microcosms, although the degree of metabolism was highly dependent on how the radiolabel was introduced to the system and the presence of suspended particulates and an established microbial community

  14. Synthesis of 14C labelled acrylic derivatives: diethyl [3-14C] methylidenemalonate and isobutyl [3-14C] cyanoacrylate

    International Nuclear Information System (INIS)

    Isobutyl [3-14C] cyanoacrylate and diethyl [3-14C] methylidenemalonate were synthesized by the intermediate of their protective Diels-Alder adduct with anthracene. These adducts were obtained in a one-pot procedure by Knoevenagel condensation of [14C] paraformaldehyde with isobutyl cyanoacetate and diethyl malonate respectively in the presence of a basic catalyst and anthracene. The adducts are stable crystalline compounds easily purified by recrystallization. The olefinic target compounds were obtained in high chemical and radiochemical purity (>99%) by thermolysis at 2200C in mineral oil in the presence of maleic anhydride. (author)

  15. Hidrocarbonetos policíclicos aromáticos (HPAS em cachaça, rum, uísque e álcool combustível Polycyclic aromatic hydrocarbons (PAHS in cachaça, rum, whiskey and alcohol fuel

    Directory of Open Access Journals (Sweden)

    Carlos Alexandre Galinaro

    2009-01-01

    Full Text Available The concentration of 15 polycyclic aromatic hydrocarbons (PAHs in 57 samples of distillates (cachaça, rum, whiskey, and alcohol fuel has been determined by HPLC-Fluorescence detection. The quantitative analytical profile of PAHs treated by Partial Least Square - Discriminant Analysis (PLS-DA provided a good classification of the studied spirits based on their PAHs content. Additionally, the classification of the sugar cane derivatives according to the harvest practice was obtained treating the analytical data by Linear Discriminant Analysis (LDA, using naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, benz[b]fluoranthene, and benz[g,h,i]perylene, as a chemical descriptors.

  16. 8-Phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18-heptaene

    Directory of Open Access Journals (Sweden)

    Eason M. Mathew

    2013-07-01

    Full Text Available In the title compound, C24H18S, the dihedral angles between the phenyl ring and the two benzene rings of the anthracene moiety are 51.92 (9 and 68.24 (9°, whereas the dihedral angle between the two anthracene benzene rings is 120.13 (9°. The three non-aromatic six-membered rings are in boat conformations, while the five-membered ring has an envelope conformation on the S atom. In the crystal, there are three C—H...π interactions, which facilitate the packing of the molecules.

  17. Application of singular value decomposition analysis to time-dependent powder diffraction data of an in-situ photodimerization reaction

    International Nuclear Information System (INIS)

    A successful application of singular value decomposition analysis to time-dependent powder diffraction data of an in-situ photodimerization reaction of some anthracene derivatives is presented. Singular value decomposition (SVD) analysis has important applications for time-dependent crystallographic data, extracting significant information. Herein, a successful application of SVD analysis of time-resolved powder diffraction data over the course of an in-situ photodimerization reaction of anthracene derivatives is introduced. SVD revealed significant results in the case of 9-methylanthracene and 1-chloroanthracene. The results support the formation of the 9-methylanthracene stable dimer phase and suggest the existence of an excimer state

  18. Triplet excitation dynamics of two keto-carotenoids in n-hexane and in methanol as studied by ns flash photolysis spectroscopy

    Science.gov (United States)

    Li, Li; Hu, Feng; Chang, Yu-Qiang; Zhou, Yan; Wang, Peng; Zhang, Jian-Ping

    2015-07-01

    Siphonaxanthin and siphonein are two keto-carotenoids. Upon anthracene-sensitizing, triplet excitation dynamics of these two carotenoids were studied in n-hexane and in methanol, respectively, by ns flash photolysis spectroscopy. In n-hexane, bleaching of the ground state absorption (GSB) and the excitation triplet (3Car*) absorption were observed. In methanol, upon the decay of the 3Car*, the cation dehydrodimer of carotenoid, #[Car]2+, generated by the same rate, while an additional GSB generated synchronously, a polar solvent assisted and anthracene-sensitized mechanism was addressed based on the discussion. The environment-sensitive triplet excitation dynamics imply their potential role in photo-protection in vivo.

  19. Hydrogen Peroxide Production as a Limiting Factor in Xenobiotic Compound Oxidation by Nitrogen-Sufficient Cultures of Bjerkandera sp. Strain BOS55 Overproducing Peroxidases

    OpenAIRE

    Kotterman, M.; Wasseveld, R. A.; Field, J. A.

    1996-01-01

    The overproduction of ligninolytic peroxidase by the N-deregulated white rot fungus Bjerkandera sp. strain BOS55 under nitrogen-sufficient conditions had no noteworthy effect on the oxidation of anthracene or the decolorization of the polymeric aromatic dye Poly R-478 in 6-day-old cultures. Only when the endogenous production of H(inf2)O(inf2) was increased by the addition of extra oxygen and glucose could a 2.5-fold increase in the anthracene oxidation rate and a 6-fold increase in the Poly ...

  20. Synthesis of Silica-anchored Sensitizer and its Application in the Preparation of Previtamin D3 from Tachysterol

    Institute of Scientific and Technical Information of China (English)

    Chang Jiang YOU; Rong XIE; Yun Yan GAO; Yong Bin HAN; Guo Qiang YANG; Yi LI

    2004-01-01

    A silica gel-anchored photosensitizer was synthesized with anthracene as sensitizer moiety. The photoisomerization of tachysterol to previtamin D3 was carried out with this heterogeneous photosensitizer in ethanol. The experiment results demonstrate that this solid phase photosensitizer is efficient for the photoisomerization and can be simply separated from the reaction mixture by filtration.

  1. Diffusion of PAH in potato and carrot slices and application for a potato model

    DEFF Research Database (Denmark)

    Trapp, Stefan; Cammarano, A.; Capri, E.;

    2007-01-01

    of water, potato tissue, and carrot tissue. Naphthalene, phenanthrene, anthracene, and fluoranthene served as model substances. Their transfer from source to sink disk was measured by HPLC to determine a velocity rate constant proportional to the diffusive conductivity. The diffusive flux through the plant...

  2. 9-(Dimethoxymethylanthracene

    Directory of Open Access Journals (Sweden)

    Cheng Yao

    2008-02-01

    Full Text Available In the title compound, C17H16O2, a dimethyl acetal of 9-anthraldehyde, the anthracene skeleton is planar and the two methoxy groups attached to the C atom at position 9 of the aromatic ring system are located above and below the ring system.

  3. Effects of Autoclaving and Mercuric Chloride Sterilization on PAHs Dissipation in a Two-Liquid-Phase Soil Slurry

    Institute of Scientific and Technical Information of China (English)

    WANG Cong-Ying; WANG Fang; WANG Tao; YANG Xing-Lun; BIAN Yong-Rong; F.O.KENGARA; LI Zeng-Bo; JIANG Xin

    2011-01-01

    A two-liquid-phase (TLP) soil slurry system was employed to quantify the efficiencies of autoclaving and mercuric chloride sterilization in the dissipation of polycyclic aromatic hydrocarbons (PAHs). The fates of 11 PAHs (naphthalene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo(a)anthracene, benzo(a)pyrene, benzo(b)fluoranthene, benzo(k)fluoranthene, dibenzo(a, h)anthracene) were recorded over 113 days of incubation. No microorganisms were detected in the HgCl2-sterilized soil slurries during the whole incubation period, indicating very effective sterilization. However, about 2%-36% losses of PAHs were observed in the HgCl2-sterilized slurry. In contrast to the HgCl2-sterilized soil slurry, some microorganisms survived in the autoclaved soil slurries. Moreover,significant biodegradation of 6 PAHs (naphthalene, fluorene, phenanthrene, anthracene, fluoranthene and pyrene) was observed in the autoclaved soil slurries. This indicated that biodegradation results of PAHs in the soil slurries, calculated on basis of the autoclaved control, would be underestimated. It could be concluded that the sterilization efficiency and effectiveness of HgCl2 on soil slurry was much higher than those of autoclaving at 121 ℃ for 45 min.

  4. Role of arbuscular mycorrhizal fungus Rhizophagus custos in the dissipation of PAHs under root-organ culture conditions

    International Nuclear Information System (INIS)

    Polycyclic aromatic hydrocarbons (PAHs) are one of the most common contaminants in soil. Arbuscular mycorrhizal (AM) fungi make host plants resistant to pollutants. This study aims to evaluate the impact of anthracene, phenanthrene and dibenzothiophene on the AM fungus Rhizophagus custos, isolated from soil contaminated by heavy metals and PAHs, under monoxenic conditions. We found a high level of tolerance in R. custos to the presence of PAHs, especially in the case of anthracene, in which no negative effect on AM-colonized root dry weight (root yield) was observed, and also a decrease in the formation of anthraquinone was detected. Increased PAH dissipation in the mycorrhizal root culture medium was observed; however, dissipation was affected by the level of concentration and the specific PAH, which lead us to a better understanding of the possible contribution of AM fungi, and in particular R. custos, to pollutant removal. -- Highlights: •The AM fungus R. custos contributes to PAH dissipation and removal from the medium. •R. custos showed high levels of tolerance to high concentrations of anthracene. •Phenanthrene negatively affects the functionality of the symbiosis. •R. custos accumulates PAHs in spores and extraradical mycelia. •R. custos is able to prevent PAHs from entering roots. -- The AM fungus Rhizophagus custos is involved in PAH dissipation in absence of other microorganisms and could be potentially effective in protecting anthracene exposed plants

  5. Detection of Neutrons with Scintillation Counters

    Science.gov (United States)

    Hofstadter, R.

    1948-11-01

    Detection of slow neutrons by: detection of single gamma rays following capture by cadmium or mercury; detection of more than one gamma ray by observing coincidences after capture; detection of heavy charged particles after capture in lithium or baron nuclei; possible use of anthracene for counting fast neutrons investigated briefly.

  6. 9-(Guanidinomethyl)-10-vinylanthracene: a suitable fluorescent monomer for MIPs

    NARCIS (Netherlands)

    Zhang, Huiqi; Verboom, Willem; Reinhoudt, David N.

    2001-01-01

    9-(Guanidinomethyl)anthracene derivatives with a bromo (6) or a vinyl group (10) at the 10-position have been prepared starting from 9-bromoanthracene (1). They show 1:1 complexation with carboxylic acids or carboxylates with K-values of 1.2–1.4×105 M−1 in deuteriomethanol. Copolymerization of 9-vin

  7. Self-assembly of diphenylalanine peptides into microtubes with "turn on" fluorescence using an aggregation-induced emission molecule.

    Science.gov (United States)

    Na, Na; Mu, Xiaoyan; Liu, Qiuling; Wen, Jiying; Wang, Fangfang; Ouyang, Jin

    2013-10-01

    The self-assembly of diphenylalanine peptides (l-Phe-l-Phe) into microtubes with "turn on" bright yellow green fluorescence was described, which was achieved using an aggregation-induced emission (AIE) molecule of 9,10-bis[4-(3-sulfonatopropoxyl)-styryl] anthracene (BSPSA) sodium. PMID:24045462

  8. The Effect of Interaction Between White-rot Fungi and Indigenous Microorganisms on Degradation of Polycyclic Aromatic Hydrocarbons in Soil

    International Nuclear Information System (INIS)

    White-rot fungi applied for soil bioremediation have to compete with indigenous soil microorganisms. The effect of competition on both indigenous soil microflora and white-rot fungi was evaluated with regard to degradation of polycyclic aromatic hydrocarbons (PAH) with different persistence in soil. Sterile and non-sterile soil was artificially contaminated with 14C-labeled PAH consisting of three (anthracene), four (pyrene, benz[a]anthracene) and five fused aromatic rings (benzo[a]pyrene, dibenz[a,h]anthracene). The two fungi tested,Dichomitus squalens and Pleurotus ostreatus, produced similar amounts of ligninolytic enzymes in soil, but PAH mineralization by P. ostreatus was significantly higher. Compared to the indigenous soil microflora, P.ostreatus mineralized 5-ring PAH to a larger extent, while the indigenous microflora was superior in mineralizing 3-ring and 4-ring PAH. In coculture the special capabilities of both soil microflora and P. ostreatus were partly restricted due to antagonistic interactions, but essentially preserved. Thus, soil inoculation with P. ostreatus significantly increased the mineralization of high-molecular-weight PAH, and at the same time reduced the mineralization of anthracene and pyrene. Regarding the mineralization of low-molecular-weight PAH, the stimulation of indigenous soil microorganisms by straw amendment was more efficient than application of white-rot fungi

  9. Uptake, translocation, and accumulation of polycyclic aromatic hydrocarbons in vegetation

    International Nuclear Information System (INIS)

    A review of the scientific literature was conducted to determine the potential for plants to take up polycyclic aromatic hydrocarbons (PAHs) from soils and the possibility of PAH movement from soils into vegetation at waste disposal sites associated with manufactured gas plants (MGP). Studies published since 1983 are considered in conjunction with previous publications and literature reviews on PAH uptake by vegetation. These studies indicate that the extent to which sorption to roots occurs is likely to be influenced by species-specific properties of the plant, physicochemical properties of each PAH, soil properties, and biodegradation rates of the PAHs in soil. PAHs containing five or more rings may sorb to plant roots but are not expected to be translocated to foliage in other than trace quantities. Uptake of naphthalene, anthracene, and benzo[a]anthracene by roots has been reported in the literature. In addition, eight PAHs of three and four rings (acenapthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, and chrysene) were isolated from leaves and roots of four plant species collected near a coal tar disposal trench in eastern Tennessee. A total concentration of 5519 ng/g was observed for the eight PAHs in roots of lamb's quarters. Coal tar, in soil, was implicated as the source of PAHs in the four plant species

  10. Detection of strand breaks in phiX 174 RFI and PM2 DNA reacted with ultimate and proximate carcinogens.

    Science.gov (United States)

    Thielmann, H W

    1977-10-01

    Supercoiled DNA duplexes of phages phiX 174 and PM2 were treated in aqueous solution at neutral pH with ultimate and proximate carcinogens. Subsequently, the carcinogen-treated phage DNAs were subjected to velocity sedimentation in neutral and alkaline sucrose to quantitative introduction of single strand breaks. Reaction of phage DNA with the ultimate carcinogens N-methyl-N-nitrosourea (MeNOUr), N-ethyl-N-nitrosourea (EtNOUr), 7-bromomethyl-benza[a]-anthracene, N-acetoxy-2-acetylaminofluorene [(Ac)2ONFln] and K-region oxides for short periods followed by sedimentation in neutral sucrose gradients led to very few breaks. Incubation with the proximate carcinogens N-hydroxy-2-acetylaminofluorene, 2-acetylaminofluorene, 7-methyl-, and 7,12-dimethyl-benza[a]anthracene did not result in breaks. However, when the phage DNAs were reacted with the ultimate carcinogens under the same conditions but subsequently alkali-denatured and sedimented in alkaline sucrose gradients, single strand breaks were readily introduced. Incubation with the proximate carcinogens followed by alkali denaturation and sedimentation in alkaline sucrose showed that only 7,12-dimethyl-benz[a]anthracene and, to a minor extent, 7-methyl-benz[]anthracene caused alkali-inducible breaks. The ability of N-methyl-N'-nitro-N-nitrosoguanidine to effect breakdown of superhelical phage DNA in alkali was found enhanced in the presence of N-acetyl-cysteine. PMID:145749

  11. CD34 EXPRESSION BY HAIR FOLLICLE STEM CELLS IS REQUIRED FOR SKIN TUMOR DEVELOPMENT IN MICE

    Science.gov (United States)

    We used knockout mice to show that a cell surface protein called CD34 is required for skin tumor formation in mice. Wild type mice treated with 7-12-Dimethylbenz(a)anthracene (DMBA) and a tumor promoter developed papillomas. When we treated CD34 knockout (KO) mice the same way, n...

  12. Physicochemical study on interactions between T-2 and HT-2 toxin derivatives and cyclodextrins

    Science.gov (United States)

    Physicochemical interactions occurring between fluorescent anthracene derivatives of T-2 and HT-2 toxins and different cyclodextrins (CDs) were investigated in aqueous solutions by means of UV-Vis absorption, fluorescence emission, and Dynamic Light Scattering. Binding constant values and physicoche...

  13. Photooxygenation and gas-phase reactivity of multiply threaded pseudorotaxanes.

    Science.gov (United States)

    Nowosinski, Karol; Warnke, Stephan; Pagel, Kevin; Komáromy, Dávid; Jiang, Wei; Schalley, Christoph A

    2016-04-01

    The solution-phase photooxygenation of multiply threaded crown/ammonium pseudorotaxanes containing anthracene spacers is monitored by electrospray ionization Fourier-transform ion-cyclotron-resonance (ESI-FTICR) mass spectrometry. The oxygenated pseudorotaxanes are mass-selected and fragmented by infrared multiphoton dissociation (IRMPD) and/or collision-induced dissociation (CID) experiments and and their behavior compared to that of the non-oxygenated precursors. [4+2]Cycloreversion reactions lead to the loss of O2, when no other reaction channel with competitive energy demand is available. Thus, the release of molecular oxygen can serve as a reference reaction for the energy demand of other fragmentation reactions such as the dissociation of the crown/ammonium binding motifs. The photooxygenation induces curvature into the initially planar anthracene and thus significantly changes the geometry of the divalent, anthracene-spacered wheel. This is reflected in ion-mobility data. Coulomb repulsion in multiply charged pseudorotaxanes assists the oxygen loss as the re-planarization of the anthracene increases the distance between the two charges. PMID:27041657

  14. Multi-color light-emitting transistors composed of organic single crystals

    NARCIS (Netherlands)

    Yomogida, Yohei; Sakai, Hayato; Sawabe, Kosuke; Gocho, Shota; Bisri, Satria Zulkarnaen; Nakanotani, Hajime; Adachi, Chihaya; Hasobe, Taku; Iwasa, Yoshihiro; Takenobu, Taishi

    2013-01-01

    We report a novel concept for multi-color light emission from an ambipolar organic single-crystal transistor using natural optical waveguides, the self-absorption effect, Davydov splitting and the unique alignment of the transition dipole moments. We used 9,10-bis(2,2-diphenylvinyl)-anthracene singl

  15. Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.

    Science.gov (United States)

    Zagotto, G; Oliva, A; Guano, F; Menta, E; Capranico, G; Palumbo, M

    1998-01-20

    New bisantrene analogues were synthesized, bearing one or two 4,5-dihydro-1H-imidazol-2-yl hydrazone side chains at positions 1,4 or 9 of the anthracene ring system. A 10-azabioisostere was also prepared. The position of substituents in structurally isomeric drugs modulates topoisomerase II poisoning and specificity, along with cytotoxicity. PMID:9871638

  16. A double-leg donor-acceptor molecular elevator: new insight into controlling the distance of two platforms.

    Science.gov (United States)

    Zhang, Zhi-Jun; Han, Min; Zhang, Heng-Yi; Liu, Yu

    2013-04-01

    A double-leg elevator with an electron-rich anthracene moiety at the platformlike component and an electron-deficient naphthalenediimide unit in the middle of a double-leg riglike component was prepared through "click chemistry", in which the reversible elevator movement between different levels could be controlled upon the addition of base and acid. PMID:23534551

  17. Predictions of Resuspension of Highway Detention Pond Deposits in Interrain Event Periods due to Wind-Induced Currents and Waves

    DEFF Research Database (Denmark)

    Bentzen, Thomas Ruby; Larsen, Torben; Rasmussen, Michael R.

    2009-01-01

    (a,h)anthracene and indeno(1,2,3-cd)pyrene (PAHs) and the heavy metals of cadmium, chromium, copper, lead, nickel, and zinc. The current and wave-generated bed-shear stresses entail a discharged bulk of pollutants corresponding to approximately 10% of the annual accumulation of pollutants in the present pond due...

  18. Characterization of polycyclic aromatic hydrocarbons in fugitive PM10 emissions from an integrated iron and steel plant.

    Science.gov (United States)

    Khaparde, V V; Bhanarkar, A D; Majumdar, Deepanjan; Rao, C V Chalapati

    2016-08-15

    Fugitive emissions of PM10 (particles <10μm in diameter) and associated polycyclic aromatic hydrocarbons (PAHs) were monitored in the vicinity of coking unit, sintering unit, blast furnace and steel manufacturing unit in an integrated iron and steel plant situated in India. Concentrations of PM10, PM10-bound total PAHs, benzo (a) pyrene, carcinogenic PAHs and combustion PAHs were found to be highest around the sintering unit. Concentrations of 3-ring and 4-ring PAHs were recorded to be highest in the coking unit whereas 5-and 6-ring PAHs were found to be highest in other units. The following indicatory PAHs were identified: indeno (1,2,3-cd) pyrene, dibenzo (a,h) anthracene, benzo (k) fluoranthene in blast furnace unit; indeno (1,2,3-cd) pyrene, dibenzo (a,h) anthracene, chrysene in sintering unit; Anthracene, fluoranthene, chrysene in coking unit and acenaphthene, fluoranthene, fluorene in steel making unit. Total-BaP-TEQ (Total BaP toxic equivalent quotient) and BaP-MEQ (Total BaP mutagenic equivalent quotient) concentration levels ranged from 2.4 to 231.7ng/m(3) and 1.9 to 175.8ng/m(3), respectively. BaP and DbA (dibenzo (a,h) anthracene) contribution to total-BaP-TEQ was found to be the highest. PMID:27099996

  19. Synthesis and Property of New Propeller Shaped Emitting Materials for Organic Light-Emitting Devices.

    Science.gov (United States)

    Kang, Seokwoo; Lee, Hayoon; Kim, Beomjin; Park, Youngil; Park, Jongwook

    2016-03-01

    New propeller type emitting compound, namely 3,6-di-anthracen-9-yl-9,10-bis-(4-anthracen-9-yi-phenyl)-phenanthrene[TAnDAP] and 3,6-bis-(10-phenyl-anthracen-9-yl)-9,10-bis-[4-(10-phenyl-anthracen-9-yl)-phenyl]-phenanthrene [TAnPDAP] were synthesized through Suzuki and McMurry reactions. We investigated their physical properties such as optical, electrochemical, and electroluminescent properties. The two compounds were used as an emitting layer in OLED devices: ITO/2-TNATA (60 nm)/NPB (15 nm)/non-doped: TAnDAP or TAnPDAP (35 nm)/Alq3 (20 nm)/LiF (1 nm)/Al (200 nm). The TAnDAP OLED device showed C.I.E. value of (0.28, 0.41) and luminance efficiency of 3.81 cd/A at 10 mA/cm2. The TAnPDAP device showed C.I.E. value of (0.20, 0.27) and high luminance efficiency of 5.40 cd/A at 10 mA/cm2. TAnPDAP was found to show better luminance efficiency and C.I.E. value than TAnDAP because it has a bulky 9-phenylanthracene. PMID:27455768

  20. Eisenia fetida increased removal of polycyclic aromatic hydrocarbons from soil

    International Nuclear Information System (INIS)

    The removal of phenanthrene, anthracene and benzo(a)pyrene added at three different concentrations was investigated with or without earthworms (Eisenia fetida) within 11 weeks. Average anthracene removal by the autochthonous micro-organisms was 23%, 77% for phenanthrene and 13% for benzo(a)pyrene, while it was 51% for anthracene, 47% for benzo(a)pyrene and 100% for phenanthrene in soil with earthworms. At 50 and 100 mg phenanthrene kg-1 E. fetida survival was 91% and 83%, but at 150 mg kg-1 all died within 15 days. Survival of E. fetida in soil amended with anthracene ≤1000 mg kg-1 and benzo(a)pyrene ≤150 mg kg-1 was higher than 80% and without weight loss compared to the untreated soil. Only small amounts of PAHs were detected in the earthworms. It was concluded that E. fetida has the potential to remove large amounts of PAHs from soil, but more work is necessary to elucidate the mechanisms involved. - Addition of earthworms, Eisenia fetida, accelara removal of polycyclic aromatic hydrocarbons from soil

  1. Purification of a New Manganese Peroxidase of the White-Rot Fungus Irpex lacteus and Degradation of Polycyclic Aromatic Hydrocarbons by the Enzyme

    Czech Academy of Sciences Publication Activity Database

    Baborová, Petra; Möder, M.; Baldrian, Petr; Cajthamlová, Kamila; Cajthaml, Tomáš

    2006-01-01

    Roč. 157, - (2006), s. 248-253. ISSN 0923-2508 R&D Projects: GA AV ČR KJB6020308; GA AV ČR KJB600200516 Institutional research plan: CEZ:AV0Z50200510 Keywords : anthracene * biodegradation * irpex lacteus Subject RIV: EE - Microbiology, Virology Impact factor: 2.504, year: 2006

  2. Photoinduced toxicity single and binary mixtures of four polycyclic aromatic hydrocarbons to the marine diatom Skeletonema costatum

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Diatom Skeletonema costatum Cleve is one of the main predominant phytoplankton species in the Changjiang Estuary in China. In order to provide some basic information for future assessment of the potential risk on phytoplankton communities in this estuary caused by polycyclic aromatic hydrocarbons(PAHs), this alga was selected as a representative to investigate the photoinduced toxicity of PAHs, in single and mixture. Four PAHs including three-ring phenanthrene and anthracene, four-ring fluoranthene and pyrene were tested in the laboratory. The single toxicity of each PAH on this microalga was compared with and without the simulated solar UV radiation. The results showed that this microalga was sensitive to PAH's photoinduced toxicity. Ratios of the 72 h median effect concentration obtained for fluorescent and UV light tests were about 8.4 for phenanthrene, 13.0 for anthracene, 6.5 for fluoranthene, and 5.7 for pyrene, indicating that UV light enhanced the PAH toxicity to this alga significantly. Under the fluorescent radiation (lacking UV), the dose-response curves based on chemical concentrations revealed that the order of toxic strength was fluoranthene greater than pyrene greater than anthracene greater than phenanthrene; while under the UV radiation (476 μW/cm2 for UVA, 6.5 μW/cm2 for UVB) it became fluoranthene approximately equaling anthracene greater than pyrene greater than phenanthrene, indicating that the UV light also changed its relative toxicity to this alga. The photoinduced toxicity of PAHs to the marine diatom S. costatum might be a synergistic effect of photosensitization reactions (e.g., generation of single-state oxygen) and photomodification (photooxidation and/or photolysis).The combined effects of six binary mixtures on the marine diatom S. costatum were investigated using the additive-index method. Four binary-mixtures (phenanthrene plus anthracene; phenanthrene plus pyrene; anthracene plus fluoranthene; anthracene plus pyrene) were found

  3. Hard Cap Espresso Machines in Analytical Chemistry: What Else?

    Science.gov (United States)

    Armenta, Sergio; de la Guardia, Miguel; Esteve-Turrillas, Francesc A

    2016-06-21

    A hard cap espresso machine has been used in combination with liquid chromatography with molecular fluorescence detection for the determination of polycyclic aromatic hydrocarbons (PAHs) from contaminated soils and sediments providing appropriate extraction efficiencies and quantitative results. Naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benz[b]fluoranthene, benz[k]fluoranthene, benz[a]pyrene, dibenz[a,h]anthracene, benz[ghi]perylene, and indeno[1,2,3-cd]pyrene were used as target compounds. It should be mentioned that the pairs benz[a]anthracene-chrysene and dibenz[a,h]anthracene-benz[ghi]perylene peaks coelute under the employed chromatographic conditions; thus, those compounds were determined together. PAHs were extracted from 5.0 g of soil, previously homogenized, freeze-dried, and sieved to 250 μm, with 50 mL of 40% (v/v) acetonitrile in water at a temperature of 72 ± 3 °C. The proposed procedure is really fast, with an extraction time of 11 s, and it reduces the required amount of organic solvent to do the sample preparation. The obtained limit of detection for the evaluated PAHs was from 1 to 38 μg kg(-1). Recoveries were calculated using clean soils spiked with 100, 500, 1000, and 2000 μg kg(-1) PAHs with values ranging from 81 to 121% and good precision with relative standard deviation values lower than 30%. The method was validated using soil and sediment certified reference materials and also using real samples by comparison with ultrasound-assisted extraction, as reference methodology, obtaining statistically comparable results. Thus, the use of hard cap espresso machines in the analytical laboratories offers tremendous possibilities as low cost extraction units for the extraction of solid samples. PMID:27224000

  4. Partition of polycyclic aromatic hydrocarbons on organobentonites

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    A series of organobentonites synthesized by exchanging organiccation such as dodecyltri-methylammonium (DTMA),benzyldimethyltetradecylammonium (BDTDA), cetyltrimethyl-ammonium (CTMA), octodeyltrimethylammonium (OTMA) on bentonite. The optimal condition, properties and mechanisms for the organobentonites to sorb phenanthrene, anthracene, naphthalene, acenaphthene in water were investigated in detail. The partition behavior was determined for four polycyclic aromatic hydrocarbons (PAHs), such as naphthalene, phenanthrene, anthracene and acenaphthene, from water to a series of organobentonites. The interlayer spacings and organic carbon contents of organobentonites, removal rate and sorption capacities for organobentonites to treat phenanthrene,anthracene, naphthalene, acenaphthene were correlated to the length of alkyl chains and the amounts of cation surfactant exchanged on Foundation item: the bentonite. Phenanthrene, anthracene, naphthalene, and acenaphthene sorption to organobentonites were characterized by linear isotherms, indicating solute partition between water and the organic phase composed of the large alkyl functional groups of quaternary ammonium cations. PAHs distribution coefficients (Kd)between organobentonites and water were proportional to the organic carbon contents of organobentonites. However, the partition coefficients (Koc) were nearly constants for PAHs in the system of organobentonite-water. The Koc of phenanthrene, anthracene,naphthalene, acenaphthene were 2.621x105, 2.106x105, 2.247x104,5.085x104, respectively. The means Koc values on the organobentonites are about ten to twenty times larger than the values on the soils/sediments, what is significant prerequisite for organobentonite to apply to remediation of pollution soil and groundwater. The sorption mechanism was also evaluated from octanol-water partition coefficients and aqueous solubility of PAHs. The correlations between lgKoc and 1gkow, 1gKoc and 1gS for PAHs in the system of water

  5. Tunneling of electrons via rotor-stator molecular interfaces: combined ab initio and model study

    CERN Document Server

    Petreska, Irina; Pejov, Ljupco; Kocarev, Ljupco

    2015-01-01

    Tunneling of electrons through rotor-stator anthracene aldehyde molecular interfaces is studied with a combined ab initio and model approach. Molecular electronic structure calculated from first principles is utilized to model different shapes of tunneling barriers. Together with a rectangular barrier, we also consider a sinusoidal shape that captures the effects of the molecular internal structure more realistically. Quasiclassical approach with the Simmons' formula for current density is implemented. Special attention is paid on conformational dependence of the tunneling current. Our results confirm that the presence of the side aldehyde group enhances the interesting electronic properties of the pure anthracene molecule, making it a bistable system with geometry dependent transport properties. We also investigate the transition voltage and we show that confirmation dependent field emission could be observed in these molecular interfaces at realistically low voltages. The present study accompanies our previ...

  6. Optimization of Large Volume Injection for Improved Detection of Polycyclic Aromatic Hydrocarbons (PAH) in Mussels

    DEFF Research Database (Denmark)

    Duedahl-Olesen, Lene; Ghorbani, Faranak

    2008-01-01

    mussel samples. Samples were extracted with Accelerated Solvent Extraction (ASE) followed by two semi-automatic clean-up steps; gel permeation chromatography (GPC) on S-X3 and solid phase extraction (SPE) on pre-packed silica columns, prior to gas chromatography-mass spectrometry (GC-MS) detection. In......-MS detection of anthracene, benz[a]anthracene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene and dibenzo[a,e]pyrene. The optimization of PTV-LVI for GC-MS analysis included the choice of liner, solvent venting, splitless time, split flow and initial inlet temperature for injection of 25 L standard solution and spiked...

  7. Synthetic Fuels Program

    International Nuclear Information System (INIS)

    Progress is reported on aquatic transport studies with regard to photolysis of polycyclic compounds in water; volatilization of PAH from water; bioaccumulation of anthracene by fathead minnows; bioaccumulation of polycyclic aromatic hydrocarbons by aquatic invertebrates; bioaccumulation of arylamines by zooplankton; availability of sediment-bound trace metals to bluegill; microbial transformation; transport and transformation of anthracene in natural waters; and microcosm studies. Progress is also reported on acute and chronic aquatic effects; acute and chronic terrestrial effects; leaching and chemical and physical characterization of solid wastes; toxicology of solid wastes; and field site task studies with regard to aquatic transport behavior of trace contaminants in wastewater discharges and airborne contaminants at coking plant field site

  8. Induction of active melanocytes in mouse skin by carcinogens: a new method for detection of skin carcinogens.

    Science.gov (United States)

    Iwata, K; Inui, N; Takeuchi, T

    1981-01-01

    Application of potent skin carcinogens, such as 7,12-dimethylbenz[a]anthracene, 3-methylcholanthrene, benzo[a]pyrene and 4-nitroquinoline-1-oxide, induced numerous dihydroxyphenylalanine (dopa)-positive cells in the interfollicular epidermis of C57BL/6 mice in a dose- and time-dependent fashion. Chrysene, a weak skin carcinogen, and croton oil, a tumor promoter, also induced 3--4 times more dopa-positive cells than acetone. Liver carcinogens, such as 3'-methyl-4-dimethylaminoazobenzene and N-2-acetylaminofluorene, and non-carcinogenic aromatic hydrocarbons, such as anthracene, fluoranthene, fluorene and pyrene, did not induce increase in these cells. These results indicate that increase in the number of dopa-positive cells after application of chemicals is well correlated with the abilities of these compounds to induce skin carcinogenesis and suppress sebaceous glands. PMID:7273337

  9. Supramolecular nanoreactors for intracellular singlet-oxygen sensitization

    Science.gov (United States)

    Swaminathan, Subramani; Fowley, Colin; Thapaliya, Ek Raj; McCaughan, Bridgeen; Tang, Sicheng; Fraix, Aurore; Burjor, Captain; Sortino, Salvatore; Callan, John F.; Raymo, Françisco M.

    2015-08-01

    An amphiphilic polymer with multiple decyl and oligo(ethylene glycol) chains attached to a common poly(methacrylate) backbone assembles into nanoscaled particles in aqueous environments. Hydrophobic anthracene and borondipyrromethene (BODIPY) chromophores can be co-encapsulated within the self-assembling nanoparticles and transported across hydrophilic media. The reversible character of the noncovalent bonds, holding the supramolecular containers together, permits the exchange of their components with fast kinetics in aqueous solution. Incubation of cervical cancer (HeLA) cells with a mixture of two sets of nanoparticles, pre-loaded independently with anthracene or BODIPY chromophores, results in guest scrambling first and then transport of co-entrapped species to the intracellular space. Alternatively, incubation of cells with the two sets of nanocarriers in consecutive steps permits the sequential transport of the anthracene and BODIPY chromophores across the plasma membrane and only then allows their co-encapsulation within the same supramolecular containers. Both mechanisms position the two sets of chromophores with complementary spectral overlap in close proximity to enable the efficient transfer of energy intracellularly from the anthracene donors to the BODIPY acceptors. In the presence of iodine substituents on the BODIPY platform, intersystem crossing follows energy transfer. The resulting triplet state can transfer energy further to molecular oxygen with the concomitant production of singlet oxygen to induce cell mortality. Furthermore, the donor can be excited with two near-infrared photons simultaneously to permit the photoinduced generation of singlet oxygen intracellularly under illumination conditions compatible with applications in vivo. Thus, these supramolecular strategies to control the excitation dynamics of multichromophoric assemblies in the intracellular environment can evolve into valuable protocols for photodynamic therapy.An amphiphilic

  10. Activation energies of photoinduced unimolecular, bimolecular and termolecular processes on silica gel surfaces.

    Science.gov (United States)

    Williams, Siân L; Worrall, David R; Kirkpatrick, Iain; Vancea, Anisoara; Pan, Jiawei

    2011-01-01

    Activation energies for energy and electron transfer have been measured in various systems on silica gel. In the case of ion-electron recombination, a facile technique involving fluorescence recovery is described which complements diffuse reflectance spectroscopy in the study of these systems. In bimolecular anthracene/azulene systems, activation energies have been shown to be independent of pre-treatment temperature in the range 25-210 °C, demonstrating that physisorbed water plays little role in determining diffusion rates on silica gel. In a ternary anthracene/azulene/perylene system, we have for the first time presented comparative activation energies for the diffusion of azulene and its radical cation, and have shown a greater activation energy for diffusion of the latter species. PMID:20978659

  11. 2-(9-Anthrylmethylideneamino-4-methylphenol

    Directory of Open Access Journals (Sweden)

    Andrés Villalpando

    2010-06-01

    Full Text Available The title compound, C22H17NO, is a novel Schiff base synthesized via a condensation reaction between 9-anthracenecarboxaldehyde and 2-amino-p-cresol. The asymmetric unit contains two independent molecules that are joined by an O—H...OH hydrogen bond. An intramolecular O—H...N hydrogen bond occurs in each molecule. π-stacking about inversion centers was observed between adjacent phenol rings [centroid–centroid distance = 3.850 (2 Å] and adjacent anthracene rings [centroid–centroid distance = 3.834 (2 Å]. The C—N=C—C torsion angles between the phenol and anthracene rings are close to 180° with values of 174.06 (15 and 179.85 (14°.

  12. Repair of DNA treated with γ-irradiation and chemical carcinogens. Comprehensive report of entire period of ERDA support from June 1, 1975--January 15, 1978

    International Nuclear Information System (INIS)

    A partially purified enzyme fraction isolated from E. coli showed an N-glycosidase activity as well as a phosphodiesterase activity on DNA treated with methylnitrosourea, and with 7-bromomethylbenz(a)anthracene and a phosphodiesterase activity against γ-irradiated DNA. Both 0-6 methyl guanine and 3-methyladenine were released from DNA treated with MNU; the adenine and guanine derivatives from the DNA treated with 7-bromomethyl-12-methylbenz(a)anthracene were also liberated. Progress is also reported on studies on Endonucleases II and VI and Exonuclease III of E. coli; methods for assay and for synthesis of substrates; attempts at purification of repair enzymes from mammalian tissues; and β-propiolactone reactions with deoxynucleosides and with DNA

  13. Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Nitrogen Heterocycles (PANHs)

    Science.gov (United States)

    Mattioda, A. L.; Hudgins, D. M.; Bauschlicher, C. W.; Allamandola, L. J.; Biemesderfer, C. D.; Rosi, M.

    2002-01-01

    The mid-infrared spectra of the nitrogen-containing heterocyclic polycyclic aromatic compounds 1-azabenz[a]-anthracene; 2-azabenz[a]anthracene; 1-azachrysene; 2-azachrysene; 4-azachrysene; 2-azapyrene, and 7,8 benzoquinoline in their neutral and cation forms were investigated. The spectra of these species isolated in an argon matrix have been measured. Band frequencies and intensities were tabulated and these data compared with spectra computed using density functional theory at the B3LYP level. The overall agreement between experiment and theory is quite good, in keeping with earlier results on homonuclear polycyclic aromatic hydrocarbons. The differences between the spectral properties of nitrogen bearing aromatics and non-substituted, neutral polycyclic aromatic hydrocarbons will be discussed.

  14. PAHs in corn grains submitted to drying with firewood.

    Science.gov (United States)

    de Lima, Rafael Friedrich; Dionello, Rafael Gomes; Peralba, Maria do Carmo Ruaro; Barrionuevo, Simone; Radunz, Lauri Lourenço; Reichert Júnior, Francisco Wilson

    2017-01-15

    Grain drying using firewood as fuel for air heating, with direct fire, is still widely used in Brazil. The combustion of organic material, such as wood, can generate polycyclic aromatic hydrocarbons (PAHs) which are known to have carcinogenic potential. In the present work corn grain drying was carried out at three drying air temperatures: 60°C, 60/80°C and 80°C. Following the drying process, the presence and quantification of PAH in the corn grains was investigated. After extracting the PAHs of the matrix, the material was subjected to analysis by gas chromatography with mass detector. he results showed the presence of seven compounds: fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo(a)anthracene and chrysene. PMID:27542463

  15. Experimental verifications on chemical carcinogenesis, a bifunctional alkylation between DNA interstrands

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    It is evidenced by the filter elution method that two carcinogenic aromatic hydrocarbons, benzo[a]pyrene and dibenzo[a,h]anthracene, two carcinogenic metal salts, beryllium chloride and cadmium chloride, four carcinogenic aromatic amines, 2-aminofluorene, β-naphthylamine, 4-aminobiphenyl and benzidine, can all induce DNA interstrand and DNA-protein cross-link in L1210 culture. However, under the same condition, the corresponding non-carcinogenic compounds, including benzo[k]fluorancene, anthracene, magnesium chloride, zinc chloride, a -naphthylamine, 2-aminobiphenyl and m-toluidine, cannot produce any cross-link adducts. All these results are consistent with the di-region theory that carcinogens are bio-bifunctional alkylation agents. This method can also be used to discriminate carcinogens and non-carcinogens.

  16. Peptide and protein sequence analysis by electron transfer dissociation mass spectrometry

    OpenAIRE

    Syka, John E. P.; Coon, Joshua J.; Schroeder, Melanie J.; Shabanowitz, Jeffrey; Hunt, Donald F.

    2004-01-01

    Peptide sequence analysis using a combination of gas-phase ion/ion chemistry and tandem mass spectrometry (MS/MS) is demonstrated. Singly charged anthracene anions transfer an electron to multiply protonated peptides in a radio frequency quadrupole linear ion trap (QLT) and induce fragmentation of the peptide backbone along pathways that are analogous to those observed in electron capture dissociation. Modifications to the QLT that enable this ion/ion chemistry are presented, and automated ac...

  17. Modeling of experimental data on trace elements and organic compounds content in industrial waste dumps.

    Science.gov (United States)

    Smoliński, Adam; Drobek, Leszek; Dombek, Václav; Bąk, Andrzej

    2016-11-01

    The main objective of the study presented was to investigate the differences between 20 mine waste dumps located in the Silesian Region of Poland and Czech Republic, in terms of trace elements and polycyclic aromatic hydrocarbons contents. The Principal Component Analysis and Hierarchical Clustering Analysis were applied in exploration of the studied data. Since the data set was affected by outlying objects, the employment of a relevant analysis strategy was necessary. The final PCA model was constructed with the use of the Expectation-Maximization iterative approach preceded by a correct identification of outliers. The analysis of the experimental data indicated that three mine waste dumps located in Poland were characterized by the highest concentrations of dibenzo(g,h,i)anthracene and benzo(g,h,i)perylene, and six objects located in Czech Republic and three objects in Poland were distinguished by high concentrations of chrysene and indeno (1.2.3-cd) pyrene. Three of studied mine waste dumps, one located in Czech Republic and two in Poland, were characterized by low concentrations of Cr, Ni, V, naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthen, benzo(a)anthracene, chrysene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo(a)pyrene, dibenzo(g,h,i)anthracene, benzo(g,h,i)perylene and indeno (1.2.3-cd) pyrene in comparison with the remaining ones. The analysis contributes to the assessment and prognosis of ecological and health risks related to the emission of trace elements and organic compounds (PAHs) from the waste dumps examined. No previous research of similar scope and aims has been reported for the area concerned. PMID:27497349

  18. 40 CFR Table 6 to Subpart Jj of... - VHAP of Potential Concern

    Science.gov (United States)

    2010-07-01

    ... aminoazobenzene 1.0 56553 Benzo (a) anthracene 0.01 205992 Benzo (b) fluoranthene 0.01 79469 2-Nitropropane 1.0...′-Methylenedianiline 1.0 90040 o-Anisidine 1.0 1746016 2,3,7,8-Tetrachlorodibenzo-p-dioxin 0.00000006 92875 Benzidine 0... carbamoyl chloride 0.002 75558 1,2-Propylenimine (2-Methyl aziridine) 0.0003 57147 1,1-Dimethyl hydrazine...

  19. Hepatotoxicity induced by the anti-oxidant food additive, butylated hydroxytoluene BHT, in rats. An electron microscopical study

    OpenAIRE

    Safer, A.M.; Al-Nughamish, A.J.

    1999-01-01

    The anti-oxidant food additive, butylated hydroxytoluene (BHT), was fed to Sprague-Dawley rats at three concentrations: 0.2%, 0.4% and 0.8% for periods of 6, 12, 18 and 24 weeks, and the results were compared with corresponging groups treated with a potent carcinogen, 7,12-dimethylbenz[a]anthracene (DMBA) groups, with olive oil, and with untreated control groups. BHT resulted in a significant increase in liver weight. The liver cells presented gradual vacuo...

  20. Melatonin attenuates lipid peroxidation and enhances circulatory antioxidants during mammary carcinogenesis in rats

    OpenAIRE

    Sankaran Mirunalini; Kandhan Karthishwaran; Ganesan Dhamodharan; Shalini Mohan

    2010-01-01

    The possible protective effect of Melatonin was investigated for its antioxidant and lipid peroxidation activity against 7,12-dimethylbenz(a)anthracene (DMBA) induced mammary carcinogenesis in female albino Wistar rats. Mammary tumor was developed to the animals by administering 5mg/kg body weight of DMBA orally at weekly intervals for one month. Intraperitoneal administration of melatonin 5mg/ml per animals for 15 days prior to the first oral administration of DMBA was continued for a month....

  1. Anticancer Effect of Rutin Isolated from the Methanolic Extract of Triticum aestivum Straw in Mice

    OpenAIRE

    Savita Dixit

    2014-01-01

    Rutin is the bioactive flavanoid isolated from the straw part of Triticum aestivum and possess various pharmacological applications. The aim of this study is to evaluate the chemopreventive potential of rutin in an experimental skin carcinogenesis mice model system. Skin tumor was induced by topical application of 7,12-dimethyl benz(a) anthracene (DMBA) and promoted by croton oil in Swiss albino mice. To assess the chemopreventive potential of rutin, it was orally administered at a concentrat...

  2. Prepubertal exposure to cow’s milk reduces susceptibility to carcinogen-induced mammary tumorigenesis in rats

    OpenAIRE

    Nielsen, Tina S.; Khan, Galam; Davis, Jennifer; Michels, Karin B; Hilakivi-Clarke, Leena

    2011-01-01

    Cow’s milk contains high levels of estrogens, progesterone and insulin-like growth factor 1 (IGF-1), all of which are associated with breast cancer. We investigated whether prepubertal milk exposure affects mammary gland development and carcinogenesis in rats. Sprague Dawley rats were given either whole milk or tap water to drink from postnatal day (PND) 14 to PND 35, and thereafter normal tap water. Mammary tumorigenesis was induced by administering 7,12-dimethylbenz[a]anthracene (DMBA) on P...

  3. Fate of polynuclear aromatic hydrocarbons in soil

    International Nuclear Information System (INIS)

    A study was performed on the persistence of selected polynuclear aromatic hydrocarbons (PAH's) in soil. Two incubation studies were performed. In the first, a mixture of eight PAH's were added to unacclimated soil at levels of 5 and 50 mg/kg and the concentrations were monitored with time. In the second, C14-labelled benzo(a)pyrene or anthracene was added to soil incubated in biometer flasks. Microbial degradation, physical and chemical degradation, volatilization and binding were assessed as mechanisms affecting benzo(a)pyrene and anthracene in soil. The disappearance of PAH's appeared to be related to molecular weight, water solubility, volatility and adsorptivity to soil. The loss during this initial period approximated first order kinetics, in some cases following a lag period. The remaining 2-6% of the added PAH's, however, was lost at a much reduced rate. With the 50 mg/kg level of application, reduced rates of disappearance in later stages resulted in levels five to ten times the background concentration which persisted throughout the 400 days. Degradation of phenanthrene, anthracene, fluoranthene and pyrene at the 5 mg/kg application rate, however, resulted in concentrations close to background levels within 400 days. Either a model other than first order or a combination of two models was required to adequately describe the loss of 99% of the added PAH's. The mechanisms leading to a decrease in PAH concentration, identified through the use of C14 labelling, were predominantly volatilization and adsorption to soil solids for anthracene and adsorption to soil solids for benzo(a)pyrene. Microbial transformation of benzo(a)pyrene was minimal. 17 refs., 10 figs., 4 tabs

  4. Extraction Optimization of Tinospora cordifolia and Assessment of the Anticancer Activity of Its Alkaloid Palmatine

    OpenAIRE

    Huma Ali; Savita Dixit

    2013-01-01

    Objective. To optimize the conditions for the extraction of alkaloid palmatine from Tinospora cordifolia by using response surface methodology (RSM) and study its anticancerous property against 7,12-dimethylbenz(a)anthracene (DMBA) induced skin carcinogenesis in Swiss albino mice. Methods. The effect of three independent variables, namely, extraction temperature, time, and cycles was investigated by using central composite design. A single topical application of DMBA (100  μ g/100  μ L of ace...

  5. In vivo nonlinear spectral imaging as a tool to monitor early spectroscopic and metabolic changes in a murine cutaneous squamous cell carcinoma model

    OpenAIRE

    Thomas, Giju; van Voskuilen, Johan; Truong, Hoa; Song, Ji-Ying; Gerritsen, Hans C.; Sterenborg, H. J. C. M.

    2014-01-01

    Timely detection of cutaneous squamous cell carcinoma with non-invasive modalities like nonlinear spectral imaging (NLSI) can ensure efficient preventive or therapeutic measures for patients. In this study, in vivo NLSI was used to study spectral characteristics in murine skin treated with 7, 12-dimethylbenz(a)anthracene. The results show that NLSI could detect emission spectral changes during the early preclinical stages of skin carcinogenesis. Analyzing these emission spectra using simulate...

  6. Use of mixed solvent systems to eliminate sorption of strongly hydrophobic organic chemicals on container walls.

    Science.gov (United States)

    Muwamba, Augustine; Nkedi-Kizza, Peter; Rhue, Roy Dean; Keaffaber, Jeffrey J

    2009-01-01

    Strongly hydrophobic organic chemicals (SHOCs) can be defined as neutral organic chemicals that have soil organic carbon (OC) normalized sorption coefficient (K(OC)) >10,000. Sorption isotherms of SHOCs are normally measured in aqueous systems to determine K(OC). Since SHOCs can adsorb on container walls leading to overestimation of K(OC), we used mixed solvent systems to characterize this potential error. Sorption coefficient (K(M)) and percent recovery (%R(M)) of anthracene, DDT, and dieldrin during sorption on centrifuge tubes made of polytetrafluoroethylene (PTFE), polycarbonate (PC), polypropylene copolymer (PPCO), and glass high pressure liquid chromatography vials (HPLCV) were measured in volume ratio-varied methanol-water mixtures until 100% recovery of the sorbate was achieved. The data were evaluated using the Solvophobic theory. The K(M) values of the entire test SHOCs decreased exponentially with increasing fraction of methanol (f(c)). For sorption on PTFE, 100% recovery of the three chemicals was at f(c) > 0.45. However, 100% recovery of DDT and anthracene from PC and PPCO was at f(c) > 0.90. The 100% recovery of dieldrin from HPLC vials was at f(c) > 0.70. In water the calculated recoveries of DDT, dieldrin, and anthracene from PTFE were 32, 43, and 48%, respectively. However, the recoveries of dieldrin from HPLC vials and DDT and anthracene from PC and PPCO ranged from 2 to 14%. The data demonstrate that sorption on container walls is a source of error that can reduce the integrity of the analyte and might be one of the causes for the large variability in literature K(OC) values for SHOCs. PMID:19398514

  7. Modification of acidity of Mo-Fe/HZSM-5 zeolite via argon plasma treatment

    Institute of Scientific and Technical Information of China (English)

    Xinli ZHU; Kailu YU; Dangguo CHENG; Yueping ZHANG; Qing XIA; Changjun LIU

    2008-01-01

    The NH3-TPD characterization was conducted to confirm that the acidity of Mo-Fe/HZSM-5 zeolite could be selectively modified via the glow discharge plasma treatment. The plasma catalyst treatment could totally change the distribution of aromatic products with higher methane conversion compared to the untreated catalyst. Some polycyclic aromatics such as anthracene, pyrene and phenanthrene were also produced over the plasma treated catalyst, in addition to benzene, toluene and naphthalene, which were normally obtained over the untreated catalyst.

  8. 2-[1-(9-Anthrylmethyl-1H-pyrazol-3-yl]pyridine

    Directory of Open Access Journals (Sweden)

    Shi-Lu Zhang

    2009-11-01

    Full Text Available The title compound, C23H17N3, can be used in coordination chemistry. The anthracene ring makes dihedral angles of 86.08 (5 and 76.63 (6°, respectively, with the pyridine and pyrazole rings. The dihedral angle between the pyrazole and pyrimidine rings is 11.79 (7°. In the structure, weak intermolecular C—H...N hydrogen bonds are observed.

  9. 10,10-Dimethylanthrone

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2010-04-01

    Full Text Available In the title compound, C16H14O, the asymmetric unit consists of three crystallographically independent molecules. The anthracene units are essentially planar, with maximum deviations of 0.165 (1, 0.153 (1 and 0.045 (1 Å in the three molecules. In the crystal structure, molecules are linked via intermolecular C—H...O hydrogen bonds. Further stabilization is provided by C—H...π interactions.

  10. Novel multiarm star block copolymer ionomers as proton conductive membranes

    OpenAIRE

    Demirel, Adem Levent; Erdoğan, Tuba; Bilir, Çiğdem; Ünveren, Elif; Tunca, Ümit

    2014-01-01

    A series of well-defined novel multiarm star block copolymer ionomers with an average of 6, 11 and 15 arms, sulfonated polystyrene-block-poly(2,2,3,3,3-pentafluoropropyl methacrylate) (SPS-b-PFPMA), were prepared via a combination of atom transfer radical polymerization (ATRP), Diels–Alder click reaction and postsulfonation reaction. First, multiarm star polymer with anthracene functionality as reactive periphery groups was prepared by a cross-linking reaction of divinyl benzene using ?-anthr...

  11. Polycyclic aromatic hydrocarbons (PAH) in Danish barbecued meat

    DEFF Research Database (Denmark)

    Duedahl-Olesen, Lene; Aaslyng, Margit Dall; Meinert, Lene;

    2015-01-01

    for the detection of 24 PAHs in barbecued meat. In total, 203 commercially barbecued meat samples (beef, pork, chicken, salmon and lamb) and 15 samples barbecued during controlled time and heat conditions were included. The sum of PAH4 (benzo[a]pyrene, benz[a]anthracene, chrysene and benzo......[b]fluoranthene) was highest for a pork tenderloin (195 μg/kg) and lowest for chicken breast (0.1 μg/kg) and controlled barbecued meat (...

  12. Synthesis of Heteroaromatic Compounds by Oxidative Aromatization Using an Activated Carbon/Molecular Oxygen System

    Directory of Open Access Journals (Sweden)

    Masahiko Hayashi

    2009-08-01

    Full Text Available A variety of heteroaromatic compounds, such as substituted pyridines, pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles and pyrimidin-2(1H-ones are synthesized by oxidative aromatization using the activated carbon and molecular oxygen system. Mechanistic study focused on the role of activated carbon in the synthesis of 2-arylbenzazoles is also discussed. In the final section, we will disclose the efficient synthesis of substituted 9,10-anthracenes via oxidative aromatization.

  13. Biological monitoring of occupational exposure to toluene diisocyanate: measurement of toluenediamine in hydrolysed urine and plasma by gas chromatography-mass spectrometry.

    OpenAIRE

    Persson, P.; Dalene, M; Skarping, G; Adamsson, M.; Hagmar, L

    1993-01-01

    Exposure to toluene diisocyanate (TDI) was studied during 48 hours and biological samples from nine subjects were taken in a factory producing flexible polyurethane (PUR) foam. Five PUR workers, two white collar workers, and two volunteers were studied. The concentrations of TDI in air were determined by high performance liquid chromatography with the 9-(N-methylaminomethyl)-anthracene reagent. Urine and plasma samples were collected and the TDI related amines, 2,4-toluenediamine (2,4-TDA) an...

  14. Bacterial Community Dynamics and Biodegradation Rates in Untreated and Oily Soils During PAH Exposure

    International Nuclear Information System (INIS)

    The approach taken in this study represents an attempt to address the possible selective effects of Polycyclic aromatic hydrocarbons (PAH) on the bacterial community structure of an untreated garden soil (S) and a chronically contaminated oily soil (CS). Untreated and chronically hydrocarbon polluted soils, collected from Egypt were enriched in shaking flasks containing 50 mg/l anthracene as a sole source of carbon over a period of 15 days. Bacterial communities in each soil were profiled by denaturing gradient gel electrophoresis (DGGE) analysis of the PCR amplified 16 S r DNA gene fragments after 0, 5, 10, and 15 days. Culture able biodegrading bacterial counts on minerals- Silica gel- Oil (MSD) plates as well as anthracene degradation for both soils were followed up at the same time intervals. Nine bacterial species were found to be dominant in the pristine soil before enrichment with the model polycyclic aromatic hydrocarbon (PAH), eight of them disappeared after live days of enrichment with the domination of one new species. It stayed dominant in soil until 15 days - exposure to anthracene. Therefore it can be used as a bio marker for PAH pollution. The chronically contaminated soil revealed a remarkable increase in the diversity directly after 5 days exposure to PAH HPLC analysis of the extracted anthracene remained in the biodegradation flasks after different degradation periods revealed that a higher biodegradation rates were accomplished by the oily soil consortium rather than by the pristine one. Before exposure to PAH, counts of culture able biodegrading bacteria were found to be higher in the untreated soil rather than in the oily one. After exposure the situation has been a bit altered as the counts in the untreated soil revealed a temporary suppression with a prolongation of the time required for growth as a result of the hydrocarbon stress

  15. Explant culture of rat colon: A model system for studying metabolism of chemical carcinogens

    DEFF Research Database (Denmark)

    Autrup, Herman; Stoner, G.D.; Jackson, F.;

    1978-01-01

    An explant culture system has been developed for the long-term maintenance of colonic tissue from the rat. Explants of 1 cm2 in size were placed in tissue-culture dishes to which was added 2 ml of CMRL-1066 medium supplemented with glucose, hydrocortisone, beta-retinyl acetate, and either 2......,12-dimethylbenz[alpha]anthracene, aflatoxin B1, dimethylnitrosamine, 1,2-dimethylhydrazine, and methylazoxymethanol acetate into chemical species that bind to cellular DNA and protein....

  16. Report on the inter-laboratory comparison organised by the European Union Reference Laboratory for Polycyclic Aromatic Hydrocarbons for the validation of a method for quantifying the four EU marker PAHs in Food

    OpenAIRE

    LERDA Donata; LOPEZ SANCHEZ Patricia; Szilagyi, Szilard; Wenzl, Thomas

    2011-01-01

    The European Union Reference Laboratory for Polycyclic Aromatic Hydrocarbons (EU-RL PAHs), operated by the Institute for Reference Materials and Methods (IRMM) of the Joint Research Centre (JRC), organised a method validation study by inter-laboratory comparison (ILC-MVS) for evaluating the effectiveness of a method based for the determination of the four marker PAHs (benz[a]anthracene, benzo[a]pyrene, benzo[b]fluoranthene, and chrysene in different food commodities within the scope of Commis...

  17. Mixture of Uncaria and Tabebuia Extracts are Potentially Chemopreventive in CBA/Ca Mice - A Long-term Experiment

    OpenAIRE

    Budán, Ferenc; Szabo, István; Varjas, Timea; Nowrasteh, Ghodratollah; Dávid, Tamás; Gergely, Péter; Varga, Zsuzsa; Molnár, Kornélia; Kádár, Balázs; Orsos, Zsuzsa; Kiss, István; Ember, István

    2010-01-01

    Abstract A long-term experimental animal model was developed by our research group for the evaluation of potential chemopreventive effects. The inhibitory effects of agents on carcinogen (7,12-Dimetilbenz[a]anthracene (DMBA)) induced molecular epidemiological biomarkers, in this case the expression of key onco/suppressor genes were investigated. Expression pattern of c-myc, Ha-ras, Bcl-2, K-ras protoonco and p53 tumoursuppressor genes were studied to elucidate early carcinogenic...

  18. Polyamine Transport as a Target for Treatment of Pneumocystis Pneumonia▿

    OpenAIRE

    Liao, Chung-Ping; Phanstiel, Otto; Lasbury, Mark E.; Zhang, Chen; Shao, Shoujin; Durant, Pamela J.; Cheng, Bi-Hua; Lee, Chao-Hung

    2009-01-01

    Polyamine levels are greatly increased in alveolar macrophages (AMs) during Pneumocystis pneumonia (PCP), leading to increased production of H2O2, which causes AMs to undergo apoptosis. One of the mechanisms by which polyamine levels in AMs are elevated is enhanced uptake of exogenous polyamines. In this study, the possibility of targeting polyamine uptake as a treatment for PCP was examined. Four anthracene- and one benzene-polyamine conjugates that are potential polyamine transport inhibito...

  19. Protective and Curative Effects of the Sea Cucumber Holothuria atra Extract against DMBA-Induced Hepatorenal Diseases in Rats

    OpenAIRE

    Dakrory, Ahmed I.; Fahmy, Sohair R; Soliman, Amel M.; Ayman S. Mohamed; Amer, Sayed A.M.

    2015-01-01

    Oxidative stress is a common mechanism contributing to the initiation and progression of hepatic damage. Hence there is a great demand for the development of agents with potent antioxidant effect. The aim of the present study is to evaluate the efficacy of Holothuria atra extract (HaE) as an antioxidant against 7,12-dimethylbenz[a]anthracene- (DMBA-) induced hepatorenal dysfunction. Experimental animals were divided into two main groups: protective and curative. Each group was then divided in...

  20. Protective Effect of Withaferin-A on Micronucleus Frequency and Detoxication Agents During Experimental Oral Carcinogenesis

    OpenAIRE

    Panjamurthy, Kuppusamy; Manoharan, Shanmugam; Balakrishnan, Subramanian; Suresh, Kathiresan; Nirmal, Madhavan R; Senthil, Namasivayam; Alias, Linsa Marry

    2008-01-01

    Our aim was to investigate the effect of Withaferin-A on bone marrow micronucleus frequency and buccal mucosa detoxication agents during 7, 12-dimethylbenz[a]anthracene (DMBA) induced hamster buccal pouch carcinogenesis. Oral squamous cell carcinoma was developed in hamsters' buccal pouches by painting 0.5% DMBA in liquid paraffin, three times per week for 14 weeks. We observed 100% tumor formation in DMBA painted hamsters. Elevated frequency of bone marrow micronucleated polychromatic erythr...

  1. Photoinduced electron transfer in porous organic salt crystals impregnated with fullerenes.

    Science.gov (United States)

    Hasegawa, Tetsuya; Ohkubo, Kei; Hisaki, Ichiro; Miyata, Mikiji; Tohnai, Norimitsu; Fukuzumi, Shunichi

    2016-06-28

    Porous organic salt (POS) crystals composed of 9-(4-sulfophenyl)anthracene (SPA) and triphenylmethylamine (TPMA) were impregnated with fullerenes (C60 and C70), which were arranged in one dimensional close contact. POS crystals of SPA and TPMA without fullerenes exhibit blue fluorescence due to SPA, whereas the fluorescence was quenched in POS with fullerenes due to electron transfer from the singlet excited state of SPA to fullerenes. PMID:27182038

  2. Photosensitization of trans-Vitamin D3 to cis-Vitamin D3 in Heterogeneous System

    Institute of Scientific and Technical Information of China (English)

    Yong Bin HAN; Jin Ping CHEN; Yun Yan GAO; Bai Ning LIU; Guo Qiang YANG; Yi LI

    2005-01-01

    Two modes of heterogeneous photoisomerization of trans-vitamin D3 to cis-vitamin D3are described. The occurrence of isomerization on the substrate bounded to the polymeric support gives us the possibility in succession synthesis of 1α-hydroxyvitamin D3. The polymer-bound anthracene can sensitize isomerization of trans-vitamin D3 to cis-vitamin D3 efficiently and ease the separation process.

  3. Molecular modeling study of intercalation complexes of tricyclic carboxamides with d(CCGGCGCCGG) and d(CGCGAATTCGCG)

    OpenAIRE

    Varvaresou, Athanasia; Iakovou, Kriton

    2010-01-01

    Abstract Tricyclic dyes with different mesoatoms such as xanthenes (fluorescein, eosin) anthracenes and acridines (proflavine) approved by the Food and Drug Administration (FDA) for use in foods, pharmaceuticals and cosmetic preparations interact with DNA, and some of them do so through intercalation. Hyperchem 7.5, Spartan 04, Yasara 10.5.14 program packages and molecular modeling, molecular mechanics and dynamics techniques with the oligonucleotides d(CCGGCGCCGG)2 and d(CGCGAATTC...

  4. Astaxanthin Inhibits JAK/STAT-3 Signaling to Abrogate Cell Proliferation, Invasion and Angiogenesis in a Hamster Model of Oral Cancer

    OpenAIRE

    Kowshik, J.; Baba, Abdul Basit; Giri, Hemant; Deepak Reddy, G.; Dixit, Madhulika; Nagini, Siddavaram

    2014-01-01

    Identifying agents that inhibit STAT-3, a cytosolic transcription factor involved in the activation of various genes implicated in tumour progression is a promising strategy for cancer chemoprevention. In the present study, we investigated the effect of dietary astaxanthin on JAK-2/STAT-3 signaling in the 7,12-dimethylbenz[a]anthracene (DMBA)-induced hamster buccal pouch (HBP) carcinogenesis model by examining the mRNA and protein expression of JAK/STAT-3 and its target genes. Quantitative RT...

  5. Preclinical evaluation of marketed sodium channel blockers in a rat model of myotonia discloses promising antimyotonic drugs

    OpenAIRE

    Desaphy, Jean-François; Carbonara, Roberta; Costanza, Teresa; Conte Camerino, Diana

    2014-01-01

    Although the sodium channel blocker mexiletine is considered the first-line drug in myotonia, some patients experiment adverse effects, while others do not gain any benefit. Other antimyotonic drugs are thus needed to offer mexiletine alternatives. In the present study, we used a previously-validated rat model of myotonia congenita to compare six marketed sodium channel blockers to mexiletine. Myotonia was induced in the rat by injection of anthracen-9-carboxylic acid, a muscle chloride chann...

  6. Organo/LDH nanocomposite as an adsorbent of polycyclic aromatic hydrocarbons in water and soil-water systems

    OpenAIRE

    Bruna González, Felipe; de Celis, R; Real Ojeda, Miguel; Cornejo, J.

    2012-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are considered as priority pollutants because of their high risk to human health. In this paper, we addressed the issue of using hydrotalcite-based nanocomposites as adsorbents of six low molecular weight PAHs (acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene and pyrene) to reduce their negative effects on the environment. A nanocomposite (HTDDS) was prepared by intercalating the organic anion dodecylsulfate (DDS) in a Mg¿Al hydrotalcite (...

  7. Polycyclic aromatic hydrocarbon degradation by the white rot fungus Bjerkandera sp. strain BOS55.

    OpenAIRE

    Kotterman, M.J.J.

    1998-01-01

    Outline of this thesisIn this thesis the conditions for optimal PAH oxidation by the white rot fungus Bjerkandera sp. strain BOS55 were evaluated. In Chapter 2, culture conditions like aeration and cosubstrate concentrations, which influenced the oxidation of the PAH compound anthracene and the ligninolytic indicator dye Poly R-478 by the white rot fungus, were studied. Two parameters were identified as the most important PAH oxidation rate-limiting factors: the hydrogen peroxide production r...

  8. Impact of Inoculation Protocols, Salinity, and pH on the Degradation of Polycyclic Aromatic Hydrocarbons (PAHs) and Survival of PAH-Degrading Bacteria Introduced into Soil

    OpenAIRE

    Kästner, Matthias; Breuer-Jammali, Maren; Mahro, Bernd

    1998-01-01

    Degradation of polycyclic aromatic hydrocarbons (PAHs) and survival of bacteria in soil was investigated by applying different inoculation protocols. The soil was inoculated with Sphingomonas paucimobilis BA 2 and strain BP 9, which are able to degrade anthracene and pyrene, respectively. CFU of soil bacteria and of the introduced bacteria were monitored in native and sterilized soil at different pHs. Introduction with mineral medium inhibited PAH degradation by the autochthonous microflora a...

  9. Inverse Secondary Deuterium Kinetic Isotope Effect in Diels-Alder Reaction of Orthonaphtho [3.3] orthoanthracenophane with Maleic Anhydride

    OpenAIRE

    Mataka, Shuntaro; Ma, Jiang; Tsuzuki, Hirohisa; Nishiyama, Kozaburo; Thiemann, Thies; Tashiro, Masashi

    1996-01-01

    The Diels-Alderreactions of rigid [3.3] orthoanthracenophanes 1 and 2 with maleic anhydride and deuterium-labeled maleic anhydride-d_2, were studied. In the reaction of naphtophane 1, a large inverse secondary kinetic isotope effect (SDKIE) (kH_2/kD_2=0.78) was observed, while benzophane 2 shows a SDKIE similar to that of anthracene itself (kH_2/kD_2=0.95 and 0.96).

  10. Environmental Remediation: Removal of polycyclic aromatic hydrocarbons

    Energy Technology Data Exchange (ETDEWEB)

    Nkansah, Marian Asantewah

    2012-11-15

    Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous persistent semi-volatile organic compounds. They are contaminants that are resistant to degradation and can remain in the environment for long periods due to their high degree of conjugation, and aromaticity. PAHs are present in industrial effluents as products of incomplete combustion processes of organic compounds. Petroleum, coal and shale oil contain extremely complex mixtures of these PAHs, and their transport and refining process can also result in the release of PAHs. It is therefore prudent that such effluents are treated before discharge into the environment. In this project, different approaches to the treatment of PAHs have been investigated. Hydrous pyrolysis has been explored as a potential technique for degrading PAHs in water using anthracene as a model compound. The experiments were performed under different conditions of temperature, substrate, redox systems and durations. The conditions include oxidising systems comprising pure water, hydrogen peroxide and Nafion-SiO2 solid catalyst in water; and reducing systems of formic acid and formic acid / Nafion-SiO2 / Pd-C catalysts to assess a range of reactivities. Products observed in GCMS analysis of the extract from the water phase include anthrone, anthraquinone, xanthone and multiple hydro-anthracene derivatives (Paper I). In addition a modified version of the Nafion-SiO2 solid catalyst in water oxidising system was tested; and reducing systems of formic acid and formic acid / Nafion-SiO2 / Pd-C catalysts were adopted for the conversion of a mixture of anthracene, fluorene and fluoranthene. The rate of conversion in the mixture was high as compared to that of only anthracene (Paper II). Also the use of LECA (Lightweight expanded clay aggregates) as an adsorbent (Paper III) for PAHs (phenanthrene, fluoranthene and pyrene) removal from water has been.(Author)

  11. Occurrence of Nitro-PAH in the Atmosphere in a Rural Area

    DEFF Research Database (Denmark)

    Nielsen, Tom; Seitz, B.; Ramdahl, T.

    1984-01-01

    By means of gas chromatography with nitrogen sensitive detection and negative ion chemical ionization mass spectrometric detection 7 mononitro-PAH, 9-nitroanthracene, x-nitro-4,5-methylene-phenanthrene, 3-nitrofluoranthene, 1- and 2-nitropyrene, 10-nitrobenz(a)anthracene and 6-nitrobenzo-(a)pyren......-nitroanthracene can be transformed during sampling at low atmospheric concentrations of NO2 and photochemical oxidants to 9,10-dinitroanthracene and 10-nitroanthrone....

  12. Isotope effects in photochemical rearrangements

    International Nuclear Information System (INIS)

    Taking anthracene resp. 9-deuteroanthracene as the initial substance, different substitution products have been prepared. The products originating by direct photolysis have been characterized and their structure has been determined. By comparing the measured kinetic isotope effect and the quantum yield of the nondeuterated and the monodeuterated fluorenes formed it could been demonstrated that the isotope effect mainly is due to the reaction rates and the influence of the deuterium substitution upon the radiationless desactivation against that is small. (HBR)

  13. Characterizing priority polycyclic aromatic hydrocarbons (PAH) in particulate matter from diesel and palm oil-based biodiesel B15 combustion

    Science.gov (United States)

    Rojas, Nestor Y.; Milquez, Harvey Andrés; Sarmiento, Hugo

    2011-11-01

    A set of 16 priority polycyclic aromatic hydrocarbons (PAH) associated with particulate matter (PM), emitted by a diesel engine fueled with petroleum diesel and a 15%-vol. palm oil methyl ester blend with diesel (B15), were determined. PM was filtered from a sample of the exhaust gas with the engine running at a steady speed and under no load. PAH were extracted from the filters using the Soxhlet technique, with dichloromethane as solvent. The extracts were then analyzed by gas chromatography using a flame ionization detector (FID). No significant difference was found between PM mass collected when fueled with diesel and B15. Ten of the 16 PAH concentrations were not reduced by adding biodiesel: Benz(a)anthracene, benzo(a)pyrene, benzo(b)fluoranthene, chrysene, dibenz(a,h)anthracene, fluoranthene, fluorene, indeno(1,2,3-c,d)pyrene, naphthalene and phenanthrene. The acenaphthene, acenaphthylene and anthracene concentrations were 45%-80% higher when using diesel, whereas those for benzo(k)fluoranthene, benzo(g,h,i)perylene and pyrene were 30%-72% higher when using the B15 blend. Even though the 16 priority-PAH cumulative concentration increased when using the B15 blend, the total toxic equivalent (TEQ) concentration was not different for both fuels.

  14. Carbon nanorings with inserted acenes: breaking symmetry in excited state dynamics.

    Science.gov (United States)

    Franklin-Mergarejo, R; Alvarez, D Ondarse; Tretiak, S; Fernandez-Alberti, S

    2016-01-01

    Conjugated cycloparaphenylene rings have unique electronic properties being the smallest segments of carbon nanotubes. Their conjugated backbones support delocalized electronic excitations, which dynamics is strongly influenced by cyclic geometry. Here we present a comparative theoretical study of the electronic and vibrational energy relaxation and redistribution in photoexcited cycloparaphenylene carbon nanorings with inserted naphthalene, anthracene, and tetracene units using non-adiabatic excited-state molecular dynamics simulations. Calculated excited state structures reflect modifications of optical selection rules and appearance of low-energy electronic states localized on the acenes due to gradual departure from a perfect circular symmetry. After photoexcitation, an ultrafast electronic energy relaxation to the lowest excited state is observed on the time scale of hundreds of femtoseconds in all molecules studied. Concomitantly, the efficiency of the exciton trapping in the acene raises when moving from naphthalene to anthracene and to tetracene, being negligible in naphthalene, and ~60% and 70% in anthracene and tetracene within the first 500 fs after photoexcitation. Observed photoinduced dynamics is further analyzed in details using induced molecular distortions, delocatization properties of participating electronic states and non-adiabatic coupling strengths. Our results provide a number of insights into design of cyclic molecular systems for electronic and light-harvesting applications. PMID:27507429

  15. Sample preparation of sewage sludge and soil samples for the determination of polycyclic aromatic hydrocarbons based on one-pot microwave-assisted saponification and extraction.

    Science.gov (United States)

    Pena, M Teresa; Pensado, Luis; Casais, M Carmen; Mejuto, M Carmen; Cela, Rafael

    2007-04-01

    A microwave-assisted sample preparation (MASP) procedure was developed for the analysis of polycyclic aromatic hydrocarbons (PAHs) in sewage sludge and soil samples. The procedure involved the simultaneous microwave-assisted extraction of PAHs with n-hexane and the hydrolysis of samples with methanolic potassium hydroxide. Because of the complex nature of the samples, the extracts were submitted to further cleaning with silica and Florisil solid-phase extraction cartridges connected in series. Naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,h]anthracene, benzo[g,h,i]perylene, and indeno[1,2,3-cd]pyrene, were considered in the study. Quantification limits obtained for all of these compounds (between 0.4 and 14.8 microg kg(-1) dry mass) were well below of the limits recommended in the USA and EU. Overall recovery values ranged from 60 to 100%, with most losses being due to evaporation in the solvent exchange stages of the procedure, although excellent extraction recoveries were obtained. Validation of the accuracy was carried out with BCR-088 (sewage sludge) and BCR-524 (contaminated industrial soil) reference materials. PMID:17268774

  16. Comparison of polycyclic aromatic hydrocarbons level between suspended solid and sediment samples of Pengkalan Chepa River, Kelantan state, Malaysia

    Science.gov (United States)

    Muslim, Noor Zuhartini Md; Babaheidari, Seyedreza Hashemi; Zakaria, Mohamad Pauzi

    2015-09-01

    Sixteen type of common Polycyclic Aromatic Hydrocarbons (PAHs) which consist of naphthalene, acenaphthene, acenaphthylene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, benzo[ghi]-perylene, indeno[1,2,3-cd]-pyrene and dibenz[a,h]-anthracene in suspended solid and sediment samples of Pengkalan Chepa River, Kelantan state, Malaysia were investigated. The analysis samples were taken from six different sites of Pengkalan Chepa River during sunny day. The samples were subjected to a series of pre-treatment before the level of PAHs can be determined. A Gas Chromatography-Mass Spectrometry (GC-MS) was the prime method for the analysis of PAHs level. A total of 16 PAHs concentration in suspended solid of the whole Pengkalan Chepa River was found to be 2144.6 ng/g dry weights. This concentration was about eight times more than 16 PAHs concentration in sediment which found to be 266.5 ng/g dry weights.

  17. Polycyclic aromatic hydrocarbons (PAHs) at traffic and urban background sites of northern Greece: source apportionment of ambient PAH levels and PAH-induced lung cancer risk.

    Science.gov (United States)

    Manoli, Evangelia; Kouras, Athanasios; Karagkiozidou, Olga; Argyropoulos, Georgios; Voutsa, Dimitra; Samara, Constantini

    2016-02-01

    Thirteen particle-phase PAHs, including nine >4-ring congeners [Benz[a]anthracene (BaAn), Chrysene (Chry), Benzo[b]fluoranthene (BbF), Benzo[k]fluoranthene (BkF), Benzo[e]pyrene (BeP), Benzo[a]pyrene (BaP), Dibenzo[a,h]anthracene (dBaAn), Benzo[g,h,i]perylene (BghiPe), Indeno(1,2,3-c,d)pyrene (IP)], listed by IARC (International Agency for Research on Cancer) as class 1, class 2A, and 2B carcinogens, plus four ≤4-ring congeners [Phenanthrene (Ph), Anthracene (An), Fluoranthene (Fl), Pyrene (Py)], were concurrently measured in inhalable and respirable particle fractions (PM10 and PM2.5) at a heavy-traffic and an urban background site in Thessaloniki, northern Greece, during the warm and the cold period of the year. Carcinogenic and mutagenic potencies of the PAH-bearing particles were calculated, and the inhalation cancer risk (ICR) for local population was estimated. Finally, Chemical Mass Balance (CMB) modeling was employed for the source apportionment of ambient PAH levels and the estimated lung cancer risk. Resulted inhalation cancer risk during winter was found to be equivalent in the city center and the urban background area suggesting that residential wood burning may offset the benefits from minor traffic emissions. PMID:26490935

  18. Abundances of PAHs in the ISM: Confronting Observations with Experimental Results

    CERN Document Server

    Gredel, R; Rouille, G; Steglich, M; Huisken, F; Henning, Th

    2011-01-01

    We present recent UV laboratory spectra of various polycyclic aromatic hydrocarbons (PAHs) and explore the potential of these molecules as carriers of the DIBs. From a detailed comparison of gas-phase and Ne-matrix absorption spectra of anthracene, phenanthrene, pyrene, 2,3-benzofluorene, benzo[ghi]perylene, and hexabenzocoronene with new interstellar spectra, we infer upper limits in the abundance of these PAHs in the interstellar medium. Upper limits in the column densities of anthracene of $0.8 - 2.8 \\times 10^{12}$\\ cm$^{-2}$ and of pyrene and 2,3-benzofluorene ranging from $2 - 8 \\times 10^{12}$\\ cm$^{-2}$ are inferred. Upper limits in the column densities of benzo[ghi]perylene are $0.9 - 2.4 \\times 10^{13}$ and $10^{14}$ cm$^{-2}$ for phenanthrene. The measurements indicate fractional abundances of anthracene, pyrene, and 2,3-benzofluorene of a few times $10^{-10}$. Upper limits in the fractional abundance of benzo[ghi]perylene of a few times $10^{-9}$ and of phenanthrene of few times $10^{-8}$ are infe...

  19. Wastewater Irrigation: Persistent Organic Pollutans in Soil and Product

    Directory of Open Access Journals (Sweden)

    Mehmet Emin AYDIN

    2015-06-01

    Full Text Available Treated or untreated wastewaters, used for irrigation purpose, contain various persistent organic pollutants. The long use of these waters for irrigation purpose results in deposition of the pollutants in soil, contaminates products and has adverse health affect on the human through food chain, and biologic activity of flora and fauna. The wastewaters of Konya were conveyed to the Salt Lake through the main drainage channel without any treatment until 2010.  During the arid period, the wastewater in the main drainage channel was used for irrigation and the products were cultivated. In this work, persistent organic pollutants i.e., polychlorinated biphenyls (PCB 28, 52, 101, 138, 153, 180 and polycyclic aromatic hydrocarbons (naphthalene, acenaphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene, dibenzo[a,h]anthracene, benzo[g,h,i]perylene are determined in wastewater irrigated agricultural soil samples and the wheat samples cultivated in the region. High alkaline properties and clay structure of Konya soil were determined. These properties of soil result in the accumulation of contaminants in top soil layer used for agricultural production. On the other hand, PCB and PAH compounds were determined in comparable concentrations in well water irrigated reference soils with wastewater irrigated soils. PCB and PAH sources other than wastewater irrigation was evidenced for the study field.

  20. Sample preparation of sewage sludge and soil samples for the determination of polycyclic aromatic hydrocarbons based on one-pot microwave-assisted saponification and extraction

    Energy Technology Data Exchange (ETDEWEB)

    Pena, M.T.; Pensado, Luis; Casais, M.C.; Mejuto, M.C.; Cela, Rafael [Universidad de Santiago de Compostela, Dpto. Quimica Analitica, Nutricion y Bromatologia. Instituto de Investigacion y Analisis Alimentario, Santiago de Compostela (Spain)

    2007-04-15

    A microwave-assisted sample preparation (MASP) procedure was developed for the analysis of polycyclic aromatic hydrocarbons (PAHs) in sewage sludge and soil samples. The procedure involved the simultaneous microwave-assisted extraction of PAHs with n-hexane and the hydrolysis of samples with methanolic potassium hydroxide. Because of the complex nature of the samples, the extracts were submitted to further cleaning with silica and Florisil solid-phase extraction cartridges connected in series. Naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,h]anthracene, benzo[g,h,i]perylene, and indeno[1,2,3-cd]pyrene, were considered in the study. Quantification limits obtained for all of these compounds (between 0.4 and 14.8 {mu}g kg{sup -1} dry mass) were well below of the limits recommended in the USA and EU. Overall recovery values ranged from 60 to 100%, with most losses being due to evaporation in the solvent exchange stages of the procedure, although excellent extraction recoveries were obtained. Validation of the accuracy was carried out with BCR-088 (sewage sludge) and BCR-524 (contaminated industrial soil) reference materials. (orig.)

  1. Metabolism and macromolecular binding of benzo(a)pyrene and its noncarcinogenic isomer benzo(e)pyrene in cell culture

    Energy Technology Data Exchange (ETDEWEB)

    Selkirk, J.K.; MacLeod, M.C.

    1978-01-01

    The carcinogenicity of the polycyclic aromatic hydrocarbon benzo(a)pyrene (B(a)P) is thought to result from the metabolic formation of a highly reactive intermediate, 7,8-dihydrodiol-9,10-oxy-B(a)P which subsequently interacts with cellular macromolecules to produce neoplasia. Evidence has been presented implicating similar bay-region diol-epoxides as the ultimate carcinogenic forms of benz(a)anthracene, 7-methyl-benz(a)anthracene, dibenz(a,h)anthracene, and chrysene. Benzo(e)pyrene (B(e)P), on the other hand, is relatively inert when tested for carcinogenicity on mouse skin and rat trachea and when tested for mutagenicity in a mammalian system. This B(e)P molecule contains two (equivalent) bay regions and quantum mechanical model calculations suggest that 9,10-dihydrodiol-11,12-oxy-B(e)P can easily form a reactive bay-region-adjacent carbonium ion. In order to explain the noncarcinogenicity of B(e)P in the context of the bay region theory, we have studied the metabolism of B(e)P by rat liver microsomes and by cultured hamster embryo fibroblasts. In both systems, the major metabolic pathways involve the K-region of B(e)P, with little or no attack on the isolated benzo ring. These results suggest that the lack of carcinogenicity of B(e)P may reflect its preferred mode of interaction with the cellular metabolic machinery.

  2. [Determination of polycyclic aromatic hydrocarbons in the working environment during aluminum production].

    Science.gov (United States)

    Brzeźnicki, S; Przybylski, H

    1996-01-01

    Polycyclic aromatic hydrocarbons (PAHs) belong to a group od chemicals responsible, to a great extent, for the contamination of the industrial and ambient air. A number of industrial processes such as coke production, coal tar processing, production of electric energy and certain rubber goods as well as metallurgy, especially aluminium metallurgy with its anodes made of coal tar pitch are the major sources of PAH emission. An attempt was made to determine PAH concentrations at selected workposts at an aluminium production plant. Breathing zone air samples were collected by individual dosimetry. Coal tar pitch volatiles were determined by a gravimetric method and individual PAHs by HPLC. The presence of naphtalene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, triphenylene, benzo/a/anthracene, chrysene, benzo/a/pyrene, benzo/b/fluorenthene, benzo/k/fluoranthene, benzo/a/pyrene, dibenzo/a,h/anthracene, benzo/g,h,i/perylene and indeno/1,2,3-c,d/pyrene was identified at all investigated workposts. The highest concentrations of benzo/a/pyrene and coal tar pitch volatiles were found at workposts of crane operators which is due to the character of the work performed. The replacement of "wet" anode material by the "dry" one should contribute to improving of the working conditions. PMID:8834591

  3. SYNTHESIS OF FUNCTIONAL MACROMOLECULE INTERMEDIATE THROUGH ACYLATION CATALYZED BY [Emim]Cl-AlCl3 IONIC LIQUID

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Acylation reaction of anthracene with oxalyl chloride in the presence of [Emim]C1-A1C13 ionic liquid has been investigated. Pure 1,2-aceanthryenedione, which is used as intermediate of functional aromatic polymer material, was obtained by recrystalling the reaction mixture with aether and was determined by GC/MS, 1HNMR and FTIR analysis. The influences of various parameters, such as the contents of AlCl3 in [Emim]C1-A1C13, the amount of acylation agent, amount of [Emim]C1-A1C13, reaction temperature and reaction time were investigated. The optimum conditions were as follows: the molar fraction of A1C13 in ionic liquid [x(AlCl3)] being 0.67 , molar ratio of ionic liquid to anthracene being 2:1 , molar ratio of oxalyl chloride to anthracene being 2:1, reaction temperature being 40℃ and reaction time being 6h. Under above conditions, the yield and selectivity of 1,2-aceanthrylenedione can reach 91.5% and 98.3% respectively. Further more, [Emim]C1-A1C13 ionic liquid, compared with metal halides such as AlCl3, was found to catalyze the reaction as a novel environmental friendly catalyst and solvent and can be reused.

  4. Rearrangement of cyclotriveratrylene (CTV) diketone: 9,10-diarylanthracenes with OLED applications.

    Science.gov (United States)

    Sarsah, Samuel R S; Lutz, Marlon R; Zeller, Matthias; Crumrine, David S; Becker, Daniel P

    2013-03-01

    Electroluminescent 9,10-diaryl anthracenes have been shown to be promising host and hole-transporting materials in organic electroluminescence due to their high thermal stability, electrochemical reversibility, and wide band gap useful for organic light-emitting diodes (OLEDs), especially blue OLEDs. Oxidation of cyclotriveratrylene (CTV) to the corresponding diketone and subsequent bromination resulted in an unexpected rearrangement to a highly functionalized 9-aryl-10-bromoanthracene derivative, which was employed in Suzuki couplings to synthesize a series of 9,10-diaryl compounds that are structural analogues of anthracene derivatives used in the preparation of OLEDs but are more highly functionalized, including electron-donating methoxy groups in addition to substitution by a carboxylic acid moiety. The UV/fluorescence solution spectra show strong emissions at 446, 438, and 479 nm, respectively, for the anthracene 10-phenyl, 10-naphthyl, and 10-pyrenyl adducts containing a benzoic acid functional group, whereas the analogues bearing the hydroxymethylene moiety from reduction of the benzoic acid to the corresponding alcohols gave much shorter emission wavelengths of 408, 417, and 476 nm, respectively, and had somewhat higher quantum yields, suggesting they are better candidates for OLED applications. PMID:23190432

  5. Validation of an analytical method for the determination of polycyclic aromatic hydrocarbons by high efficiency liquid chromatography in PM10 and PM2,5 particles

    International Nuclear Information System (INIS)

    An analytical method was validated for polycyclic aromatic hydrocarbons in PM10 and PM2,5 particles collected from air by high performance liquid chromatography (HPLC) was validated. The PAHs analyzed in the methodology include: Naphthalene, Acenaphthylene, Fluorene, Acenaphthene, Phenanthrene, Anthracene, fluoranthene, pyrene, Benzo (a)anthracene, Chrysene, Benzo (b)fluoranthene, Benzo (k)fluoranthene, Benzo (a)pyrene, Dibenzo (a, h)anthracene, Benzo (g, h, i)perylene and Indeno (1,2,3-CD)pyrene. For these compounds, the detection limit and quantification limit have been between 0,02 and 0,1 mg/l. An equipment DIONEX, ICS 3000 model is used, that has two in series detectors: one ultraviolet model VWD-1, and fluorescence detector, model RF-2000, separating the different absorption and emission signals for proper identification of individual compounds. For all the compounds analyzed, the recovery factor has found not significantly different from each other and the repeatability and reproducibility has been to be suitable for an analytical method, especially for the lighter PAHs. (author)

  6. Biodegradation of polycyclic aromatic hydrocarbons by arbuscular mycorrhizal leek plants

    International Nuclear Information System (INIS)

    A study was conducted to examine the response of arbuscular mycorrhizal fungi (AMF) on the degradation of polycyclic aromatic hydrocarbon (PAH), nutrient uptake, and leek growth under greenhouse conditions. This experiment included 3 mycorrhizal treatments, 2 microorganism treatments, 2 PAH chemicals, and 4 concentrations of PAHs. Plant growth was greatly reduced by the addition of anthracene or phenanthrene in soil, whereas mycorrhizal inoculation not only increased plant growth, but also enhanced uptake of nitrogen and phosphorus. PAH concentrations in soil was lowered through the inoculation of two different strains of the species G. intraradices and G. versiforme. In 12 weeks of pot cultures, anthracene and phenanthrene concentrations decreased for all 3 PAH levels tested. However, the reduced amount of phenanthrene in soil was greater than that of anthracene. The addition of a soil microorganism extract into pot cultures accelerated the PAH degradation. The inoculation of AMF in a hydrocarbon contaminated soil was shown to enhance PAHs soil decontamination. It was concluded that a soil colonized with AMF can not only improve plant growth but can also stimulate soil microflora abundance and diversity. AMF may therefore directly influence PAH soil decontamination through plant growth enhancement

  7. Carbon nanorings with inserted acenes: breaking symmetry in excited state dynamics

    Science.gov (United States)

    Franklin-Mergarejo, R.; Alvarez, D. Ondarse; Tretiak, S.; Fernandez-Alberti, S.

    2016-08-01

    Conjugated cycloparaphenylene rings have unique electronic properties being the smallest segments of carbon nanotubes. Their conjugated backbones support delocalized electronic excitations, which dynamics is strongly influenced by cyclic geometry. Here we present a comparative theoretical study of the electronic and vibrational energy relaxation and redistribution in photoexcited cycloparaphenylene carbon nanorings with inserted naphthalene, anthracene, and tetracene units using non-adiabatic excited-state molecular dynamics simulations. Calculated excited state structures reflect modifications of optical selection rules and appearance of low-energy electronic states localized on the acenes due to gradual departure from a perfect circular symmetry. After photoexcitation, an ultrafast electronic energy relaxation to the lowest excited state is observed on the time scale of hundreds of femtoseconds in all molecules studied. Concomitantly, the efficiency of the exciton trapping in the acene raises when moving from naphthalene to anthracene and to tetracene, being negligible in naphthalene, and ~60% and 70% in anthracene and tetracene within the first 500 fs after photoexcitation. Observed photoinduced dynamics is further analyzed in details using induced molecular distortions, delocatization properties of participating electronic states and non-adiabatic coupling strengths. Our results provide a number of insights into design of cyclic molecular systems for electronic and light-harvesting applications.

  8. Biodegradation of polycyclic aromatic hydrocarbons by arbuscular mycorrhizal leek plants

    Energy Technology Data Exchange (ETDEWEB)

    Liu, A.; Dalpe, Y. [Agriculture Canada, Ottawa, ON (Canada). Grain and Oilseeds Branch

    2005-07-01

    A study was conducted to examine the response of arbuscular mycorrhizal fungi (AMF) on the degradation of polycyclic aromatic hydrocarbon (PAH), nutrient uptake, and leek growth under greenhouse conditions. This experiment included 3 mycorrhizal treatments, 2 microorganism treatments, 2 PAH chemicals, and 4 concentrations of PAHs. Plant growth was greatly reduced by the addition of anthracene or phenanthrene in soil, whereas mycorrhizal inoculation not only increased plant growth, but also enhanced uptake of nitrogen and phosphorus. PAH concentrations in soil was lowered through the inoculation of two different strains of the species G. intraradices and G. versiforme. In 12 weeks of pot cultures, anthracene and phenanthrene concentrations decreased for all 3 PAH levels tested. However, the reduced amount of phenanthrene in soil was greater than that of anthracene. The addition of a soil microorganism extract into pot cultures accelerated the PAH degradation. The inoculation of AMF in a hydrocarbon contaminated soil was shown to enhance PAHs soil decontamination. It was concluded that a soil colonized with AMF can not only improve plant growth but can also stimulate soil microflora abundance and diversity. AMF may therefore directly influence PAH soil decontamination through plant growth enhancement.

  9. Synthesis and modification of reduced graphene oxide aerogels for biofuel cell applications

    Directory of Open Access Journals (Sweden)

    Kondratowicz Izabela

    2015-06-01

    Full Text Available We have carried out the preparation of reduced graphene oxide aerogels using eco-friendly method that is based on the Hummers method of graphite oxidation without the use of NaNO3 that produces toxic gases. To obtain a porous 3D structure of reduced graphene oxide, we performed the hydrothermal reduction at elevated temperature. We also prepared the rGO aerogel/CNT composite using multiwalled carbon nanotubes as linkers. The rGO aerogels are promising materials as they possess good electrical conductivity (up to 100 S/m and high surface area and porous structure (~500 m2/g. The main goal was to obtain the material for electrodes in enzymatic biofuel cells. Thus, the proper modification was performed using free radical functionalization. It was shown that in order to synthesize rGO aerogels modified with anthracene, the proper order of reactions needs to be provided. The morphology of anthracene modified electrodes was analyzed using scanning electron microscopy, which confirmed their porous structure with non-uniform pore size distribution that ranged between few nanometers to microns. Data obtained by Raman spectroscopy confirmed the successful oxidation and reduction of analyzed materials. UV-Vis spectra revealed the presence of anthracene moieties in examined materials. We also recorded preliminary cyclic voltammograms that confirm an electric conductivity of the obtained structures.

  10. MONITORING POLYNUCLEAR AROMATIC HYDROCARBONS IN SEDIMENT POREWATER BY SPMD

    Institute of Scientific and Technical Information of China (English)

    朱亚先; 张勇; 庄一廷; Ka-FaiPoon; MichaelH.W.Lam; 洪华生; RudolfS.S.Wu

    2001-01-01

    A new mimic biological Semi-permeable Membrane Device (SPMD) introduced for sampling organic pollutants yielded satisfactory results when it was frrst used as a passive sampler to concentrate and determine 16 kinds of polynuclear aromatic hydrocarbons (PAHs) by means of capillary GC on an HP 5890 GC-FID in coastal sediment perewater. The concentration of PAHs in sediment porewater for naphthalene(N), acenaphthlene(AL), acenaphthene (AE), fluorene (F), phenaphthene(P), anthracene(A), fluoranthene(FA), pyrene(Py), benzo[a]anthracene(B[a]A), chrysene(Chr), benzo[b] fluor- anthene(B[b]F), benzo[k]fluoranthene(B[k]F), benzo[a]pyrene(B[a]P),indeno[1,2,3,-cd]-Pyrene(I[123]P), dibenz[a,h]anthracene(D[ab]A) and benzo[g,h,i] perylene(B[ghi]P) were:50.36, under detection limits(UD), 18.19, 8.41, 8.40, 1.44, UD, 8.01, 524.15, 168.47, 50.13,123.66, 63.48, 27.40, 82.04 and 58,81 ng/L, respectively.

  11. Isolation, fingerprinting and genetic identification of indigenous PAHs degrading bacteria from oil-polluted soils.

    Science.gov (United States)

    Alrumman, Sulaiman A; Hesham, Abd El-Latif; Alamri, Saad A

    2016-01-01

    In the present study, thirty five bacterial isolates were obtained from hydrocarbon-contaminated soil samples using an enrichment method. These isolates were tested to grow on mineral salt medium containing anthracene or phenanthrene as sole carbon source. Only five isolates showed the ability to degrade these compounds. RAPD-PCR fingerprinting was carried out for the five isolates, and the DNA patterns revealed that there was no similarity among the examined bacteria whenever the RFLP using four restriction enzymes HaeIII, Msp1, Hinf1 and Taq1 failed to differentiate among them. Five bacterial isolates were grown in high concentration of anthracene and phenanthrene (4% w/v). Two bacterial isolates were selected due to their high ability to grow in the presence of high concentrations of anthracene and phenanthrene. The isolates were identified as Bacillus flexus and Ochrobactrum anthropi, based on DNA sequencing of amplified 16S rRNA gene and phylogenetic analysis. Finally, the ability of these bacterial strains to tolerate and remove different PAHs looked promising for application in bioremediation technologies. PMID:26930863

  12. Exchangeable cations-mediated photodegradation of polycyclic aromatic hydrocarbons (PAHs) on smectite surface under visible light

    International Nuclear Information System (INIS)

    Graphical abstract: Roles of exchangeable cations in PAHs photodegradation on clay surafces under visible light. - Highlights: • Photolysis rate are strongly dependent on the type of cations on clay surface. • The strength of “cation–π” interactions governs the photodegradation rate of PAHs. • Several exchangeable cations could cause a shift in the absorption spectrum of PAHs. • Exchangeable cations influence the type and amount of reactive intermediates. - Abstract: Clay minerals saturated with different exchangeable cations are expected to play various roles in photodegradation of polycyclic aromatic hydrocarbons (PAHs) via direct and/or indirect pathways on clay surfaces. In the present study, anthracene and phenanthrene were selected as molecule probes to investigate the roles of exchangeable cations on their photodegradation under visible light irradiation. For five types of cation-modified smectite clays, the photodegradation rate of anthracene and phenanthrene follows the order: Fe3+ > Al3+ > Cu2+ >> Ca2+ > K+ > Na+, which is consistent with the binding energy of cation–π interactions between PAHs and exchangeable cations. The result suggests that PAHs photolysis rate depends on cation–π interactions on clay surfaces. Meanwhile, the deposition of anthracene at the Na+-smectite and K+-smectite surface favors solar light absorption, resulting in enhanced direct photodecomposition of PAHs. On the other hand, smectite clays saturated with Fe3+, Al3+, and Cu2+ are highly photoreactive and can act as potential catalysts giving rise to oxidative radicals such as O2−· , which initiate the transformation of PAHs. The present work provides valuable insights into understanding the transformation and fate of PAHs in the natural soil environment and sheds light on the development of technologies for contaminated land remediation

  13. Content determination and health risk assessment of polycyclic aromatic hydrocarbon in fish tissue samples from Perhentian Island, Malaysia

    International Nuclear Information System (INIS)

    The concentration of polycyclic aromatic hydrocarbon (PAH) in three fish species with different feeding habits and habitat for examples Lolong (Selar boops), Kerisi (Nemipterus peronii) dan Mengkarong (Trachinocephalus myops) from offshore of Perhentian Island, Malaysia was determined. Three individuals from each species were taken at random and the PAHs contents were determined in the muscles. Ten PAH compounds, phenanthrene, anthracene, fluoranthene, pyrene, benzo(a)anthracene, chrysene, benzo(b)fluoranthene, benzo(k)fluoranthene, benzo(e)pyrene and dibenzo(a,h)anthracene were determined. PAH in fish tissues was extracted using Soxhlet method and detected using gas chromatography - mass spectrometry (GC-MS). The level of PAH in fish tissue ranged from 17.89 - 42.18 ng/ g wet weight and 393.98 - 511.07 ng/ g lipid weight. The order of PAH concentration in wet weight was Kerisi (511.07 ng/ g)> Mengkarong (409.50 ng/ g)> Lolong (393.98 ng/ g) but in terms of lipid weight, the order was Kerisi (511.07 ng/ g)> Mengkarong (409.50 ng/ g)> Lolong (393.98 ng/ g). Kerisi has the lowest lipid content of 3.5 % compared to Lolong (6.5 %) and Mengkarong (10.3 %). No obvious significant difference (p > 0.05) of PAH levels in three fish species was observed (ANOVA, p > 0.05). There was no significant relationship between lipid content and PAH accumulation in fish. Based on fish consumption rate of 142.2 g/ day, the Potency Equivalent Concentration (PEC), which is a carcinogenic potency value for PAH, was found to be ranged from 0.41 - 0.63 ng/ g wet weight in all three species of fish. This value is below the limit set by USEPA, which is 0.67 ng/ g wet weight for human consumption. (author)

  14. Exchangeable cations-mediated photodegradation of polycyclic aromatic hydrocarbons (PAHs) on smectite surface under visible light

    Energy Technology Data Exchange (ETDEWEB)

    Jia, Hanzhong, E-mail: jiahz@ms.xjb.ac.cn [Laboratory of Environmental Sciences and Technology, Xinjiang Technical Institute of Physics & Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011 (China); Li, Li [Laboratory of Environmental Sciences and Technology, Xinjiang Technical Institute of Physics & Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011 (China); Chen, Hongxia; Zhao, Yue [Laboratory of Environmental Sciences and Technology, Xinjiang Technical Institute of Physics & Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011 (China); School of Geology and Mining Engineering, Xinjiang University, Urumqi 830046 (China); Li, Xiyou [Laboratory of Environmental Sciences and Technology, Xinjiang Technical Institute of Physics & Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011 (China); Wang, Chuanyi, E-mail: cywang@ms.xjb.ac.cn [Laboratory of Environmental Sciences and Technology, Xinjiang Technical Institute of Physics & Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011 (China)

    2015-04-28

    Graphical abstract: Roles of exchangeable cations in PAHs photodegradation on clay surafces under visible light. - Highlights: • Photolysis rate are strongly dependent on the type of cations on clay surface. • The strength of “cation–π” interactions governs the photodegradation rate of PAHs. • Several exchangeable cations could cause a shift in the absorption spectrum of PAHs. • Exchangeable cations influence the type and amount of reactive intermediates. - Abstract: Clay minerals saturated with different exchangeable cations are expected to play various roles in photodegradation of polycyclic aromatic hydrocarbons (PAHs) via direct and/or indirect pathways on clay surfaces. In the present study, anthracene and phenanthrene were selected as molecule probes to investigate the roles of exchangeable cations on their photodegradation under visible light irradiation. For five types of cation-modified smectite clays, the photodegradation rate of anthracene and phenanthrene follows the order: Fe{sup 3+} > Al{sup 3+} > Cu{sup 2+} >> Ca{sup 2+} > K{sup +} > Na{sup +}, which is consistent with the binding energy of cation–π interactions between PAHs and exchangeable cations. The result suggests that PAHs photolysis rate depends on cation–π interactions on clay surfaces. Meanwhile, the deposition of anthracene at the Na{sup +}-smectite and K{sup +}-smectite surface favors solar light absorption, resulting in enhanced direct photodecomposition of PAHs. On the other hand, smectite clays saturated with Fe{sup 3+}, Al{sup 3+}, and Cu{sup 2+} are highly photoreactive and can act as potential catalysts giving rise to oxidative radicals such as O{sub 2}{sup −}· , which initiate the transformation of PAHs. The present work provides valuable insights into understanding the transformation and fate of PAHs in the natural soil environment and sheds light on the development of technologies for contaminated land remediation.

  15. A screening method for polycyclic aromatic hydrocarbons determination in water by headspace SPME with GC-FID

    Energy Technology Data Exchange (ETDEWEB)

    Zuazagoitia, D.; Millan, E.; Garcia, R. [Univ. of Pais Vasco, Donostia-San Sebastian (Spain). Dept. of Applied Chemistry

    2007-11-15

    A simple method for determination of polycyclic aromatic hydrocarbons (PAHs) in water using headspace solid-phase microextraction (HS-SPME) with gas chromatography-flame ionisation detector (GC-FID) was developed. In order to obtain the convenient experimental conditions for HS-SPME extraction an experimental design with two steps was accomplished. A 2{sup 6-2} fractional factorial design and central composite design (CCD) considering three significant factors were used. Naphthalene, anthracene and fluoranthene were chosen as representatives of two, three and four aromatic rings, and the global response of three PAHs was used for the results, evaluation. The chosen extraction conditions were: 85 {mu}m polyacrylate fibre; 50 C temperature; 60 min time; 20 mL-dissolution volume (in 40 mL glass vial); without salt addition; and 2 min desorption time. The procedure was extended to other seven PAHs (acenaphthylene, acenaphthene, fluorene, phenanthrene, pyrene, chrysene and benzo(a)anthracene) and the analytical characteristics were checked. The limit of detection (LOD) was from 0.08 (anthracene) to 0.20 {mu}g L{sup -1} (naphthalene). The precision expressed as relative standard deviation (RSD in %) using 50 {mu}g L{sup -1} of each analyte ranged from 6.8 to 17 %. The method was applied to the analysis of the surface waters and leaching waters of contaminated soils from Gipuzkoa (North Spain). The PAHs were not detected in surface water samples. Most of the PAHs were found in the leachates from contaminated soils showing a maximum global value of 75.5 {mu}g L{sup -1}. (orig.)

  16. Characterization of parent and oxygenated-polycyclic aromatic hydrocarbons (PAHs) in Xi'an, China during heating period: An investigation of spatial distribution and transformation.

    Science.gov (United States)

    Wang, Jingzhi; Hang Ho, Steven Sai; Huang, Rujin; Gao, Meiling; Liu, Suixin; Zhao, Shuyu; Cao, Junji; Wang, Gehui; Shen, Zhenxing; Han, Yongming

    2016-09-01

    Polycyclic aromatic hydrocarbons (PAHs) and its oxygenated derivatives (OPAHs) are toxins in PM2.5. Little information has been known for their transformation in the ambient airs. In this study, PM2.5 samples were collected at 19 sampling sites in Xi'an, China during the heating period, which is classified into: urban residential, university, commercial area, suburban region, and industry. Organic compounds including PAHs, OPAHs, hopanes and cholestanes were quantified. The average of total quantified PAHs and OPAHs concentrations were 196.5 ng/m(3) and 29.4 ng/m(3), respectively, which were consistent with other northern cities in China. Statistical analyses showed that there were significant differences on the distributions of PAHs between urban and suburban regions. The industry also had distinguishable profiles compared with urban residential and commercial area for OPAHs. The greater diversity of OPAHs than PAHs might be due to different primary emission sources and transformation and degradation pathways. The ratios of OPAHs to the corresponding parent PAHs, including 9-fluorenone/fluorene, anthraquinone/anthracene, benz[a]anthracene-7,12-dione/benzo[a]anthracene were 6.2, 12.7, and 1.4, respectively, which were much higher than those for the fresh emissions from coal combustion and biomass burning. These prove the importance of secondary formation and transformation of OPAHs in the ambient airs. Biomarkers such as retene, cyclopenta[CD]pyrene and αα-homohopane were characterized for the source apportionment. With Positive Matrix Factorization (PMF) model analysis, biomass burning was recognized as the most dominant pollution sources for PAHs during the heading period, which accounted for a contribution of 37.1%. Vehicle emission (22.8%) and coal combustion (22.6%) were also contributors in Xi'an. PMID:27323290

  17. Degradation and mineralization of high-molecular-weight polycyclic aromatic hydrocarbons by defined fungal-bacterial cocultures

    International Nuclear Information System (INIS)

    This study investigated the biodegradation of high-molecular-weight polycyclic aromatic hydrocarbons (PAHs) in liquid media and soil by bacteria (Stenotrophomonas maltophilia VUN 10,010 and bacterial consortium VUN 10,009) and a fungus (Penicillium janthinellum VUO 10,201) that were isolated from separate creosote- and manufactured-gas plant-contaminated soils. The bacteria could use pyrene as their sole carbon and energy source in a basal salts medium (BSM) and mineralized significant amounts of benzo[a]pyrene cometabolically when pyrene was also present in BSM. P. janthinellum VUO 10,201 could not utilize any high-molecular-weight PAH as sole carbon and energy source but could partially degrade these if cultured in a nutrient broth. Although small amounts of chrysene, benz[a]pyrene, and dibenz[a,h]anthracene were degraded by axenic cultures of these isolates in BSM containing a single PAH, such conditions did not support significant microbial growth or PAH mineralization. However, significant degradation of, and microbial growth on, pyrene, chrysene, benz[a]anthracene, benzo[a]pyrene, and dibenz[a,h]anthracene, each as a single PAH in BSM, occurred when P. janthinellum VUO 10,201 and either bacterial consortium VUN 10,009 or S. maltophilia VUN 10,010 were combined in the one culture, i.e., fungal-bacterial cocultures: 25% of the benzo[a]pyrene was mineralized to CO2 by these cocultures over 49 days, accompanied by transient accumulation and disappearance of intermediates detected by high-pressure liquid chromatography. Inoculation of fungal-bacterial cocultures into PAH-contaminated soil resulted in significantly improved degradation of high-molecular-weight PAHs, benzo[a]pyrene mineralization, and reduction in the mutagenicity of organic soil extracts, compared with the indigenous microbes and soil amended with only axenic inocula

  18. A novel analytical approach for visualizing and tracking organic chemicals in plants.

    Science.gov (United States)

    Wild, Edward; Dent, John; Barber, Jonathan L; Thomas, Gareth O; Jones, Kevin C

    2004-08-01

    Vegetation plays a key role in the environmental fate of many organic chemicals, from pesticides applied to plants, to the air-vegetation exchange and global cycling of atmospheric organic contaminants. Our ability to locate such compounds in plants has traditionally relied on inferences being made from destructive chemical extraction techniques or methods with potential artifacts. Here, for the first time, two-photon excitation microscopy (TPEM) is coupled with plant autofluorescence to visualize and track trace levels of an organic contaminant in living plant tissue, without any form of sample modification or manipulation. Anthracene-a polynuclear aromatic hydrocarbon (PAH)-was selected for study in living maize (Zea mays) leaves. Anthracene was tracked over 96 h, where amounts as low as approximately 0.1-10 pg were visible, as it moved through the epicuticular wax and plant cuticle, and was observed reaching the cytoplasm of the epidermal cells. By this stage, anthracene was identifiable in five separate locations within the leaf: (1) as a thin (approximately 5 microm) diffuse layer, in the upper surface of the epicuticular wax; (2) as thick (approximately 28 microm) diffuse bands extending from the epicuticular wax through the cuticle, to the cell walls of the epidermal cells; (3) on the external surface of epidermal cell walls; (4) on the internal surface of epidermal cell walls; and (5) within the cytoplasm of the epidermal cells. This technique provides a powerful nonintrusive tool for visualizing and tracking the movement, storage locations, and degradation of organic chemicals within vegetation using only plant and compound autofluorescence. Many other applications are envisaged for TPEM, in visualizing organic chemicals within different matrixes. PMID:15352460

  19. Risk Assessment for Children Exposed to Beach Sands Impacted by Oil Spill Chemicals

    Directory of Open Access Journals (Sweden)

    Jennifer C. Black

    2016-08-01

    Full Text Available Due to changes in the drilling industry, oil spills are impacting large expanses of coastlines, thereby increasing the potential for people to come in contact with oil spill chemicals. The objective of this manuscript was to evaluate the health risk to children who potentially contact beach sands impacted by oil spill chemicals from the Deepwater Horizon disaster. To identify chemicals of concern, the U.S. Environmental Protection Agency’s (EPA’s monitoring data collected during and immediately after the spill were evaluated. This dataset was supplemented with measurements from beach sands and tar balls collected five years after the spill. Of interest is that metals in the sediments were observed at similar levels between the two sampling periods; some differences were observed for metals levels in tar balls. Although PAHs were not observed five years later, there is evidence of weathered-oil oxidative by-products. Comparing chemical concentration data to baseline soil risk levels, three metals (As, Ba, and V and four PAHs (benzo[a]pyrene, benz[a]anthracene, benzo[b]fluoranthene, and dibenz[a,h]anthracene were found to exceed guideline levels prompting a risk assessment. For acute or sub-chronic exposures, hazard quotients, computed by estimating average expected contact behavior, showed no adverse potential health effects. For cancer, computations using 95% upper confidence limits for contaminant concentrations showed extremely low increased risk in the 10−6 range for oral and dermal exposure from arsenic in sediments and from dermal exposure from benzo[a]pyrene and benz[a]anthracene in weathered oil. Overall, results suggest that health risks are extremely low, given the limitations of available data. Limitations of this study are associated with the lack of toxicological data for dispersants and oil-spill degradation products. We also recommend studies to collect quantitative information about children’s beach play habits, which are

  20. UVA Photoirradiation of Halogenated-Polycyclic Aromatic Hydrocarbons Leading to Induction of Lipid Peroxidation

    Directory of Open Access Journals (Sweden)

    Peter P. Fu

    2006-06-01

    Full Text Available Since the finding in the 1930s, a large number of polycyclic aromatic hydrocarbons (PAHs of different structures have been tested for potential tumorigenicity. Structure-activity relationships of halo-PAHs have been investigated to determine the regions of a PAH that may be involved in cancer initiation. From these studies, a number of halo-PAHs were found to be tumorigenic in experimental animals. It was not until the 1980s that halo-PAHs were found to be present in the environment, including municipal incinerator fly ash, urban air, coal combustion, soil, snow, automobile exhausts, and tap water. Due to their widespread presence in the environment and their genotoxic activities, including carcinogenicity, many of these compounds may pose a health risk to humans. Although the biological activities, including metabolism, mutagenicity, and carcinogenicity, of halo-PAHs have been studied their phototoxicity and photo-induced biological activity have not been well examined. In this study, we study the photoirradiation of a series of structure-related halo-PAHs by UVA light in the presence of a lipid, methyl linoleate, and determine as to whether or not these compounds can induce lipid peroxidation. The halo-PAHs chosen for study include 2-bromonaphthalene, 1-chloroanthracene, 9,10-dibromoanthracene, 9-chlorophenanthrene, 9-bromophenanthrene, 7-chlorobenz[a]anthracene, 7-bromobenz[a]anthracene, 7-bromo-5-methylbenz[a]anthracene, 6-chlorobenzo[a]pyrene, and 6-bromobenzo[a]pyrene. The results indicate that upon photoirradiation by UVA all these compounds induced lipid peroxidation at different levels. These results suggest that halo-PAHs may be harmful to human health.

  1. A Potential Impact on the Chemical Composition in the Marine Boundary Layer in the Arctic Ocean by Ship Emissions

    Science.gov (United States)

    Xie, Z.; Wang, X.; Blum, J. D.; Sun, L.

    2005-12-01

    Samples of aerosols in the marine boundary layer (MBL) of the Arctic Ocean were collected aboard R/V ()Xuelong during the summer on the Second Chinese Arctic Research Expedition (July-September, 2003). Chemical compositions including major and trace elements and polycyclic aromatic hydrocarbons (PAHs) in aerosol particles were analyzed. Results showed that significant amounts of S, Fe, V and Ni are emitted from ship diesel engines and contaminate the ambient air. The total amount of Fe, which plays a significant role in the ocean ()biological pump, emitted from ships in the Arctic is estimated at 4.33-A106 kg yr-1. Sulfur emitted into the atmosphere may be transformed to sulfur acid and result in a chlorine depletion in sea-salt. Because the global inventory of sulfur from ship exhausts is large and halogens may have important consequences in possible tropospheric ozone destruction, the role of ships in effecting halogen depression in sea-salt should be evaluated. For organic compounds, 17 PAHs including Fluoranthene, Phenanthrene, Chrysene, Indeno[123-cd]pyrene, Pyrene, Benzo[b]fluoranthene, Benzo[ghi]pyrene, Naphthalene, Benzo[a]anthracene, Benzo[k]fluoranthene, Coronene, Fluorene, Benzo[a]pyrene, Acenaphthene, Anthracene, Dibenzo[a,h]anthracene and Acenaphthylene were detected. The average levels of subspecies of PAHs in ambient air ranged from 0.003 to 0.089 ng/m3. Among the 17 PAHs, fluoranthene had a relative high level, while the level of acenaphthylene was relative low. The aerosols contaminated by the ship, which were commonly excluded in previous investigations, thus provide an opportunity to investigate and understand the role of ship emissions in the atmospheric chemistry of the marine boundary layer, especially in the Arctic Ocean.

  2. Determination of octanol-air partition coefficients and supercooled liquid vapor pressures of PAHs as a function of temperature: Application to gas-particle partitioning in an urban atmosphere

    Science.gov (United States)

    Odabasi, Mustafa; Cetin, Eylem; Sofuoglu, Aysun

    Octanol-air partition coefficients ( KOA) for 14 polycyclic aromatic hydrocarbons (PAHs) were determined as a function of temperature using the gas chromatographic retention time method. log KOA values at 25° ranged over six orders of magnitude, between 6.34 (acenaphthylene) and 12.59 (dibenz[ a,h]anthracene). The determined KOA values were within factor of 0.7 (dibenz[ a,h]anthracene) to 15.1 (benz[ a]anthracene) of values calculated as the ratio of octanol-water partition coefficient to dimensionless Henry's law constant. Supercooled liquid vapor pressures ( PL) of 13 PAHs were also determined using the gas chromatographic retention time technique. Activity coefficients in octanol calculated using KOA and PL ranged between 3.2 and 6.2 indicating near-ideal solution behavior. Atmospheric concentrations measured in this study in Izmir, Turkey were used to investigate the partitioning of PAHs between particle and gas-phases. Experimental gas-particle partition coefficients ( Kp) were compared to the predictions of KOA absorption and KSA (soot-air partition coefficient) models. Octanol-based absorptive partitioning model predicted lower partition coefficients especially for relatively volatile PAHs. Ratios of measured/modeled partition coefficients ranged between 1.1 and 15.5 (4.5±6.0, average±SD) for KOA model. KSA model predictions were relatively better and measured to modeled ratios ranged between 0.6 and 5.6 (2.3±2.7, average±SD).

  3. Levels and distributions of polycyclic aromatic hydrocarbons in agricultural soils in an emerging e-waste recycling town in Taizhou area, China.

    Science.gov (United States)

    Tang, Xianjin; Shen, Chaofeng; Cheema, Sardar Alam; Chen, Lei; Xiao, Xi; Zhang, Congkai; Liu, Wenli; Li, Feng; Chen, Yingxu

    2010-01-01

    The present study investigated the levels, distributions, profiles and possible sources of polycyclic aromatic hydrocarbons (PAHs) in agricultural soils around Zeguo, an emerging e-waste recycling town in Taizhou area, China. Concentrations of sixteen USEPA priority PAHs and soil organic matter were analyzed in 59 agricultural soil samples. The total PAH concentrations ranged from 262.6 to 3,420.2 microg/kg, with the average values in a gradually descending order: agricultural soil near e-waste recycling plants and workshops (1,336.0 microg/kg) > agricultural soil in villages with open burning and e-waste recycling activities (945.8 microg/kg) > agricultural soil in other villages (466.5 microg/kg). Analysis of the distribution patterns of the PAHs showed that phenanthrene, anthracene, fluoranthene and pyrene were the dominant species. The significant correlations among individual, low-molecular-weight (LMW), high-molecular-weight (HMW) and total PAHs and the very similar PAH profiles in the three sampling areas indicated that the PAHs might have come from similar sources. The ratios of Anthracene to sum of Anthracene and Phenanthrene concentrations (Ant/(Ant+Phe)) and fluoranthene to sum of fluoranthene and pyrene concentrations (Flt/(Flt+Pyr)) were calculated and principal component analysis (PCA) was performed and the results suggested that an anthropogenic source such as the combustion of a petroleum product or coal during the e-waste recycling process seemed to be the main source of PAHs in the Zeguo agricultural soil. In conclusion, soils taken from Zeguo agricultural areas were considered to be heavily polluted, and the emerging e-waste recycling activities had definite effects on PAH soil concentrations. PMID:20535879

  4. Soil pollution by PAHs in urban soils: a comparison of three European cities.

    Science.gov (United States)

    Morillo, E; Romero, A S; Maqueda, C; Madrid, L; Ajmone-Marsan, F; Grcman, H; Davidson, C M; Hursthouse, A S; Villaverde, J

    2007-09-01

    The purpose of this study was to determine the degree of contamination with polycyclic aromatic hydrocarbons (PAHs) in samples of urban soil from three European cities: Glasgow (UK), Torino (Italy) and Ljubljana (Slovenia). Fifteen PAHs (naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenzo[a,h]anthracene, benzo[g,h,i]perylene, indeno[1,2,3-c,d]pyrene) were measured in urban soil samples, using harmonised sampling, sample extraction and analyte quantification methods. Although the mean concentration of each PAH in urban soils of each city showed a wide range of values, high levels of contamination were only evident in Glasgow, where the sum of concentrations of 15 PAHs was in the range 1487-51,822 microg kg(-1), cf. ranges in the other two cities were about ten-fold lower (89.5-4488 microg kg(-1)). The three predominant PAHs were phenanthrene, fluoranthene and pyrene, with the sum of these compounds about 40% of the total PAH content. These data, together with some special molecular indices based on ratios of selected PAHs, suggest pyrogenic origins, especially motor vehicle exhausts, to be the major sources of PAHs in urban soils of the three cities. The largest concentrations for PAHs were often found in sites close to the historic quarters of the cities. Overall, the different climatic conditions, the organic carbon contents of soil, and the source apportionment were the dominant factors affecting accumulation of PAHs in soil. PMID:17726562

  5. Effect of irradiance spectra on the photoinduced toxicity of three polycyclic aromatic hydrocarbons

    Energy Technology Data Exchange (ETDEWEB)

    Diamond, S.A.; Mount, D.R.; Burkhard, L.P.; Ankley, G.T.; Makynen, E.A.; Leonard, E.N.

    2000-05-01

    Photoinduced toxicity of polycyclic aromatic hydrocarbons (PAHs) is dependent on the concentration of compounds present and the dose of light received. Of the light present, only those wavelengths absorbed by the compound have the potential to initiate the photochemical events underlying phototoxicity. This suggests that variation in light spectra present in natural waters, arising from variation in dissolved organic carbon composition, is an important determinant of phototoxicity risk in specific, PAH-contaminated waterbodies. To quantify the effect of environmentally realistic variation in light spectra on toxicity, brine shrimp (Artemia salina) assays were conducted under various light spectra and with three PAHs (pyrene, fluoranthene, and anthracene) of known phototoxicity potential. In these spectral assays, the total ultraviolet light present was equivalent; only the spectral characteristics varied. Based on the absorbance spectra of these PAHs, it was predicted that toxicity, quantified using immobilization as the endpoint, would vary significantly among light spectra in pyrene assays, but not in anthracene assays, and that variation in toxicity in fluoranthene assays would be intermediate. The results supported these assumptions. In the pyrene exposures, the glass filter time to 50% population immobilization (IT50) (39.5 min) was 117% longer than the KCr filter IT50 (18.2 min). In the fluoranthene exposures, the glass filter IT50 (49.5 min) was 27% longer than the KCr filter IT50 (39.1 min). In the anthracene exposures, the glass filter IT50 (62.2 min) was not statistically different from the KCr filter IT50 (63.8 min). Comparison of these results with the results of assays conducted under neutral-density filters (that change intensity but not spectral distribution) demonstrate that multiplying spectral intensity by wavelength-specific absorbance accurately predicts relative photoinduced toxicity among the experimental treatments. These results indicate

  6. Chemoprevention of DMBA-induced mammary carcinogenesis in rats by low-dose EPA and DHA.

    OpenAIRE

    Noguchi, M.; Minami, M; Yagasaki, R.; Kinoshita, K; Earashi, M.; Kitagawa, H; Taniya, T.; Miyazaki, I.

    1997-01-01

    We investigated the effects of low-dose eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) on the incidence and growth of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary carcinoma in rats fed a high-fat (HF) diet. We also examined the effects of these treatments on the fatty acid composition of tumour and serum. Tumour incidence was significantly decreased by the administration of low-dose EPA and DHA, whereas their inhibitory effects on tumour growth did not reach significance....

  7. Influence of the supramolecular order on the electrical properties of 1D coordination polymers based materials

    Science.gov (United States)

    Musumeci, Chiara; Osella, Silvio; Ferlauto, Laura; Niedzialek, Dorota; Grisanti, Luca; Bonacchi, Sara; Jouaiti, Abdelaziz; Milita, Silvia; Ciesielski, Artur; Beljonne, David; Hosseini, Mir Wais; Samorì, Paolo

    2016-01-01

    The generation, under self-assembly conditions, of coordination polymers on surface based combinations of a terpyridine-antracene-pyridine based tecton and Co(ii) or Pd(ii) cations is primarily governed by the coordination geometry of the metal center (octahedral and square planar respectively). While the octahedral Co(ii) based polymer self-assembles in insulating films exhibiting randomly oriented crystalline domains, the planarity of Pd(ii) based polymers leads to the formation of conductive π-π stacked fibrillar structures exhibiting anisotropically oriented domains. In the latter case, the favorable Pd-Pd and anthracene-anthracene wavefunction overlaps along the fiber direction are responsible for the large electronic couplings between adjacent chains, whereas small electronic couplings are instead found along individual polymer chains. These results provide important guidelines for the design of conductive metal coordination polymers, highlighting the fundamental role of both intra- as well as inter-chain interactions, thus opening up new perspectives towards their application in functional devices.The generation, under self-assembly conditions, of coordination polymers on surface based combinations of a terpyridine-antracene-pyridine based tecton and Co(ii) or Pd(ii) cations is primarily governed by the coordination geometry of the metal center (octahedral and square planar respectively). While the octahedral Co(ii) based polymer self-assembles in insulating films exhibiting randomly oriented crystalline domains, the planarity of Pd(ii) based polymers leads to the formation of conductive π-π stacked fibrillar structures exhibiting anisotropically oriented domains. In the latter case, the favorable Pd-Pd and anthracene-anthracene wavefunction overlaps along the fiber direction are responsible for the large electronic couplings between adjacent chains, whereas small electronic couplings are instead found along individual polymer chains. These results

  8. PEG-Biscyanoacrylate Crosslinker for Octyl Cyanoacrylate Bioadhesive.

    Science.gov (United States)

    Basu, Arijit; Veprinsky-Zuzulia, Ilana; Levinman, Mira; Barkan, Yoav; Golenser, Jacob; Domb, Abraham J

    2016-02-01

    PEG400 (polyethylene glycol, MW 400) biscyanoacrylate is synthesized and copolymerized with 2-octyl cyanoacrylate for potential use as bioadhesive. PEG400 biscyanoacrylate is synthesized from the esterification of anthracenyl cyanoacrylic acid where the anthracene unit serves as vinyl-protecting group. Copolymerization increases the plasticity, mechanical strength, and resilience of the resulted polymer as determined by dynamic mechanical analysis. Peeling test confirms its superior bioadhesive properties. Surface morphology is characterized by SEM imaging. The formulations are cytocompatible and safe. This cyanoacrylate composition may provide improved bioadhesive cyanoacrylates. PMID:26572088

  9. Wetland treatment of oil and gas well wastewaters. Quarterly technical report, May 25, 1992---August 24, 1992

    Energy Technology Data Exchange (ETDEWEB)

    Kadlec, R.H.; Srinivasan, K.R.

    1995-11-01

    The purpose of this study is to extend the knowledge base for wetland treatment to include processes and substances of particular importance to small, on-site systems receiving oil and gas well waste water. Collection of data on the sorption of heavy metals and the degradation of toxic organics is one of the key tasks. The toxic organics phenolics and anthracene, and chromium and copper have been selected as target adsorbates. An information search was performed on oil refinery waste treatment wetland systems.

  10. Occurrence of Nitro-PAH in the Atmosphere in a Rural Area

    DEFF Research Database (Denmark)

    Nielsen, Tom; Seitz, B.; Ramdahl, T.

    1984-01-01

    -(a)pyrene have been identied in samples of airborne particulate matter. Furthermore, 8-nitrofluoranthene has been tentatively identified. The amounts of mononitro-PAH are one to two orders of magnitude lower than the most common carcinogenic PAH, as e.g. benzo(a)pyrene. Filter effects have been studied, 9......By means of gas chromatography with nitrogen sensitive detection and negative ion chemical ionization mass spectrometric detection 7 mononitro-PAH, 9-nitroanthracene, x-nitro-4,5-methylene-phenanthrene, 3-nitrofluoranthene, 1- and 2-nitropyrene, 10-nitrobenz(a)anthracene and 6-nitrobenzo...

  11. 3-(9-Anthrylmethyl-1-benzylperimidinium hexafluorophosphate

    Directory of Open Access Journals (Sweden)

    Gui-Yu Wang

    2009-06-01

    Full Text Available In the title compound, C33H25N2+·PF6−, the naphthalene ring system is twisted with respect to the anthracene and benzene rings, making dihedral angles of 72.40 (3 and 71.39 (4°, respectively. The crystal structure is stabilized by intermolecular C—H...F hydrogen bonding. Four F atoms of the hexafluorophosphate anion are disordered over two sets of sites in a 0.645 (4:0.355 (4 ratio.

  12. Avaliação da eficiência de degradação de hidrocarbonetos aromáticos por bactérias provinientes de estação de tratamento de efluente de refinaria de petróleo

    Directory of Open Access Journals (Sweden)

    Fernanda R. Pinhati

    2014-01-01

    Full Text Available Three bacterial strains were isolated from the activated sludge system of petroleum refinery wastewater, identified by partial sequencing of 16S rDNA, and classified as Acinetobacter genomospecies 3, Bacillus pumilus, and Bacillus flexus. The degradation efficiency of aromatic hydrocarbons was evaluated by gas chromatography with a flame ionization detector. In a mineral medium containing anthracene and phenanthrene and the consortium of microorganisms, the removal efficiency was 96% and 99%, respectively, after 30 days. The good rate of hydrocarbon degradation proves the operational efficiency of the microbial consortium in treating effluents containing these compounds.

  13. 4-(9-Anthryl-1-(4-methoxyphenylspiro[azetidin-3,9′-xanthen]-2-one

    Directory of Open Access Journals (Sweden)

    Orhan Büyükgüngör

    2008-05-01

    Full Text Available In the title molecule, C36H25NO3, the β-lactam ring is essentially planar, with a dihedral angle of 3.3 (2° between the two separate three-atom N/C/C planes. The β-lactam ring makes dihedral angles of 28.45 (14, 87.4 (1 and 51.8 (1° with the mean planes of the benzene, xanthene and anthracene ring systems, respectively. In addition to a weak intramolecular C—H...N hydrogen bond, the crystal structure is stabilized by two weak intermolecular C—H...O hydrogen bonds.

  14. Thermally-generated reactive intermediates: Trapping of the parent ferrocene-based o-quinodimethane and reactions of diradicals generated by hydrogen-atom transfers

    International Nuclear Information System (INIS)

    Ferrocenocyclobutene is prepared by flash vacuum pyrolysis (FVP) of the N-amino-2-phenylaziridine hydrazone of 2-methylferrocenealdehyde. In the second section of this dissertation, a series of hydrocarbon rearrangements were observed. FVP of o-allyltoluene at 0.1 Torr (700--900 C) gives 2-methylindan and indene, accompanied by o-propenyltoluene. FVP of 2-methyl-2'-vinylbiphenyl gives 9-methyl-9,10-dihydrophenanthrene, which fits the proposed mechanism. However, FVP of 2-(o-methylbenzyl)styrene gives mainly anthracene and 1-methylanthracene. This cyclization reaction was also successful with o-allylphenol and o-(2-methylallyl)phenol

  15. Understanding anionic Chugaev elimination in pericyclic tetracene formation

    OpenAIRE

    Burroughs, Laurence; Ritchie, John; Woodward, Simon

    2016-01-01

    The reaction pathway for the formation of tetracenes from the diols 1,2-C6H4(CHOHC≡CAr)2 , LiHDMS, CS2 and MeI has been modelled by computational methods at the CBS-QB3 level of theory. Comparison of PhCHOC(=S)YCCPh (Y = S- or SMe) indicates a slight kinetic advantage for the anionic system towards [3,3]-sigmatropic rearrangement [Eact(calc.) 19.7 vs 21.8 kcal mol-1]. Using anthracene-based models, 10-{SC(=O)Y}-4a,10-dihydroanthracene (Y = S- or SMe), allows direct comparison of both syn and...

  16. Temperature Effects on Retention and Separation of PAHs in Reversed-Phase Liquid Chromatography Using Columns Packed with Fully Porous and Core-Shell Particles

    OpenAIRE

    Christophe Waterlot; Anaïs Goulas

    2016-01-01

    Effects of temperature on the reversed-phase chromatographic behavior of PAHs were investigated on three columns. The first was the recent C18 column (250 mm × 4.6 mm) packed with 5 µm core-shell particles while the others were more conventional C18 columns (250 mm × 4.6 mm) packed with fully porous particles. Among the 16 PAHs studied, special attention has been paid to two pairs of PAHs, fluorene/acenaphthene and chrysene/benzo[a]anthracene, which often present coeluting problems. Due to th...

  17. Laser-induced fluorescence studies of polycyclic aromatic hydrocarbons (PAH) vapors at high temperatures.

    Science.gov (United States)

    Chi, Z; Cullum, B M; Stokes, D L; Mobley, J; Miller, G H; Hajaligol, M R; Vo-Dinh, T

    2001-06-01

    In this work, we present the fluorescence spectra of anthracene and pyrene vapors at different elevated temperatures (from 150 to 650 degrees C) excited with the 337 nm line of a nitrogen laser. We describe the high temperature effects on the resulting spectral properties including spectral intensity, spectral bandwidth and spectral shift. We found that the PAH fluorescence spectral bandwidths become very broad as the temperature increases. The broadening is mainly due to thermal vibrational sequence congestion. We also have found that the fluorescence intensity of pyrene vapor increases with increasing temperature, which results from the increase of the pyrene vapor absorption cross section at 337 nm. PMID:11446693

  18. Ultrafast cyclic voltammetry with asymmetrical potential scan

    Institute of Scientific and Technical Information of China (English)

    Zhi Yong Guo; Xiang Qin Lin

    2008-01-01

    Based on the perfect ohmic drop compensation by online electronic positive feedback, ultrafast cyclic voltammetry withasymmetrical potential scan is achieved for the first time, with the reduction of anthracene acting as the test system. Compared withthe traditional cyclic voltammetry utilizing symmetrical triangular waveform as the excitation one, the new method allows a simplerapproach to mechanistic analysis of ultrafast chemical reactions coupled with a charge transfer. And perhaps more important, it alsoprovides a way to eliminate the interference of the adsorbed product in dynamic monitoring.

  19. Palladium(II)-Catalyzed Tandem Synthesis of Acenes Using Carboxylic Acids as Traceless Directing Groups.

    Science.gov (United States)

    Kim, Kiho; Vasu, Dhananjayan; Im, Honggu; Hong, Sungwoo

    2016-07-18

    A straightforward synthetic strategy for generating useful anthracene derivatives was developed involving palladium(II)-catalyzed tandem transformation with carboxylic acids as traceless directing groups. Carboxyl-directed C-H alkenylation, carboxyl-directed secondary C-H activation and rollover, intramolecular C-C bond formation, and decarboxylative aromatization are proposed as the key steps in the tandem reaction pathway. This novel synthetic route utilizes a broad range of substrates and provides a convenient synthetic tool that allows access to acenes. PMID:27244536

  20. Aggregate Formed by a Cationic Fluorescence Probe

    Institute of Scientific and Technical Information of China (English)

    TIAN, Juan; SANG, Da-Yong; JI, Guo-Zhen

    2007-01-01

    The aggregation behavior of a cationic fluorescence probe 10-(4,7,10,13,16-pentaoxa-1-azacyclooctadecyl-methyl)anthracen-9-ylmethyl dodecanoate (1) was observed and studied by a fluorescence methodology in acidic and neutral conditions. By using the Py scale, differences between simple aggregates and micelles have been discussed. The stability of simple aggregates was discussed in terms of hydrophobic interaction and electrostatic repulsion. The absence of excimer emission of the anthrancene moiety of probe 1 in neutral condition was attributed to the photoinduced electron transfer mechanism instead of photodimerization.