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Sample records for fluorophore chloro phenyl

  1. {5-Chloro-2-[(4-chlorobenzylideneamino]phenyl}(phenylmethanone

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    Shazia Yasmeen

    2012-03-01

    Full Text Available In the title compound, C20H13Cl2NO, the C=N bond adopts an E conformation. The chloro-substituted rings form a dihedral angle of 11.99 (9° with each other and form dihedral angles of 74.95 (9 and 83.26 (10° with the unsubstituted ring. In the crystal, molecules are connected into dimers by pairs of weak C—H...O hydrogen bonds and the dimers are arranged in columns parallel to the a axis.

  2. Synthesis and Biological Activity of 3-Chloro-1-(4-perimidine methylcarbonylamino-4-phenyl-azetidin-2-one

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    Dinesh R. Panchasara

    2009-01-01

    Full Text Available Perimidine-1-acetic acid hydrazide (1 undergoes facile condensation with aromatic aldehydes to afford the corresponding azomethine (i.e. Schiff base derivatives (2a-h in good yield. Cyclocondensation of compounds (2a-h with chloro acetyl chloride affords 3-chloro-1-(4-perimidine methylcarbonylamino-4-phenyl-azetidin-2-ones (3a-h. The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.

  3. Poly[methyl(phenyl)silanediyl] modified with dansyl fluorophore: synthesis and photophysics

    Czech Academy of Sciences Publication Activity Database

    Cimrová, Věra; Výprachtický, Drahomír; Hörhold, H. H.

    2011-01-01

    Roč. 49, č. 10 (2011), s. 2233-2244 ISSN 0887-624X R&D Projects: GA MŠk(CZ) 1M06031; GA AV ČR IAA4050409 Institutional research plan: CEZ:AV0Z40500505 Keywords : conjugated polymer s * dansyl fluorophore * polysilanes Subject RIV: JA - Electronics ; Optoelectronics, Electrical Engineering Impact factor: 3.919, year: 2011

  4. Synthesis and Characterization of Ferroelectric Liquid Crystalline Organosiloxanes Containing 4-(4-undecanyloxy bi-phenyl-1-carboxyloxyphenyl (2S,3S-2-chloro-3-methylvalerate and 4-(4-undecanyloxybenzoyloxybiphenyl (2S,3S-2-chloro-3-methylvalerate

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    Chih-Hung Lin

    2013-10-01

    Full Text Available A series of new organosiloxane ferroelectric liquid crystalline (FLC materials have been synthesized, and their mesomorphic and physical properties have been characterized. Four new disiloxanes and trisiloxanes, containing biphenyl 4-hydroxybenzoate and phenyl 4-hydroxybiphenylcarboxylate as mesogenic units and eleven methylene unit as spacers and (2S,3S-2-chloro-3-methylvalerate unit as chiral end groups. The molecule, using three phenyl ring as a mesogenic unit, formulates much wider liquid crystalline phase temperature ranges than that of a two phenyl ring unit. The phenyl arrangement differences of mesogenic unit result in the greater differences of the liquid crystal phase formation. The siloxane molecule induction is helpful to the more regular smectic phase formation and smectic phase stabilization, such as chiral SC (SC* and SB phases. The siloxane molecule is helpful to reduce the phase transition temperature and broaden the liquid crystal temperature range of the SC* phase and, simultaneously, it will not induce chain crystallization phenomenon and dilute the Ps value. The synthesis and characterization of the new FLCs materials, which exhibit a room temperature SC* phase and higher spontaneous polarization are presented.

  5. Synthesis and Antifungal Activities of 5-(o-Hydroxy phenyl-2-[4'aryl-3'chloro-2'azetidinon-1-yl]-1,3,4-thiadiazole

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    Shiv K. Gupta

    2011-01-01

    Full Text Available New series of 5-(o-hydroxy phenyl-2-[4'aryl-3'chloro-2'azetidinon-1-yl]-1,3,4-thiadiazole have been synthesized and the structures of the new compounds were established on the basis of IR, 1H NMR spectral data. In vitro antifungal activity (MIC activity was evaluated and compared with standard drugs of ketoconazole. Compounds 3c in the series has shown interesting antifungal activity against both C. albicans and A. niger fungus. In the gratifying result, most of the compounds were found to have moderate antifungal activity.

  6. Quantum mechanical and spectroscopic (FT-IR, 13C, 1H NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide.

    Science.gov (United States)

    Vitnik, Vesna D; Vitnik, Željko J; Banjac, Nebojša R; Valentić, Nataša V; Ušćumlić, Gordana S; Juranić, Ivan O

    2014-01-03

    This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wavenumber showed very good agreement with the experimental values. The (1)H and (13)C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the σ(*) and π(*) antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent DFT (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule. Copyright © 2013 Elsevier B.V. All rights reserved.

  7. 1-[(6-Chloro-3-pyridylmethyl]-N-(4-ethoxyphenyl-3-phenyl-1H-pyrazole-5-carboxamide

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    Zheng Tang

    2009-04-01

    Full Text Available In the title compound, C24H21ClN4O2, the pyrazole ring makes dihedral angles of 7.70 (11, 89.17 (11 and 40.68 (11° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H...O and C—H...π bonds giving rigidity to the molecule, while weak intermolecular N—H...N and C—H...π hydrogen bonds link the molecules into a two-dimensional structure.

  8. Crystal structure of bis-(4-nitro-aniline-κN (1))(5,10,15,20-tetra-phenyl-por-phy-rin-ato-κ(4) N)cobalt(III) chloride di-chloro-methane monosolvate.

    Science.gov (United States)

    Belghith, Yassine; Mansour, Anissa; Nasri, Habib

    2014-09-01

    The reaction of [Co(III)(TPP)Cl] (TPP is the dianion of 5,10,15,20-tetra-phenyl-porphyrin) with an excess of 4-nitro-aniline in di-chloro-methane leads to the title compound, [Co(III)(C44H28N4)(C6H6N2O2)2]Cl·CH2Cl2. The Co(III) ion lies on an inversion centre and is octa-hedrally coordinated by two N atoms of the NH2 groups of the two 4-nitro-aniline trans-axial ligands and four pyrrole N atoms of the porphyrin. The asymmetric unit contains one half of the [Co(III)(TPP)(4-nitro-aniline)2](+) ion complex, one chloride counter-ion (lying on a twofold rotation axis) and one half di-chloro-methane solvent mol-ecule, where the C atom lies on a twofold rotation axis. The average equatorial Co-N(pyrrole) distance (Co-Np) is 1.982 (2) Å and the axial Co-N(4-nitro-aniline) bond length is 2.006 (2) Å. The crystal packing is stabilized by an N-H⋯Cl hydrogen bond between the N atom of the amino group of the 4-nitro-aniline axial ligand and the chloride counter-ion. The supra-molecular architecture is further stabilized by weak C-H⋯π inter-actions.

  9. Crystal structures of nitrato-(2-[2-(1-pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazolo) aquacopper and chloro-(2-[2-phenyl(pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazolo) copper

    Energy Technology Data Exchange (ETDEWEB)

    Chumakov, Yu. M. [Academy of Sciences of Moldova, Institute of Applied Physics (Moldova, Republic of); Paholnitcaia, A. Yu. [State University of Moldova (Moldova, Republic of); Petrenko, P. A. [Academy of Sciences of Moldova, Institute of Applied Physics (Moldova, Republic of); Tsapkov, V. I., E-mail: vtsapkov@gmail.com [State University of Moldova (Moldova, Republic of); Poirier, D. [Centre Hospitalier Universitaire de Quebec (Canada); Gulea, A. P. [State University of Moldova (Moldova, Republic of)

    2015-01-15

    Two crystal modifications of nitrato-(2-[2-(1-pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazolo) aquacopper (I and II) and two modifications of chloro-(2-[2-phenyl(pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazolo) copper (III and IV) have been synthesized and studied by X-ray diffraction. In structures I and II, the copper atoms coordinate a monodeprotonated molecule of the organic ligand, nitrate ions, and a water molecule. In crystals of I, the complexes are monomeric, whereas complexes II are linked via nitrate ions to form polymeric chains. In both structures the coordination polyhedron of the copper atom can be described as a distorted tetragonal bipyramid—(4 + 1 + 1) in I and (4 + 2) in II. These coordination polyherdra have different compositions. In structures III and IV, the metal atoms coordinate a monodeprotonated (2-[2-phenyl(pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazole molecule and chloride ions. In III the complex-forming ion has square-planar coordination geometry, whereas structure IV consists of centrosymmetric dimers with two bridging chlorine atoms. It was found that nitrato-(2-[2-(1-pyridine-2-ylethylidene)hydrazine]-1,3-benzothiazolo) aquacopper possesses antitumor activity.

  10. Synthesis, crystal structure, vibrational profiling, DFT studies and molecular docking of N-(4-chloro-2-{[2-(1H-indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamide.DMSO: A new antiproliferative agent

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    Al-Wabli, Reem I.; Salman, Asmaa; Shyni, V.; Ghabbour, Hazem A.; Joe, I. Hubert; Almutairi, Maha S.; Maklad, Yousreya A.; Attia, Mohamed I.

    2018-03-01

    Cancer is one of the most serious health problems worldwide and it is considered the second major cause of mankind deaths. We report the synthesis and spectroscopic characterization of N-(4-chloro-2-{[2-(1H-indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamide (CICHOPA, 5) as a new antiproliferative glyoxylamide derivative. Molecular structure of CICHOPA (5) was unequivocally confirmed via X-ray analysis and it was crystallized in the monoclinic, P21/c, a = 14.3956 (4) Å, b = 8.9307 (3) Å, c = 34.9507 (10) Å, β = 94.439 (1)°, V = 4479.9 (2) Å3, Z = 8. The in vitro anticancer potential of the title molecule 5 was examined toward four types of human cancer cell lines. Vibrational profile of the CICHOPA molecule was investigated with the aid of density functional theory approach. Natural bond orbital, and natural population analyses as well as HOMO and LUMO molecular orbitals studies were carried out in order to explore the possible intermolecular delocalization or hyperconjugation in the title compound. The binding mode of compound 5 to its target protein was predicted through a molecular docking investigation. The in vitro antiproliferative activity of the title compound 5 was examined against four human cancer cell lines and showed growth inhibitory activity at concentrations of 25 and 50 μM.

  11. N-[4-(3-Methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]- N'-pyridin-2-ylmethylene-chloro-acetic acid hydrazide: Synthesis and configurational assignment based on X-ray, 1H, and 13C NMR and theoretical calculations

    Science.gov (United States)

    Demir, Sibel; Dinçer, Muharrem; Çukurovali, Alaaddin; Yılmaz, Ibrahim

    2017-11-01

    In this study, quantum chemical calculations based on the density functional theory have been carried out to examine the effects of N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]- N'-pyridin-2-ylmethylene- chloro-acetic acid hydrazide. The calculated values are compared with the experimental data available for these molecules as a mean of validation of our proposed chemistry model. Aided by normal coordinate analysis and potential energy distributions, a confident vibrational assignment of all fundamentals is proposed herein. Additional support is given by 1H and 13C NMR spectra recorded with the sample dissolved in CDCl3 and by predicted chemical shifts at the B3LYP/6-31G( d)/6-311G+( d) levels obtained using the gauge-invariant atomic orbital method. The calculated HOMO and LUMO energies also confirm that the charge transfer occurs within the molecule. Thiazole-based compounds are potential storehouse for exploiting CH···O and CH···N hydrogen bonding interactions for molecular self-assembly.

  12. 6-Chloro-3-[5-(3-methoxy-8-methyl-4-quinolyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenylquinoline

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    Hoong-Kun Fun

    2009-11-01

    Full Text Available In the title compound, C36H29ClN4O, the dihydropyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018 Å are oriented at a dihedral angle of 71.43 (4°. One of the quinoline rings makes a dihedral angle of 65.40 (7° with the phenyl substituent. In the crystal, molecules are linked into chains along the b axis by intermolecular C—H...N hydrogen bonds. In addition, C—H...π and π–π [centroid–centroid distance = 3.7325 (8 Å] interactions are observed.

  13. Crystal structure of bis­(4-nitro­aniline-κN 1)(5,10,15,20-tetra­phenyl­por­phy­rin­ato-κ4 N)cobalt(III) chloride di­chloro­methane monosolvate

    OpenAIRE

    Belghith, Yassine; Mansour, Anissa; Nasri, Habib

    2014-01-01

    The reaction of [CoIII(TPP)Cl] (TPP is the dianion of 5,10,15,20-tetra­phenyl­porphyrin) with an excess of 4-nitro­aniline in di­chloro­methane leads to the title compound, [CoIII(C44H28N4)(C6H6N2O2)2]Cl·CH2Cl2. The CoIII ion lies on an inversion centre and is octa­hedrally coordinated by two N atoms of the NH2 groups of the two 4-nitro­aniline trans-axial ligands and four pyrrole N atoms of the porphyrin. The asymmetric unit contains one half of the [CoIII(TPP)(4-nitro­aniline)2]+ ion comple...

  14. Crystal structure of bis­(4-nitro­aniline-κN 1)(5,10,15,20-tetra­phenyl­por­phy­rin­ato-κ4 N)cobalt(III) chloride di­chloro­methane monosolvate

    Science.gov (United States)

    Belghith, Yassine; Mansour, Anissa; Nasri, Habib

    2014-01-01

    The reaction of [CoIII(TPP)Cl] (TPP is the dianion of 5,10,15,20-tetra­phenyl­porphyrin) with an excess of 4-nitro­aniline in di­chloro­methane leads to the title compound, [CoIII(C44H28N4)(C6H6N2O2)2]Cl·CH2Cl2. The CoIII ion lies on an inversion centre and is octa­hedrally coordinated by two N atoms of the NH2 groups of the two 4-nitro­aniline trans-axial ligands and four pyrrole N atoms of the porphyrin. The asymmetric unit contains one half of the [CoIII(TPP)(4-nitro­aniline)2]+ ion complex, one chloride counter-ion (lying on a twofold rotation axis) and one half di­chloro­methane solvent mol­ecule, where the C atom lies on a twofold rotation axis. The average equatorial Co—N(pyrrole) distance (Co—Np) is 1.982 (2) Å and the axial Co—N(4-nitro­aniline) bond length is 2.006 (2) Å. The crystal packing is stabilized by an N—H⋯Cl hydrogen bond between the N atom of the amino group of the 4-nitro­aniline axial ligand and the chloride counter-ion. The supra­molecular architecture is further stabilized by weak C—H⋯π inter­actions. PMID:25309176

  15. Synthesis and characterization of high quantum yield and oscillator strength 6-chloro-2-(4-cynophenyl)-4-phenyl quinoline (cl-CN-DPQ) organic phosphor for solid-state lighting.

    Science.gov (United States)

    Ghate, Minakshi; Dahule, H K; Thejo Kalyani, N; Dhoble, S J

    2018-03-01

    A novel blue luminescent 6-chloro-2-(4-cynophenyl) substituted diphenyl quinoline (Cl-CN DPQ) organic phosphor has been synthesized by the acid-catalyzed Friedlander reaction and then characterized to confirm structural, optical and thermal properties. Structural properties of Cl-CN-DPQ were analyzed by Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) spectroscopy, X-ray diffraction technique (XRD) and scanning electron microscopy (SEM) and energy dispersive analysis of X-ray (EDAX) spectroscopy. FTIR spectra confirmed the presence of different functional groups and bond stretching. 1 H-NMR and 13 C-NMR confirmed the formation of an organic Cl-CN-DPQ compound. X-ray diffraction study provided its crystalline nature. The surface morphology of Cl-CN-DPQ was analyzed by SEM, while EDAX spectroscopy revealed the elemental analysis. Differential thermal analysis (TGA/DTA) disclosed its thermal stability up to 250°C. The optical properties of Cl-CN-DPQ were investigated by UV-vis absorption and photoluminescence (PL) measurements. Cl-CN-DPQ exhibits intense blue emission at 434 nm in a solid-state crystalline powder with CIE co-ordinates (0.157, 0.027), when excited at 373 nm. Cl-CN-DPQ shows remarkable Stokes shift in the range 14800-5100 cm -1 , which is the characteristic feature of intense light emission. A narrow full width at half-maximum (FWHM) value of PL spectra in the range 42-48 nm was observed. Oscillator strength, energy band gap, quantum yield, and fluorescence energy yield were also examined using UV-vis absorption and photoluminescence spectra. These results prove its applications towards developing organic luminescence devices and displays, organic phosphor-based solar cells and displays, organic lasers, chemical sensors and many more. Copyright © 2017 John Wiley & Sons, Ltd.

  16. 3-[Chloro(phenylmethyl]-6-methyl-1,2-benzoxazole

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    M. Kayalvizhi

    2011-11-01

    Full Text Available The title compound, C15H12ClNO, is a functionalized 1,2-benzoxazole with a chloro(phenylmethyl substituent. The molecule is V-shaped, the dihedral angle between the mean plane of the 1,2-benzoxazole system [maximum deviation = 0.023 (3 Å for the N atom] and the phenyl ring being 70.33 (14°. There are no hydrogen-bonding interactions in the crystal structure, which is stabilized by van der Waals interactions only.

  17. Antibacterial Activity of Coumarine Derivatives Synthesized from 4-Chloro-chromen-2-one. The Comparison with Standard Drug.

    OpenAIRE

    Aziz Behrami

    2014-01-01

    This work reports the synthesis of some new derivatives from 4-Chloro-chromen-2-one and describe the results of antibacterial activity of purified compounds. Compounds 4-Butylamino-chromen-2-one (1a) , 4-Butylamino-2-oxo-2H-chromene-3-sulfonyl chloride (2a) , 4-Butylamino-2-oxo-2H-chromene-3-sulfonic acid (2-hydroxy-phenyl)-amide (3a), 4-Butylamino-5-ethyl-2-oxo-7-(N'-phenyl-hydrazino)-2H-chromene-3-sulfonic acid (2-hydroxy-phenyl)-amide (4a) , have been synthesized and characterized using me...

  18. Synthesis and Characterization of Some Mono Chloro-S- Triazine ...

    African Journals Online (AJOL)

    A series of ten bifunctional mono-chloro-s-triazine vinyl sulphone reactive dyes were synthesized based on Hacid with varied substituents coded as (BRD). These dyes were characterized by IR spectroscopy. The results revealed an incorporation of various substituents. The visible absorption spectra of these dyes were ...

  19. 5-Chloro-2-methyl-3-phenylsulfonyl-1-benzofuran

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    Hong Dae Choi

    2008-07-01

    Full Text Available The title compound, C15H11ClO3S, was prepared by the oxidation of 5-chloro-2-methyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. There are two symmetry-independent molecules in the asymmetric unit. The dihedral angles formed by the phenyl ring and the plane of the benzofuran system are 77.80 (8 and 78.34 (8°. The crystal structure is stabilized by aromatic π–π stacking interactions between the furan ring and the benzene rings of neighbouring benzofuran fragments from two symmetry-independent molecules; the centroid–centroid distances within the stacks are 3.689 (4, 3.702 (4, 3.825 (4 and 3.826 (4 Å. Additionally, the stacked molecules exhibit inter- and intramolecular C—H...O interactions.

  20. Alkynyl-naphthalimide Fluorophores: Gold Coordination Chemistry and Cellular Imaging Applications.

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    Langdon-Jones, Emily E; Lloyd, David; Hayes, Anthony J; Wainwright, Shane D; Mottram, Huw J; Coles, Simon J; Horton, Peter N; Pope, Simon J A

    2015-07-06

    A range of fluorescent alkynyl-naphthalimide fluorophores has been synthesized and their photophysical properties examined. The fluorescent ligands are based upon a 4-substituted 1,8-naphthalimide core and incorporate structural variations (at the 4-position) to tune the amphiphilic character: chloro (L1), 4-[2-(2-aminoethoxy)ethanol] (L2), 4-[2-(2-methoxyethoxy)ethylamino] (L3), piperidine (L4), morpholine (L5), 4-methylpiperidine (L6), and 4-piperidone ethylene ketal (L7) variants. The amino-substituted species (L2-L7) are fluorescent in the visible region at around 517-535 nm through a naphthalimide-localized intramolecular charge transfer (ICT), with appreciable Stokes' shifts of ca. 6500 cm(-1) and lifetimes up to 10.4 ns. Corresponding two-coordinate Au(I) complexes [Au(L)(PPh3)] were isolated, with X-ray structural studies revealing the expected coordination mode via the alkyne donor. The Au(I) complexes retain the visible fluorescence associated with the coordinated alkynyl-naphthalimide ligand. The ligands and complexes were investigated for their cytotoxicity across a range of cell lines (LOVO, MCF-7, A549, PC3, HEK) and their potential as cell imaging agents for HEK (human embryonic kidney) cells and Spironucleus vortens using confocal fluorescence microscopy. The images reveal that these fluorophores are highly compatible with fluorescence microscopy and show some clear intracellular localization patterns that are dependent upon the specific nature of the naphthalimide substituent.

  1. Deuterium isotopic effects connected with unimolecular and concerted mechanisms. The case of 1-deutero-2-chloro alcohols

    International Nuclear Information System (INIS)

    Jambon, C.

    1962-01-01

    After a bibliographic analysis of the probable causes of isotopic effects and their comparison, with the simplifications provided by the athermal model, a discussion of the isotopic effect of deuterium in organic molecules in terms of structural influences is presented, showing the important role of the C-D bond length which is shorter than the C-H bond length, and of the D atom's Van der Waals radius, shorter than that of the H atom. Kinetic measurements were carried out on some reactions involving the mechanisms proposed: unimolecular ionizations and halogen concentrates. The structural models chosen are: 2-chloro-cyclo-hexanols cis and trans 1-H and 2-D; 2-chloro-cyclo-pentanols cis trans 1-H and 1-D; 1-phenyl-l-chloro-2-propanol threo 2-H and 2-D. (author) [fr

  2. Deuterium isotopic effects connected with unimolecular and concerted mechanisms. The case of 1-deutero-2-chloro alcohols; Effets isotopiques du deuterium attaches a des mecanismes unimoleculaires et concertes. Cas des deutero-1-chloro-2 alcools

    Energy Technology Data Exchange (ETDEWEB)

    Jambon, C

    1962-07-01

    After a bibliographic analysis of the probable causes of isotopic effects and their comparison, with the simplifications provided by the athermal model, a discussion of the isotopic effect of deuterium in organic molecules in terms of structural influences is presented, showing the important role of the C-D bond length which is shorter than the C-H bond length, and of the D atom's Van der Waals radius, shorter than that of the H atom. Kinetic measurements were carried out on some reactions involving the mechanisms proposed: unimolecular ionizations and halogen concentrates. The structural models chosen are: 2-chloro-cyclo-hexanols cis and trans 1-H and 2-D; 2-chloro-cyclo-pentanols cis trans 1-H and 1-D; 1-phenyl-l-chloro-2-propanol threo 2-H and 2-D. (author) [French] Apres une analyse bibliographique des causes probables d'effets isotopiques et leur comparaison, avec les simplifications qu'apporte le modele athermique, on a entrepris l'etude de la discussion isotopique du deuterium dans des molecules organiques en termes d'influences structurelles, cherchant a degager le role important de la longueur de la liaison C-D plus courte que C-H, et du rayon de Van der Waals de l'atome de D plus petit que celui de H. On a effectue des mesures cinetiques sur quelques reactions invoquant les mecanismes envisages: ionisations unimoleculaires et concentrees d'halogenes. Les modeles structuraux choisis sont: chloro 2 - cyclohexanols cis et trans H 1 et D 1; chloro 2 - cyclopentanols cis et trans H 1 et D 1; phenyl 1 - chloro 1 - propanol 2 threo H 2 et D 2. (auteur)

  3. Cobalamin-fluorophores' photochemistry and biomedical applications

    Science.gov (United States)

    Rodgers, Zachary Lewis

    As science focuses on the finer details of complex processes occurring in biology, the need for tools responsive to researcher control have become critical to communicate with cellular functions in both a spatial and temporal manner. To this end, light responsive "caging groups" have been used to generate molecular constructs with which researchers can activate using directed irradiation to elicit biological responses where and when they want. This advancement in molecular control has greatly improved our ability to study biological systems in their dynamically intricate form. Most of these photoresponsive moieties perform well within a petri dish, but their application is limited in vivo. Current photochemical tools require high energy light for their activation. Dermal tissue contains bio chromophores that absorb this light and prevents its penetration to less than a few millimeters making photoactivation impossible. However, tissue has an "optical window" in the red and near infrared (600 -- 1000 nm) where light penetrates efficiently to clinically relevant depths. Therefore, researchers have sought long wavelength responsive caging groups but have had little success to date. Herein, I report the development of an entire class of red and near infrared responsive (600 -- 800 nm) caging groups based on Vitamin B12 or cobalamin. Upon modification with a fluorophore antenna, these metal complexes can capture long wavelength light to perform photochemical work in the form of bond scission reactions. The effect is compatible with a range of fluorophores covering the entire near infrared spectrum, and bond scission proceeds rapidly with extremely high efficiencies. In this work, the initial development and characterization of these molecules as photoactivateable groups will be discussed. Furthermore, I will demonstrate how these molecules can be applied for clinical applications, such as drug delivery and tissue scaffold formation, to provide safer and less invasive

  4. Synthesis and antimicrobial activity of N1-(3-chloro-4-fluorophenyl-N4-substituted semicarbazone derivatives

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    Mohamed Jawed Ahsan

    2016-09-01

    Full Text Available A series of 16 N1-(3-chloro-4-fluorophenyl-N4-substituted semicarbazone derivatives were synthesized and subjected to computational pharmacokinetic studies to predict molecular properties. All the title compounds (4a–p followed the Lipinski “Rule of Five”. The synthesized compounds were characterized by elemental analyses and spectral data and the compounds (4a–p were evaluated for antimicrobial activities. Among them the compound 2-(4-hydroxybenzylidene-N-(3-chloro-4-fluorolphenylhydrazinecarboxamide (4f was found to be the most active compound that showed good antibacterial activity while the compound 2-(4-methoxybenzylidene-N-(3-chloro-4-fluorolphenylhydrazinecarboxamide (4g was moderately active against fungal strains. We have noticed that the compounds, (4f, 4k and 4d bearing OH and NO2 groups on the phenyl ring at position 4 exhibited good antibacterial activity while compound (4g bearing OCH3 on the phenyl ring at position 4 exhibited moderate antifungal activity.

  5. Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro-form monosolvate.

    Science.gov (United States)

    Wenger, Emmanuel; Moulat, Laure; Legrand, Baptiste; Amblard, Muriel; Calmès, Monique; Didierjean, Claude

    2015-10-01

    In the title compound, phenyl (S)-2-[(S)-(1-{2-[(S)-(1-{[(tert-but-oxy)carbon-yl]amino}-bicyclo-[2.2.2]octan-2-yl)formamido]-propanamido}-bicyclo-[2.2.2]octan-2-yl)formamido]-3-phenyl-propano-ate chloro-form monosolvate, C42H56N4O7·CHCl3, the α,β-hybrid peptide contains two non-proteinogenic amino acid residues of (S)-1-amino-bicyclo-[2.2.2]octane-2-carb-oxy-lic acid [(S)-ABOC], two amino acid residues of (S)-2-amino-propanoic acid [(S)-Ala] and (S)-2-amino-3-phenyl-propanoic acid [(S)-Phe], and protecting groups of tert-but-oxy-carbonyl (Boc) and benzyl ester (OBn). The tetra-mer folds into a right-handed mixed 11/9 helix stabilized by intra-molecular i,i + 3 and i,i - 1 C=O⋯H-N hydrogen bonds. In the crystal, the oligomers are linked by N-H⋯O=C hydrogen bonds into chains along the a-axis direction. The chloro-form solvent mol-ecules are inter-calated between the folded chains via C-H⋯O=C inter-actions.

  6. 4-Chloro-2-((E-{3-[1-(hydroxyiminoethyl]phenyl}iminomethylphenol

    Directory of Open Access Journals (Sweden)

    Lei Wu

    2009-12-01

    Full Text Available The title compound, C15H13ClN2O2, adopts an E conformation with respect to the azomethine C=N bond. The aniline and phenol rings are almost coplanar, making a dihedral angle of 3.33 (2°. In the crystal, the molecules lie about inversion centers, forming dimers that are connected by intermolecular O—H...N hydrogen bonds, resulting in six-membered rings with graph-set motif R22(6. In addition, there is a strong intermolecular O—H...N hydrogen-bonding interaction, resulting in an S(6 ring motif. Weak π–π interactions between the benzene rings [centroid–centroid distance = 3.809 (1 Å] further stabilize the crystal structure.

  7. Size dependent studies of metal nanoparticles with bio-fluorophores

    Science.gov (United States)

    Patil, Ajeetkumar; Ballary, Steffy; George, Sajan D.; Chidangil, Santhosh

    2017-06-01

    Interaction of noble metal nanoparticles (NPs) with fluorophores has been an important research area in the field of material science and biomedical field. In the proximity of a metal nanoparticle, there is a quenching or enhancement in the intrinsic fluorescence of the fluorophore . The conditional quenching of the fluorescence can be used for negative sensing whereas enhancement in the fluorescence can be used to gain greater sensitivity and high signal to noise ratio in the molecular sensing/imaging. The current work deals with the systematic studies to understand the fluorescence quenching for few bio-fluorophores (NADH and FAD) when interacted with different sized silver nano-particles of (10nm, 40nm and 100nm). Home assembled Laser Induced Fluorescence (LIF) set-up was used to study the fluorescence quenching of NADH and FAD for different sized silver nanoparticles.

  8. Bright photoactivatable fluorophores for single-molecule imaging.

    Science.gov (United States)

    Grimm, Jonathan B; English, Brian P; Choi, Heejun; Muthusamy, Anand K; Mehl, Brian P; Dong, Peng; Brown, Timothy A; Lippincott-Schwartz, Jennifer; Liu, Zhe; Lionnet, Timothée; Lavis, Luke D

    2016-12-01

    Small-molecule fluorophores are important tools for advanced imaging experiments. We previously reported a general method to improve small, cell-permeable fluorophores which resulted in the azetidine-containing 'Janelia Fluor' (JF) dyes. Here, we refine and extend the utility of these dyes by synthesizing photoactivatable derivatives that are compatible with live-cell labeling strategies. Once activated, these derived compounds retain the superior brightness and photostability of the JF dyes, enabling improved single-particle tracking and facile localization microscopy experiments.

  9. Spectroscopic identification of individual fluorophores using photoluminescence excitation spectra.

    Science.gov (United States)

    Czerski, J; Colomb, W; Cannataro, F; Sarkar, S K

    2018-01-25

    The identity of a fluorophore can be ambiguous if other fluorophores or nonspecific fluorescent impurities have overlapping emission spectra. The presence of overlapping spectra makes it difficult to differentiate fluorescent species using discrete detection channels and unmixing of spectra. The unique absorption and emission signatures of fluorophores provide an opportunity for spectroscopic identification. However, absorption spectroscopy may be affected by scattering, whereas fluorescence emission spectroscopy suffers from signal loss by gratings or other dispersive optics. Photoluminescence excitation spectra, where excitation is varied and emission is detected at a fixed wavelength, allows hyperspectral imaging with a single emission filter for high signal-to-background ratio without any moving optics on the emission side. We report a high throughput method for measuring the photoluminescence excitation spectra of individual fluorophores using a tunable supercontinuum laser and prism-type total internal reflection fluorescence microscope. We used the system to measure and sort the photoluminescence excitation spectra of individual Alexa dyes, fluorescent nanodiamonds (FNDs), and fluorescent polystyrene beads. We used a Gaussian mixture model with maximum likelihood estimation to objectively separate the spectra. Finally, we spectroscopically identified different species of fluorescent nanodiamonds with overlapping spectra and characterized the heterogeneity of fluorescent nanodiamonds of varying size. © 2018 The Authors Journal of Microscopy © 2018 Royal Microscopical Society.

  10. Interactions of carbohydrates and proteins by fluorophore-assisted ...

    Indian Academy of Sciences (India)

    A sensitive, specific, and rapid method for the detection of carbohydrate-protein interactions is demonstrated by fluorophore-assisted carbohydrate electrophoresis (FACE). The procedure is simple and the cost is low. The advantage of this method is that carbohydrate-protein interactions can be easily displayed by FACE, ...

  11. Naphthyl azomesogens with lateral chloro groups

    Indian Academy of Sciences (India)

    Unknown

    2003-10-11

    Oct 11, 2003 ... 4-Hydroxybenzoic acid, the appropriate n-alkyl halides, SOCl2, KOH, 2-naphthol, 3-chloro aniline,. NaNO2, CuSO45H2O, anhydrous K2CO3 etc. were used as received. Solvents were dried and distilled prior to use. 2.2a 4-n-Alkoxybenzoic acids [A] and 4-n- alkoxybenzoyl chlorides [B]: These were synthe-.

  12. L-shaped benzimidazole fluorophores: synthesis, characterization and optical response to bases, acids and anions.

    Science.gov (United States)

    Lirag, Rio Carlo; Le, Ha T M; Miljanić, Ognjen Š

    2013-05-14

    Nine L-shaped benzimidazole fluorophores have been synthesized, computationally evaluated and spectroscopically characterized. These "half-cruciform" fluorophores respond to bases, acids and anions through changes in fluorescence that vary from moderate to dramatic.

  13. Exposure characteristics of positive tone electron beam resist containing p-chloro-α-methylstyrene

    Science.gov (United States)

    Ochiai, Shunsuke; Takayama, Tomohiro; Kishimura, Yukiko; Asada, Hironori; Sonoda, Manae; Iwakuma, Minako; Hoshino, Ryoichi

    2017-07-01

    The positive tone resist consisted of methyl-α-chloroacrylate (ACM) and α-methylstyrene (MS) has higher sensitivity and higher dry etching resistance than poly (methylmethacrylate) (PMMA) due to the presence of a chlorine atom and a phenyl group. Copolymers consisted of ACM and p-chloro-α-methylstyrene (PCMS), where the additional chlorine atom is introduced in phenyl group compared with ACM-MS resist are synthesized and their exposure characteristics are investigated. ACM-PCMS resist with the ACM:PCMS composition ratio of 49:51 indicates the high solubility for amyl acetate developer. As the ACM composition ratio increases, the solubility of ACM-PCMS resist is suppressed. In both ACM-PCMS and ACM-MS resists, the sensitivity decreases while the contrast increases with increasing ACM ratio. When the composition ratio of ACM:PCMS is 69:31, 100/100 nm line and space pattern having a good shape is obtained at 120 μC/cm2 which is comparable to the required exposure dose for conventional ACM-MS resist with ACM:MS=50:50. Dry etching resistance of ACM:PCMS resists for Ar gas is also presented.

  14. NIR FRET Fluorophores for Use as an Implantable Glucose Biosensor

    Directory of Open Access Journals (Sweden)

    Majed DWEIK

    2008-12-01

    Full Text Available Development of an in vivo optical sensor requires the utilization of Near Infra Red (NIR fluorophores due to their ability to operate within the biological tissue window. Alexa Fluor 750 (AF750 and Alexa Fluor 680 (AF680 were examined as potential NIR fluorophores for an in vivo fluorescence resonance energy transfer (FRET glucose biosensor. AF680 and AF750 found to be a FRET pair and percent energy transfer was calculated. Next, the tested dye pair was utilized in a competitive binding assay in order to detect glucose. Concanavalin A (Con A and dextran have binding affinity, but in the presence of glucose, glucose displaces dextran due to its higher affinity to Con A than dextran. Finally, the percent signal transfer through porcine skin was examined. The results showed with approximately 4.0 mm porcine skin thickness, 1.98 % of the fluorescence was transmitted and captured by the detector.

  15. Structure-activity relationship of nerve-highlighting fluorophores.

    Directory of Open Access Journals (Sweden)

    Summer L Gibbs

    Full Text Available Nerve damage is a major morbidity associated with numerous surgical interventions. Yet, nerve visualization continues to challenge even the most experienced surgeons. A nerve-specific fluorescent contrast agent, especially one with near-infrared (NIR absorption and emission, would be of immediate benefit to patients and surgeons. Currently, there are only three classes of small molecule organic fluorophores that penetrate the blood nerve barrier and bind to nerve tissue when administered systemically. Of these three classes, the distyrylbenzenes (DSBs are particularly attractive for further study. Although not presently in the NIR range, DSB fluorophores highlight all nerve tissue in mice, rats, and pigs after intravenous administration. The purpose of the current study was to define the pharmacophore responsible for nerve-specific uptake and retention, which would enable future molecules to be optimized for NIR optical properties. Structural analogs of the DSB class of small molecules were synthesized using combinatorial solid phase synthesis and commercially available building blocks, which yielded more than 200 unique DSB fluorophores. The nerve-specific properties of all DSB analogs were quantified using an ex vivo nerve-specific fluorescence assay on pig and human sciatic nerve. Results were used to perform quantitative structure-activity relationship (QSAR modeling and to define the nerve-specific pharmacophore. All DSB analogs with positive ex vivo fluorescence were tested for in vivo nerve specificity in mice to assess the effect of biodistribution and clearance on nerve fluorescence signal. Two new DSB fluorophores with the highest nerve to muscle ratio were tested in pigs to confirm scalability.

  16. Enhanced Fluorescence from Fluorophores on Fractal Silver Surfaces

    OpenAIRE

    Parfenov, Alexandr; Gryczynski, Ignacy; Malicka, Joanna; Geddes, Chris D.; Lakowicz, Joseph R.

    2003-01-01

    Recent reports have shown enhanced fluorescence for fluorophores in close proximity to chemically deposited silver islands or colloids. To expand the usefulness of metal-enhanced fluorescence we tested fractal silver structures formed on, or near, silver electrodes by passage of electric currents. The emission intensity of fluorescein-labeled human serum albumin (FITC-HSA) was enhanced over 100-fold when adsorbed to the fractal silver structures as compared to glass. The amplitude-weighted li...

  17. Selective modification of layered silicate nanoparticle edges with fluorophores

    Czech Academy of Sciences Publication Activity Database

    Bujdák, J.; Danko, M.; Chorvát Jr., D.; Czímerová, A.; Sýkora, Jan; Lang, Kamil

    65-66, SEP 2012 (2012), s. 152-157 ISSN 0169-1317 R&D Projects: GA ČR GAP207/10/1447; GA ČR GBP208/12/G016 Institutional research plan: CEZ:AV0Z40320502; CEZ:AV0Z40400503 Keywords : fluorescence * fluorophore * grafited day minerals Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 2.342, year: 2012

  18. Simulated evolution of fluorophores for light emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Shu, Yinan; Levine, Benjamin G., E-mail: levine@chemistry.msu.edu [Department of Chemistry, Michigan State University, East Lansing, Michigan 48824 (United States)

    2015-03-14

    Organic light emitting diodes based on fluorophores with a propensity for thermally activated delayed fluorescence (TADF) are able to circumvent limitations imposed on device efficiency by spin statistics. Molecules with a propensity for TADF necessarily have two properties: a small gap between the lowest lying singlet and triplet excited states and a large transition dipole moment for fluorescence. In this work, we demonstrate the use of a genetic algorithm to search a region of chemical space for molecules with these properties. This algorithm is based on a flexible and intuitive representation of the molecule as a tree data structure, in which the nodes correspond to molecular fragments. Our implementation takes advantage of hybrid parallel graphics processing unit accelerated computer clusters to allow efficient sampling while retaining a reasonably accurate description of the electronic structure (in this case, CAM-B3LYP/6-31G{sup ∗∗}). In total, we have identified 3792 promising candidate fluorophores from a chemical space containing 1.26 × 10{sup 6} molecules. This required performing electronic structure calculations on only 7518 molecules, a small fraction of the full space. Several novel classes of molecules which show promise as fluorophores are presented.

  19. Synthesis of Two Novel 3-Amino-5-[4-chloro-2-phenoxyphenyl]-4H-1,2,4-triazoles with Anticonvulsant Activity

    OpenAIRE

    Mahdavi, Mohammad; Akbarzadeh, Tahmineh; Sheibani, Vahid; Abbasi, Maryam; Firoozpour, Loghman; Tabatabai, Sayyed Abbas; Shafiee, Abbas; Foroumadi, Alireza

    2010-01-01

    Two novel 3-amino-5-(4-choloro-2-phenoxyphenyl)-4H-1,2,4-triazole derivatives were prepared and their anticonvulsant activity was measured by evaluation of the ability of these compounds to protect mice against convulsion induced by lethal doses of pentylenetetrazole (PTZ). Diazepam (Sigma) was considered as a positive control drug with anticonvulsant effect [ED50 = 1.2 (0.5-1.9) mg/Kg]. Amongst the compounds tested, compound 3, 3-amino-5- [4-chloro-2-(2-flurophenoxy)phenyl]-4H-1,2,4-triazole...

  20. 3-Substituted 2-phenyl-indoles

    DEFF Research Database (Denmark)

    Johansson, Karl Henrik; Jørgensen, T.B.; Gloriam, D.E.

    2013-01-01

    -indoles with a variety of substituents at the indole 3-position. Herein we describe the development of optimised and efficient synthetic routes to a series of new 2-phenyl-indole building blocks 3 to 9 and show that these can be used to generate a broad variety of 3-substituted 2-phenyl-indoles of interest to medicinal...

  1. Discovery, understanding, and bioapplication of organic fluorophore: a case study with an indolizine-based novel fluorophore, Seoul-Fluor.

    Science.gov (United States)

    Kim, Eunha; Lee, Youngjun; Lee, Sanghee; Park, Seung Bum

    2015-03-17

    Owing to its high sensitivity and great applicability, the fluorescence phenomenon has been considered as an inevitable research tool in the modern scientific fields of chemistry, biology, materials science, biomedical science, and their interfaces. Many strategies have been pursued to understand and manipulate the photophysical properties of fluorescent materials, but the scientific community has been focused on the repeated application of existing organic fluorophores or the identification of unique fluorescence properties in a trial-and-error basis without systematic studies. Moreover, recent studies are emphasizing the necessity of deeper understanding about the structure-photophysical property relationship of organic fluorophores for the development of better fluorescent probes. Herein, we provide an overview of a novel fluorescent molecular framework, Seoul-Fluor, which can be rationally engineered to furnish a wide variety of fluorophores in terms of the photophysical properties. Seoul-Fluor is built on an indolizine-based fluorescent platform with three different positions to introduce various substituents: R(1) and R(2) substituents for electronic perturbation; R(3) substituent as a functional handle for bioconjugation. Over the past decade, we have demonstrated that the Seoul-Fluor system has (i) tunable and predictable emission wavelength covering a full visible-color range; (ii) controllable quantum yield via photoinduced electron transfer phenomenon; and (iii) environment-sensitive fluorogenic properties that can be modified through intramolecular charge transfer processes. We convincingly demonstrated the prediction of photophysical properties, that is, emission wavelength and quantum yield, through the construction of a systematic set of analogues and the subsequent analysis of their photophysical properties without the highly sophisticated theoretical support. Guided by quantifiable parameters such as the Hammett substituent constants or energy

  2. Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives

    Directory of Open Access Journals (Sweden)

    Lucjan Strekowski

    2010-03-01

    Full Text Available Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinylpyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethylpyrimidines and 2-chloro-4-(2-substituted ethylquinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted pyrimidines and quinazolines.

  3. Thermotropic liquid crystalline polyesters derived from 2-chloro ...

    Indian Academy of Sciences (India)

    NAGESH MANURKAR

    2017-08-24

    -hydroxy benzoyloxy]-. 2-chloro-1,4-benzene (BHBOCB) and aliphatic dicarboxylic acid chlorides by interfacial polycondensation methodology is presented. Synthesised polyesters consist of bis[4-hydroxy ...

  4. Thermotropic liquid crystalline polyesters derived from 2-chloro ...

    Indian Academy of Sciences (India)

    Home; Journals; Journal of Chemical Sciences; Volume 129; Issue 9. Thermotropic liquid crystalline polyesters derived from 2-chloro ... These polyesters exhibited thermotropic liquid crystalline behavior and showed nematic texture except decamethylene spacer. Decamethylene spacer based polyester showed marble ...

  5. Electrochemistry of silicon in chloro-fluoride and carbonate melts

    Directory of Open Access Journals (Sweden)

    Devyatkin S.V.

    2003-01-01

    Full Text Available The electrochemical behavior of K2SiF6 in chloro-fluoride melts and that of SiO2 in carbonate melts has been studied. Silicon, titanium silicides, boron silicide and ternary compounds Ti-Si-B have been deposited from chloro-fluoride melts. Only SiC was deposited from carbonate-silica melts under carbon dioxide atmosphere (that is, excessive pressure of CO2.

  6. Single Molecule Study of Photoconversion and Spectral Heterogeneities of Fluorophores

    DEFF Research Database (Denmark)

    Liao, Zhiyu

    of conformational changes and dynamics. The photophysical properties of organic dyes directly determine the quality of the experiments. So the better understanding of the photophysical properties of organic dyes, the better we are able to design the experiments and interpret the data, especially in single molecule...... 104 single molecule measurements. A simple and practical method is introduced to study the characteristics of the photoproducts at the ensemble level. Control experiments reveal that the reaction leading to photobleaching is oxygen related, but the composition of the photoproducts remains inconclusive...... stimulate new pathways in engineering and designing photoconvertible fluorophores, based on the reaction with oxygen or other chemicals. Besides, this results show that dyes that convert into other emissive species could give problems when interpreting single molecule FRET systems. The revealed mechanism...

  7. Characterization of UV fluorophores for application to luminescent solar concentrators

    Science.gov (United States)

    Hellier, Kaitlin; Carter, Sue

    The implementation of solar as an alternative energy source faces many challenges, including the competition for space with agriculture and the environmental impacts of solar farms in deserts. As a solution to these problems, the Carter Lab has developed Luminescent Solar Concentrator (LSC) panels for applications to greenhouses. These panels utilize a luminescent dye compatible with the spectrum used in photosynthesis for the plants below and front-facing PV cells, achieving power enhancement of greater than 20% compared with the cells alone. To increase this enhancement, additional portions of the unused spectrum must be harvested. In this talk, we will discuss the characterization of UV absorbing fluorophores, including spectra, quantum yield, and the enhancement of light output and power generation. We will also address the combination of these UV dyes with the original LSC dye in low and high concentration, and the FRET efficiency and potential applications associated with high concentration films.

  8. Probing protein-lipid interactions by FRET between membrane fluorophores

    Science.gov (United States)

    Trusova, Valeriya M.; Gorbenko, Galyna P.; Deligeorgiev, Todor; Gadjev, Nikolai

    2016-09-01

    Förster resonance energy transfer (FRET) is a powerful fluorescence technique that has found numerous applications in medicine and biology. One area where FRET proved to be especially informative involves the intermolecular interactions in biological membranes. The present study was focused on developing and verifying a Monte-Carlo approach to analyzing the results of FRET between the membrane-bound fluorophores. This approach was employed to quantify FRET from benzanthrone dye ABM to squaraine dye SQ-1 in the model protein-lipid system containing a polycationic globular protein lysozyme and negatively charged lipid vesicles composed of phosphatidylcholine and phosphatidylglycerol. It was found that acceptor redistribution between the lipid bilayer and protein binding sites resulted in the decrease of FRET efficiency. Quantification of this effect in terms of the proposed methodology yielded both structural and binding parameters of lysozyme-lipid complexes.

  9. Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging.

    Science.gov (United States)

    Cosco, Emily D; Caram, Justin R; Bruns, Oliver T; Franke, Daniel; Day, Rachael A; Farr, Erik P; Bawendi, Moungi G; Sletten, Ellen M

    2017-10-09

    Bright fluorophores in the near-infrared and shortwave infrared (SWIR) regions of the electromagnetic spectrum are essential for optical imaging in vivo. In this work, we utilized a 7-dimethylamino flavylium heterocycle to construct a panel of novel red-shifted polymethine dyes, with emission wavelengths from 680 to 1045 nm. Photophysical characterization revealed that the 1- and 3-methine dyes display enhanced photostability and the 5- and 7-methine dyes exhibit exceptional brightness for their respective spectral regions. A micelle formulation of the 7-methine facilitated SWIR imaging in mice. This report presents the first polymethine dye designed and synthesized for SWIR in vivo imaging. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives

    Science.gov (United States)

    Galal, Alaaeldin M. F.; Shalaby, Elsayed M.; Abouelsayed, Ahmed; Ibrahim, Medhat A.; Al-Ashkar, Emad; Hanna, Atef G.

    2018-01-01

    The absolute configuration of 5-chloro-2-methoxy-N-phenylbenzamide single crystal [compound (1)] and the effect of introducing -[CH2]n-, n = 1,2 group adjacent to the amide group [compounds (2) and (3)], were studied. Furthermore, the replacement of the methoxy group with a hydroxy group [compound (4)] was defined. Proton and carbon-13 NMR spectrometer were used to record the structural information of the prepared compounds. X-ray single crystal diffractometer were used to elucidate the 3D structural configurations. Intensity data for the studied compounds were collected at room temperature. The X-ray data prove that compound (1) is almost planar, with maximum r.m.s. deviations of 0.210(3) Å corresponds to C13. This planarity starts to disturb by adding -[CH2]n-, n = 1,2 groups between the NH group and the phenyl ring in compounds (2) and (3), respectively. By replacing the OCH3 group by an OH group in compound (4), the plane of the chlorophenyl moiety is nearly perpendicular to that of the phenyl ring. Such new structural configurations were further illustrated by the infrared, and ultraviolet-visible spectroscopy measurements in the frequency range 400-4000 cm-1 and 190-1100 nm, respectively. Spectroscopic analyses were verified with the help of molecular modeling using density functional theory. The estimated total dipole moment for the prepared compounds reflects its ability to interact with its surrounding molecules. The higher dipole moment for a given structures is combined with the higher reactivity for potential use in medicinal applications.

  11. Mapping absolute tissue endogenous fluorophore concentrations with chemometric wide-field fluorescence microscopy

    Science.gov (United States)

    Xu, Zhang; Reilley, Michael; Li, Run; Xu, Min

    2017-06-01

    We report chemometric wide-field fluorescence microscopy for imaging the spatial distribution and concentration of endogenous fluorophores in thin tissue sections. Nonnegative factorization aided by spatial diversity is used to learn both the spectral signature and the spatial distribution of endogenous fluorophores from microscopic fluorescence color images obtained under broadband excitation and detection. The absolute concentration map of individual fluorophores is derived by comparing the fluorescence from "pure" fluorophores under the identical imaging condition following the identification of the fluorescence species by its spectral signature. This method is then demonstrated by characterizing the concentration map of endogenous fluorophores (including tryptophan, elastin, nicotinamide adenine dinucleotide, and flavin adenine dinucleotide) for lung tissue specimens. The absolute concentrations of these fluorophores are all found to decrease significantly from normal, perilesional, to cancerous (squamous cell carcinoma) tissue. Discriminating tissue types using the absolute fluorophore concentration is found to be significantly more accurate than that achievable with the relative fluorescence strength. Quantification of fluorophores in terms of the absolute concentration map is also advantageous in eliminating the uncertainties due to system responses or measurement details, yielding more biologically relevant data, and simplifying the assessment of competing imaging approaches.

  12. Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate

    Directory of Open Access Journals (Sweden)

    Jian-Kang Jiang

    2002-10-01

    Full Text Available In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.

  13. 5'-C-Ethyl-tetrazolyl-N(6)-substituted adenosine and 2-chloro-adenosine derivatives as highly potent dual acting A1 adenosine receptor agonists and A3 adenosine receptor antagonists.

    Science.gov (United States)

    Petrelli, Riccardo; Torquati, Ilaria; Kachler, Sonja; Luongo, Livio; Maione, Sabatino; Franchetti, Palmarisa; Grifantini, Mario; Novellino, Ettore; Lavecchia, Antonio; Klotz, Karl-Norbert; Cappellacci, Loredana

    2015-03-12

    A series of N(6)-substituted-5'-C-(2-ethyl-2H-tetrazol-5-yl)-adenosine and 2-chloro-adenosine derivatives was synthesized as novel, highly potent dual acting hA1AR agonists and hA3AR antagonists, potentially useful in the treatment of glaucoma and other diseases. The best affinity and selectivity profiles were achieved by N(6)-substitution with a 2-fluoro-4-chloro-phenyl- or a methyl- group. Through an in silico receptor-driven approach, the molecular bases of the hA1- and hA3AR recognition and activation of this series of 5'-C-ethyl-tetrazolyl derivatives were explained.

  14. Adaptive optics two-photon excited fluorescence lifetime imaging ophthalmoscopy of exogenous fluorophores in mice.

    Science.gov (United States)

    Feeks, James A; Hunter, Jennifer J

    2017-05-01

    In vivo cellular scale fluorescence lifetime imaging of the mouse retina has the potential to be a sensitive marker of retinal cell health. In this study, we demonstrate fluorescence lifetime imaging of extrinsic fluorophores using adaptive optics fluorescence lifetime imaging ophthalmoscopy (AOFLIO). We recorded AOFLIO images of inner retinal cells labeled with enhanced green fluorescent protein (EGFP) and capillaries labeled with fluorescein. We demonstrate that AOFLIO can be used to differentiate spectrally overlapping fluorophores in the retina. With further refinements, AOFLIO could be used to assess retinal health in early stages of degeneration by utilizing lifetime-based sensors or even fluorophores native to the retina.

  15. (1-Adamantyl{4-[(2-chloro-9-isopropyl-9H-purin-6-ylaminomethyl]phenyl}methanone trichloromethane solvate

    Directory of Open Access Journals (Sweden)

    Michal Rouchal

    2009-06-01

    Full Text Available In the title compound, C26H30ClN5O·CHCl3, the purine molecule consists of essentially planar benzene and purine ring systems [maximum deviation 0.010 (4 Å for both ring systems] forming a dihedral angle of 85.52 (9°. Intermolecular N—H...N hydrogen bonds link adjacent molecules into centrosymmetric dimers. The structure also contains intermolecular C—H...O and C—H...N interactions. The benzene rings form offset face-to-face π–π stacking interactions with an interplanar distance of 3.541 (4 Å and a centroid-to-centroid distance of 4.022 (4 Å.

  16. 2-(1-Adamantyl-1-{4-[(2-chloro-9-isopropyl-9H-purin-6-ylaminomethyl]phenyl}ethanone

    Directory of Open Access Journals (Sweden)

    Robert Vícha

    2009-02-01

    Full Text Available The structure of the title compound, C27H32ClN5O, consists of two crystallographically independent conformers differing slightly in all geometric parameters. Both contain nearly planar purine and benzene ring systems [maximum deviations of 0.046 (3 and 0.005 (2 Å, respectively], the dihedral angles between them being 76.44 (6 and 82.39 (6°, and an adamantane cage consisting of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.7 (2–110.6 (2°. The carbonyl plane and the benzene ring are almost coplanar [dihedral angles of 6.43 (9 and 0.64 (8° in the two conformers]. The crystal structure is stabilized by intermolecular N—H...N interactions that link adjacent molecules into dimers and by some non-bonding contacts of the C—H...Cl type.

  17. Cannizzaro reaction of 2-chloro-3-formylquinolines and its synthetic ...

    Indian Academy of Sciences (India)

    to give 4-(2-methoxy-quinolin-3-yl)-but-3-en-2-ones which in turn were bromocyclized and dehydrobromi- nated to get 2-acetylfuro[2,3-b]quinolines. Keywords. Cannizzaro reaction; bromocyclisation; 2-methoxy-3-formylquinolines; furoquinolines;. 2-chloro-3-formylquinolines. 1. Introduction. Natural products bearing furo[2 ...

  18. 21 CFR 177.2210 - Ethylene polymer, chloro-sulfonated.

    Science.gov (United States)

    2010-04-01

    ... reference. Copies of the ASTM method may be obtained from the American Society for Testing Materials, 100... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Ethylene polymer, chloro-sulfonated. 177.2210... (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: POLYMERS Substances for Use Only...

  19. 4-Chloro-2,3,5-trifluorobenzoic Acid

    Directory of Open Access Journals (Sweden)

    Shuitao Yu

    2015-11-01

    Full Text Available A new tetrahalogenated benzoic acid 4-chloro-2,3,5-trifluorobenzoic acid was synthesized from methyl 2,3,4,5-tetrafluorobenzoate via three steps. The structure of the newly synthesized compound was established by FTIR, NMR, MS and elemental analysis.

  20. Influence of molecules with chloro group on the associative liquid ...

    Indian Academy of Sciences (India)

    Influence of molecules with chloro group on the associative liquid methanol: A dielectric relaxation approach. V P PAWAR1, G S RAJU2 and S C MEHROTRA3. 1Department of Electronics, Maharashtra Udayagiri College, Udgir 413 517, India. 2Department of Physics, Dr. B.A. Marathwada University, Aurangabad 431 004, ...

  1. Genotype-Independent Transmission of Transgenic Fluorophore Protein by Boar Spermatozoa

    Science.gov (United States)

    Garrels, Wiebke; Holler, Stephanie; Taylor, Ulrike; Herrmann, Doris; Struckmann, Christina; Klein, Sabine; Barg-Kues, Brigitte; Nowak-Imialek, Monika; Ehling, Christine; Rath, Detlef; Ivics, Zoltán; Niemann, Heiner; Kues, Wilfried A.

    2011-01-01

    Recently, we generated transposon-transgenic boars (Sus scrofa), which carry three monomeric copies of a fluorophore marker gene. Amazingly, a ubiquitous fluorophore expression in somatic, as well as in germ cells was found. Here, we characterized the prominent fluorophore load in mature spermatozoa of these animals. Sperm samples were analyzed for general fertility parameters, sorted according to X and Y chromosome-bearing sperm fractions, assessed for potential detrimental effects of the reporter, and used for inseminations into estrous sows. Independent of their genotype, all spermatozoa were uniformly fluorescent with a subcellular compartmentalization of the fluorophore protein in postacrosomal sheath, mid piece and tail. Transmission of the fluorophore protein to fertilized oocytes was shown by confocal microscopic analysis of zygotes. The monomeric copies of the transgene segregated during meiosis, rendering a certain fraction of the spermatozoa non-transgenic (about 10% based on analysis of 74 F1 offspring). The genotype-independent transmission of the fluorophore protein by spermatozoa to oocytes represents a non-genetic contribution to the mammalian embryo. PMID:22110672

  2. Experimental validation of a theoretical model of dual wavelength photoacoustic (PA) excitation in fluorophores

    Science.gov (United States)

    Märk, Julia; Theiss, Christoph; Schmitt, Franz-Josef; Laufer, Jan

    2015-03-01

    Fluorophores, such as exogenous dyes and genetically expressed proteins, exhibit radiative relaxation with long excited state lifetimes. This can be exploited for PA detection based on dual wavelength excitation using pump and probe wavelengths that coincide with the absorption and emission spectra, respectively. While the pump pulse raises the fluorophore to a long-lived excited state, simultaneous illumination with the probe pulse reduces the excited state lifetime due to stimulated emission (SE).This leads to a change in thermalized energy, and hence PA signal amplitude, compared to single wavelength illumination. By introducing a time delay between pump and probe pulses, the change in PA amplitude can be modulated. Since the effect is not observed in endogenous chromophores, it provides a contrast mechanism for the detection of fluorophores via PA difference imaging. In this study, a theoretical model of the PA signal generation in fluorophores was developed and experimentally validated. The model is based on a system of coupled rate equations, which describe the spatial and temporal changes in the population of the molecular energy levels of a fluorophore as a function of pump-probe energy and concentration. This allows the prediction of the thermalized energy distribution, and hence the time-resolved PA signal amplitude. The model was validated by comparing its predictions to PA signals measured in solutions of rhodamine 6G, a well-known laser dye, and Atto680, a NIR fluorophore.

  3. chromic transitions in phenyl-substituted polythiophenes

    African Journals Online (AJOL)

    The solvatochromic and thermochromic behaviours of phenyl-substituted polythiophenes were studied. The pristine polymers, upon dissolution in chloroform, exhibited blue-shifted absorption. The solid films of the polymers showed significant blue-shifted as well as red-shifted absorptions when heated. While the addition of ...

  4. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject to...

  5. Tetra-butyl-ammonium hydrogen phenyl-arsonate-phenyl-arsonic acid (1/1).

    Science.gov (United States)

    Reck, Lukas; Schmitt, Wolfgang

    2012-09-01

    The structure of the title salt adduct, (C(4)H(9))(4)N(+)·C(6)H(5)AsO(3)H(-)·C(6)H(5)AsO(3)H(2), features chains along the a axis comprising alternating hydrogen phenyl-arsonate anions and phenyl-arsonic acid mol-ecules linked by O-H⋯O hydrogen bonds.

  6. Different Fluorophore Labeling Strategies and Designs Affect Millisecond Kinetics of DNA Hairpins

    Directory of Open Access Journals (Sweden)

    Andreas Hartmann

    2014-09-01

    Full Text Available Changes in molecular conformations are one of the major driving forces of complex biological processes. Many studies based on single-molecule techniques have shed light on conformational dynamics and contributed to a better understanding of living matter. In particular, single-molecule FRET experiments have revealed unprecedented information at various time scales varying from milliseconds to seconds. The choice and the attachment of fluorophores is a pivotal requirement for single-molecule FRET experiments. One particularly well-studied millisecond conformational change is the opening and closing of DNA hairpin structures. In this study, we addressed the influence of base- and terminal-labeled fluorophores as well as the fluorophore DNA interactions on the extracted kinetic information of the DNA hairpin. Gibbs free energies varied from ∆G0 = −3.6 kJ/mol to ∆G0 = −0.2 kJ/mol for the identical DNA hairpin modifying only the labeling scheme and design of the DNA sample. In general, the base-labeled DNA hairpin is significantly destabilized compared to the terminal-labeled DNA hairpin and fluorophore DNA interactions additionally stabilize the closed state of the DNA hairpin. Careful controls and variations of fluorophore attachment chemistry are essential for a mostly undisturbed measurement of the underlying energy landscape of biomolecules.

  7. Synthesis and Antimicrobial activity 2-chloro-6-methylquinoline Hydrazone derivatives

    Directory of Open Access Journals (Sweden)

    Rajiv Kumar

    2009-12-01

    Full Text Available

    A series of 2-chloro-6-methylquinoline hydrazones (3a-o were synthesized by the condensation of substituted acyl
    hydrazines, semicarbazide, thiosemicarbazide and INH with 2-chloro-3-formyl-6-methylquinoline in absolute alcohol.
    The structures of compounds were established using spectral data and elemental analysis. All the compounds were
    evaluated for their antibacterial activity against Escherichia coli (NCTC, 10418, Staphylococcus aureus (NCTC, 65710
    and Pseudomonas aeruginosa (NCTC, 10662. Compounds were also tested for antifungal activity aganist Aspergillus
    niger (MTCC, 281, Aspergillus flavus (MTCC, 277, Monascus purpureus (MTCC, 369 and Penicillium citrinum
    (NCIM, 768 by cup-plate method.

  8. Radiation decomposition of alcohols and chloro phenols in micellar systems

    International Nuclear Information System (INIS)

    Moreno A, J.

    1998-01-01

    The effect of surfactants on the radiation decomposition yield of alcohols and chloro phenols has been studied with gamma doses of 2, 3, and 5 KGy. These compounds were used as typical pollutants in waste water, and the effect of the water solubility, chemical structure, and the nature of the surfactant, anionic or cationic, was studied. The results show that anionic surfactant like sodium dodecylsulfate (SDS), improve the radiation decomposition yield of ortho-chloro phenol, while cationic surfactant like cetyl trimethylammonium chloride (CTAC), improve the radiation decomposition yield of butyl alcohol. A similar behavior is expected for those alcohols with water solubility close to the studied ones. Surfactant concentrations below critical micellar concentration (CMC), inhibited radiation decomposition for both types of alcohols. However radiation decomposition yield increased when surfactant concentrations were bigger than the CMC. Aromatic alcohols decomposition was more marked than for linear alcohols decomposition. On a mixture of alcohols and chloro phenols in aqueous solution the radiation decomposition yield decreased with increasing surfactant concentration. Nevertheless, there were competitive reactions between the alcohols, surfactants dimers, hydroxyl radical and other reactive species formed on water radiolysis, producing a catalytic positive effect in the decomposition of alcohols. Chemical structure and the number of carbons were not important factors in the radiation decomposition. When an alcohol like ortho-chloro phenol contained an additional chlorine atom, the decomposition of this compound was almost constant. In conclusion the micellar effect depend on both, the nature of the surfactant (anionic or cationic) and the chemical structure of the alcohols. The results of this study are useful for wastewater treatment plants based on the oxidant effect of the hydroxyl radical, like in advanced oxidation processes, or in combined treatment such as

  9. In vitro bactericidal activity of 4- and 5-chloro-2-hydroxy-N-[1-oxo-1-(phenylamino)alkan-2-yl]benzamides against MRSA.

    Science.gov (United States)

    Zadrazilova, Iveta; Pospisilova, Sarka; Pauk, Karel; Imramovsky, Ales; Vinsova, Jarmila; Cizek, Alois; Jampilek, Josef

    2015-01-01

    A series of nine substituted 2-hydroxy-N-[1-oxo-1-(phenylamino)alkan-2-yl]benzamides was assessed as prospective bactericidal agents against three clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) and S. aureus ATCC 29213 as the reference and quality control strain. The minimum bactericidal concentration was determined by subculturing aliquots from MIC determination onto substance-free agar plates. The bactericidal kinetics of compounds 5-chloro-2-hydroxy-N-[(2S)-3-methyl-1-oxo-1-{[4-(trifluoromethyl)phenyl]amino}butan-2-yl]benzamide (1f), N-{(2S)-1-[(4-bromophenyl)amino]-3-methyl-1-oxobutan-2-yl}-4-chloro-2-hydroxybenzamide (1g), and 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide (1h) was established by time-kill assay with a final concentration of the compound equal to 1x, 2x, and 4x MIC; aliquots were removed at 0, 4, 6, 8, and 24 h time points. The most potent bactericidal agent was compound 1f exhibiting remarkable rapid concentration-dependent bactericidal effect even at 2x MIC at 4, 6, and 8 h (with a reduction in bacterial count ranging from 3.08 to 3.75 log10 CFU/mL) and at 4x MIC at 4, 6, 8, and 24 h (5.30 log10 CFU/mL reduction in bacterial count) after incubation against MRSA 63718. Reliable bactericidal effect against other strains was maintained at 4x MIC at 24 h.

  10. Synthesis of new N-(5-chloro-2-methoxyphenyl-4-(5-substituted-1,3,4-oxadiazol-2-ylthiobutanamide derivatives as suitable lipoxygenase inhibitors

    Directory of Open Access Journals (Sweden)

    Aziz-ur-Rehman

    2016-09-01

    Full Text Available Heterocyclic compounds are the most attractive class for researchers due to their biological activities. In the undertaken research, a number of N-(5-chloro-2-methoxyphenyl-4-(5-substituted-1,3,4-oxadiazol-2-ylthiobutanamide (6a–k compounds were prepared by converting multifarious phenyl/aryl/aralkyl/heterocyclic organic acids (1a–k consecutively into the corresponding esters (2a–k, hydrazides (3a–k and 5-substituted-1,3,4-oxadiazol-2-thiols (4a–k. Finally, the target compounds 6a–k were synthesized by stirring 5-substituted-1,3,4-oxadiazol-2-thiols (4a–k with N-(5-chloro-2-methoxyphenyl-4-bromobutanamide (5 in the presence of N,N-dimethylformamide (DMF and sodium hydride (NaH. The structure elucidation of the synthesized compounds was processed through 1H-NMR, IR and mass spectral data. The synthesized compounds were screened against lipoxygenase enzyme (LOX and showed moderately good activities relative to the reference standard Baicalein.

  11. Eigen-analysis reveals components supporting super-resolution imaging of blinking fluorophores.

    Science.gov (United States)

    Agarwal, Krishna; Prasad, Dilip K

    2017-06-30

    This paper presents eigen-analysis of image stack of blinking fluorophores to identify the components that enable super-resolved imaging of blinking fluorophores. Eigen-analysis reveals that the contributions of spatial distribution of fluorophores and their temporal photon emission characteristics can be completely separated. While cross-emitter cross-pixel information of spatial distribution that permits super-resolution is encoded in two matrices, temporal statistics weigh the contribution of these matrices to the measured data. The properties and conditions of exploitation of these matrices are investigated. Con-temporary super-resolution imaging methods that use blinking for super-resolution are studied in the context of the presented analysis. Besides providing insight into the capabilities and limitations of existing super-resolution methods, the analysis shall help in designing better super-resolution techniques that directly exploit these matrices.

  12. Multicolor imaging of cancer cells with fluorophore-tagged aptamers for single cell typing.

    Science.gov (United States)

    Wang, Song; Kong, Hao; Gong, Xiaoyun; Zhang, Sichun; Zhang, Xinrong

    2014-08-19

    The discrimination of the type of cancer cells remains challenging due to the subtle differences in their expression of membrane receptors. In this work, we developed a multicolor cell imaging method for distinguishing the type of cancer cells with fluorophore-tagged aptamers. We found that the interaction between aptamers and cancer cells was affected by both of the sequence of aptamers and the labeled dyes. As the co-ownership of biomarkers for different cancer cell lines, the fluorophore-tagged aptamers interacted with different cancer cell lines in different degree, resulting in a distinct color to discriminate the type of cancer cells at single cell level. Taking advantage of the cross-reactive ability of the fluorophore-tagged aptamers, we could not only distinguish the cancerous cells quickly from large quantities of noncancerous cells, but also identify the type of the cancerous cells. This work has potential application for cancer diagnostic and therapy in the future.

  13. Selective Activation of N,N'-Diacyl Rhodamine Pro-fluorophores Paired with Releasing Enzyme, Porcine Liver Esterase (PLE).

    Science.gov (United States)

    Abney, Kristopher K; Ramos-Hunter, Susan J; Romaine, Ian M; Godwin, J Shawn; Sulikowski, Gary A; Weaver, Charles David

    2018-04-21

    This study reports the synthesis and testing of a family of rhodamine pro-fluorophores and an enzyme capable of converting pro-fluorophores to Rhodamine 110. We prepared a library of simple N,N'-diacyl rhodamines and investigated Porcine Liver Esterase (PLE) as an enzyme to activate rhodamine-based pro-fluorophores. A PLE-expressing cell line generated an increase in fluorescence rapidly upon pro-fluorophore addition demonstrating the rhodamine pro-fluorophores are readily taken up and fluorescent upon PLE-mediated release. Rhodamine pro-fluorophore amides trifluoroacetamide (TFAm) and proponamide (PAm) appeared to be the best substrates using a cell-based assay using PLE expressing HEK293. Our pro-fluorophore series showed diffusion into live cells and resisted endogenous hydrolysis. The use of our engineered cell line containing the exogenous enzyme PLE demonstrated the rigorousness of amide masking when compared to cells not containing PLE. This simple and selective pro-fluorophore rhodamine pair with PLE offers the potential to be used in vitro and in vivo fluorescence based assays. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  14. Cobalt (II, nickel (II, copper (II and zinc (II complexes of 1-(phenyl(phenylamino methylpyrrolidine-2,5-dione and 2-((phenylaminomethyl isoindoline-1,3-dione and their biological activity

    Directory of Open Access Journals (Sweden)

    D. Tamil Vendan

    2010-12-01

    Full Text Available The new Mannich bases 1-(phenyl(phenylaminomethylpyrrolidine-2,5-dione (SBA was synthesized from the condensation of succinimide, benzaldehyde and aniline. 2-((phenylaminomethylisoindoline-1,3-dione (PFA was derived from pthalimide, formaldehyde and aniline. The general formula of the Co (II, Ni (II, Cu (II and Zn (II chloro complexes, ML2X2 are reported. The ligands and the complexes have been characterized by various physical-chemical techniques such as elemental analysis, molar conductance, magnetic susceptibility measurements, infrared and electronic spectra. The spectral analysis to ascertain mode of bonding and overall geometry of the complexes revealed octahedral geometries.

  15. Asymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethyleneglycinamides across α-chloro-N-sulfinylimines

    Directory of Open Access Journals (Sweden)

    Gert Callebaut

    2012-12-01

    Full Text Available The asymmetric synthesis of new chiral γ-chloro-α,β-diaminocarboxylamide derivatives by highly diastereoselective Mannich-type reactions of N-(diphenylmethyleneglycinamides across chiral α-chloro-N-p-toluenesulfinylaldimines was developed. The resulting (SS,2S,3S-γ-chloro-α,β-diaminocarboxylamides were formed with the opposite enantiotopic face selectivity as compared to the (SS,2R,3R-γ-chloro-α,β-diaminocarboxyl esters obtained via Mannich-type addition of analogous N-(diphenylmethyleneglycine esters across a chiral α-chloro-N-p-toluenesulfinylaldimine. Selective deprotection under different acidic reaction conditions and ring closure of the γ-chloro-α,β-diaminocarboxylamides was optimized, which resulted in Nα-deprotected syn-γ-chloro-α,β-diaminocarboxylamides, N-sulfinyl-β,γ-aziridino-α-aminocarboxylamide derivatives, a trans-imidazolidine, and an Nα,Nβ-deprotected syn-γ-chloro-α,β-diaminocarboxylamide.

  16. Structure-Inherent Targeting of Near-Infrared Fluorophores for Image-Guided Surgery.

    Science.gov (United States)

    Jo, Danbi; Hyun, Hoon

    2017-05-01

    Although various clinical imaging modalities have been developed to visualize internal body structures and detect abnormal tissues prior to surgical procedures, most medical imaging modalities do not provide disease-specific images in real-time. Optical imaging can provide the surgeon with real-time visualization of the surgical field for intraoperative image-guided surgery. Imaging in the near-infrared (NIR) window (650-900 nm), also known as the "therapeutic window" has high potential by offering low absorbance and scattering in tissues resulting in minimized background autofluorescence. Clinically, optical fluorescence imaging with the targeted contrast agents provides opportunities for significant advances in intraoperative image-guided surgery. There are only two clinically available NIR fluorophores, indocyanine green (ICG) and methylene blue (MB), that support the image-guided surgery. However, neither of them perform in vivo by providing optimum specificity and stability for targeted image guidance. Therefore, it is of paramount importance to develop targeted NIR fluorophores for unmet clinical needs. Using the right combination of an NIR fluorescence imaging system and a targeted fluorophore, the desired target tissues can be imaged to provide real-time fluorescence guidance without changing the field-of-view during surgery. Thus, in a clinical discipline, the development of NIR fluorophores for 'structure-inherent targeting' is an unmet need for early phase diagnostics with accurate targeting.

  17. Photoinduced electron transfer between anionic fluorophores and methyl viologen in homogeneous and microheterogeneous media

    Energy Technology Data Exchange (ETDEWEB)

    Burai, Tarak Nath; Panda, Debashis; Iyer, E Siva Subramaniam [Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076 (India); Datta, Anindya, E-mail: anindya@chem.iitb.ac.in [Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076 (India)

    2012-11-15

    The rate and extent of photoinduced electron transfer change significantly as a result of confinement in nanovolumes. Study of such processes is an active area of research in physical chemistry. The effect is most interesting when the molecules that participate in PET are charged. In the present article, the modulation of PET has been studied for two anionic fluorophores: Lucifer Yellow CH and chlorin p{sub 6} with Methylviologen dication. PET, manifested in the quenching of fluorescence of the fluorophores, has been modulated by incorporating the molecules in organized assemblies like micelles, reverse micelles and supramolecular hosts. The dynamics of the process has been monitored in the femtosecond to nanosecond timescale. The modulation of the electron transfer has been found to be occurring mainly due to the disruption of contact ion pairs formed between the fluorophores and the quencher. - Highlights: Black-Right-Pointing-Pointer Modulation of PET of biologically active fluorophores and Methyl viologen. Black-Right-Pointing-Pointer Static and Dynamic Quenching present. Black-Right-Pointing-Pointer PET enhanced upon encapsulation, studied through Fluorescence upconversion experiments. Black-Right-Pointing-Pointer Rotational anisotropy has significant contribution in quenching.

  18. Photoinduced electron transfer between anionic fluorophores and methyl viologen in homogeneous and microheterogeneous media

    International Nuclear Information System (INIS)

    Burai, Tarak Nath; Panda, Debashis; Iyer, E Siva Subramaniam; Datta, Anindya

    2012-01-01

    The rate and extent of photoinduced electron transfer change significantly as a result of confinement in nanovolumes. Study of such processes is an active area of research in physical chemistry. The effect is most interesting when the molecules that participate in PET are charged. In the present article, the modulation of PET has been studied for two anionic fluorophores: Lucifer Yellow CH and chlorin p 6 with Methylviologen dication. PET, manifested in the quenching of fluorescence of the fluorophores, has been modulated by incorporating the molecules in organized assemblies like micelles, reverse micelles and supramolecular hosts. The dynamics of the process has been monitored in the femtosecond to nanosecond timescale. The modulation of the electron transfer has been found to be occurring mainly due to the disruption of contact ion pairs formed between the fluorophores and the quencher. - Highlights: ► Modulation of PET of biologically active fluorophores and Methyl viologen. ► Static and Dynamic Quenching present. ► PET enhanced upon encapsulation, studied through Fluorescence upconversion experiments. ► Rotational anisotropy has significant contribution in quenching.

  19. Photoactivatable Drug-Caged Fluorophore Conjugate Allows Direct Quantification of Intracellular Drug Transport

    Science.gov (United States)

    Kohler, Rainer H.; Weissleder, Ralph

    2013-01-01

    We report here a method that utilizes photoactivatable drug-caged fluorophore conjugate to quantify intracellular drug trafficking processes at single cell resolution. Photoactivation is performed in labeled cellular compartments to visualize intracellular drug exchange at physiologic conditions, without the need for washing, facilitating its translation to in vivo cancer models. PMID:24135896

  20. Chemistry of polycyclic aromatic hydrocarbons formation from phenyl radical pyrolysis and reaction of phenyl and acetylene.

    Science.gov (United States)

    Comandini, A; Malewicki, T; Brezinsky, K

    2012-03-15

    An experimental investigation of phenyl radical pyrolysis and the phenyl radical + acetylene reaction has been performed to clarify the role of different reaction mechanisms involved in the formation and growth of polycyclic aromatic hydrocarbons (PAHs) serving as precursors for soot formation. Experiments were conducted using GC/GC-MS diagnostics coupled to the high-pressure single-pulse shock tube present at the University of Illinois at Chicago. For the first time, comprehensive speciation of the major stable products, including small hydrocarbons and large PAH intermediates, was obtained over a wide range of pressures (25-60 atm) and temperatures (900-1800 K) which encompass the typical conditions in modern combustion devices. The experimental results were used to validate a comprehensive chemical kinetic model which provides relevant information on the chemistry associated with the formation of PAH compounds. In particular, the modeling results indicate that the o-benzyne chemistry is a key factor in the formation of multi-ring intermediates in phenyl radical pyrolysis. On the other hand, the PAHs from the phenyl + acetylene reaction are formed mainly through recombination between single-ring aromatics and through the hydrogen abstraction/acetylene addition mechanism. Polymerization is the common dominant process at high temperature conditions.

  1. The lowest excited singlet state of isolated 1-phenyl-butadiene and 1-phenyl-hexatriene

    NARCIS (Netherlands)

    Kohler, B.E.; Shaler, T.A.; Buma, W.J.; Song, K.; Nuss, J.M.

    1992-01-01

    We report vibrationally resolved S0S1 excitation spectra and vibronic level decay times for the phenyl-substituted polyenes 1-phenylbutadiene and 1-phenylhexatriene seeded in supersonic He expansions. This information was obtained using one- and two-color resonance-enhanced multiphoton ionization

  2. beta-Chloro-L-alanine inhibition of the Escherichia coli alanine-valine transaminase.

    OpenAIRE

    Whalen, W A; Wang, M D; Berg, C M

    1985-01-01

    beta-Chloro-L-alanine, an amino acid analog which inhibits a number of enzymes, reversibly inhibited the Escherichia coli K-12 alanine-valine transaminase, transaminase C. This inhibition, along with the inhibition of transaminase B, accounted for the isoleucine-plus-valine requirement of E. coli in the presence of beta-chloro-L-alanine.

  3. 40 CFR 721.3560 - Derivative of tetra-chloro-ethy-lene.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Derivative of tetra-chloro-ethy-lene... Substances § 721.3560 Derivative of tetra-chloro-ethy-lene. (a) Chemical substance and significant new uses... described in paragraph (a)(2) of this section: Derivative of tetrachloroethylene, P-82-684. (2) The...

  4. A new class of efficient 4-[(nitro substituted-phenyl ...

    Indian Academy of Sciences (India)

    A new class of efficient colorimetric chemosensors derived from 4-[(nitro substituted-phenyl)-hydrazonomethyl]-1-phenyl-1H-pyrazole-3-carboxylate have been synthesized and characterized. The synthesized receptors exhibit instant color change from yellow to dark purple along with significant bathochromicshifts when ...

  5. Proton Induced Modulation of ICT and PET Processes in an Imidazo-phenanthroline Based BODIPY Fluorophores.

    Science.gov (United States)

    Thakare, Shrikant S; Chakraborty, Goutam; Kothavale, Shantaram; Mula, Soumyaditya; Ray, Alok K; Sekar, Nagaiyan

    2017-11-01

    BODIPY fluorophores linked with an imidazo-phenanthroline donor at α and β positions have been synthesized. Intriguing intramolecular charge transfer phenomenon is observed in both the dyes which has been extensively investigated using UV-vis absorption, steady-state and time-resolved fluorescence measurements. H-bonding and intrinsic polarity of the solvents has modulated the absorption and emission bands of these fluorophores strongly causing significant increase in the Stokes shifts. In spite of having difference only in terms of the position of donor subunit, the photophysics of these dyes are not only significantly different from each other, but contradictory too. Interestingly, acidochromic studies revealed the shuttling mechanism between ICT and PET processes for BDP 2. Quantum chemical calculations have been employed further to support experimental findings. DFT and TD-DFT method of analysis have been used to optimize ground and excited state geometries of the synthesized dyes.

  6. Photo-physical characterization of fluorophore Ru(bpy32+ for optical biosensing applications

    Directory of Open Access Journals (Sweden)

    E.L. Sciuto

    2015-12-01

    Full Text Available We studied absorption, emission and lifetime of the coordination compound tris(2,2′-bipyridylruthenium(II fluorophore (Ru(bpy32+ both dissolved in water solutions and dried. Lifetime measurements were carried out using a new detector, the Silicon Photomultiplier (SiPM, which is more sensitive and physically much smaller than conventional optical detectors, such as imager and scanner. Through these analyses and a morphological characterization with transmission electron microscopy, revealed its usability for sensor applications, in particular, as dye in optical DNA-chip technology, a viable alternative to the conventional CY5 fluorophore. The use of Ru(bpy32+ would solve some of the typical disadvantages related to Cy5’s application, such as self-absorption of fluorescence and photobleaching. In addition, the Ru(bpy32+ longer lifetime may play a key role in the definition of new optical DNA-chip.

  7. Investigation of porous silicon nanopowders functionalized by antibiotic Kanamycin, fluorophore Indocyanine Green

    Science.gov (United States)

    Bespalova, K.; Somov, P. A.; Spivak, Yu M.

    2017-11-01

    Porous silicon nanopowders for target drug delivery were obtained by electrochemical anodic etching in a hydrofluoric acid solution using the monocrystalline silicon n-type conductivity. Porous silicon powders were obtained by sonification of porous silicon layers. The powders were functionalized by antibiotic Kanamycin and fluorophore Indocyanine Green by the passive adsorption method. The peculiarities of absorption spectra in 190-600 nm region were revealed for functionalized porous silicon powders dispersions in water.

  8. Graphene oxide from silk cocoon: a novel magnetic fluorophore for multi-photon imaging

    OpenAIRE

    Roy, Manas; Kusurkar, Tejas Sanjeev; Maurya, Sandeep Kumar; Meena, Sunil Kumar; Singh, Sushil Kumar; Sethy, Niroj; Bhargava, Kalpana; Sharma, Raj Kishore; Goswami, Debabrata; Sarkar, Sabyasachi; Das, Mainak

    2013-01-01

    In this work, we synthesized graphene oxide from silk cocoon embarking its new dimension as a magnetic fluorophore when compared with its present technical status, which at best is for extracting silk as a biomaterial for tissue engineering applications. We produced graphene oxide by pyrolysing the silk cocoon in an inert atmosphere. The collected raw carbon is oxidized by nitric acid that readily produces multilayer graphene oxide with nano carbon particulates. Structural properties of the g...

  9. Single-step generation of fluorophore-encapsulated gold nanoparticle core-shell materials

    International Nuclear Information System (INIS)

    Sardar, R; Shem, P M; Pecchia-Bekkum, C; Bjorge, N S; Shumaker-Parry, J S

    2010-01-01

    We report a simple route to produce fluorophore-encapsulated gold nanoparticles (AuNPs) in a single step under aqueous conditions using the fluorophore 1-pyrenemethylamine (PMA). Different amounts of PMA were used and the resulting core-shell gold nanoparticles were analyzed using UV-visible absorption spectroscopy, fluorescence spectroscopy, and transmission and scanning electron microscopy. Electron microscopy analysis shows nanoparticles consisting of a gold nanoparticle core which is encapsulated with a lower contrast shell. In the UV-visible spectra, we observed a significant red shift (37 nm) of the localized surface plasmon resonance (LSPR) absorption maximum (λ max ) compared to citrate-stabilized AuNPs of a similar size. We attribute the prominent LSPR wavelength shift for PMA-AuNP conjugates to the increase in the local dielectric environment near the gold nanoparticles due to the shell formation. This simple, aqueous-based synthesis is a new approach to the production of fluorophore-encapsulated AuNPs that could be applicable in biological sensing systems and photonic device fabrication.

  10. The use of nanocrystal quantum dot as fluorophore reporters in molecular beacon-based assays

    Science.gov (United States)

    Adegoke, Oluwasesan; Park, Enoch Y.

    2016-12-01

    The utilization of molecular beacon (MB) biosensor probes to detect nucleic acid targets has received enormous interest within the scientific community. This interest has been stimulated by the operational qualities of MB-based probes with respect to their unique sensitivity and specificity. The design of MB biosensors entails not only optimizing the sequence of the loop to hybridize with the nucleic acid target or optimization of the length of the stem to tune the sensitivity but also the selection of the appropriate fluorophore reporter to generate the signal transduction read-out upon hybridization of the probe with the target sequence. Traditional organic fluorescent dyes are mostly used for signal reporting in MB assays but their optical properties in comparison to semiconductor fluorescent quantum dot (Qdot) nanocrystals are at a disadvantage. This review highlights the progress made in exploiting Qdot as fluorophore reporters in MB-based assays with the aim of instigating further development in the field of Qdot-MB technology. The development reported to date indicates that unparalleled fluorescence signal reporting in MB-based assays can be achieved using well-constructed Qdot fluorophores.

  11. Circumvention of fluorophore photobleaching in fluorescence fluctuation experiments: a beam scanning approach.

    Science.gov (United States)

    Satsoura, Dmitri; Leber, Brian; Andrews, David W; Fradin, Cécile

    2007-04-23

    Photobleaching is a fluorophore-damaging process that commonly afflicts single-molecule fluorescence studies. It becomes an especially severe problem in fluorescence fluctuation experiments when studying slowly diffusing particles. One way to circumvent this problem is to use beam scanning to decrease the residence time of the fluorophores in the excitation volume. We report a systematic study of the effects of circular beam scanning on the photobleaching of fluorescent particles as observed in single-photon excitation fluorescence fluctuation experiments. We start by deriving a simple expression relating the average detected fluorescence to the photobleaching cross section of the fluorophores. We then perform numerical calculations of the spatial distribution of fluorescent particles in order to understand under which conditions beam scanning can prevent the formation of a photobleaching hole. To support these predictions, we show experimental results obtained for large unilamellar vesicles containing a small amount of the fluorescent lipophilic tracer DiD. We establish the required scanning radius and frequency range in order to obtain sufficient reduction of the photobleaching effect for that system. From the detected increase in fluorescence upon increase in scanning speed, we estimate the photobleaching cross section of DiD.

  12. Molecular Counting with Localization Microscopy: A Bayesian Estimate Based on Fluorophore Statistics.

    Science.gov (United States)

    Nino, Daniel; Rafiei, Nafiseh; Wang, Yong; Zilman, Anton; Milstein, Joshua N

    2017-05-09

    Superresolved localization microscopy has the potential to serve as an accurate, single-cell technique for counting the abundance of intracellular molecules. However, the stochastic blinking of single fluorophores can introduce large uncertainties into the final count. Here we provide a theoretical foundation for applying superresolved localization microscopy to the problem of molecular counting based on the distribution of blinking events from a single fluorophore. We also show that by redundantly tagging single molecules with multiple, blinking fluorophores, the accuracy of the technique can be enhanced by harnessing the central limit theorem. The coefficient of variation then, for the number of molecules M estimated from a given number of blinks B, scales like ∼1/N l , where N l is the mean number of labels on a target. As an example, we apply our theory to the challenging problem of quantifying the cell-to-cell variability of plasmid copy number in bacteria. Copyright © 2017 Biophysical Society. Published by Elsevier Inc. All rights reserved.

  13. The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy)-N-phenylbenzamide derivatives

    OpenAIRE

    IOANA M. C. IENAŞCU; ALFA X. LUPEA; IULIANA M. POPESCU; MIRABELA A. PĂDURE; ALINA D. ZAMFIR

    2009-01-01

    To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzamide structure was performed. The ethyl esters 4–6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzamide and chloro-substituted acid ethyl esters 1–3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7–8. The hydrazones 11–14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9–10. All t...

  14. The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy-N-phenylbenzamide derivatives

    Directory of Open Access Journals (Sweden)

    IOANA M. C. IENAŞCU

    2009-08-01

    Full Text Available To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzamide structure was performed. The ethyl esters 4–6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzamide and chloro-substituted acid ethyl esters 1–3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7–8. The hydrazones 11–14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9–10. All the newly synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, MS and elemental analyses.

  15. A general synthetic strategy for the design of new BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents.

    Science.gov (United States)

    Schmidt, Elena Yu; Zorina, Nadezhda V; Dvorko, Marina Yu; Protsuk, Nadezhda I; Belyaeva, Kseniya V; Clavier, Gilles; Méallet-Renault, Rachel; Vu, Thanh T; Mikhaleva, Al'bina I; Trofimov, Boris A

    2011-03-07

    BODIPYrrole: A general strategy for the design of novel BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents has been developed. The strategy involves the acylation of the condensed substituent and treatment of the acylated derivative (as oxime) with acetylene in MOH/DMSO (M = alkali metal) to give pyrroles that were then used for assembly of the BODIPY fluorophores (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Doping chloro boron subnaphthalocyanines and chloro boron subphthalocyanine in simple OLED architectures yields warm white incandescent-like emissions

    Science.gov (United States)

    Plint, Trevor G.; Lessard, Benoît H.; Bender, Timothy P.

    2018-01-01

    We have incorporated chloro boron subphthalocyanine (Cl-BsubPc) and chloro boron subnapthalocyanines (Cl-ClnBsubNcs) into organic light emitting diodes (OLEDs) that enabled an overall warm white emission with CIE coordinates close to that of a 60 W incandescent lightbulb. More specifically, we have shown that Cl-BsubPc and Cl-ClnBsubNcs can be used as dopant emitters in a simple host-dopant architecture, and we have compared the use of NPB and Alq3 as potential hosts for these materials. When doped into Alq3, Cl-BsubPc shows a strong orange emission, and Cl-ClnBsubNcs shows a moderately strong red emission. We have further demonstrated that Cl-BsubPc and Cl-ClnBsubNcs can be co-doped into the same layer giving combined orange and red emission peaks. A "cascade" energy transfer mechanism of sequential absorption and re-emission is proposed. Device performance characteristics such as luminance, current efficiency, photoluminescence efficiency, and external quantum efficiency are tabulated. Additionally, in view of ongoing research into white emitting OLEDs for indoor lighting purposes, the Colour Rendering Index (CRI), R9 values, and CIE co-ordinates for these devices are also discussed. We conclude from this study that the BsubNc chromophore has potential application as a red dopant in OLEDs including for indoor lighting. Additionally, given the scope for axial and peripheral derivatization of the BsubNc motif, we believe that this chromophore has many unexplored molecular design handles that will affect its ultimate performance and application in OLEDs and other opto-electronic devices.

  17. 5-Chloro-2-(2'-((dimethylamino)methyl)-4'-iodophenylthio)benzenamine: a new serotonin transporter ligand

    International Nuclear Information System (INIS)

    Oya, Shunichi; Choi, Seok-Rye; Kung, Mei-Ping; Kung, Hank F.

    2007-01-01

    Two novel ligands with 4' substitution on the Phenyl Ring B of biphenylthiol, 5-chloro-2-(2'-((dimethylamino)methyl)-4'-iodophenylthio)benzenamine (7) and 2-(2'-((dimethylamino)methyl)-4'-methoxyphenylthio)-5-iodobenzenamine (8), were prepared and tested as potential serotonin transporter (SERT) imaging agents. The new ligands displayed extremely high binding affinities to SERT (K i =0.22±0.09 and 0.11±0.04 nM, respectively), with very low binding affinities to dopamine and norepinephrine transporters (K i >1000 nM). The corresponding [ 125 I]7 and [ 125 I]8 were successfully prepared from tri-n-butyltin derivatives. They showed good brain uptakes and prolonged retention after intravenous injection in rats (brain uptake was 1.77% and 0.98% dose/g for [ 125 I]7, and 0.92% and 0.29% dose/g for [ 125 I]8, at 2 and 120 min, respectively). Significantly, [ 125 I]7 showed excellent uptake and prolonged retention in the hypothalamus, where SERT concentration was highest. The hypothalamus/cerebellum (HY/CB) ratios (target/background ratios) were 4.24, 7.10, 8.24 and 12.6 at 2, 4, 6 and 12 h, respectively. The HY/CB ratios for [ 125 I]8 were 3.97, 5.57 and 5.06 at 1, 2 and 4 h, respectively. Adding the 4'-iodo group to the Phenyl Ring B of Compound (7) appeared to reduce the rate of clearance from the brain, and kinetics favored uptake and retention in the hypothalamus. The localization of [ 125 I]7 in the hypothalamus region in the rat brain could be blocked by pretreatment with (+)McN5652, escitalopram and ADAM (2), which are all selective SERT ligands (at 2 mg/kg iv, 5 min pretreatment). Ex vivo autoradiograms of rat brain sections (at 4 h after intravenous injection of [ 125 I]7) showed intense labeling in regions of the brain known to have high SERT density. The excellent selective uptake and retention in the hypothalamus region suggest that [ 123 I]7 is a potential lead compound for developing new imaging agents targeting SERT-binding sites with single

  18. 5-Chloro-2-(2'-((dimethylamino)methyl)-4'-iodophenylthio)benzenamine: a new serotonin transporter ligand

    Energy Technology Data Exchange (ETDEWEB)

    Oya, Shunichi [Department of Radiology, University of Pennsylvania, Philadelphia, PA 19104 (United States); Choi, Seok-Rye [Department of Radiology, University of Pennsylvania, Philadelphia, PA 19104 (United States); Kung, Mei-Ping [Department of Radiology, University of Pennsylvania, Philadelphia, PA 19104 (United States); Kung, Hank F. [Department of Radiology, University of Pennsylvania, Philadelphia, PA 19104 (United States); Department of Pharmacology, University of Pennsylvania, Philadelphia, PA 19104 (United States)

    2007-02-15

    Two novel ligands with 4' substitution on the Phenyl Ring B of biphenylthiol, 5-chloro-2-(2'-((dimethylamino)methyl)-4'-iodophenylthio)benzenamine (7) and 2-(2'-((dimethylamino)methyl)-4'-methoxyphenylthio)-5-iodobenzenamine (8), were prepared and tested as potential serotonin transporter (SERT) imaging agents. The new ligands displayed extremely high binding affinities to SERT (K {sub i}=0.22{+-}0.09 and 0.11{+-}0.04 nM, respectively), with very low binding affinities to dopamine and norepinephrine transporters (K {sub i}>1000 nM). The corresponding [{sup 125}I]7 and [{sup 125}I]8 were successfully prepared from tri-n-butyltin derivatives. They showed good brain uptakes and prolonged retention after intravenous injection in rats (brain uptake was 1.77% and 0.98% dose/g for [{sup 125}I]7, and 0.92% and 0.29% dose/g for [{sup 125}I]8, at 2 and 120 min, respectively). Significantly, [{sup 125}I]7 showed excellent uptake and prolonged retention in the hypothalamus, where SERT concentration was highest. The hypothalamus/cerebellum (HY/CB) ratios (target/background ratios) were 4.24, 7.10, 8.24 and 12.6 at 2, 4, 6 and 12 h, respectively. The HY/CB ratios for [{sup 125}I]8 were 3.97, 5.57 and 5.06 at 1, 2 and 4 h, respectively. Adding the 4'-iodo group to the Phenyl Ring B of Compound (7) appeared to reduce the rate of clearance from the brain, and kinetics favored uptake and retention in the hypothalamus. The localization of [{sup 125}I]7 in the hypothalamus region in the rat brain could be blocked by pretreatment with (+)McN5652, escitalopram and ADAM (2), which are all selective SERT ligands (at 2 mg/kg iv, 5 min pretreatment). Ex vivo autoradiograms of rat brain sections (at 4 h after intravenous injection of [{sup 125}I]7) showed intense labeling in regions of the brain known to have high SERT density. The excellent selective uptake and retention in the hypothalamus region suggest that [{sup 123}I]7 is a potential lead compound for

  19. CCDC 940297: Experimental Crystal Structure Determination : (mu~2~-Chloro)-(mu~2~-2-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-2-phenyl-1-(phenyl(phenylethynyl)phosphanyl)ethenyl)-chloro-(2-(1-(dimethylamino)ethyl)phenyl)-palladium-platinum dichloromethane solvate

    KAUST Repository

    Chen, Shuli

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  20. CCDC 940298: Experimental Crystal Structure Determination : (mu~2~-Chloro)-(mu~2~-2-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-2-phenyl-1-(phenyl(phenylethynyl)phosphanyl)ethenyl)-chloro-(2-(1-(dimethylamino)ethyl)phenyl)-palladium-platinum acetone solvate

    KAUST Repository

    Chen, Shuli

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  1. The zeolite mediated isomerization of allyl phenyl ether

    Science.gov (United States)

    Pebriana, R.; Mujahidin, D.; Syah, Y. M.

    2017-04-01

    Allyl phenyl ether is an important starting material in organic synthesis that has several applications in agrochemical industry. The green transformation of allyl phenyl ether assisted by heterogeneous catalyst is an attractive topic for an industrial process. In this report, we investigated the isomerization of allyl phenyl ether by heating it in zeolite H-ZSM-5 and Na-ZSM-5. The conversion of allyl phenyl ether (neat) in H-ZSM-5 was 67% which produced 40% of 2-allylphenol, 17% of 2-methyldihydrobenzofuran, and other product (4:1.7:1), while in Na-ZSM-5 produced exclusively 2-allylphenol with 52% conversion. These results showed that zeolite properties can be tuned to give a selective transformation by substitution of metal ion into the zeolite interior.

  2. 1-{6-Chloro-2-[(2-chloro-8-methyl-3-quinolylmethoxy]-4-phenylquinolin-3-yl}ethanone

    Directory of Open Access Journals (Sweden)

    F. Nawaz Khan

    2010-08-01

    Full Text Available In the title molecule, C28H20Cl2N2O2, the dihedral angle between the 2-chloroquinoline and 6-chloroquinoline rings is 7.55 (6°. The dihedral angle between the phenyl ring and its attached quinoline ring is 62.59 (4°. In the crystal, aromatic π–π stacking interactions [centroid–centroid distances = 3.771 (3 and 3.612 (3 Å] help to establish the packing.

  3. Confirmation of vinyl chloride in foods by conversion to 1-chloro-1,2-dibromoethane.

    Science.gov (United States)

    Williams, D T

    1976-01-01

    A semiquantitative method has been developed for the confirmation of vinyl chloride (VC) in foodstuffs. The VC was brominated to give 1-chloro-1,2-dibromoethane which was analyzed by gas-liquid chromatography, using an electron capture detector. The yield of 1-chloro-1,2-dibromoethane varied between 40 and 55%, which permitted a lower limit of confirmation of VC of 15 ppb for vinegar and sherry and 50 ppb for peanut oil.

  4. N-(3-Chloro-2-methylphenyl-4-(4-fluorophenyl-1,3-thiazol-2-amine

    Directory of Open Access Journals (Sweden)

    Nadine Uwabagira

    2018-01-01

    Full Text Available The two precursors 3-chloro-2-methylphenylthiourea 2 and 4-fluorophenacyl bromide 4 are reacted under Hantzsch thiazole synthesis condition to yield the new compound N-(3-chloro-2-methylphenyl-4-(4-fluorophenyl-1,3-thiazol-2-amine 5. The IR, 1H-NMR, 13C-NMR and mass spectral data are presented, along with its in vitro antibacterial activity against Staphylococcus aureus and Chromobacterium violaceum.

  5. Reversible addition-fragmentation chain transfer polymerization of 2-chloro-1,3-butadiene

    OpenAIRE

    Pullan, Nikki; Liu, Max; Topham, Paul D.

    2013-01-01

    Controlled polymerization of 2-chloro-1,3-butadiene using reversible addition–fragmentation chain transfer (RAFT) polymerization has been demonstrated for the first time. 2-Chloro-1,3-butadiene, more commonly known as chloroprene, has significant industrial relevance as a crosslinked rubber, with uses ranging from adhesives to integral automotive components. However, problems surrounding the inherent toxicity of the lifecycle of the thiourea-vulcanized rubber have led to the need for control ...

  6. Syntheses and Antibacterial Studies of Some 1-Phenyl-3-(4-(2-ethanoloxy phenyl-5-aryl-1H-pyrazoles

    Directory of Open Access Journals (Sweden)

    Anju Goyal

    2013-01-01

    Full Text Available A series of 1-phenyl-3-(4-(2-ethanoloxy phenyl-5-aryl-1H-pyrazoles were synthesized from chalcones, that is, 3-aryl-1-(4-hydroxyphenyl prop-2-en-1-ones and studied for their in vitro antibacterial activity. Chalcones 1 on reaction with phenyl hydrazine in the presence of acetic acid and few drops of hydrochloric acid yielded the corresponding 1-phenyl-3-(4-hydroxyphenyl-5-aryl-1H-pyrazoles 2 which on further reaction with 2-chloroethanol furnished the title compounds 3. These compounds were characterized by CHN analyses, IR, mass and 1H NMR spectral data. All the compounds were evaluated for their in vitro antibacterial activity against two Gram positive strains (Bacillus subtilis and Staphylococcus aureus and two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa, and their minimum inhibitory concentration (MIC was determined.

  7. Tetra­butyl­ammonium hydrogen phenyl­arsonate–phenyl­arsonic acid (1/1)

    Science.gov (United States)

    Reck, Lukas; Schmitt, Wolfgang

    2012-01-01

    The structure of the title salt adduct, (C4H9)4N+·C6H5AsO3H−·C6H5AsO3H2, features chains along the a axis comprising alternating hydrogen phenyl­arsonate anions and phenyl­arsonic acid mol­ecules linked by O—H⋯O hydrogen bonds. PMID:22969495

  8. Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C-H Bond Activation.

    Science.gov (United States)

    Hu, Jundie; Guan, Mingyu; Han, Jian; Huang, Zhi-Bin; Shi, Da-Qing; Zhao, Yingsheng

    2015-08-21

    A highly regioselective palladium-catalyzed ester-directed ortho-olefination of phenyl acetic and propionic esters with olefins via C-H bond activation has been developed. A wide variety of phenyl acetic and propionic esters were tolerated in this transformation, affording the corresponding olefinated aromatic compounds. The ortho-olefination of heterocyclic acetic and propionic esters also took place smoothly giving the products in good yields, thus proving the potential utility of this protocol in synthetic chemistry.

  9. Fluorophore-tagged pharmacophores for antitumor cytotoxicity: Modified chiral lipidic dialkynylcarbinols for cell imaging.

    Science.gov (United States)

    Listunov, Dymytrii; Mazères, Serge; Volovenko, Yulian; Joly, Etienne; Génisson, Yves; Maraval, Valérie; Chauvin, Remi

    2015-10-15

    Chiral lipidic dialkynylcarbinols (DACs), recently highlighted as antitumoral pharmacophores, have been conjugated to difluoroboron-dipyrromethene (bodipy), 7-hydroxy-coumarine, and 7-nitro-benzoxadiazole (NBD) fluorophore motifs through triazole clips. The labeled lipids preserve cytotoxic activity against HCT116 cells, and fluorescence microscopy of the stained cells showed clear signals in the intra-cellular membrane system. While the bodipy conjugate also labels lipid droplets very brightly, as expected, the coumarine and NBD probes appear as promising specific tools for the identification of the intra-cellular targets of DACs' cytotoxicity. Copyright © 2015 Elsevier Ltd. All rights reserved.

  10. Spectrofluorometric Determination of Putrescine Using Orthophthaldehyde as a Fluorophore: A Novel Method.

    Science.gov (United States)

    Oyelakin, Oladele; Traoré, Moumouny; Mbaye, El Hadji Babacar; Konté, Abdourahmane; Cissé, Lamine; Faye, Abdoulaye N; Faye, Ousman; Mbaye, Moussa; Kital, Khemesse; Seye, Gaye; Coly, Atanasse; Tine, Alphonse; Delattre, François

    2016-01-01

    This paper concerns spectrofluorometric analysis of putrescine using orthophthaladehyde as a fluorophore in aqueous alkaline medium. Wavelengths of excitation and emission in acid, neutral, and alkaline media were different. There is a maximum intensity of fluorescence in alkaline medium 24 h after complexation compared with other media. Putrescine and orthophthaladehyde are used at an equimolar ratio, and the product is kinetically stable in alkaline medium. Calibration curves obtained gave limits of detection and quantification of 39 and 65 ng/mL, respectively. The correlation coefficient obtained in alkaline medium was 0.992 at pH 12. Results obtained largely showed a good reproducibility of our method.

  11. Dye doped Eosin yellowish silica nanoparticles as novel fluorophore for a peroxyoxalate chemiluminescence system.

    Science.gov (United States)

    Yari, Abdollah; Saidikhah, Marzieh

    2012-05-01

    In this work, we report the preparation and characterization of novel dye doped fluorophore Eosin yellowish silica nanoparticles (ESNPs). We synthesized ESNPs by the Stöber method via encapsulation of Eosin Yellowish in silica particles by the condensation of tetraethyl orthosilicate under alkaline condition at room temperature. The resulted ESNPs were characterized by transmission electron microscopy, atomic force microscopy; UV-Visible, fluorescence and Fourier transform infrared spectroscopy. The sizes of the nanoparticles have been found to be 300.0 (±1.0), 400.0 (±1.1) and 500.0 (±5.2) nm depending the reaction conditions under which they were synthesized. Furthermore, because of intense light emission, the ESNPs were used as fluorophore in a peroxyoxalate chemiluminescence system. The effect of solvent and concentrations of necessary reagents, bis(2,4,6-trichlorophenyl)oxalate, sodium salicylate, hydrogen peroxide and the effects of size of the ESNP and temperature on the luminescence efficiency of the system were examined. The activation kinetic parameters of the system were also evaluated from the temperature investigation.

  12. Characterization of fluorescent-dissolved organic matter and identification of specific fluorophores in textile effluents.

    Science.gov (United States)

    Li, Wentao; Xu, Zixiao; Wu, Qian; Li, Yan; Shuang, Chendong; Li, Aimin

    2015-03-01

    This study focused on the characterization of fluorescent-dissolved organic matter and identification of specific fluorophores in textile effluents. Samples from different textile wastewater treatment plants were characterized by high-performance liquid chromatography and size exclusion chromatography as well as fluorescence excitation-emission matrix spectra. Despite the highly heterogeneous textile effluents, the fluorescent components and their physicochemical properties were found relatively invariable, which is beneficial for the combination of biological and physicochemical treatment processes. The humic-like substance with triple-excitation peaks (excitation (Ex) 250, 310, 365/emission (Em) 460 nm) presented as the specific fluorescence indicator in textile effluents. It was also the major contributor to UV absorbance at 254 nm and resulted in the brown color of biologically treated textile effluents. By spectral comparison, the specific fluorophore in textile effluents could be attributed to the intermediate structure of azo dyes 1-amino-2-naphthol, which was transferred into the special humic-like substances during biological treatment.

  13. Multiple fluorophore-analysis (MFA) for qualitative tissue diagnosis in the oral cavity

    Science.gov (United States)

    Pauli, Romana; Betz, Christian; Havel, Miriam; Sroka, Ronald; Stepp, Herbert; Leunig, Andreas; Assmann, Walter

    2007-07-01

    Early diagnosis of head and neck tumors is usually achieved via surgical tissue biopsy. By measuring the specific autofluorescence of endogenous fluorophores with tumor-specific distributions, it might be possible to non-invasively judge tissue dignities ("optical biopsy"). A total of 22 patients with suspicious lesions of the oral cavity and 7 healthy volunteers were included into the study. Using a mercury vapour lamp as a light source, excitation and detection of endogenous fluorophores (tryptophan, NADH, FAD) was achieved using corresponding filter sets in an automated system. By including simultaneously recorded remission spectra into the analysis, it was possible to calculate "intrinsic" fluorescence spectra. Subsequently, the histopathological results of the lesions were compared to the spectroscopic findings. In a quantitative analysis, the intrinsic fluorescence spectra from (pre)malignant mucosal lesions regularly differed in fluorescence intensities when compared to healthy tissue. Whereas NADH and FAD yielded tumor specific intensity profiles with statistically significant differences in Student's t-test (p<=0.05), no definite spectral differences were found for tryptophan (p=0.22). The mucosa of the healthy volunteers showed a similar spectral pattern as the non-cancerous control areas in tumor patients. With regards to the results in this pilot study, MFA might serve as a helpful tool in early diagnosis of malignant lesions of head and neck.

  14. Graphene oxide from silk cocoon: a novel magnetic fluorophore for multi-photon imaging.

    Science.gov (United States)

    Roy, Manas; Kusurkar, Tejas Sanjeev; Maurya, Sandeep Kumar; Meena, Sunil Kumar; Singh, Sushil Kumar; Sethy, Niroj; Bhargava, Kalpana; Sharma, Raj Kishore; Goswami, Debabrata; Sarkar, Sabyasachi; Das, Mainak

    2014-02-01

    In this work, we synthesized graphene oxide from silk cocoon embarking its new dimension as a magnetic fluorophore when compared with its present technical status, which at best is for extracting silk as a biomaterial for tissue engineering applications. We produced graphene oxide by pyrolysing the silk cocoon in an inert atmosphere. The collected raw carbon is oxidized by nitric acid that readily produces multilayer graphene oxide with nano carbon particulates. Structural properties of the graphene oxide were analyzed using scanning electron microscopy, transmission electron microscopy, Fourier transform infra-red spectroscopy, and Raman spectroscopy. The oxidized sample shows remarkable fluorescence, multi-photon imaging and magnetic properties. On increasing the excitation wavelength, the fluorescence emission intensity of the graphene oxide also increases and found maximum emission at 380 nm excitation wavelength. On studying the two photon absorption (TPA) property of aqueous graphene oxide using Z-scan technique, we found significant TPA activity at near infrared wavelength. In addition, the graphene oxide shows ferromagnetic behavior at room temperature. The observed fluorescence and magnetic property were attributed to the defects caused in the graphene oxide structure by introducing oxygen containing hydrophilic groups during the oxidation process. Previously silk cocoon has been used extensively in deriving silk-based tissue engineering materials and as gas filter. Here we show a novel application of silk cocoon by synthesizing graphene oxide based magnetic-fluorophore for bio-imaging applications.

  15. Quantification of hyaluronan (HA) using a simplified fluorophore-assisted carbohydrate electrophoresis (FACE) procedure.

    Science.gov (United States)

    Midura, Ronald J; Cali, Valbona; Lauer, Mark E; Calabro, Anthony; Hascall, Vincent C

    2018-01-01

    Hyaluronan (HA) exhibits numerous important roles in physiology and pathologies, and these facts necessitate an ability to accurately and reproducibly measure its quantities in tissues and cell cultures. Our group previously reported a rigorous and analytical procedure to quantify HA (and chondroitin sulfate, CS) using a reductive amination chemistry and separation of the fluorophore-conjugated, unsaturated disaccharides unique to HA and CS on high concentration acrylamide gels. This procedure is known as fluorophore-assisted carbohydrate electrophoresis (FACE) and has been adapted for the detection and quantification of all glycosaminoglycan types. While this previous FACE procedure is relatively straightforward to implement by carbohydrate research investigators, many nonglycoscience laboratories now studying HA biology might have difficulties establishing this prior FACE procedure as a routine assay for HA. To address this need, we have greatly simplified our prior FACE procedure for accurate and reproducible assessment of HA in tissues and cell cultures. This chapter describes in detail this simplified FACE procedure and, because it uses an enzyme that degrades both HA and CS, investigators will also gain additional insight into the quantities of CS in the same samples dedicated for HA analysis. © 2018 Elsevier Inc. All rights reserved.

  16. Combination probes with intercalating anchors and proximal fluorophores for DNA and RNA detection.

    Science.gov (United States)

    Qiu, Jieqiong; Wilson, Adam; El-Sagheer, Afaf H; Brown, Tom

    2016-09-30

    A new class of modified oligonucleotides (combination probes) has been designed and synthesised for use in genetic analysis and RNA detection. Their chemical structure combines an intercalating anchor with a reporter fluorophore on the same thymine nucleobase. The intercalator (thiazole orange or benzothiazole orange) provides an anchor, which upon hybridisation of the probe to its target becomes fluorescent and simultaneously stabilizes the duplex. The anchor is able to communicate via FRET to a proximal reporter dye (e.g. ROX, HEX, ATTO647N, FAM) whose fluorescence signal can be monitored on a range of analytical devices. Direct excitation of the reporter dye provides an alternative signalling mechanism. In both signalling modes, fluorescence in the unhybridised probe is switched off by collisional quenching between adjacent intercalator and reporter dyes. Single nucleotide polymorphisms in DNA and RNA targets are identified by differences in the duplex melting temperature, and the use of short hybridization probes, made possible by the stabilisation provided by the intercalator, enhances mismatch discrimination. Unlike other fluorogenic probe systems, placing the fluorophore and quencher on the same nucleobase facilitates the design of short probes containing multiple modifications. The ability to detect both DNA and RNA sequences suggests applications in cellular imaging and diagnostics. © The Author(s) 2016. Published by Oxford University Press on behalf of Nucleic Acids Research.

  17. Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

    Directory of Open Access Journals (Sweden)

    Markus Börgardts

    2017-04-01

    Full Text Available The covalent attachment of organic fluorophores in mesoporous silica matrices for usage as energy down converting phosphors without employing inorganic transition or rare earth metals is reported in this article. Triethoxysilylpropyl-substituted derivatives of the blue emitting perylene, green emitting benzofurazane, and red emitting Nile red were synthesized and applied in the synthesis of mesoporous hybrid materials by postsynthetic grafting to commercially available MCM-41. These individually dye-functionalized hybrid materials are mixed in variable ratios to furnish a powder capable of emitting white light with CIE chromaticity coordinates of x = 0.33, y = 0.33 and an external quantum yield of 4.6% upon irradiation at 410 nm. Furthermore, as a proof of concept two different device setups of commercially available UV light emitting diodes, are coated with silica monoliths containing the three triethoxysilylpropyl-substituted fluorophore derivatives. These coatings are able to convert the emitted UV light into light with correlated color temperatures of very cold white (41100 K, 10700 K as well as a greenish white emission with correlated color temperatures of about 5500 K.

  18. Ultimate use of two-photon fluorescence microscopy to map orientational behavior of fluorophores.

    Science.gov (United States)

    Ferrand, Patrick; Gasecka, Paulina; Kress, Alla; Wang, Xiao; Bioud, Fatma-Zohra; Duboisset, Julien; Brasselet, Sophie

    2014-06-03

    The orientational distribution of fluorophores is an important reporter of the structure and function of their molecular environment. Although this distribution affects the fluorescence signal under polarized-light excitation, its retrieval is limited to a small number of parameters. Because of this limitation, the need for a geometrical model (cone, Gaussian, etc.) to effect such retrieval is often invoked. In this work, using a symmetry decomposition of the distribution function of the fluorescent molecules, we show that polarized two-photon fluorescence based on tunable linear dichroism allows for the retrieval of this distribution with reasonable fidelity and without invoking either an a priori knowledge of the system to be investigated or a geometrical model. We establish the optimal level of detail to which any distribution can be retrieved using this technique. As applied to artificial lipid vesicles and cell membranes, the ability of this method to identify and quantify specific structural properties that complement the more traditional molecular-order information is demonstrated. In particular, we analyze situations that give access to the sharpness of the angular constraint, and to the evidence of an isotropic population of fluorophores within the focal volume encompassing the membrane. Moreover, this technique has the potential to address complex situations such as the distribution of a tethered membrane protein label in an ordered environment. Copyright © 2014 Biophysical Society. Published by Elsevier Inc. All rights reserved.

  19. Förster resonance energy transfer: Role of diffusion of fluorophore orientation and separation in observed shifts of FRET efficiency.

    Directory of Open Access Journals (Sweden)

    Bram Wallace

    Full Text Available Förster resonance energy transfer (FRET is a widely used single-molecule technique for measuring nanoscale distances from changes in the non-radiative transfer of energy between donor and acceptor fluorophores. For macromolecules and complexes this observed transfer efficiency is used to infer changes in molecular conformation under differing experimental conditions. However, sometimes shifts are observed in the FRET efficiency even when there is strong experimental evidence that the molecular conformational state is unchanged. We investigate ways in which such discrepancies can arise from kinetic effects. We show that significant shifts can arise from the interplay between excitation kinetics, orientation diffusion of fluorophores, separation diffusion of fluorophores, and non-emitting quenching.

  20. Radioiodinated N-(2-aminoethyl)-2-chloro-4-iodobenzamide

    International Nuclear Information System (INIS)

    Ohmomo, Yoshiro; Murakami, Katsuhiko; Tanaka, Chiaki; Hirata, Masahiko; Magata, Yasuhiro; Yokoyama, Akira.

    1994-01-01

    In developing monoamine oxidase (MAO)-B specific radioligands, N-(2-aminoethyl)-2-chloro-4-[ 125 I]iodobenzamide ([ 125 I]FIBA) was conveniently synthesized from its tributylstannyl precursor by an iododestannylation reaction using sodium [ 125 I]iodide and hydrogen peroxide with high radiochemical yield. The method should be applicable for labeling with 123 I, a suitable radioisotope for in vivo imaging with single photon emission computed tomography (SPECT). In vitro binding studies using mouse brain mitochondrial preparations showed that the specific binding of [ 125 I]FIBA was saturable and of high affinity. Calculated values for K D and B max were 201 nM and 9.5 pmol/mg protein, respectively. The [ 125 I]FIBA binding was effectively prevented by MAO-B specific inhibitors (l-deprenyl, Ro 16-6491, FIBA) or substrate (β-phenethylamine). However, MAO-A specific inhibitor (clorgyline) and substrate (serotonin) had no significant effect. After an intravenous injection into mice, [ 125 I]FIBA showed high brain uptake (1.64% dose/g at 15-30 min post injection) and long retention (1.11% dose/g at 120 min post injection) in the brain. Good brain-to-blood radioactivity ratios of 2.19 and 2.41 at 60 and 120 min after injection, respectively, were obtained. The in vitro binding data and in vivo characteristics suggested that [ 125 I]FIBA is potentially useful as a probe for biological studies including specific labeling of MAO-B in vivo as well as in vitro. Moreover, the 123 I-labeled counterpart, [ 123 I]FIBA, might be valuable for non-invasive imaging and mapping of MAO-B in the living brain with SPECT. (author)

  1. Synthesis, characterization and antibacterial investigation of divalent metal complexes of NO-donor ligand: {5-chloro-2-[(4-chlorobenzylidene-amino]phenyl}(phenylmethanone

    Directory of Open Access Journals (Sweden)

    Muhammad Aslam

    2015-05-01

    Full Text Available A ligand L has been synthesized by the condensation of 4-chlorobenzaldehyde and 2-amino-5-chlorobenzophenone. The complexes 1–5 of Pb+2, Ni+2, Co+2, Cu+2 and Cd+2 with ligand were prepared. The newly synthesized ligand L and its complexes 1–5 were characterized on the basis of elemental analyses, molar conductance, 1H NMR, IR and MS spectral data. The ligand was also characterized by X-ray crystallography. By electronic spectra and magnetic moment data, the square planar geometry for complex 1 and the octahedral geometry for complexes 2–5 were proposed. The conductivity data suggests non-electrolytic nature of the complexes 1–5. The complexes have higher antibacterial activity than the parent ligand L.

  2. CCDC 879685: Experimental Crystal Structure Determination : Chloro-(3,5-di-t-butyl-2,6-bis((di-t-butylphosphino)oxy)phenyl)-nickel(ii)

    KAUST Repository

    Chen, Tao

    2012-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  3. Synthesis and biological activities of 3-1-(3-(2-chloro-3,3,3-trifluoro-prop-1-enyl) 2,2-dimethylcyclopropanecarbonyl)-3substituted phenyl thiourea

    International Nuclear Information System (INIS)

    Sun, N.B.; Lei, C.; Jin, J.Z.; Zhang, J.F.

    2013-01-01

    Some thiourea compounds containing pyrethroids are synthesized. Their structures were confirmed by 1H-NMR, MS and elemental analysis. The bioassay results indicated that they showed moderate insecticidal and fungicidal activity. (author)

  4. CCDC 879684: Experimental Crystal Structure Determination : chloro-(2,6-bis((bis(cyclopentyl)phosphino)oxy)-4-(ethoxycarbonyl)phenyl)-nickel(ii)

    KAUST Repository

    Chen, Tao

    2012-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  5. CCDC 926491: Experimental Crystal Structure Determination : Chloro-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)imidazol-2-ylidene)-gold

    KAUST Repository

    Collado, Alba

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  6. Synthesis, Characterization and Antimicrobial Activity of Metal Chelates of 5-[4-Chloro phenyl(1, 3, 4thiadiazol-2-ylamino methylene]-8-hydroxy quinoline

    Directory of Open Access Journals (Sweden)

    Divyesh K. Patel

    2009-01-01

    Full Text Available 5-Chloromethyl-8-quinolinol was condensed stoichiometrically with 5-(4-chlorophenyl-(1,3,4 thiadiazol-2-ylamine in the presence of sodium bicarbonate. The resulting 5-[4-chlorophenyl-(1,3,4thiadiazol-2-ylamino methylene]-8-quinolinol (CTAQ was characterized by elemental analysis and spectral studies. The transition metal chelates viz. Cu2+, Ni2+, Co2+, Mn2+ and Zn2+ of CTAQ were prepared and characterized by metal-ligand (M:L ratio, IR and reflectance spectroscopies and magnetic properties. The antifungal activity of CTAQ and its metal chelates was screened against various fungi. The results show that all these samples are good antifungal agents.

  7. On the bioactive conformation of R(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

    Science.gov (United States)

    Verdonk, M. L.; Voogd, K.; Kanters, J. A.; Kroon, J.; van Duijneveldt, F. B.

    1994-07-01

    A redetermination of the X-ray structure of the title compound is reported. In this structure a partially occupied position of a water molecule was found that was not observed in an earlier structure determination. This water molecule appears to have an important role in the crystal packing. Molecular mechanics calculations were performed on 12 conformations of the protonated title compound, complexed to a chloride anion. This anion represents the anionic binding site of the receptors at which the title compound exerts its biological activity. Crystal-structure statistics and ab initio calculations were used to generate starting geometries for the molecular mechanics calculations. It appears that the conformation that is assumed to be the active conformation for the D 1 receptor is the lowest-energy conformation. It is concluded that this conformation may, therefore, also be the active conformation for other receptors.

  8. Chloro({2-[mesityl(quinolin-8-yl-κNboryl]-3,5-dimethyl-phenyl}methyl-κCpalladium(II as a Catalyst for Heck Reactions

    Directory of Open Access Journals (Sweden)

    Sem Raj Tamang

    2015-07-01

    Full Text Available We recently reported an air and moisture stable 16-electron borapalladacycle formed upon combination of 8-quinolyldimesitylborane with bis(benzonitriledichloropalladium(II. The complex features a tucked mesityl group formed upon metalation of an ortho-methyl group on a mesityl; however it is unusually stable due to contribution of the boron pz orbital in delocalizing the carbanion that gives rise to an η4-boratabutadiene fragment coordinated to Pd(II, as evidenced from crystallographic data. This complex was observed to be a highly active catalyst for the Heck reaction. Data of the catalyst activity are presented alongside data found in the literature, and initial comparison reveals that the borapalladacycle is quite active. The observed catalysis suggests the borapalladacycle readily undergoes reductive elimination; however the Pd(0 complex has not yet been isolated. Nevertheless, the ambiphilic ligand 8-quinolyldimesitylborane may be able to support palladium in different redox states.

  9. 3-Phenyl-1-(pyrrol-2-ylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Zhen-Qi Gong

    2008-01-01

    Full Text Available The title molecule, C13H11NO, is almost flat, the angle between the pyrrole and the phenyl rings being 10.9 (1°. The atoms of the central C3O unit are coplanar, with a mean deviation from the plane of 0.001 (1 Å. The angles between this plane and the pyrrole and phenyl rings are 3.3 (1 and 8.0 (1°, respectively. The molecules form centrosymmetric dimers through a pair of N—H...O hydrogen bonds with an R22(10 motif.

  10. 2-Methyl-4-phenyl-3,4-dihydroquinazoline

    Directory of Open Access Journals (Sweden)

    Arto Valkonen

    2011-04-01

    Full Text Available The title compound, C15H14N2, was formed during the lithiation of 2-methylquinazoline with phenyllithium followed by hydrolysis of the intermediate lithium 2-methyl-4-phenyl-4H-quinazolin-3-ide. NMR spectra as well as single-crystal X-ray structural data indicate that the reaction product to have the same structure in chloroform solution as in the crystalline state. The phenyl substituent is twisted out of the plane of the 3,4-dihydroquinazoline ring system by 86.47 (7°. In the crystal, intermolecular N—H...N interactions connect the molecules into infinite chains.

  11. Reaction of 1,2,4-triazole-3-thiones with 1-chloro-2,3-epoxypropane

    International Nuclear Information System (INIS)

    Trzhtsinskaya, B.V.; Kositsyna, E.I.; Pertsikov, B.Z.; Rudakova, E.V.; Voronov, V.K.; Skvortsova, G.G.

    1987-01-01

    Addition of 1-chloro-2,3-epoxypropane to 1,2,4-triazole-3-thiones depending on the ratio of the reactants leads to the formation of 3-(1-chloro-2-hydroxypropyl)-3-(1-chloro-2-hydroxypropylthio)-1,2,4-triazoles. 3-Hydroxy-1,2,4-triazolo[2,3-b] tetrahydro-1,3-triazines have been synthesized by intramolecular cyclization of the monoadducts. IR spectra were recorded on a Specord 75-IR instrument as a thin layer, in KBr pellets, an in chloroform solution; PMR spectra were recorded on a Tesla BS-497 instrument (100 MHz) at 20 0 C in CD 3 OD with TMS as internal standard

  12. 4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

    Science.gov (United States)

    Eren, Bilge; Demir, Selçuk; Dal, Hakan; Hökelek, Tuncer

    2014-01-01

    The whole mol­ecule of the title compound, C20H19NO4S2, is generated by twofold rotational symmetry. The N atom is located on the twofold rotation axis and has a trigonal-planar geometry. It is bonded by two S atoms of two symmetry-related 4-methyl­phenyl­sulfonyl groups and by the C atom of the phenyl ring, which is bis­ected by the twofold rotation axis. The benzene and phenyl rings are oriented at a dihedral angle of 51.48 (5)° while the pendant benzene rings are inclined to one another by 87.76 (9)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network. PMID:24764960

  13. Cu(II) recognition materials: Fluorophores grafted on mesoporous silica supports

    Science.gov (United States)

    Kledzik, Krzysztof; Orłowska, Maja; Patralska, Dorota; Gwiazda, Marcin; Jezierska, Julia; Pikus, Stanisław; Ostaszewski, Ryszard; Kłonkowski, Andrzej M.

    2007-11-01

    There were designed and synthesized naphthalene and pyrene derivatives consisting of fluorophore group and of receptor fragment with donor N and O atoms. These fluorosensors were covalently attached by grafting carboxyl group to surfaces of silica xerogel or mesoporous silicas (MCM-41 and MCM-48) functionalized either with 3-aminopropyl or 3-glycidoxypropyl groups. The pyrene derivatives 2 and 3 covalently grafted on MCM-48 silica functionalized with 3-aminopropyl groups are potential recognition elements of a fluorescence chemical sensor. Fluorescence emission of the prepared recognition materials is quenched specifically owing to photoinduced electron transfer (PET) effect after coordination reactions with Cu(II) ions. Moreover, both the materials exhibit selectivity for Cu(II) ions in aqueous solutions in presence of such metal ions as: alkali, alkaline earth and transition. During UV irradiation the studied recognition elements undergo slowly photochemical degradation.

  14. A promising solution to the limits of microscopes for smooth surfaces: fluorophore-aided scattering microscopy.

    Science.gov (United States)

    Li, Liang; Liu, Jian; Liu, Yan; Liu, Chenguang; Zhang, He; You, Xiaoyu; Gu, Kang; Wang, Yuhang; Tan, Jiubin

    2018-04-06

    Reflected light escape and mesoscopic penetration are two serious problems for optical characterization using microscopes. For specular samples with steep slopes, the detector does not receive enough light and the detection algorithm is not be able to detect the peak position, and would generate non-measured points. Moreover, the mesoscopic penetration phenomenon has been ignored when measuring and observing the shapes of samples with multi-layer structures. But this phenomenon, due to the transparency of materials to certain wavelengths of light, may result in serious errors in the measurements of the heights of samples, as well as errors in the descriptions of their shapes. Here we describe the use of fluorophore-aided scattering microscopy to significantly extend the magnitudes of slopes that can be detected, and to essentially eliminate errors in measurements of height caused by mesoscopic penetration.

  15. Selenium as an alternative peptide label - comparison to fluorophore-labelled penetratin

    DEFF Research Database (Denmark)

    Hyrup Møller, Laura; Bahnsen, Jesper Søborg; Nielsen, Hanne Mørck

    2015-01-01

    lysates, primarily the intact peptide (PenMSe, TAMRA-PenMSe or TAMRA-Pen) was observed. Selenium labelling caused minimal alteration of the physicochemical properties of the peptide and allowed for absolute quantitative determination of cellular uptake by inductively coupled plasma mass spectrometry......In the present study, the impact on peptide properties of labelling peptides with the fluorophore TAMRA or the selenium (Se) containing amino acid SeMet was evaluated. Three differently labelled variants of the cell-penetrating peptide (CPP) penetratin (Pen) were synthesized, PenMSe, TAMRA....... Selenium is thus proposed as a promising alternative label for quantification of peptides in general, altering the properties of the peptide to a minor extent as compared to commonly used peptide labels....

  16. Synthesis and electrical conductivity studies of metal chloro and nitroxide group containing styrene butadiene rubber

    Science.gov (United States)

    Anilkumar, T.; Ramesan, M. T.

    2014-10-01

    The introduction of different functional group in SBR was done by a simple reaction between sodium nitrite and mercuric chloride in the presence of phase transfer catalyst. The attachment of chlorine and NO2 functional group in the double bond of the butadiene was monitored by FTIR and UV spectroscopy. The structure and morphology of chloro nitro SBR was studied by SEM and XRD. Flame retardency studies revealed that the chemical modification imparts better flame resistance to chemically modified SBR. AC conductivity and dielectric properties of chloro- nitro SBR was higher than that of SBR and conductivity increases with the level of chemical modification.

  17. A green-light-emitting, spontaneously blinking fluorophore based on intramolecular spirocyclization for dual-colour super-resolution imaging.

    Science.gov (United States)

    Uno, Shin-Nosuke; Kamiya, Mako; Morozumi, Akihiko; Urano, Yasuteru

    2017-12-19

    We have developed the first green-light-emitting, spontaneously blinking fluorophore (SBF), HEtetTFER. In combination with our near-infrared-light-emitting SBF (HMSiR), HEtetTFER allows dual-colour single-molecule localization microscopy (SMLM) in buffer solution without any additive and without photoactivation.

  18. Experimental recovery of intrinsic fluorescence and fluorophore concentration in the presence of hemoglobin: spectral effect of scattering and absorption on fluorescence.

    Science.gov (United States)

    Du Le, Vinh Nguyen; Patterson, Michael S; Farrell, Thomas J; Hayward, Joseph E; Fang, Qiyin

    2015-01-01

    The ability to recover the intrinsic fluorescence of biological fluorophores is crucial to accurately identify the fluorophores and quantify their concentrations in the media. Although some studies have successfully retrieved the fluorescence spectral shape of known fluorophores, the techniques usually came with heavy computation costs and did not apply for strongly absorptive media, and the intrinsic fluorescence intensity and fluorophore concentration were not recovered. In this communication, an experimental approach was presented to recover intrinsic fluorescence and concentration of fluorescein in the presence of hemoglobin (Hb). The results indicated that the method was efficient in recovering the intrinsic fluorescence peak and fluorophore concentration with an error of 3% and 10%, respectively. The results also suggested that chromophores with irregular absorption spectra (e.g., Hb) have more profound effects on fluorescence spectral shape than chromophores with monotonic absorption and scattering spectra (e.g., black India ink and polystyrene microspheres).

  19. Synthesis of 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole and 1-(4-sulfonamide-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole as novel carbon-14 anticonvulsant

    International Nuclear Information System (INIS)

    Saemian, N.; Shirvani, G.; Matloubi, H.

    2006-01-01

    Two 1,2,3-triazole anticonvulsants, 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole and 1-(4-sulfonamide-phenyl)-5-(4- fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole, both labeled with carbon-14 in the 5-position were prepared from para-fluoro-benzonitrile-[cyano- 14 C]. (author)

  20. 4-Bromo-3-methoxy-1-phenyl-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2009-11-01

    Full Text Available The title compound was prepared by treatment of 4-bromo-1-phenyl-1H-pyrazol-3-ol with sodium hydride/methyl iodide in good yield. Detailed spectroscopic data (1H NMR, 13C NMR, 15N NMR, IR, MS are presented.

  1. Chemistry of the pyrazolidines. 26. Alkylation of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines

    International Nuclear Information System (INIS)

    Moldarev, B.L.; Aronzon, M.E.; Adanin, V.M.; Zyakun, A.M.

    1986-01-01

    The reaction of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines with alkyl halides in the presence of sodium alkoxide gave 1-phenyl-2-alkyl-4-benzyliden- and 1-phenyl-2,4-dialkyl-4-(α-alkoxybenzyl)-3,4-dioxopyrazolines. The structures of these compounds were confirmed by UV, IR, and PMR spectroscopy, and by mass-spectrometry

  2. Electrochemical characterization of azo dye (E)-1-(4-((4-(phenylamino)phenyl)diazenyl)phenyl)ethanone (DPA)

    International Nuclear Information System (INIS)

    Surucu, Ozge; Abaci, Serdar; Seferoğlu, Zeynel

    2016-01-01

    Highlights: • Electrochemical characterization of azo dye DPA was performed. • Pencil graphite electrode was used as working electrode. • Cyclic voltammetry was used to determine the effect of scan rate and pH. • Chronoamperometry was used to determine diffusion constant. • Square wave voltammetry verified the results of cyclic voltammetry. - Abstract: An enormous range of possible dyes are available, especially as the starting molecules are readily available and cheap. As other dye classes become less viable from either an environmental or economic reasons, azo dyes come to the forefront. Therefore, electrochemical characterization of a novel synthesized azo dye (E)-1-(4-((4-(phenylamino) phenyl)diazenyl)phenyl)ethanone was achieved for the first time. Cyclic voltammetry, chronoamperometry and square wave voltammetry techniques were used to investigate the electrochemical behavior and electrocatalytic effect of azo dye (E)-1-(4-((4-(phenylamino) phenyl)diazenyl)phenyl)ethanone at pencil graphite electrode. Cyclic voltammograms were utilized to determine the effect of scan rate and pH on the peak current and peak potential. Chronoamperometry technique was used to determine diffusion constant, D and the type of adsorption isotherms. The kinetics parameters which were the apparent electron transfer rate constant, k s and charge transfer coefficient, α were calculated. Square wave voltammetry was used to verify responses of cyclic voltammetry technique.

  3. Gelation Behavior of 5-Chloro-8-hydroxyquinoline, an Antituberculosis Agent in Aqueous Alcohol Solutions

    Directory of Open Access Journals (Sweden)

    Jukka Korpela

    2012-09-01

    Full Text Available It was shown that 5-chloro-8-hydroxyquinoline, an antituberculosis agent, gels aqueous alcohol solutions efficiently. Thermal stability and gel-to-sol transition temperature of 1% gel in CD3OD/D2O (2:1 was studied by 1H-NMR. Fibrous structures of four xerogels have been characterized by scanning electron microscope.

  4. Iron(III) porphyrin-catalysed oxidation reactions by m-chloro ...

    Indian Academy of Sciences (India)

    Unknown

    Dedicated to the memory of the late Professor Bhaskar G Maiya. *For correspondence. Iron(III) porphyrin-catalysed oxidation reactions by m-chloro- perbenzoic acid: Nature of reactive intermediates. A AGARWALA, V BAGCHI and D BANDYOPADHYAY*. Department of Chemistry, Indian Institute of Technology, New Delhi ...

  5. Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

    Energy Technology Data Exchange (ETDEWEB)

    Vieira, Andreia A.; Gomes, Niele M.; Matheus, Maria E.; Figueroa-Villar, Jose D., E-mail: figueroa@ime.eb.b [Instituto Militar de Engenharia (IME), Rio de Janeiro, RJ (Brazil). Dept. de Chemistry. Medicinal Chemistry Grupo; Fernandes, Patricia D. [Universidade Federal do Rio de Janeiro (UFRJ), RJ (Brazil). Inst. de Ciencias Biomedicas. Lab. de Farmacologia da Inflamacao e do Oxido Nitrico

    2011-07-01

    A new family of barbiturates, 5-chloro-5-benzylbarbituric acids, was prepared using a simple efficient synthetic method from aromatic aldehydes and barbituric acid, followed by reduction and chlorination with trichloro-isocyanuric acid, affording overall yields of 53 to 70%. The in vivo evaluation with mice showed that these compounds present tranquilizing activity. (author)

  6. Gelation Behavior of 5-Chloro-8-hydroxyquinoline, an Antituberculosis Agent in Aqueous Alcohol Solutions.

    Science.gov (United States)

    Kolehmainen, Erkki; Salo, Hannu; Korpela, Jukka

    2012-09-19

    It was shown that 5-chloro-8-hydroxyquinoline, an antituberculosis agent, gels aqueous alcohol solutions efficiently. Thermal stability and gel-to-sol transition temperature of 1% gel in CD₃OD/D₂O (2:1) was studied by ¹H-NMR. Fibrous structures of four xerogels have been characterized by scanning electron microscope.

  7. New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides

    DEFF Research Database (Denmark)

    Hawata, Mohamed A.M.; El-Torgoman, Abdel M.; El-Kousy, Salah M.

    2002-01-01

    The pyridine-catalyzed reaction between a number of propanedioic acid derivatives 1 and thionyl chloride has been investigated in detail. Contrary to popular belief the straightforward formation of the corresponding alpha-chloro sulfenyl chlorides 2 is the exception rather than the rule. The prop...

  8. Kinetic studies on substitution of cis-diaqua-chloro-tris-(dimethyl ...

    Indian Academy of Sciences (India)

    4, July 2012, pp. 801–807. c Indian Academy of Sciences. Kinetic studies on substitution of cis-diaqua-chloro-tris-(dimethyl sulphoxide)-ruthenium(II) complex with some dipeptides in aqueous medium. ARUP MANDAL, PARNAJYOTI KARMAKAR, SUBHASIS MALLICK, BIPLAB K BERA,. SUBALA MONDAL, SUMON RAY ...

  9. Novel 2-Chloro-8-arylthiomethyldipyridodiazepinone Derivatives with Activity against HIV-1 Reverse Transcriptase

    Directory of Open Access Journals (Sweden)

    Supanna Techasakul

    2007-02-01

    Full Text Available Based on the molecular modeling analysis against Y181CHIV-1 RT, dipyridodiazepinone derivatives containing an unsubstituted lactamnitrogen and 2-chloro-8-arylthiomethyl were synthesized via an efficientroute. Some of them were evaluated for their antiviral activity against HIV-1RT subtype E and were found to exhibit virustatic activity comparable to some clinically usedtherapeutic agents.

  10. ChloroMitoCU: Codon patterns across organelle genomes for functional genomics and evolutionary applications.

    Science.gov (United States)

    Sablok, Gaurav; Chen, Ting-Wen; Lee, Chi-Ching; Yang, Chi; Gan, Ruei-Chi; Wegrzyn, Jill L; Porta, Nicola L; Nayak, Kinshuk C; Huang, Po-Jung; Varotto, Claudio; Tang, Petrus

    2017-06-01

    Organelle genomes are widely thought to have arisen from reduction events involving cyanobacterial and archaeal genomes, in the case of chloroplasts, or α-proteobacterial genomes, in the case of mitochondria. Heterogeneity in base composition and codon preference has long been the subject of investigation of topics ranging from phylogenetic distortion to the design of overexpression cassettes for transgenic expression. From the overexpression point of view, it is critical to systematically analyze the codon usage patterns of the organelle genomes. In light of the importance of codon usage patterns in the development of hyper-expression organelle transgenics, we present ChloroMitoCU, the first-ever curated, web-based reference catalog of the codon usage patterns in organelle genomes. ChloroMitoCU contains the pre-compiled codon usage patterns of 328 chloroplast genomes (29,960 CDS) and 3,502 mitochondrial genomes (49,066 CDS), enabling genome-wide exploration and comparative analysis of codon usage patterns across species. ChloroMitoCU allows the phylogenetic comparison of codon usage patterns across organelle genomes, the prediction of codon usage patterns based on user-submitted transcripts or assembled organelle genes, and comparative analysis with the pre-compiled patterns across species of interest. ChloroMitoCU can increase our understanding of the biased patterns of codon usage in organelle genomes across multiple clades. ChloroMitoCU can be accessed at: http://chloromitocu.cgu.edu.tw/. © The Author 2017. Published by Oxford University Press on behalf of Kazusa DNA Research Institute.

  11. Multimodal fluorescence molecular imaging for in vivo characterization of skin cancer using endogenous and exogenous fluorophores

    Science.gov (United States)

    Miller, Jessica P.; Habimana-Griffin, LeMoyne; Edwards, Tracy S.; Achilefu, Samuel

    2017-06-01

    Similarity of skin cancer with many benign skin pathologies requires reliable methods to detect and differentiate the different types of these lesions. Previous studies have explored the use of disparate optical techniques to identify and estimate the invasive nature of melanoma and basal cell carcinoma with varying outcomes. Here, we used a concerted approach that provides complementary information for rapid screening and characterization of tumors, focusing on squamous cell carcinoma (SCC) of the skin. Assessment of in vivo autofluorescence lifetime (FLT) imaging of endogenous fluorophores that are excitable at longer wavelengths (480 nm) than conventional NADH and FAD revealed a decrease in the short FLT component for SCC compared to normal skin, with mean values of 0.57±0.026 ns and 0.61±0.021 ns, respectively (p=0.004). Subsequent systemic administration of a near-infrared fluorescent molecular probe in SCC bearing mice, followed by the implementation of image processing methods on data acquired from two-dimensional and three-dimensional fluorescence molecular imaging, allowed us to estimate the tumor volume and depth, as well as quantify the fluorescent probe in the tumor. The result suggests the involvement of lipofuscin-like lipopigments and riboflavin in SCC metabolism and serves as a model for staging SCC.

  12. A laser scanner for imaging fluorophore labeled molecules in electrophoretic gels

    Energy Technology Data Exchange (ETDEWEB)

    Fisk, D.J.; Sutherland, J.C. [Brookhaven National Lab., Upton, NY (United States). Biology Dept.

    1995-08-01

    A laser scanner for imaging electrophoretic gels was constructed and tested. The scanner incorporates a green helium-neon (HeNe) laser (543.5nm wavelength) and can achieve a spatial resolution of 19{micro}m. The instrument can function in two modes : snap-shot and finish-line. In snapshot mode, all samples are electrophoresed for the same time and the gel is scanned after completion of electrophoresis, while in finish-line mode, fluorophore labeled samples are electrophoresed for a constant distance and the image is formed as the samples pass under the detector. The resolving power of the finish-line mode of imaging is found to be greater than that of the snapshot mode of imaging. This laser scanner is also compared with a Charge Coupled Device (CCD) camera and in terms of resolving power is found to be superior. Sensitivity of the instrument is presented in terms of the minimum amount of DNA that can be detected verses its molecular length.

  13. Rapid Differential Diagnosis of Breast Microcalcification Using Targeted Near-Infrared Fluorophores.

    Science.gov (United States)

    Park, Min Ho; Lim, Wonbong; Jo, Danbi; Jung, Jin Seok; Kim, Subin; Kim, Jangho; Lim, Hyo Soon; Lee, Ji Shin; Min, Jung-Joon; Hyun, Hoon

    2017-12-06

    Early detection and differential diagnosis of breast microcalcifications are of significant importance in effective treatment of early breast cancer, because mineral composition of breast calcification is directly associated with different pathological states. However, applying image-based modalities for component identification in breast calcification remains challenging, because no calcification-specific contrast agent is available to distinguish between benign and malignant (type I and type II, respectively) calcifications of breast lesions. In this study, real-time near-infrared (NIR) fluorescence imaging of breast microcalcifications using targeted NIR fluorophores in combination with dual-channel NIR fluorescence imaging system is reported. This strategy can be used to solve major problem in mammography and ultrasonography methods for the differentiation of benign and malignant microcalcifications. Thus, this novel technology shows significant potential for breast cancer diagnosis and image-guided surgery performed with increased precision and efficiency by providing differential diagnosis of breast microcalcifications. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  14. Isolation and analysis of sugar nucleotides using solid phase extraction and fluorophore assisted carbohydrate electrophoresis.

    Science.gov (United States)

    Barnes, Jarrod; Tian, Liping; Loftis, Jacqueline; Hiznay, James; Comhair, Suzy; Lauer, Mark; Dweik, Raed

    2016-01-01

    The building blocks of simple and complex oligosaccharides, termed sugar nucleotides, are often overlooked for their role in metabolic diseases and may hold the key to the underlying disease pathogenesis. Multiple reasons may account for the lack of analysis and quantitation of these sugar nucleotides, including the difficulty in isolation and purification as well as the required expensive instrumentation such as a high performance liquid chromatography (HPLC), mass spectrometer, or capillary electrophoresis. We have established a simple yet effective way to purify and quantitate sugar nucleotides using solid phase extraction (SPE) chromatography combined with fluorophore assisted carbohydrate electrophoresis (FACE). The simplicity of use, combined with the ability to run multiple samples at one time, give this technique a distinct advantage over the established methods for isolation and analysis of sugar nucleotides from cell culture models. •Sugar nucleotides can be easily purified with solid phase extraction chromatography.•FACE can be used to analyze multiple nucleotide sugar extracts with a single run.•The proposed method is simple, affordable, and uses common everyday research labware.

  15. Sulfonation of alkyl phenyl ether self-assembled monolayers.

    Science.gov (United States)

    Katash, Irit; Luo, Xianglin; Sukenik, Chaim N

    2010-02-02

    The sulfonation of phenyl ether decorated self-assembled monolayers (SAMs) was studied with an eye toward creating surfaces with a particularly high negative charge density based on a close-packed array of phenyl rings with more than one sulfonic acid group per molecule. The product distribution and kinetics of this process were studied by ultraviolet, infrared, and photoelectron spectroscopies and by monitoring changes in the thickness and wetting properties of the SAM. The sulfonation chemistry could be effected without undermining monolayer integrity and the isomer distribution of ortho- and para-monosulfonated material, along with the percentages of mono- and disulfonated molecules could be established throughout the process. As doubly sulfonated molecules appeared, the reaction slowed drastically. Ultimately, sulfonation stops completely with approximately 60% of the molecules disulfonated and 20% each of the two monosulfonated isomers. This striking constraint on monolayer reactivity and the relationship between the surface chemistry and variations in SAM structure are discussed.

  16. Synthesis of (1,213C)-2-chloroethyl phenyl sulfide

    International Nuclear Information System (INIS)

    Taber, D.F.; Yanong Wang

    1995-01-01

    Incorporation of a double 13 C label into the mustard 2-chloroethyl phenyl sulfide is straightforward, but analysis is complicated by 13 C- 13 C coupling. An alternative is reported, in which the ease of scrambling of sulfur mustards is used to advantage to prepare precisely 50% (1, 2- 13 C) enriched with each carbon of the ethyl chain labelled to provide optimal signal to noise in the 13 C spectrum. (author)

  17. High-resolution of particle contacts via fluorophore exclusion in deep-imaging of jammed colloidal packings

    Science.gov (United States)

    Kyeyune-Nyombi, Eru; Morone, Flaviano; Liu, Wenwei; Li, Shuiqing; Gilchrist, M. Lane; Makse, Hernán A.

    2018-01-01

    Understanding the structural properties of random packings of jammed colloids requires an unprecedented high-resolution determination of the contact network providing mechanical stability to the packing. Here, we address the determination of the contact network by a novel strategy based on fluorophore signal exclusion of quantum dot nanoparticles from the contact points. We use fluorescence labeling schemes on particles inspired by biology and biointerface science in conjunction with fluorophore exclusion at the contact region. The method provides high-resolution contact network data that allows us to measure structural properties of the colloidal packing near marginal stability. We determine scaling laws of force distributions, soft modes, correlation functions, coordination number and free volume that define the universality class of jammed colloidal packings and can be compared with theoretical predictions. The contact detection method opens up further experimental testing at the interface of jamming and glass physics.

  18. The mechanochemical production of phenyl cations through heterolytic bond scission.

    Science.gov (United States)

    Shiraki, Tomohiro; Diesendruck, Charles E; Moore, Jeffrey S

    2014-01-01

    High mechanical forces applied to polymeric materials typically induce unselective chain scission. For the last decade, mechanoresponsive molecules, mechanophores, have been designed to harness the mechanical energy applied to polymers and provide a productive chemical response. The selective homolysis of chemical bonds was achieved by incorporating peroxide and azo mechanophores into polymer backbones. However, selective heterolysis in polymer mechanochemistry is still mostly unachieved. We hypothesized that highly polarized bonds in ionic species are likely to undergo heterolytic bond scission. To test this, we examined a triarylsulfonium salt (TAS) as a mechanophore. Poly(methyl acrylate) possessing TAS at the center of the chain (PMA-TAS) is synthesized by a single electron transfer living radical polymerization (SET-LRP) method. Computational and experimental studies in solution reveal the mechanochemical production of phenyl cations from PMA-TAS. Interestingly, the generated phenyl cation reacts with its counter-anion (trifluoromethanesulfonate) to produce a terminal trifluoromethyl benzene structure that, to the best of our knowledge, is not observed in the photolysis of TAS. Moreover, the phenyl cation can be trapped by the addition of a nucleophile. These findings emphasize the interesting reaction pathways that become available by mechanical activation.

  19. Fragrance material review on 4-phenyl-3-buten-2-ol.

    Science.gov (United States)

    Scognamiglio, J; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 4-phenyl-3-buten-2-ol when used as a fragrance ingredient is presented. 4-Phenyl-3-buten-2-ol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a secondary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 4-phenyl-3-buten-2-ol were evaluated then summarized and includes physical properties, and genotoxicity data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. Copyright © 2011 Elsevier Ltd. All rights reserved.

  20. Fragrance material review on 2-methyl-4-phenyl-2-butanol.

    Science.gov (United States)

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butanol when used as a fragrance ingredient is presented. 2-methyl-4-phenyl-2-butanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenyl-2-butanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, and skin sensitization data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. assessment of aryl alkyl alcohols when used as fragrance ingredients. Copyright © 2011 Elsevier Ltd. All rights reserved.

  1. Synthesis and Characterization of 9-Phenyl-9H-purin-6-amines from 5-Amino-1-phenyl-1H-imidazole-4-carbonitriles

    Directory of Open Access Journals (Sweden)

    Asieh Yahyazadeh

    2007-01-01

    Full Text Available 9-Phenyl-9H-purin-6-amine derivatives have been synthesized in high yields by reaction between 5-amino-1-phenyl-1H-imidazole-4-carbonitrile with HC(OEt3 and Ac2O followed by reaction with ammonia.

  2. Solid-state circularly polarised luminescence of atropisomeric fluorophores embedded in achiral myo-inositol-containing polyurethanes.

    Science.gov (United States)

    Amako, Tomoyuki; Nakabayashi, Kazuki; Sudo, Atsushi; Fujiki, Michiya; Imai, Yoshitane

    2015-03-14

    We investigated the ground- and photoexcited-state chiralities of two chiral fluorophores with a rigid framework embedded in two achiral polyurethanes as the solid matrices. As the fluorophores, we used two pairs of atropisomeric binaphthyl derivatives, (R)-(−)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate [(R)-1a] and (R)-(−)-(3,5-dioxa-4-phosphacyclohepta-[2,1-a:3,4-a′]dinaphthalen-4-yl)-dimethylamine [(R)-1b], and for comparison, their optical antipodes (S)-1a and (S)-1b. As the solid matrices, we used two soluble achiral polyurethanes (2a and 2b) derived from the naturally occurring myo-inositol as the building block, because these polymers had a high glass transition temperature of ~150 °C. The chiral fluorophores in the polyurethanes emitted circularly polarised luminescence with a high circular anisotropy of ~0.6–1.5 × 10(-3). Regardless of the matrix, (R)- and (S)-1a had nearly mirror-image chiroptical properties in the ground and photoexcited states, as did (R)- and (S)-1b.

  3. Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid.

    Science.gov (United States)

    Forsch, Ronald A; Wright, Joel E; Rosowsky, Andre

    2002-06-01

    N-[5-[N-(2-Amino-5-chloro-3,4-dihydro-4-oxoquinazolin-6-yl)methylamino]-2-thenoyl]-L-glutamic acid (6) and N-[5-[N-(5-chloro-3,4-dihydro-2-methyl-4-oxoquinazolin-6-yl)methylamino]-2-thenoyl]-L-glutamic acid (7), the first reported thiophene analogues of 5-chloro-5,8-dideazafolic acid, were synthesized and tested as inhibitors of tumor cell growth in culture. 4-Chloro-5-methylisatin (10) was converted stepwise to methyl 2-amino-5-methyl-6-chlorobenzoate (22) and 2-amino-5-chloro-3,4-dihydro-6-methyl-4-oxoquinazoline (19). Pivaloylation of the 2-amino group, followed by NBS bromination, condensation with di-tert-butyl N-(5-amino-2-thenoyl)-L-glutamate (28), and stepwise cleavage of the protecting groups with ammonia and TFA yielded. Treatment of 9 with acetic anhydride afforded 2,6-dimethyl-5-chlorobenz[1,3-d]oxazin-4-one (31), which on reaction with ammonia, NaOH was converted to 2,6-dimethyl-5-chloro-3,4-dihydroquinazolin-4-one (33). Bromination of, followed by condensation with and ester cleavage with TFA, yielded. The IC(50) of and against CCRF-CEM human leukemic lymphoblasts was 1.8+/-0.1 and 2.1+/-0.8 microM, respectively.

  4. Resonance energy transfer between fluorescent BSA protected Au nanoclusters and organic fluorophores.

    Science.gov (United States)

    Raut, Sangram; Rich, Ryan; Fudala, Rafal; Butler, Susan; Kokate, Rutika; Gryczynski, Zygmunt; Luchowski, Rafal; Gryczynski, Ignacy

    2014-01-07

    Bovine serum albumin (BSA) protected nanoclusters (Au and Ag) represent a group of nanomaterials that holds great promise in biophysical applications due to their unique fluorescence properties and lack of toxicity. These metal nanoclusters have utility in a variety of disciplines including catalysis, biosensing, photonics, imaging and molecular electronics. However, they suffer from several disadvantages such as low fluorescence quantum efficiency (typically near 6%) and broad emission spectrum (540 nm to 800 nm). We describe an approach to enhance the apparent brightness of BSA Au clusters by linking them with a high extinction donor organic dye pacific blue (PB). In this conjugate PB acts as a donor to BSA Au clusters and enhances its brightness by resonance energy transfer (RET). We found that the emission of BSA Au clusters can be enhanced by a magnitude of two-fold by resonance energy transfer (RET) from the high extinction donor PB, and BSA Au clusters can act as an acceptor to nanosecond lifetime organic dyes. By pumping the BSA Au clusters using a high extinction donor, one can increase the effective brightness of less bright fluorophores like BSA Au clusters. Moreover, we prepared another conjugate of BSA Au clusters with the near infrared (NIR) dye Dylight 750 (Dy750), where BSA Au clusters act as a donor to Dy750. We observed that BSA Au clusters can function as a donor, showing 46% transfer efficiency to the NIR dye Dy750 with a long lifetime component in the acceptor decay through RET. Such RET-based probes can be used to prevent the problems of a broad emission spectrum associated with the BSA Au clusters. Moreover, transferring energy from BSA Au clusters to Dy750 will result in a RET probe with a narrow emission spectrum and long lifetime component which can be utilized in imaging applications.

  5. High-spin intermediates of the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine

    Directory of Open Access Journals (Sweden)

    Sergei V. Chapyshev

    2013-04-01

    Full Text Available In contrast to theoretical expectations, the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine in argon at 5 K gives rise to EPR peaks of just two triplet mononitrenes, two quintet dinitrenes, and a septet trinitrene. EPR spectral simulations in combination with DFT calculations show that observable nitrenes can be assigned to triplet 2,4-diazido-3-chloro-5-fluoropyridyl-6-nitrene (DT = 1.026 cm−1, ET = 0, triplet 2,6-diazido-3-chloro-5-fluoropyridyl-4-nitrene (DT = 1.122 cm−1, ET = 0.0018 cm−1, quintet 4-azido-3-chloro-5-fluoropyridyl-2,6-dinitrene (DQ = 0.215 cm−1, EQ = 0.0545 cm−1, quintet 2-azido-3-chloro-5-fluoropyridyl-4,6-dinitrene (DQ = 0.209 cm−1, EQ = 0.039 cm−1 and septet 3-chloro-5-fluoropyridyl-2,4,6-trinitrene (DS = −0.1021 cm−1, ES = −0.0034 cm−1. Preferential photodissociation of the azido groups located in ortho-positions to the fluorine atom of pyridines is associated with strong π-conjugation of these groups with the pyridine ring. On photoexcitation, such azido groups are more efficiently involved in reorganization of the molecular electronic system and more easily adopt geometries of the locally excited predissociation states.

  6. Combining regio- and enantioselectivity of lipases for the preparation of (R)-4-chloro-2-butanol.

    Science.gov (United States)

    Méndez, Jonh J; Oromi, Mireia; Cervero, Maria; Balcells, Mercè; Torres, Mercè; Canela, Ramon

    2007-01-01

    Preparation of 98% ee (R)-4-chloro-2-butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435), C. rugosa, Rhizomucor miehei (Lipozyme IM), Burkolia cepacia, and resting cells of Rhizopus oryzae and Aspergillus flavus. The influence of the enzyme, the solvent, the temperature, and the alkyl chain length on the selectivity of hydrolyzes of isomeric mixtures of chlorohydrin esters is described. Regioselectivity was higher than 95% for some of the tested lipases. Novozym 435 allowed preparation of the (R)-4-chloro-2-butanol after 15 min of reaction at 30-40 degrees C. (c) 2006 Wiley-Liss, Inc.

  7. CCDC 940299: Experimental Crystal Structure Determination : (mu~2~-Chloro)-(mu~2~-2-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-2-phenyl-1-(phenyl(phenylethynyl)phosphanyl)ethenyl)-chloro-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-palladium-platinum benzene solvate

    KAUST Repository

    Chen, Shuli

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  8. CCDC 940295: Experimental Crystal Structure Determination : (mu~2~-Chloro)-(mu~2~-2-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-2-phenyl-1-(phenyl(phenylethynyl)phosphanyl)ethenyl)-chloro-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-di-palladium acetone dichloromethane solvate

    KAUST Repository

    Chen, Shuli

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  9. CCDC 940296: Experimental Crystal Structure Determination : (mu~2~-Chloro)-(mu~2~-2-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-2-phenyl-1-(phenyl(phenylethynyl)phosphanyl)ethenyl)-chloro-(1-(1-(dimethylamino)ethyl)naphthalen-2-yl)-palladium-platinum acetone dichloromethane solvate

    KAUST Repository

    Chen, Shuli

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  10. Derivatives of benzimidazole: vasodilator activity of 2-(p-chloro-alpha-hydroxybenzyl)-benzimidazole hydrochloride. Preliminary study.

    Science.gov (United States)

    Demenge, P; Carraz, G; Luu Duc, C; Silice, C

    1979-01-01

    The effects of 2-(p-chloro-alpha-hydroxybenzyl)-benzimidazole hydrochloride (HBBPC) have been studied in the rabbit and rat. Most of these studies were performed comparatively with reference vasodilators and papaverine. HBBPC vasodilator activity is nearly the same as that of papaverine in the isolated rabbit ear. The characteristic of the vasoactive action of HBBPC seems to reside in its duration. The mechanism of action of HBBPC seems of peripheral type, that is to say it acts on the vascular smooth muscle.

  11. Growth and characterization of 4-chloro-3-nitrobenzophenone single crystals using vertical Bridgman technique

    Energy Technology Data Exchange (ETDEWEB)

    Aravinth, K., E-mail: anandcgc@gmail.com; Babu, G. Anandha, E-mail: anandcgc@gmail.com; Ramasamy, P., E-mail: anandcgc@gmail.com [Centre for Crystal Growth, SSN College of Engineering, Kalavakkam -603110, Tamilnadu (India)

    2014-04-24

    4-chloro-3-nitrobenzophenone (4C3N) has been grown by using vertical Bridgman technique. The grown crystal was confirmed by Powder X-ray diffraction analysis. The crystalline perfection of the grown crystal was examined by high-resolution X-ray diffraction study. The fluorescence spectra of grown 4C3N single crystals exhibit emission peak at 575 nm. The micro hardness measurements were used to analyze the mechanical property of the grown crystal.

  12. Fourier transform infrared and FT-Raman spectra, assignment, ab initio, DFT and normal co-ordinate analysis of 2-chloro-4-methylaniline and 2-chloro-6-methylaniline.

    Science.gov (United States)

    Arjunan, V; Mohan, S

    2009-03-01

    The Fourier transform infrared (FTIR) and FT-Raman spectra of 2-chloro-4-methylaniline and 2-chloro-6-methylaniline have been measured in the range 4000-400 and 4000-100cm(-1), respectively. Utilising the observed FTIR and FT-Raman data, a complete vibrational assignment and analysis of the fundamental modes of the compounds were carried out. The vibrational frequency which were determined experimentally are compared with those obtained theoretically from ab initio HF and DFT gradient calculations employing the HF/6-31G(d,p) and B3LYP/6-31G(d,p) methods for optimised geometries. The geometries and normal modes of vibration obtained from the HF and DFT methods are in good agreement with the experimental data. The normal co-ordinate analysis was also carried out on the basis of ab initio force fields utilising Wilson's FG matrix method. The manifestations of NH-pi interactions and the influence of bulky chlorine and methyl group on the vibrational modes of the amino group are investigated.

  13. Ruthenium(II) carbonyl compounds with the 4'-chloro-2,2':6',2''-terpyridine ligand.

    Science.gov (United States)

    Tatikonda, Rajendhraprasad; Haukka, Matti

    2017-04-01

    Two ruthenium carbonyl complexes with the 4'-chloro-2,2':6',2''-terpyridine ligand (tpy-Cl, C 15 H 10 ClN 3 ), i.e. [RuCl(tpy-Cl)(CO) 2 ][RuCl 3 (CO) 3 ] (I) [systematic name: cis -di-carbonyl-chlorido(4'-chloro-2,2':6',2''-terpyridine-κ 3 N )ruthenium(II) fac -tricarbonyltri-chlorido-ruthenate(II)], and [RuCl 2 (tpy-Cl)(CO) 2 ] (II) [ cis -dicarbonyl- trans -di-chlorido(4'-chloro-2,2':6',2''-terpyridine-κ 2 N 1 , N 1' )ruthenium(II)], were synthesized and characterized by single-crystal X-ray diffraction. The Ru II atoms in both centrosymmetric structures (I) and (II) display similar, slightly distorted octa-hedral coordination spheres. The coordination sphere in the complex cation in compound (I) is defined by three N atoms of the tridentate tpy-Cl ligand, two carbonyl carbon atoms and one chlorido ligand; the charge is balanced by an octa-hedral [Ru(CO) 3 Cl 3 ] - counter-anion. In the neutral compound (II), the tpy-Cl ligand coordinates to the metal only through two of its N atoms. The coordination sphere of the Ru II atom is completed by two carbonyl and two chlorido ligands. In the crystal structures of both (I) and (II), weak C-H⋯Cl inter-actions are observed.

  14. Catecholamine uptake sites: characterization, localization, and a role in the production of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinsonism

    International Nuclear Information System (INIS)

    Javitch, J.A.

    1985-01-01

    Dopamine and norepinephrine are inactivated by specific high affinity transport systems which mediate the recapture of the amines into presynaptic nerve terminals. [ 3 H]Maxindol labels neuronal dopamine uptake sites in corpus striatum membranes and neuronal norepinephrine uptake sites in cerebral cortex and submaxillary/sublingual gland membranes. The potencies of various inhibitors of biogenic amine uptake in reducing [ 3 H]mazindol binding in striatal membranes correlate with their potencies for inhibition of neurona [ 3 H]dopamine accumulation, whereas their potencies in reducing [ 3 H]mazindol binding to cortical and salivary gland membranes correlate with their potencies for inhibition of neuronal [ 3 H]norepinephrine accumulation. The association of [ 3 H]mazindol binding sites with neuronal dopamine uptake sites in the corpus striatum is further supported by the reduction of [ 3 H]mazindol binding sites in striatal membranes following destruction of dopaminergic neurons by 6-hydroxydopamine. Similarly, destruction of noradrenergic neurons by N-(2-chloro-ethyl)-N-ethyl-2-bromobenzylamine(DSP-4) decreases [ 3 H]mazindol binding to cortical membranes. Dopamine and norepinephrine uptake sites in rat brain have been differentially visualized using [ 3 H]mazindol autoradiography. N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) produces neuropathologic and clinical abnormalities in humans and animals that closely resemble idiopathic Parkinson disease. [ 3 H]MPTP binds with high affinity to brain membranes. The chemical specificity of the binding sites corresponds to structure-activity requirements for neurotoxicity

  15. 1-Acetyl-5-ferrocenyl-3-phenyl-2-pyrazoline

    Directory of Open Access Journals (Sweden)

    Orhan Büyükgüngör

    2009-02-01

    Full Text Available In the title compound, [Fe(C5H5(C16H15N2O], the pyrazoline ring and the phenyl ring are nearly coplanar, making a dihedral angle of 6.54 (2°, while the substituted cyclopentadienyl ring is twisted out of the pyrazoline ring plane by 81.32 (1°. The molecules in the crystal structure are held together by weak C—H...O intermolecular hydrogen bonds and two C—H...π interactions.

  16. N-{2-[N-(4-Methylphenyloxamoyl]phenyl}propanamide

    Directory of Open Access Journals (Sweden)

    Humayun Pervez

    2010-07-01

    Full Text Available The title compound, C18H18N2O3, is the product of the heterocyclic ring cleavage at position 2 of 1-propionylisatin. Two centrosymmetric cyclic motifs, viz. R22(14 and R22(18, are formed by N—H...O hydrogen bonds with the propanamide and aminophenyl units, respectively, as the N—H donors. These motifs combine into two C22(8 chain motifs parallel to the b axis. The chain structure is stabilized by C—H...π interactions between the benzene rings, where C—H is from the phenyl ring of the cleaved part of 1-propionylisatin.

  17. Polymerization of N-(fluoro phenyl) maleimides. [. gamma. radiation

    Energy Technology Data Exchange (ETDEWEB)

    Barrales-Rienda, J.M.; Ramos, J.G.; Chaves, M.S.

    1979-01-01

    Poly(N-aryl maleimide)s of characteristic structures have been synthesized and some of their physical properties studied. The polymerization of N-(fluoro phenyl) maleimides by free-radical initiation in bulk or in solution and by anionic catalyst have been studied to compare the characteristics of polymerization by ..gamma..-ray irradiation with that by free-radical initiation. The polymers were characterized by elemental analysis, intrinsic viscosity, spectroscopy (IR and NMR), programmed thermogravimetric analysis, and x-ray diffraction. Spectra of polymers prepared by radiation and anionic polymerization were nearly identical with those of polymers prepared by free-radical polymerization initiated by azobisisobutyronitrile in bulk or in solution and by the self-initiated thermal polymerization. A variety of reaction conditions were tried, but all attempts to change the molecular structure of the polymers were unsuccessful. Rates of thermal degradation for poly(N-(fluoro phenyl) maleimide)s have been analyzed by using a multiple-heating-rate procedure. Overall activation energy, order of reaction, and frequency factor have been evaluated. 6 figures, 8 tables.

  18. Thermolysis of surface-immobilized phenethyl phenyl ether

    Energy Technology Data Exchange (ETDEWEB)

    Britt, P.F.; Buchanan, A.C. III; Hitsman, V.M.

    1991-01-01

    Our research has focused on modeling the constraints on free-radical reactions that might be imposed in coal as a consequence of its cross-linked macromolecular structure by covalently bonding diphenylalkanes to an inert silica surface. A surface-immobilized phenethyl phenyl ether ({approx}PhCH{sub 2}CH{sub 2}POh, or {approx}PPE-3) has been prepared as a model for ether linkages in lignin by the condensation of p-HOPhCH{sub 2}CH{sub 2}OPh with the surface hydroxyls of a high purity fumed silica. Thermolysis of {approx}PPE-3 at saturation surface coverage at 375{degree}C produces {approx}PhCH = CH{sub 2} and PhOH as the major products which are consistent with the proposed free-radical chain mechanism for the decomposition of fluid-phase phenethyl phenyl ether. However, significant quantities of {approx}PhCH{sub 3} and PhCHO (ca. 18% of the products) are produced indicating the emergence of a new reaction pathway on the surface. The mechanism for the decomposition of {approx}PPE-3 will be discussed in light of this new information. 18 refs., 1 fig.

  19. Red Emitting Phenyl-Polysiloxane Based Scintillators for Neutron Detection

    International Nuclear Information System (INIS)

    Dalla Palma, Matteo; Quaranta, Alberto; Marchi, Tommaso; Gramegna, Fabiana; Cinausero, Marco; Carturan, Sara; Collazuol, Gianmaria

    2013-06-01

    In this work, the performances of new red emitting phenyl- substituted polysiloxane based scintillators are described. Three dyes were dispersed in a phenyl-polysiloxane matrix in order to shift the scintillation wavelength towards the red part of the visible spectrum. PPO, Lumogen Violet (BASF) and Lumogen Red (BASF) were mixed to the starting resins with different wt. % and the analysis of the different samples was performed by means of fluorescence measurements. The scintillation yield to alpha particles at the different dye ratios was monitored by detecting either the full spectrum or the red part of the emitted light. Finally, thin red scintillators with selected compositions were coupled to Avalanche Photodiode sensors, which are usually characterized by higher efficiency in the red part of the spectrum. An increased light output of about 17% has been obtained comparing the red scintillators to standard blue emitting systems. Preliminary results on the detection of fast neutrons with the APD-red scintillator system are also presented. (authors)

  20. Ideal gas thermodynamic properties for the phenyl, phenoxy, and o-biphenyl radicals

    Science.gov (United States)

    Burcat, A.; Zeleznik, F. J.; Mcbride, B. J.

    1985-01-01

    Ideal gas thermodynamic properties of the phenyl and o-biphenyl radicals, their deuterated analogs and the phenoxy radical were calculated to 5000 K using estimated vibrational frequencies and structures. The ideal gas thermodynamic properties of benzene, biphenyl, their deuterated analogs and phenyl were also calculated.

  1. 2-(4-Methylpiperazin-1-yl-4-phenyl-6-(thiophen-2-yl-pyridine-3-carbonitrile

    Directory of Open Access Journals (Sweden)

    Nawal Mishriky

    2013-02-01

    Full Text Available 2-(4-Methylpiperazin-1-yl-4-phenyl-6-(thiophen-2-yl-pyridine-3-carbonitrile (4 was synthesized via nucleophilic substitution reaction of 1-methylpiperazine with 2-bromo analogue 3. The latter was obtained through bromination (Br2/AcOH of 2-[3-oxo-1-phenyl-3-(thiophen-2-ylpropyl]malononitrile (2.

  2. Synthesis, characterization and crystal structure of 6-Chloro-4,4‧-dimethyl-2,2‧-bipyridine and 4,4‧-Dimethyl 2,2‧-bipyridine N-Oxide

    Science.gov (United States)

    Conterosito, Eleonora; Magistris, Claudio; Barolo, Claudia; Croce, Gianluca; Milanesio, Marco

    2016-03-01

    The synthesis, the NMR characterization and the crystal structure of 6-Chloro 4,4‧-dimethyl 2,2‧-bipyridine and of the reaction intermediate 4,4‧-Dimethyl 2,2‧-bipyridine N-Oxide are here reported. The target compound crystallizes in the orthorhombic system while the intermediate is monoclinic. In both structures, the molecules are linked by weak interactions. The structure of the reaction intermediate N-oxide is characterized by a dihedral angle between the two phenyl rings of 161.77° while the other is almost planar with a dihedral angle of 179.15°. The crystal packing was investigated, also with the aid of Hirshfeld surface analysis. In the N-oxide reaction intermediate the packing is governed by CH-O interactions, while in the product the packing is simply driven by minimizing the voids and thus maximizing the density, with a prevalence of H•••H and C•••H contacts, as indicated by fingerprint decomposition analysis.

  3. Cytotoxicity, genotoxicity, and mutagenicity of 1-chloro-2-hydroxy-3-butene and 1-chloro-3-buten-2-one, two alternative metabolites of 1,3-butadiene.

    Science.gov (United States)

    Liu, Xin-Jie; Zeng, Fang-Mao; An, Jing; Yu, Ying-Xin; Zhang, Xin-Yu; Elfarra, Adnan A

    2013-08-15

    The cytotoxicity, genotoxicity, and mutagenicity of 1-chloro-2-hydroxy-3-butene (CHB), a known in vitro metabolite of the human carcinogen 1,3-butadiene, have not previously been investigated. Because CHB can be bioactivated by alcohol dehydrogenases to yield 1-chloro-3-buten-2-one (CBO), a bifunctional alkylating agent that caused globin-chain cross-links in erythrocytes, in the present study we investigated the cytotoxic and genotoxic potential of CHB and CBO in human normal hepatocyte L02 cells using the MTT assay, the relative cloning efficiency assay and the comet assay. We also investigated the mutagenic potential of these compounds with the Ames test using Salmonella strains TA1535 and TA1537. The results provide clear evidence for CHB and CBO being both cytotoxic and genotoxic with CBO being approximately 100-fold more potent than CHB. Interestingly, CHB generated both single-strand breaks and alkali-labile sites on DNA, whereas CBO produced only alkali-labile sites. CHB did not directly result in DNA breaks, whereas CBO was capable of directly generating breaks on DNA. Interestingly, both compounds did not induce DNA cross-links as examined by the comet assay. The Ames test results showed that CHB induced point mutation but not frameshift mutation, whereas the toxic effects of CBO made it difficult to reliably assess the mutagenic potential of CBO in the two strains. Collectively, the results suggest that CHB and CBO may play a role in the mutagenicity and carcinogenicity of 1,3-butadiene. Copyright © 2013 Elsevier Inc. All rights reserved.

  4. Synthesis, characterization and corrosion inhibition properties of benzamide-2-chloro-4-nitrobenzoic acid and anthranilic acid-2-chloro-4-nitrobenzoic acid for mild steel corrosion in acidic medium

    Science.gov (United States)

    Pandey, Archana; Verma, Chandrabhan; Singh, B.; Ebenso, Eno E.

    2018-03-01

    The present study deals with the synthesis of two new compounds namely, benzamide - 2-chloro-4-nitrobenzoic acid (BENCNBA) and anthranilic acid-2-chloro-4-nitrobenzoic acid (AACNBA) using solid phase reactions. The phase diagram studies revealed that formation of the investigated compounds occurs in 1:1 molar ratio. The synthesized compounds were characterized using several spectral techniques such as FT-IR, 1H and 13C NMR, UV-Vis, powder X-ray diffraction (PXRD). Single crystal XRD (SCXRD) study showed that both BENCNBA and AACNBA compounds crystallize in triclinic crystal system with P-1 space group. Further, the presence of intermolecular hydrogen bonding between the constituent components was also supported by single crystal X-ray diffraction (SCXRD) method. Heat of mixing, entropy of fusion, roughness parameter, interfacial energy and excess thermodynamic functions have also been computed using the enthalpy of fusion values derived from differential scanning calorimeter (DSC) study. The inhibition effect of BENCNBA and AACNBA on the mild steel corrosion in hydrochloric acid solution was tested using electrochemical methods. Electrochemical impedance spectroscopy (EIS) study revealed that both BENCNBA and AACNBA behaved as interface corrosion inhibitors and showed maximum inhibition efficiencies of 95.71% and 96.42%, respectively at 400 ppm (1.23 × 10-3 M) concentration. Potentiodynamic polarization (PDP) measurements suggested that BENCNBA and AACNBA acted as mixed type corrosion inhibitors. EIS and PDP results showed that BENCNBA and AACNBA act as efficient corrosion inhibitors for mild steel and their inhibition efficiencies enhances on increasing their concentrations.

  5. Phenyl-β-D-glucopyranoside and Phenyl-β-D-galactopyranoside Dimers: Small Structural Differences but Very Different Interactions

    Directory of Open Access Journals (Sweden)

    Imanol Usabiaga

    2018-02-01

    Full Text Available We report a combination of laser spectroscopy in molecular jets and quantum mechanical calculations to characterize the aggregation preferences of phenyl-β-D-glucopyranoside (β-PhGlc and phenyl-β-D-galactopyranoside (β-PhGal homodimers. At least two structures of β-PhGlc dimer were found maintaining the same intramolecular interactions of the monomers, but with additional intermolecular interactions between the hydroxyl groups. Several isomers were also found for the dimer of β-PhGal forming extensive hydrogen bond networks between the interacting molecules, of very different shape. All the species found present several CH•••π and OH•••π interactions that add stability to the aggregates. The results show how even the smallest change in a substituent, from axial to equatorial position, plays a decisive role in the formation of the dimers. These conclusions reinforce the idea that the small structural changes between sugar units are amplified by formation of intra and intermolecular hydrogen bond networks, helping other molecules (proteins, receptors to easily read the sugar code of glycans.

  6. Development of homogeneous binding assays based on fluorescence resonance energy transfer between quantum dots and Alexa Fluor fluorophores.

    Science.gov (United States)

    Nikiforov, Theo T; Beechem, Joseph M

    2006-10-01

    We studied the fluorescence resonance energy transfer (FRET) between quantum dots emitting at 565, 605, and 655 nm as energy donors and Alexa Fluor fluorophores with absorbance maxima at 594, 633, 647, and 680 nm as energy acceptors. As a first step, we prepared covalent conjugates between all three types of quantum dots and each of the Alexa Fluor fluorophores that could act as an energy acceptor. All of these conjugates displayed efficient resonance energy transfer. Then we prepared covalent conjugates of these quantum dots with biotin, fluorescein, and cortisol and established that the binding of these conjugates to suitable Alexa Fluor-labeled antibodies and streptavidin (in the case of biotin) can be efficiently detected by measuring the resonance energy transfer in homogeneous solutions. Finally, based on these observations, competitive binding assays for these three small analytes were developed. The performance of these assays as a function of the degree of labeling of the quantum dots was evaluated. It was found that decreasing the degree of loading of the quantum dots leads to decreases of the limits of detection. The results show the great potential of this FRET system for the development of new homogeneous binding assays.

  7. Purification and characterization of the 3-chloro-4-hydroxy-phenylacetate reductive dehalogenase of Desulfitobacterium hafniense

    DEFF Research Database (Denmark)

    Christensen, Nina; Ahring, Birgitte Kiær; Wohlfarth, Gert

    1998-01-01

    The membrane-bound 3-chloro-4-hydroxyphenylacetate (Cl-OHPA) reductive dehalogenase from the chlorophenol- educing anaerobe Desulfitobacterium hafniense was purified 11.3-fold to apparent homogeneity in the presence of the detergent CHAPS. The purified dehalogenase catalyzed the reductive...... dechlorination of Cl-OHPA to 4-hydroxyphenylacetate with reduced methyl viologen as the electron donor at a specific activity of 103.2 nkat/mg protein. SDS-PAGErevealed a single protein band with an apparent molecular mass of 46.5 kDa. The enzyme contained 0.68±0.2 mol corrinoid, 12.0±0.7 mol iron, and 13...

  8. Biophysical properties of phenyl succinic acid derivatised hyaluronic acid

    DEFF Research Database (Denmark)

    Neves-Petersen, Maria Teresa; Klitgaard, Søren; Skovsen, Esben

    2010-01-01

    Modification of hyaluronic acid (HA) with aryl succinic anhydrides results in new biomedical properties of HA as compared to non-modified HA, such as more efficient skin penetration, stronger binding to the skin, and the ability to blend with hydrophobic materials. In the present study, hyaluronic...... acid has been derivatised with the anhydride form of phenyl succinic acid (PheSA). The fluorescence of PheSA was efficiently quenched by the HA matrix. HA also acted as a singlet oxygen scavenger. Fluorescence lifetime(s) of PheSA in solution and when attached to the HA matrix has been monitored...... with ps resolved streak camera technology. Structural and fluorescence properties changes induced on HA-PheSA due to the presence of singlet oxygen were monitored using static light scattering (SLS), steady state fluorescence and ps time resolved fluorescence studies. SLS studies provided insight...

  9. SYNTHESIS OF ALLYL PHENYL ETHER AND CLAISEN REARRANGEMENT

    Directory of Open Access Journals (Sweden)

    Gagik Torosyan

    2011-12-01

    Full Text Available It has been established the possibility for phenol allylation on natural zeolites and them analogs. Here is demonstrated the synthesis of allyl phenol, which has wide industrial applications. The offered method in comparison with the traditional methods has more advantages – higher selectivity, smaller material and power resources consumption. It has been obtained the mixture of allylating phenols (30% in general with allyl phenyl ether (1 with 80% yields. At 600 K is obtained allylphenyl ether, at 700 K beginning the formation of allyl phenols, which is the result of direct C-allylation of the aromatic ring. It has been investigated the possibility of Claisen rearrangement in the same conditions. All of that are established by gas-liquid chromatography and liquid chromatography data.

  10. The Exotic Excited State Behavior of 3-PHENYL-2-PROPYNENITRILE

    Science.gov (United States)

    Jawad, Khadija M.; Viquez Rojas, Claudia I.; Slipchenko, Lyudmila V.; Zwier, Timothy S.

    2017-06-01

    3-phenyl-2-propynenitrile (Ph-C≡C-C≡N) is of interest to the study of Titan's atmosphere as it is a likely product of the photochemical reaction between two known species in that environment: benzene and cyanoacetylene. The gas phase jet-cooled resonant two-photon ionization, laser induced fluorescence, and preliminary dispersed fluorescence spectra were previously reported without firm assignments due to the scarcity of totally symmetric vibrations and the prevalence of strong bands of b2 and b1 symmetry vibrations. These had called into question the identity and geometry of the excited state(s) involved in the transitions. We will here present the completed set of dispersed fluorescence data along with an analysis of the potential energy surfaces and vibronic coupling characteristic of the close-lying excited states in this intriguing molecule.

  11. Enhanced biological activity of carotenoids stabilized by phenyl groups.

    Science.gov (United States)

    You, Ji Suk; Jeon, Sunhwa; Byun, Youn Jung; Koo, Sangho; Choi, Shin Sik

    2015-06-15

    Carotenoids are lipid soluble food ingredients with multifunction including antioxidant and anticancer activities. However, carotenoids are destructively oxidized upon reaction with radicals resulting in toxic effects on biological systems. Two synthetic carotenoids (BAS and BTS) containing the aromatic phenyl groups with a para-substituent (OMe and Me, respectively) at C-13 and C-13' position were prepared in order to overcome a structural instability of carotenoid. Both BAS and BTS exerted stronger radical scavenging activity than β-carotene in DPPH and ABTS assays. In particular, BTS significantly reduced in vivo ROS (reactive oxygen species) levels and improved body growth and reproduction of Caenorhabditiselegans. BTS has a great potential for the advanced and modified carotenoid material with stability leading to enhanced bioavailability. Copyright © 2015 Elsevier Ltd. All rights reserved.

  12. 1-Methyl-5-nitro-3-phenyl-1H-indazole

    Directory of Open Access Journals (Sweden)

    Mohammed Naas

    2016-06-01

    Full Text Available The title compound, C14H11N3O2, crystallizes with two molecules in the asymmetric unit. The indazole ring system and the nitro group are nearly coplanar, with the largest deviations from the mean plane being 0.070 (4 Å in one molecule and 0.022 (3 Å in the second. The dihedral angle between the mean plane through the phenyl ring and the mean plane of the indazole ring system is of 23.24 (18° in the first molecule and 26.87 (18° in the second. In the crystal, molecules are linked by two C—H...O hydrogen bonds, forming linear zigzag tapes running along the c-axis direction, and by π–π stacking of molecules along the b axis, generating a three-dimensional structure.

  13. Cleavage reactions of the lead-carbon bond II. The reaction of tetraorganolead compounds with 1-chloro-1,2,3-benzotriazole

    NARCIS (Netherlands)

    Pant, Bhuvan C.; Noltes, J.G.

    1972-01-01

    1-(Triorganoplumbyl)-1,2,3-benzotriazoles were synthesized in excellent yields by the cleavage of an organic group from tetraorganolead derivatives with 1-chloro-1,2,3-benzotriazole in benzene at 50–60°. The order of ease of cleavage of organic groups by 1-chloro-l,2,3-benzotriazole in the case of

  14. Design of NIR Chromenylium-Cyanine Fluorophore Library for "Switch-ON" and Ratiometric Detection of Bio-Active Species In Vivo.

    Science.gov (United States)

    Wei, Yanfen; Cheng, Dan; Ren, Tianbing; Li, Yinhui; Zeng, Zebing; Yuan, Lin

    2016-02-02

    The real-time monitoring of key biospecies in the living systems has received thrusting attention during the past decades. Specifically, fluorescent detection based on near-infrared (NIR) fluorescent probes is highly favorable for live cells, live tissues, and even animal imaging, owing to the substantial merits of the NIR window, such as minimal phototoxicity, deep penetration into tissues, and low autofluorescence background. Nevertheless, developing potent NIR fluorescent probes still poses serious challenges to the chemists because traditional NIR fluorophores are less tunable than visible-wavelength fluorophores. To address this issue, here we report a set of novel NIR hybrid fluorophores, namely, the hybrid chromenylium-cyanine fluorophore (CC-Fluor), in which both the fluorescence intensity and the emission wavelength can be easily adjusted by the conformational changes and substitution groups. Compared to known NIR fluorophores, the new CC-Fluors are substantially advantageous for NIR probe development: (1) CC-Fluors display tunable and moderate Stokes shifts and quantum yields; (2) the fluorophores are stable at physiological conditions after long-term incubation; (3) the absorption maxima of CC-Fluors coincide with the common laser spectral lines in mainstream in vivo imaging systems; (4) most importantly, CC-Fluors can be easily modified to prepare NIR probes targeting various biospecies. To fully demonstrate the practical utility of CC-Fluors, we report two innovative NIR probes, a ratiometric pH probe and a turn-on Hg(2+) probe, both are successfully employed in live animal imaging. Hence, the detailed studies allow us to confirm that CC-Fluors can work as an excellent platform for developing NIR probes for the detection of species in living systems.

  15. Identification of α-Chloro-2,2',4,4',6,6'-Hexanitrobibenzyl as an Impurity in Hexanitrostilbene

    Science.gov (United States)

    Bellamy, A. J.

    2010-01-01

    The final intermediate in the Shipp synthesis of 2,2‧,4,4‧,6,6‧-hexanitrostilbene (HNS) from TNT, α-chloro-2,2‧,4,4‧,6,6‧-hexanitrobibenzyl, has been extracted and characterized by nuclear magnetic resonance (NMR) spectroscopy, chlorine elemental analysis, and high-performance liquid chromatography (HPLC). It has also been shown that digestion in NMP of HNS containing α-chlorohexanitrobibenzyl generates another chlorine-containing by-product, 2-chloro-2‧,4,4‧,6,6‧-pentanitrostilbene. This too has been characterized by NMR spectroscopy, chlorine elemental analysis, and HPLC.

  16. Crystal structures and quantum chemical calculations of dichloro[4-(dimethylamino)phenyl]arsine and tris[4-(dimethylamino)phenyl]arsine

    Science.gov (United States)

    Bani-Fwaz, Mutasem Z.; Fazary, Ahmed E.; Becker, Gerd

    2017-12-01

    Dichloro[4-(dimethylamino)phenyl]arsine (1) and tris[4-(dimethylamino)phenyl]arsine (2) were synthesized and characterized using single crystal X-ray diffraction studies, NMR spectroscopy, IR spectroscopy and elemental analyses techniques. The X-ray structure analysis of 1 (P1bar , triclinic, Z = 4; R1 = 0.0478) revealed two crystallographically independent molecules in the asymmetric part of the unit cell. The average Assbnd Cl bond (220.6 p.m.) is found to be slightly longer than that of arsenic(III) chloride (216.1 or 216.2 p.m.), but to be rather similar to that in the orthorhombic modification of chlorobis[2,4,6-tris(trifluoromethyl)phenyl]arsine (219.2 p.m.). Mean As-Caryl (191.7 p.m.) and Caryl-N bond lengths (135.9 p.m.) suggest extended electronic interactions between the dichloroarsanyl group, the π-electron system of the arene ring and the nitrogen lone pair. In both molecules the nitrogen atoms are found in a planar coordination sphere; the sums of bond angles vary only slightly between 359.1° for 1a and 359.9° for 1b. In contrast to these observations, sums of bond angles of 292.7° for 1a and 293.98° for 1b indicate a pyramidal coordination sphere at arsenic. As well, the X-ray structure analysis of 2 (P1bar , triclinic, Z = 2; R1 = 0.0347) reveals bond lengths and angles at arsenic (Assbnd C 194.9 p.m., Csbnd Assbnd C 99.3°, Assbnd Csbnd C 121.3°) as to be expected and obtained for similar compounds such as triphenyl arsine or triphenyl arsine derivatives. The sums of angles at two of the nitrogen atoms amount to values of 353.6° and 356.1° and deviate significantly from the value of the third (348.1°). Hence, two of three dimethylamino groups are found to be almost planar, whereas the third group shows a coordination sphere which has to be classified as an intermediate between trigonal planar and trigonal pyramidal. The molecule shows a high degree of C3 pseudosymmetry; the sum of angles at arsenic amounts to 298.0°. The average Caryl

  17. Crystal structure of fac-[2-(4-methyl-5-phenyl-pyridin-2-yl)phenyl-κ2C1,N]bis-[2-(pyridin-2-yl)phenyl-κ2C1,N]iridium(III).

    Science.gov (United States)

    Lee, Chi-Heon; Moon, Suk-Hee; Park, Ki-Min; Kang, Youngjin

    2016-12-01

    In the title compound, [Ir(C 11 H 8 N) 2 (C 18 H 14 N)], the Ir III ion adopts a distorted octa-hedral coordination environment defined by three C , N -chelating ligands, one stemming from a 2-(4-phenyl-5-methyl-pyridin-2-yl)phenyl ligand and two from 2-(pyridin-2-yl)phenyl ligands, arranged in a facial manner. The Ir III ion lies almost in the equatorial plane [deviation = 0.0069 (15) Å]. In the crystal, inter-molecular π-π stacking inter-actions, as well as inter-molecular C-H⋯π inter-actions, are present, leading to a three-dimensional network.

  18. Phenyl galactopyranosides – {sup 13}C CPMAS NMR and conformational analysis using genetic algorithm

    Energy Technology Data Exchange (ETDEWEB)

    Wałejko, Piotr, E-mail: pwalejko@uwb.edu.pl [University of Bialystok, Institute of Chemistry, Pilsudskiego 11/4, 15-443 Bialystok (Poland); Paradowska, Katarzyna, E-mail: katarzyna.paradowska@wum.edu.pl [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland); Bukowicki, Jarosław [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland); Witkowski, Stanisław [University of Bialystok, Institute of Chemistry, Pilsudskiego 11/4, 15-443 Bialystok (Poland); Wawer, Iwona [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland)

    2015-08-18

    Highlights: • The structures of phenyl galactosides were studied by {sup 13}C CPMAS NMR. • The GAAGS method was used in conformational analysis of phenyl galactosides. • The rotation of the aglycone was investigated. • {sup 13}C CPMAS NMR supported by GIAO DFT calculations was used as a verification method. - Abstract: Structural analyses of four compounds (phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (1), phenyl β-D-galactopyranoside (2), phenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (3) and phenyl α-D-galactopyranoside (4)) have been performed using solid-state {sup 13}C MAS NMR spectroscopy and theoretical methods. Conformational analysis involved grid search and genetic algorithm (GAAGS). Low-energy conformers found by GAAGS were further optimized by DFT and chemical shifts were calculated using GIAO/DFT approach. {sup 13}C CPMAS NMR chemical shift of carbon C2 is indicative of the glycoside torsional angle. Separated or merged resonances of C2 and C6 suggest free rotation of phenyl ring in the solid phase.

  19. Chloro-1,4-dimethyl-9H-carbazole Derivatives Displaying Anti-HIV Activity

    Directory of Open Access Journals (Sweden)

    Carmela Saturnino

    2018-01-01

    Full Text Available Background: Despite the progress achieved by anti-retroviral drug research in the last decades, the discovery of novel compounds endowed with selective antiviral activity and reduced side effects is still a necessity. At present, the most urgent requirement includes the improvement of HIV (Human Immunodeficiency Virus prevention and sexual transmission and the development of new drugs to treat the chronic lifelong infection. Methods: Six chloro-1,4-dimethyl-9H-carbazoles (2a,b–4a,b have been prepared following opportunely modified known chemical procedures and tested in luciferase and Escherichia coli β-galactosidase expressing CD4+, CXCR4+, CCR5+ TZM-bl cells. Results and Conclusion: a preliminary biological investigation on the synthesized small series of chloro-1,4-dimethyl-9H-carbazoles has been carried out. Among all tested compounds, a nitro-derivative (3b showed the most interesting profile representing a suitable lead for the development of novel anti-HIV drugs.

  20. Metabolism of chinoform(5-chloro-7-iodo-8-quinolinol)-14C in dog

    International Nuclear Information System (INIS)

    Urakubo, Goro; Kido, Yasumasa; Ikebuchi, Hideharu; Nagamatsu, Kunisuke

    1975-01-01

    Chinoform (6-chloro-7-iodo-8-quinolinol)- 14 C (302.4μCi/83 mg) packed in a capsule was given orally to a dog weighing 10.5 kg, and the urine and feces were collected for 5 days after dosing. Excretion of a large portion of the radioactivity in urine and feces was observed on the 1st day and 3rd day after dosing. The total radioactivity in both excreta in 5 days was about 70% of dose. The urine was used for the study of metabolites. The urine was extracted with a mixture of benzene and pyridine (9:1), and an organic layer and an aqueous layer were obtained. Intact chinoform and 5-chloro-8-quinolinol (a deiodinated product of chinoform) were identified in the organic layer by radiochromatography and by an isotope dilution method. From the water layer of urine, glucuronides of chinoform and the deiodinated product, and sulfate of chinoform were identified as the metabolites. (author)

  1. 3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H-one

    Directory of Open Access Journals (Sweden)

    Orhan Büyükgüngör

    2012-05-01

    Full Text Available In the title compound, C14H11ClN2O2, the 2,3-dihydro-1,3-benzoxazole ring system is essentially planar [maximum deviation = 0.009 (2 Å] and makes a dihedral angle of 79.15 (7° with the phenyl ring. Intermolecular N—H...O and weak C—H...Cl hydrogen bonds occur in the crystal structure.

  2. 3,5-Bis(4-methoxyphenyl-1-phenyl-4,5-dihydro-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Zeliha Baktır

    2011-02-01

    Full Text Available In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å and it makes a dihedral angle of 18.5 (2° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2 and 80.6 (2°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [centriod–centroid distance = 3.891 (2 Å].

  3. Fast screening of glycosaminoglycan disaccharides by fluorophore-assisted carbohydrate electrophoresis (FACE): applications to biologic samples and pharmaceutical formulations.

    Science.gov (United States)

    Karousou, Evgenia; Asimakopoulou, Athanasia P; Zafeiropoulou, Vassiliki; Viola, Manuela; Monti, Luca; Rossi, Antonio; Passi, Alberto; Karamanos, Nikos

    2015-01-01

    Hyaluronan (HA), chondroitin sulfate (CS), and heparan sulfate (HS) are glycosaminoglycans (GAGs) with a great importance in biological processes as they participate in functional cell properties, such as migration, adhesion, and proliferation. A perturbation of the quantity and/or the sulfation of GAGs is often associated with pathological conditions. In this chapter, we present valuable and validated protocols for the analysis of HA-, CS-, and HS-derived disaccharides after derivatization with 2-aminoacridone and by using the fluorophore-assisted carbohydrate electrophoresis (FACE). FACE is a well-known technique and a reliable tool for a fast screening of GAGs, as it is possible to analyze 16 samples at the same time with one electrophoretic apparatus. The protocols for the gel preparation are based on the variations of the acrylamide/bisacrylamide and buffer concentrations. Different approaches for the extraction and purification of the disaccharides of various biologic samples and pharmaceutical preparations are also stressed.

  4. Nanoparticle-encapsulated vis- and NIR-emissive fluorophores with different fluorescence decay kinetics for lifetime multiplexing.

    Science.gov (United States)

    Hoffmann, Katrin; Behnke, Thomas; Grabolle, Markus; Resch-Genger, Ute

    2014-05-01

    Bioanalytical, clinical, and security applications increasingly require simple, efficient, and versatile strategies to measure an ever increasing number of analytes or events in parallel in a broad variety of detection formats as well as in conjunction with chromatographic separation techniques or flow cytometry. An attractive alternative to common optical multiplexing and encoding methods utilizing spectral multiplexing/color encoding and intensity encoding is lifetime multiplexing, which relies on the discrimination between different fluorescent reporters based on their fluorescence decay kinetics. Here, we propose a platform of surface-functionalizable polymeric nanoparticles stained with fluorophores differing in their fluorescence lifetimes as a new multiplexing and encoding approach. Proof-of-concept measurements with different sets of lifetime-encoded polystyrene nanoparticles are presented, obtained via staining of preformed particles with visible (vis)- and near-infrared (NIR)-emissive organic dyes, which display very similar absorption and emission spectra to enable excitation and detection at the same wavelengths, yet sufficiently different fluorescence decay kinetics in suspension, thereby minimizing instrumentation costs. Data analysis was performed with a linear combination approach in the lifetime domain. Our results and first cell experiments with these reporter sets underline the suitability of our multiplexing strategy for the discrimination between and the quantification of different labels. This simple and versatile concept can be extended to all types of fluorophores, thereby expanding the accessible time scale, and can be used, e.g., for the design of labels and targeted probes for fluorescence assays and molecular imaging, cellular imaging studies, and barcoding applications, also in conjunction with spectral and intensity encoding.

  5. An LED light source and novel fluorophore combinations improve fluorescence laparoscopic detection of metastatic pancreatic cancer in orthotopic mouse models.

    Science.gov (United States)

    Metildi, Cristina A; Kaushal, Sharmeela; Lee, Claudia; Hardamon, Chanae R; Snyder, Cynthia S; Luiken, George A; Talamini, Mark A; Hoffman, Robert M; Bouvet, Michael

    2012-06-01

    The aim of this study was to improve fluorescence laparoscopy of pancreatic cancer in an orthotopic mouse model with the use of a light-emitting diode (LED) light source and optimal fluorophore combinations. Human pancreatic cancer models were established with fluorescent FG-RFP, MiaPaca2-GFP, BxPC-3-RFP, and BxPC-3 cancer cells implanted in 6-week-old female athymic mice. Two weeks postimplantation, diagnostic laparoscopy was performed with a Stryker L9000 LED light source or a Stryker X8000 xenon light source 24 hours after tail-vein injection of CEA antibodies conjugated with Alexa 488 or Alexa 555. Cancer lesions were detected and localized under each light mode. Intravital images were also obtained with the OV-100 Olympus and Maestro CRI Small Animal Imaging Systems, serving as a positive control. Tumors were collected for histologic analysis. Fluorescence laparoscopy with a 495-nm emission filter and an LED light source enabled real-time visualization of the fluorescence-labeled tumor deposits in the peritoneal cavity. The simultaneous use of different fluorophores (Alexa 488 and Alexa 555), conjugated to antibodies, brightened the fluorescence signal, enhancing detection of submillimeter lesions without compromising background illumination. Adjustments to the LED light source permitted simultaneous detection of tumor lesions of different fluorescent colors and surrounding structures with minimal autofluorescence. Using an LED light source with adjustments to the red, blue, and green wavelengths, it is possible to simultaneously identify tumor metastases expressing fluorescent proteins of different wavelengths, which greatly enhanced the signal without compromising background illumination. Development of this fluorescence laparoscopy technology for clinical use can improve staging and resection of pancreatic cancer. Copyright © 2012 American College of Surgeons. Published by Elsevier Inc. All rights reserved.

  6. Exploring selectivity requirements for COX-2 versus COX-1 binding of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines using topological and physico-chemical parameters.

    Science.gov (United States)

    Chakraborty, Santanu; Sengupta, Chandana; Roy, Kunal

    2005-04-01

    Considering the current need for development of selective cyclooxygenase-2 (COX-2) inhibitors, an attempt has been made to explore physico-chemical requirements of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines for binding with COX-1 and COX-2 enzyme subtypes and also to explore the selectivity requirements. In this study, E-states of different common atoms of the molecules (calculated according to Kier & Hall), first order valence connectivity and physicochemical parameters (hydrophobicity pi, Hammett sigma and molar refractivity MR of different ring substituents) were used as independent variables along with suitable dummy parameters in the stepwise regression method. The best equation describing COX-1 binding affinity [n = 25, Q2 = 0.606, R(a)2 = 0.702, R2 = 0.752, R = 0.867, s = 0.447, F = 15.2 (df 4, 20)] suggests that the COX-1 binding affinity increases in the presence of a halogen substituent at R1 position and a p-alkoxy or p-methylthio substituent at R2 position. Furthermore, a difluoromethyl group is preferred over a trifluoromethyl group at R position for the COX-1 binding. The best equation describing COX-2 binding affinity [n = 32, Q2 = 0.622, R(a)2= 0.692, R2 = 0.732, R = 0.856, s = 0.265, F = 18.4 (df 4, 27)] shows that the COX-2 binding affinity increases with the presence of a halogen substituent at R1 position and increase of size of R2 substituents. However, it decreases in case of simultaneous presence of 3-chloro and 4-methoxy groups on the phenyl nucleus and in the presence of highly lipophilic R2 substituents. The best selectivity relation [n = 25, Q2 = 0.455, R(a)2 = 0.605, R2 = 0.670, R = 0.819, s = 0.423, F = 10.2 (df 4, 20)] suggests that the COX-2 selectivity decreases in the presence of p-alkoxy group and electron-withdrawing para substituents at R2 position. Again, a trifluoro group is conductive for the selectivity instead of a difluoromethyl group at R position. Furthermore, branching may also play significant role in

  7. 40 CFR 721.9750 - 2-Chloro-4,6-bis(substituted)-1,3,5-triazine, dihydrochloride.

    Science.gov (United States)

    2010-07-01

    ... terrestrial organisms and plants. Notice to users: Release to water restrictions apply. (ii) Disposal... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 2-Chloro-4,6-bis(substituted)-1,3,5-triazine, dihydrochloride. 721.9750 Section 721.9750 Protection of Environment ENVIRONMENTAL PROTECTION...

  8. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester. 721.304 Section 721.304 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances ...

  9. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  10. NMR study of the epoxidation of liquid hydrolyzed poly-butadiene and meta-chloro-per-benzoic acid

    International Nuclear Information System (INIS)

    Aguiar, Marcelo; Akcelrud, L.; Menezes, Sonia Cabral de

    1993-01-01

    This work presents a study concerning the selectivity of the different configurations of the double bond present in liquid hydrolyzed poly-butadiene towards the epoxidation reaction with meta-chloro-per-benzoic acid through hydrogen-1, carbon-13 NMR aiming the production of new materials, varying the epoxidation level

  11. A facile one-pot synthesis of (Z-α-chloro-α,β-unsaturated esters from alcohols

    Directory of Open Access Journals (Sweden)

    U. Karama

    2017-05-01

    Full Text Available Treatment of N-Chlorosuccinimide with (ethoxycarbonylmethylene-triphenylphosphorane followed by oxidation of alcohol using DMSO/SO3.Pyridine complex as a mild oxidant and trapping of the aldehydes constitutes a stereoselective single flask procedure for the preparation of Z-configured α-chloro-α,β-unsaturated esters.

  12. Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride

    DEFF Research Database (Denmark)

    Vilhelmsen, Mie Højer; Østergaard, Lars Frøsig; Nielsen, Mogens Brøndsted

    2008-01-01

    The reduction of 2-chloro-N-phenylpropanamide with LiAlH4 has been re-examined. In contrast to previous findings, we obtain in almost equal quantities two amines from this reaction, namely N-propylaniline and the rearranged product N-isopropylaniline. 2-Methyl-N-phenylaziridine is an intermediate...

  13. Effective photo-enhancement of cellular activity of fluorophore-octaarginine antisense PNA conjugates correlates with singlet oxygen formation, endosomal escape and chromophore lipophilicity

    DEFF Research Database (Denmark)

    Yarani, Reza; Shiraishi, Takehiko; Nielsen, Peter E.

    2018-01-01

    Photochemical internalization (PCI) is a cellular drug delivery method based on the generation of light-induced reactive oxygen species (ROS) causing damage to the endosomal membrane and thereby resulting in drug release to the cytoplasm. In our study a series of antisense fluorophore octaarginine...

  14. Studies on Novel N4-[4,6-Diaryl-2-pyrimidinyl]-7-chloro-4-quinolinamine and their Microbicidal Efficacy

    OpenAIRE

    Mehta, Arvind G.; Patel, Avnish A.

    2009-01-01

    The required chalcones 1a-h were prepared by reaction of substituted acetophenone with different aryl aldehyde, which in turn treated with guanidine nitrate, yielded 4-(substituted phenyl)-6-(substituted phenyl)-2-pyrimidinamine 2a-h. Novel pyrimidine quinoline clubbed molecules 3a-h have been prepared by reaction of 2a-h with 4,7-dichloroquinoline. All the compounds were characterized by elemental analysis and spectral studies. The newly synthesized compounds were evaluated for their antibac...

  15. The study of antimicrobial properties of immobilized fibrous N-chloro sulfonamides

    Directory of Open Access Journals (Sweden)

    V. N. Toropіn

    2016-12-01

    Full Text Available Aim. The determination of antibacterial and antifungal action of nonwoven form of N-chloro sulfonamides immobilized on a polypropylene fiber with a graft copolymer of styrene and divinylbenzene. Materials and methods. The object of the study was a non-woven form of sodium N-chloro sulfonamides immobilized on a polypropylene fiber with a graft copolymer of styrene and divinylbenzene. Determination of antibacterial and antifungal action of the material was carried out by the "agar plate" at the meat peptone agar (МPA. As the test cultures of microorganisms we used: E.coli, S.aureus and C.albicans. Microbial load was 1х107 TEM/ml. Results. The growing delay for such test microorganisms as E. coli strains, S.aureus and C.albicans fungi has been observed only for samples of material. Lack of microbial growth delay zones outside the samples occurs due to poor contact with the surface of the MPA. The method of "agar plate" has been changed to obtain reliable results of antibacterial and antifungal action of the material. The test material samples were placed in uncured MPA, the further experiment was carried out according to standard procedures of the "agar plates" method. Latency test microorganism growth around the sample material lies in the range 6,0 -7,0 mm – for E.coli; 16,0 -25,0 mm – for S.aureus; 4,0 -6,0 mm – for C.albicans. These results are explained by activation with the help of ammonium salts and amino acids, which release the active material of chlorine in case when the material contacts with the liquid nutrient medium. Evidently, this way the material will behave in contact with the skin of human (or animal. In contact with the dry skin covering the material will remain inactive, but in contact with the wound the release of active chlorine will occur within a specified period of time, whereby the material can protect the wound from infection. Conclusions. Antibacterial and antifungal properties of non-woven form of sodium N-chloro

  16. Theoretical investigation of tautomeric equilibrium in ortho-hydroxy phenyl Schiff bases

    Science.gov (United States)

    Kluba, M.; Lipkowski, P.; Filarowski, A.

    2008-10-01

    This Letter presents a study of the tautomeric equilibrium in ortho-hydroxy phenyl Schiff bases. The influence of substitution and solvent (simulated by the self-consistent reaction field model, SCRF) on the energy barrier of the transition state and on proton transfer is investigated. Dependencies of the HOMA and HOSE aromaticity indices on the molecular, transition state, and proton transfer forms were obtained. The state of chelate chain and phenyl ring aromaticity depending on the tautomeric equilibrium is studied.

  17. Aromatically C6- and C9-Substituted Phenanthro[9,10-d]imidazole Blue Fluorophores: Structure-Property Relationship and Electroluminescent Application.

    Science.gov (United States)

    Chen, Wen-Cheng; Yuan, Yi; Xiong, Yuan; Rogach, Andrey L; Tong, Qing-Xiao; Lee, Chun-Sing

    2017-08-09

    In this study, a series of aromatically substituted phenanthro[9,10-d]imidazole (PI) fluorophores at C6 and C9 (no. 6 and 9 carbon atoms) have been synthesized and systematically characterized by theoretical, thermal, photophysical, electrochemical, and electroluminescent (EL) studies. C6 and C9 modifications have positive influences on the thermal properties of the new materials. Theoretical calculations suggest that the C6 and the C9 positions of PI are electronically different. Theoretical and experimental evidences of intramolecular charge transfer (ICT) between two identical moieties attaching to the C6 and the C9 positions are observed. Photophysical properties of the fluorophores are greatly influenced by size and conjugation extent of the substituents as well as linking steric hindrance. It is found that the C6 and C9 positions afford moderate conjugated extension compared to the C2 modification. Moreover, ICT characteristics of the new fluorophores increase as the size of the substituted aromatic group, and are partially influenced by steric hindrance, with the anthracene and the pyrene derivatives having the strongest ICT excited properties. EL performances of the fluorophores were evaluated as host emitters or dopants in organic light-emitting devices (OLEDs). Most of the devices showed significantly improved efficiencies compared to the OLED using the nonmodified emitter. Among all the devices, a 5 wt % TPI-Py doped device exhibited excellent performances with an external quantum efficiency >5% at 1000 cd/m 2 and a deep-blue color index of (0.155, 0.065), which are comparable to the most advanced deep-blue devices. Our study can give useful information for designing C6/C9-modificated PI fluorophores and provide an efficient approach for constructing high-performance deep-blue OLEDs.

  18. Catecholamine uptake sites: characterization, localization, and a role in the production of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinsonism

    Energy Technology Data Exchange (ETDEWEB)

    Javitch, J.A.

    1985-01-01

    Dopamine and norepinephrine are inactivated by specific high affinity transport systems which mediate the recapture of the amines into presynaptic nerve terminals. (/sup 3/H)Maxindol labels neuronal dopamine uptake sites in corpus striatum membranes and neuronal norepinephrine uptake sites in cerebral cortex and submaxillary/sublingual gland membranes. The potencies of various inhibitors of biogenic amine uptake in reducing (/sup 3/H)mazindol binding in striatal membranes correlate with their potencies for inhibition of neurona (/sup 3/H)dopamine accumulation, whereas their potencies in reducing (/sup 3/H)mazindol binding to cortical and salivary gland membranes correlate with their potencies for inhibition of neuronal (/sup 3/H)norepinephrine accumulation. The association of (/sup 3/H)mazindol binding sites with neuronal dopamine uptake sites in the corpus striatum is further supported by the reduction of (/sup 3/H)mazindol binding sites in striatal membranes following destruction of dopaminergic neurons by 6-hydroxydopamine. Similarly, destruction of noradrenergic neurons by N-(2-chloro-ethyl)-N-ethyl-2-bromobenzylamine(DSP-4) decreases (/sup 3/H)mazindol binding to cortical membranes. Dopamine and norepinephrine uptake sites in rat brain have been differentially visualized using (/sup 3/H)mazindol autoradiography. N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) produces neuropathologic and clinical abnormalities in humans and animals that closely resemble idiopathic Parkinson disease. (/sup 3/H)MPTP binds with high affinity to brain membranes. The chemical specificity of the binding sites corresponds to structure-activity requirements for neurotoxicity.

  19. Solubility of 3-chloro-N-phenylphthalimide in ten organic solvents from T = (288.15 to 323.15) K: Determination and modelling

    International Nuclear Information System (INIS)

    Du, Cunbin; Xu, Renjie; Han, Shuo; Xu, Jian; Meng, Long; Wang, Jian; Zhao, Hongkun

    2016-01-01

    Highlights: • Solubility of 3-chloro-N-phenylphthalimide in ten solvents were determined. • The solubility were correlated with four models. • The solution properties were evaluated. - Abstract: The solubility of 3-chloro-N-phenylphthalimide in acetonitrile, methanol, n-propanol, isopropanol, n-butanol, 2-methyl-1-propanol, ethyl acetate, acetone, 1,4-dioxane and acetic acid were obtained experimentally with the high-performance liquid chromatography analysis at temperature ranging from (288.15 to 323.15) K under 0.1 MPa. The solubility values of 3-chloro-N-phenylphthalimide in those solvents increased with an increase in temperature, and decreased from high to low based on the following order: 1,4-dioxane > acetone > ethyl acetate > acetonitrile > acetic acid > (n-propanol, n-butanol) > (methanol, 2-methyl-1-propanol) > isopropanol. The obtained solubility data of 3-chloro-N-phenylphthalimide in the studied solvents were correlated by using four models, the modified Apelblat equation, λh equation, Wilson model and NRTL model. The calculated solubility using the modified Apelblat equation provided better agreement with those evaluated by the other three models. In general, the four models were all acceptable for correlating the solubility data of 3-chloro-N-phenylphthalimide in the studied solvents. In addition, the change of molar Gibbs energy, molar solution enthalpy, molar solution entropy and excess enthalpy of the solution for per 1 mol of mixture of 3-chloro-N-phenylphthalimide in these solvents were evaluated at mean harmonic temperature. The dissolution process of 3-chloro-N-phenylphthalimide in the selected solvents was exothermic and entropy-driving. The study concerning the solubility of 3-chloro-N-phenylphthalimide in the selected solvents and solution properties can provide fundamental data in the manufacturing and separating process of 3-chloro-N-phenylphthalimide.

  20. The fluorescence and electronic structure of phenyl-substituted tetraazachlorin molecules

    Science.gov (United States)

    Pershukevich, P. P.; Volkovich, D. I.; Gladkov, L. L.; Dudkin, S. V.; Stupak, A. P.; Kuzmitsky, V. A.; Makarova, E. A.; Solovyov, K. N.

    2014-11-01

    The effect of the addition of phenyl groups to pyrrole rings of tetraazachlorins, a new class of tetrapyrroles, on the photophysical properties and electronic structure of the molecules has been investigated by a complex of experimental and theoretical methods. Characteristics of fluorescence at 293 and 77 K have been determined for phenyl-substituted tetraazachlorins. The objects of this study include unsubstituted tetraazaporphine. The introduction of phenyl groups affords a marked increase in the fluorescence quantum yield. For tetraazaporphine and phenyl-substituted tetraazachlorins, fluorescence buildup occurs as the temperature is decreased from 293 to 77 K, but to a lesser extent than for tetraazachlorins having no phenyl groups, which were earlier studied by the authors. The fluorescence buildup mechanism is discussed. The singlet oxygen generation quantum yield has been determined for the tetrapyrroles examined. This characteristic increases upon tetrapyrrole is phenylation. The electronic structure and absorption spectra of unsubstituted porphine and chlorin, tetraazaporphine, tetraazachlorin, octaphenyltetraazaporphine, and tetramethylhexaphenyltetraazachlorin have been calculated by the INDO/Sm method (original modification of the INDO/S method) with molecular geometry optimization using DFT. The results of the quantum-chemical calculation of the absorption spectra are in good agreement with experimental data for transitions to the lowest excited electronic states Q x( S 1) and Q y( S 2).

  1. An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones from 2-Halobenzoic Acids

    International Nuclear Information System (INIS)

    Song, Yoon Ju; Choi, Jin Sun; Lee, Jae In

    2013-01-01

    The present method offers an efficient synthesis of 1-alkyl-2-phenyl-4-quinolones from 2-haloben-zoic acids. It has the advantages with respect to (i) synthesis of 2 equiv of alkynones 5 from 1 equiv of 4,6-pyrimidyl di(2-halobenzoates) 3, (ii) synthesis of versatile 1-alkyl-2-phenyl-4-quinolones in high overall yields, and (iii) use of readily available and cheap starting materials. Therefore, this method could be utilized as a practical synthesis of 1-alkyl-2-phenyl-4-quinolones. Several methods have been developed to synthesize 1-alkyl-2-phenyl-4-quinolones from 2'-substituted acetophenones, anilines, and 2-halobenzoyl chlorides as starting materials. The reaction of N-methylisatoic anhydride with the lithium enolate of an 4'-methoxyacetophenone afforded the 1-methyl-2-phenyl-4-quinolone in a short sequence, but the yield was low. N-(2-Acetylphenyl)benzamides, prepared by Friedel-Crafts acylation of N-phenyl benzamides with acetyl chloride or benzoylation of 2'-aminoacetophenones with benzoyl chlorides,8 were cyclized with potassium t-butoxide to yield 2-aryl-4-quinolones, which were further alkylated with alkyl iodides to give 1-alkyl-2-aryl-4-quinolones

  2. [3-Chloro-N′-(2-oxidonaphthalen-1-ylmethylidenebenzohydrazidato]methanol(methanolatooxidovanadium(V

    Directory of Open Access Journals (Sweden)

    Fu-Ming Wang

    2011-09-01

    Full Text Available In the title complex, [V(C18H11ClN2O2(CH3OO(CH3OH], the VV ion is coordinated by a tridendate 3-chloro-N′-(2-oxidonaphthalen-1-ylmethylidenebenzohydrazidate ligand, one oxido ligand and by O atoms from a methanol and a methoxide ligand, forming a distorted octahedral geometry. The dihedral angle between the benzene ring and the naphthylene ring system is 6.4 (3°. The deviation of the VV ion from the plane defined by the three donor atoms of the tridentate ligand and the methoxy O atom towards the oxido O atom is 0.323 (2 Å. In the crystal, pairs of intermolecular O—H...N hydrogen bonds form centrosymmetric dimers.

  3. Rotational study on the van der Waals complex 1-chloro-1,1-difluoroethane-argon.

    Science.gov (United States)

    Wang, Juan; Chen, Junhua; Feng, Gang; Xia, Zhining; Gou, Qian

    2018-03-15

    The rotational spectrum of the van der Waals complex formed between 1-chloro-1,1-difluoroethane and argon has been investigated by using a pulsed jet Fourier transform microwave spectrometer. Only one set of rotational transitions belonging to the lowest energy conformer has been observed and assigned, although theoretical calculations suggest six stable conformers that might be observed. The observed conformer, according to the experimental evidence from two isotopologues ( 35 Cl and 37 Cl), adopts a configuration in which the argon atom is located, close to the CF 2 Cl top, between the CCF and CCCl planes (the dihedral angle ∠ArCCCl is 65.2°). The distance between argon atom and the center of mass of CH 3 CF 2 Cl is 3.949(2) Å. The dissociation energy, with pseudo diatomic approximation, is evaluated to be 2.4kJmol -1 . Copyright © 2017 Elsevier B.V. All rights reserved.

  4. Degradation of 4-Chloro phenol by gamma radiation of 137Cs and X-rays

    International Nuclear Information System (INIS)

    Gonzalez J, J. C.; Jimenez B, J.; Cejudo A, J.

    2010-01-01

    This paper presents results of radiolytic degradation of 4-chloro phenol in the presence of TiO 2 , Al 2 O 3 and SiO 2 , using different radiation sources than 60 Co, which is so common in this type of experiment. The radiation sources used were X-rays with energy of 100 keV and radiation from 137 Cs (662 keV). After irradiation with a dose of 50 c Gy X-ray and TiO 2 obtained a degradation of about 5%, no degradation was obtained with 137 Cs source and other oxides. This may be due to the fact that X-rays have a linear energy transfer greater value, and in the case of TiO 2 present a crystalline structure, whereas the other two oxides are amorphous. Both characteristics result in better formation of a reactive species that allows the degradation of the compound. (Author)

  5. Synthesis, antileishmanial activity and QSAR studies of 2-chloro- N -arylacetamides

    Directory of Open Access Journals (Sweden)

    Stefânia Neiva Lavorato

    2017-04-01

    Full Text Available ABSTRACT We describe herein the synthesis and evaluation of the antileishmanial activity against promastigote forms of Leishmania amazonensis and cytotoxicity to murine macrophages of a series of 2-chloro-N-arylacetamide derivatives. All compounds were active, except one (compound 3. Compound 5 presented the most promising results, showing good antileishmanial activity (CI50=5.39±0.67 µM and moderate selectivity (SI=6.36, indicating that further development of this class is worthwhile. Preliminary QSAR studies, although not predictive, furnished some insights on the importance of electronic character of aryl substituent to biological activity, as well as an indirect influence of hydrophobicity on activity.

  6. Fluorescence and physical properties of the organic salt 2-chloro-4-nitrobenzoate–3-ammonium-phenol

    Energy Technology Data Exchange (ETDEWEB)

    Mani, Rajaboopathi, E-mail: mrajaboopathi@gmail.com [Department of Physics, Periyar University, Salem 636 011, Tamilnadu (India); Rietveld, Ivo B.; Nicolaï, Béatrice [Laboratoire de Chimie Physique, Faculté de Pharmacie, Université Paris Descartes, 75006 Paris (France); Varadharajan, Krishnakumar, E-mail: vkrishna_kumar@yahoo.com [Department of Physics, Periyar University, Salem 636 011, Tamilnadu (India); Louhi-Kultanen, Marjatta [Department of Chemical Technology, Lappeenranta University of Technology, Lappeenranta 53851 (Finland); Narasimhan, Surumbarkuzhali [Department of Physics, Government Arts College (Autonomous), Salem 636 007, Tamilnadu (India)

    2015-09-08

    Highlights: • Organic salt of 2-chloro-4-nitrobenzoate–3-ammonium-phenol (CNBA{sup −} · AP{sup +}) was grown by solution growth technique. • Single crystal X-ray diffraction demonstrate that two molecules were linked via N{sup +}–H⋯O{sup −} interactions. • The narrow spatial overlap between HOMO and LUMO leads to low ΔE{sub ST} = 73 meV. • The fluorescence emission was observed at ≈338 nm with Stokes shift of 53 nm. • The melting point of CNBA{sup −} · AP{sup +} is 187 °C which is higher than the individual components. - Abstract: Organic salt 2-chloro-4-nitrobenzoate (CNBA{sup −}) 3-ammonium-phenol (AP{sup +}) exhibits fluorescence at 338 nm in solution and frontier molecular orbitals generated from TDDFT calculations indicate that the ground state and the excited state are physically separated on AP{sup +} and CNBA{sup −}. The crystal structure and physical–chemical properties of the CNBA{sup −} · AP{sup +} were investigated using X-ray single crystal and powder diffraction, SEM, FTIR, UV–Vis–NIR, and fluorescence spectrometry. X-ray diffraction demonstrates that the two molecules are linked via N{sup +}–H⋯O{sup −} ammonium–carboxylate interactions, as expected considering their interaction propensities. Proton transfer has been confirmed by FTIR analysis. The melting point of CNBA{sup −} · AP{sup +} was observed at 186 °C, which is higher than pure CNBA (140 °C) or AP (120 °C). The observation of a spatially separated HOMO and LUMO possessing a narrow ΔE{sub ST} = 73.3 meV and an emission in the blue region is promising as an alternative method for the production of OLED materials.

  7. Bioactivation mechanism of the cytotoxic and nephrotoxic S-conjugate S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine.

    OpenAIRE

    Dekant, W; Lash, L H; Anders, M W

    1987-01-01

    The bioactivation of S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine (CTFC) was studied with purified bovine kidney cysteine conjugate beta-lyase and with N-dodecylpyridoxal bromide in cetyltrimethylammonium bromide micelles as a pyridoxal model system. The beta-lyase and the pyridoxal model system converted CTFC to chlorofluoroacetic acid and inorganic fluoride, which were identified by 19F NMR spectrometry. 2-Chloro-1,1,2-trifluoroethanethiol and chlorofluorothionoacetyl fluoride were formed a...

  8. Synthesis and antimicrobial evaluation of 2-(2-butyl- 4-chloro-1H-imidazol-5-yl-methylene-substituted-benzofuran-3-ones

    Directory of Open Access Journals (Sweden)

    Bhaskar S. Dawane

    2010-05-01

    Full Text Available In the present study, the oxidation of 3-(4-chloro-1H-imidazol-5-yl-1-(2-hydroxyphenylprop-2-en-1-ones with mercuric(II acetate in in polyethylene glycol (PEG-400 gave the corresponding 2-((4-chloro-1H-imidazol-5-ylmethylenebenzofuran-3(2H-ones. Newly synthesized compounds were tested for their in vitro antimicrobial activity.

  9. Removal of P-chloro Phenol from Aqueous Solutions Using Chestnut Shell Modified by Sulfuric Acid: Study of Adsorption Kinetic and Isotherm

    Directory of Open Access Journals (Sweden)

    Hatam Godini

    2015-06-01

    Full Text Available Background: Present of p-chloro phenol in the environment due to high toxicity, mutagenic and carcinogenic effects, powerful odor production and stability in the environment caused to be categorized as priority pollutants. The aim of this study was to investigate the removal of p-chloro phenol from aqueous solution using chestnut shell modified by sulfuric acid. Methods: This study was an experimental study and chestnut shell (Quercus brantii Var. persica was used as an adsorbent. The effects of pH, contact time, adsorbent dosage, and initial concentration on the adsorption process were evaluated, in a batch scale. The characterizations of the raw and modified adsorbent were investigated by Fourier transform infrared (FTIR spectroscopy, scanning electron microscopy (SEM and X-ray diffractometer (XRD. Langmuir and Fruindlich isotherm models and pseudo-first order kinetic, pseudo-second order kinetic were evaluated by experimental data. Results: The results showed that the removal efficiency of p-chloro phenol increased with increasing of the contact time and adsorbent dosage, and had a reverse effect with increasing of pH and p-chloro phenol initial concentration. The maximum adsorption capacity of p-chloro phenol by modified chestnut shell adsorbent was achieved of 3.33 mg/g and the maximum removal efficiency of p-chloro phenol was 87 percent at pH=4. The experimental data were well descripted by Freundlich isotherm (R2>0.92 and pseudo-second order kinetic (R2>0.94. Conclusion: This study showed that the chestnut shell could be effectively used at removal of p-chloro phenol from aqueous solutions. As the chestnut shell is a waste, so it can be applied as an adsorbent for removal of pollutants such as p-chloro phenol.

  10. Synthesis of highly fluorescent silica nanoparticles in a reverse microemulsion through double-layered doping of organic fluorophores

    International Nuclear Information System (INIS)

    Yoo, Hyojong; Pak, Joonsung

    2013-01-01

    Water-soluble, highly fluorescent double-layered silica nanoparticles (FL-DLSN) have been successfully synthesized through a reverse (water-in-oil) microemulsion method. The microemulsion was prepared by mixing a surfactant (Brij35), co-surfactant, organic solvent, water, and fluorescein as an organic fluorophore. The sizes of the silica nanoparticles were successfully controlled in the reverse microemulsion using Brij35 by changing the water-to-Brij35 ratio and by adding HCl. Initially, tetraethylorthosilicate was hydrolyzed by adding NH 4 OH as a catalyst and then polymerized to generate core fluorescent silica nanoparticles with fluorescein. 3-(Aminopropyl)triethoxysilane (APTS) was sequentially added into the reaction mixture, and reacted on the surface of pre-generated core silica nanoparticles to form the second layer in the form of a shell. The second silica layer that was derived from the condensation of APTS effectively protected the fluorescein dye within the silica matrix. This is a novel and simple synthetic approach to generate highly fluorescent, monodispersed silica nanoparticles by doping organic molecules into a silica matrix.Graphical Abstract

  11. Functionalized tricyclic cytosine analogues provide nucleoside fluorophores with improved photophysical properties and a range of solvent sensitivities.

    Science.gov (United States)

    Rodgers, Brittney J; Elsharif, Nada A; Vashisht, Nisha; Mingus, Macy M; Mulvahill, Mark A; Stengel, Gudrun; Kuchta, Robert D; Purse, Byron W

    2014-02-10

    Tricyclic cytosines (tC and tC(O) frameworks) have emerged as a unique class of fluorescent nucleobase analogues that minimally perturb the structure of B-form DNA and that are not quenched in duplex nucleic acids. Systematic derivatization of these frameworks is a likely approach to improve on and diversify photophysical properties, but has not so far been examined. Synthetic methods were refined to improve on tolerance for electron-donating and electron-withdrawing groups, resulting in a series of eight new, fluorescent cytidine analogues. Photophysical studies show that substitution of the framework results in a pattern of effects largely consistent across tC and tC(O) and provides nucleoside fluorophores that are brighter than either parent. Moreover, a range of solvent sensitivities is observed, offering promise that this family of probes can be extended to new applications that require reporting on the local environment. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Surface plasmon enhanced energy transfer between gold nanorods and fluorophores: application to endocytosis study and RNA detection.

    Science.gov (United States)

    Zhang, Yinan; Wei, Guoke; Yu, Jun; Birch, David J S; Chen, Yu

    2015-01-01

    Previously we have demonstrated surface plasmon enhanced energy transfer between fluorophores and gold nanorods under two-photon excitation using fluorescence lifetime imaging microscopy (FLIM) in both solution and intracellular phases. These studies demonstrated that gold nanoparticle-dye energy transfer combinations are appealing, not only in Förster resonance energy transfer (FRET) imaging, but also energy transfer-based fluorescence lifetime sensing of bio-analytes. Here, we apply this approach to study the internalization of gold nanorods (GNRs) in HeLa cells using the early endosome labeling marker GFP. The observed energy transfer between GFP and the GNRs indicates the involvement of endocytosis in GNR uptake. Moreover, a novel nanoprobe based on oligonucleotide functionalized gold nanorods for nucleic acid sensing via dye-GNRs energy transfer is demonstrated, potentially opening up new possibilities in cancer diagnosis and prognosis. The influence of oligonucleotide design on such nanoprobe performance was studied for the first time using time-resolved fluorescence spectroscopy, bringing new insights to the optimization of the nanoprobe.

  13. Identification of nodal tissue in the living heart using rapid scanning fiber-optics confocal microscopy and extracellular fluorophores.

    Science.gov (United States)

    Huang, Chao; Kaza, Aditya K; Hitchcock, Robert W; Sachse, Frank B

    2013-09-01

    Risks associated with pediatric reconstructive heart surgery include injury of the sinoatrial node (SAN) and atrioventricular node (AVN), requiring cardiac rhythm management using implantable pacemakers. These injuries are the result of difficulties in identifying nodal tissues intraoperatively. Here we describe an approach based on confocal microscopy and extracellular fluorophores to quantify tissue microstructure and identify nodal tissue. Using conventional 3-dimensional confocal microscopy we investigated the microstructural arrangement of SAN, AVN, and atrial working myocardium (AWM) in fixed rat heart. AWM exhibited a regular striated arrangement of the extracellular space. In contrast, SAN and AVN had an irregular, reticulated arrangement. AWM, SAN, and AVN tissues were beneath a thin surface layer of tissue that did not obstruct confocal microscopic imaging. Subsequently, we imaged tissues in living rat hearts with real-time fiber-optics confocal microscopy. Fiber-optics confocal microscopy images resembled images acquired with conventional confocal microscopy. We investigated spatial regularity of tissue microstructure from Fourier analysis and second-order image moments. Fourier analysis of fiber-optics confocal microscopy images showed that the spatial regularity of AWM was greater than that of nodal tissues (37.5 ± 5.0% versus 24.3 ± 3.9% for SAN and 23.8 ± 3.7% for AVN; Pfiber-optics confocal microscopy. Application of the approach in pediatric reconstructive heart surgery may reduce risks of injuring nodal tissues.

  14. Phenyl-doped graphitic carbon nitride: photoluminescence mechanism and latent fingerprint imaging.

    Science.gov (United States)

    Song, Zhiping; Li, Zhihong; Lin, Lihua; Zhang, Yongfan; Lin, Tianran; Chen, Ling; Cai, Zhuang; Lin, Sen; Guo, Liangqia; Fu, Fengfu; Wang, Xinchen

    2017-11-23

    The photoluminescence (PL) emission mechanism of graphitic carbon nitride (g-C 3 N 4 ) is still ambiguous and the application of PL g-C 3 N 4 powder as a solid sensing platform has not been explored. Herein we highlight a strategy to prepare g-C 3 N 4 powder with strong green PL by doping phenyl groups in a carbon nitride network. Compared with pristine g-C 3 N 4 , doping of phenyl groups greatly enhances the PL efficiency and Stokes shift. Theoretical calculations based on density function theory indicate that phenyl groups change the electronic structure of the carbon nitride network and have an obvious contribution to the LUMO of phenyl-doped g-C 3 N 4 , which may be the main reason for the enhancement of the PL efficiency and Stokes shift. Taking advantage of the high PL efficiency, large Stokes shift and high photo-stability, phenyl-doped g-C 3 N 4 powder shows promising application for the imaging of latent fingerprints.

  15. Synthesis and anticonvulsant activity of 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p-substituted benzal) hydrazone derivatives.

    Science.gov (United States)

    Gökçe, Mehtap; Geciken, Ahmet Emin; Yildirim, Engin; Tosuni, Ali Ulvi

    2008-01-01

    It is well known that some hydrazone derivatives of both 2-oxobenzoxazoline and 2-oxobenzothiazoline exhibit potent anticonvulsant activity. In order to investigate the effects of structural modifications on the biological properties, 14 new hydrazones of 5-chloro-2(3H)-benzox-azolinone-3-acetyl hydrazide were synthesized. The chemical structures of the synthesized compounds were established by IR, 1H-NMR spectral analyses and elementary analyses. The anticonvulsant activities of the title compounds were tested by the penthylenetetrazole induced seizure test. 5-Chloro-2(3H)-benz-oxazolinone-3-acetyl-2-(o-methoxy-benzaldehyde)-hydrazone 4d, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o-methybenzaldehyde)-hydrazone 4g, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(p-methylbenzaldehyde)-hydrazone 4h, 5-chloro-2(3H)-benzoxazolino-ne-3-acetyl-2-(p-nitrobenzaldehyde)-hydrazone 4m, and 5-chloro-2(3H)-benzox-azolinone-3-acetyl-2-(p-dimethylaminobenzaldehyde)-hydrazone 4n were found more active than phenytoin (CAS 57-41-0) in the tests.

  16. Synthesis of 1-chloro-1-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization

    DEFF Research Database (Denmark)

    Ivan, Bela; Chen, Xianyi; Kops, Jørgen

    1998-01-01

    1-Chloro-1-phenylethyl-telechelic polyisobutylene (PIB) was synthesized by living carbocationic polymerization (LCCP). LCCP of isobutylene was induced by a difunctional initiator in conjunction with TiCl4 as coinitiator in the presence of N,N-dimethylacetamide in CH2Cl2/hexane (40:60 v/v) solvent...... mixture at -78 degrees C. After complete isobutylene conversion a small amount of styrene was added leading to a rapid crossover reaction and thus to the attachment of short outer polystyrene (PSt) blocks to the PIB segment. Quenching the living polymerization of styrene yielded 1-chloro-1-phenylethyl...... terminal groups. The resulting telechelic polymer (Cl-PSt-PIB-PSt-Cl) is a potential new macroinitiator for atom transfer radical polymerization of a variety of vinyl monomers....

  17. Pulse-radiolytic one-electron reduction of anthraquinone and chloro-anthraquinones in aqueous-isopropanol-acetone mixed solvent

    International Nuclear Information System (INIS)

    Rath, M.C.; Pal, H.; Mukherjee, T.

    1996-01-01

    One-electron reduction of 9,10-anthraquinone and some chloro-anthraquinones and the characteristics of the semiquinones thus formed have been investigated in aqueous-isipropanol-acetone mixed solvent using electron pulse radiolysis technique. Spectroscopic characteristics, kinetic parameters of formation and decay, and the acid/base behaviour of the semiquinones have been investigated. The one-electron reduction potential of the quinones have been measured following electron transfer equilibria with a reference redox system (methyl viologen) and the values thus obtained have been compared with those of some other anthrasemiquinone systems. An analysis of the characteristics of the semiquinones shows that α-chloro substituents adjacent to the C=O group act as electron withdrawing groups. (author)

  18. Identification of cysteine as the reactive group in pyruvate kinase alkylated by 5-chloro-4-oxopentanoic acid.

    Science.gov (United States)

    Chalkley, R A; Bloxham, D P

    1976-11-01

    4-Hydroxypentanoic acid alanine thioether was synthesized and characterized by n.m.r. spectroscopy. This derivative corresponded to the modified amino acid obtained by allowing 5-chloro-4-oxo[3,5-3H]pentanoic acid to react with rabbit muscle pyruvate kinase. Performic acid oxidation of 4-oxo[3,5-3H]pentanoic acid alanine thioether in pyruvate kinase gave [3H]succinate (67%) and [3H]carboxymethylcysteine (33%) as expected. Evidence is presented to show that NaBH4 reduction followed by periodate oxidation and analysis of radioactive formaldehyde production may provide a convenient method for distinguishing between thiol and amino alkylation by halogenomethyl ketone compounds. Peptide 'mapping' confirms that the modification by 5-chloro-4-oxopentanoic acid occurs primarily at one region of pyruvate kinase.

  19. Radiation decomposition of alcohols and chloro phenols in micellar systems; Descomposicion por irradiacion de alcoholes y clorofenoles en sistemas micelares

    Energy Technology Data Exchange (ETDEWEB)

    Moreno A, J

    1998-12-31

    The effect of surfactants on the radiation decomposition yield of alcohols and chloro phenols has been studied with gamma doses of 2, 3, and 5 KGy. These compounds were used as typical pollutants in waste water, and the effect of the water solubility, chemical structure, and the nature of the surfactant, anionic or cationic, was studied. The results show that anionic surfactant like sodium dodecylsulfate (SDS), improve the radiation decomposition yield of ortho-chloro phenol, while cationic surfactant like cetyl trimethylammonium chloride (CTAC), improve the radiation decomposition yield of butyl alcohol. A similar behavior is expected for those alcohols with water solubility close to the studied ones. Surfactant concentrations below critical micellar concentration (CMC), inhibited radiation decomposition for both types of alcohols. However radiation decomposition yield increased when surfactant concentrations were bigger than the CMC. Aromatic alcohols decomposition was more marked than for linear alcohols decomposition. On a mixture of alcohols and chloro phenols in aqueous solution the radiation decomposition yield decreased with increasing surfactant concentration. Nevertheless, there were competitive reactions between the alcohols, surfactants dimers, hydroxyl radical and other reactive species formed on water radiolysis, producing a catalytic positive effect in the decomposition of alcohols. Chemical structure and the number of carbons were not important factors in the radiation decomposition. When an alcohol like ortho-chloro phenol contained an additional chlorine atom, the decomposition of this compound was almost constant. In conclusion the micellar effect depend on both, the nature of the surfactant (anionic or cationic) and the chemical structure of the alcohols. The results of this study are useful for wastewater treatment plants based on the oxidant effect of the hydroxyl radical, like in advanced oxidation processes, or in combined treatment such as

  20. Genetic and Biochemical Characterization of 2-Chloro-5-Nitrophenol Degradation in a Newly Isolated Bacterium,Cupriavidussp. Strain CNP-8.

    Science.gov (United States)

    Min, Jun; Chen, Weiwei; Wang, Jinpei; Hu, Xiaoke

    2017-01-01

    Compound 2-chloro-5-nitrophenol (2C5NP) is a typical chlorinated nitroaromatic pollutant. To date, the bacteria with the ability to degrade 2C5NP are rare, and the molecular mechanism of 2C5NP degradation remains unknown. In this study, Cupriavidus sp. strain CNP-8 utilizing 2-chloro-5-nitrophenol (2C5NP) and meta -nitrophenol (MNP) via partial reductive pathways was isolated from pesticide-contaminated soil. Biodegradation kinetic analysis indicated that 2C5NP degradation by this strain was concentration dependent, with a maximum specific degradation rate of 21.2 ± 2.3 μM h -1 . Transcriptional analysis showed that the mnp genes are up-regulated in both 2C5NP- and MNP-induced strain CNP-8. Two Mnp proteins were purified to homogeneity by Ni-NTA affinity chromatography. In addition to catalyzing the reduction of MNP, MnpA, a NADPH-dependent nitroreductase, also catalyzes the partial reduction of 2C5NP to 2-chloro-5-hydroxylaminophenol via 2-chloro-5-nitrosophenol, which was firstly identified as an intermediate of 2C5NP catabolism. MnpC, an aminohydroquinone dioxygenase, is likely responsible for the ring-cleavage reaction of 2C5NP degradation. Gene knockout and complementation indicated that mnpA is necessary for both 2C5NP and MNP catabolism. To our knowledge, strain CNP-8 is the second 2C5NP-utilizing bacterium, and this is the first report of the molecular mechanism of microbial 2C5NP degradation.

  1. Genetic and Biochemical Characterization of 2-Chloro-5-Nitrophenol Degradation in a Newly Isolated Bacterium, Cupriavidus sp. Strain CNP-8

    Directory of Open Access Journals (Sweden)

    Jun Min

    2017-09-01

    Full Text Available Compound 2-chloro-5-nitrophenol (2C5NP is a typical chlorinated nitroaromatic pollutant. To date, the bacteria with the ability to degrade 2C5NP are rare, and the molecular mechanism of 2C5NP degradation remains unknown. In this study, Cupriavidus sp. strain CNP-8 utilizing 2-chloro-5-nitrophenol (2C5NP and meta-nitrophenol (MNP via partial reductive pathways was isolated from pesticide-contaminated soil. Biodegradation kinetic analysis indicated that 2C5NP degradation by this strain was concentration dependent, with a maximum specific degradation rate of 21.2 ± 2.3 μM h−1. Transcriptional analysis showed that the mnp genes are up-regulated in both 2C5NP- and MNP-induced strain CNP-8. Two Mnp proteins were purified to homogeneity by Ni-NTA affinity chromatography. In addition to catalyzing the reduction of MNP, MnpA, a NADPH-dependent nitroreductase, also catalyzes the partial reduction of 2C5NP to 2-chloro-5-hydroxylaminophenol via 2-chloro-5-nitrosophenol, which was firstly identified as an intermediate of 2C5NP catabolism. MnpC, an aminohydroquinone dioxygenase, is likely responsible for the ring-cleavage reaction of 2C5NP degradation. Gene knockout and complementation indicated that mnpA is necessary for both 2C5NP and MNP catabolism. To our knowledge, strain CNP-8 is the second 2C5NP-utilizing bacterium, and this is the first report of the molecular mechanism of microbial 2C5NP degradation.

  2. Oxidative alkylation of azoles. 1. Reaction of N-chloro-3-nitro-1,2,4-triazoles with methyl iodide

    International Nuclear Information System (INIS)

    Pevzner, M.S.; Kurunkov, A.A.; Trubitsin, A.E.

    1994-01-01

    By the methods of chemical analysis, IR and NMR spectroscopy it has been ascertained that interaction of methyl iodide with N-chloro-3-nitro- and 5-methyl-3-nitro-1,2,4-triazols results in iodine isolation and formation of a mixture of compounds: nonsubstituted in terms of nitrogen 3-nitro-1,2,4-triazols, N-mono- and N,N-dimethylated derivatives and products of their further transformations (1,4-dimethyl-5-triazolons)

  3. Metabolism of 4-chloro-2-nitrophenol in a Gram-positive bacterium, Exiguobacterium sp. PMA

    Directory of Open Access Journals (Sweden)

    Arora Pankaj

    2012-11-01

    Full Text Available Abstract Background Chloronitrophenols (CNPs are widely used in the synthesis of dyes, drugs and pesticides, and constitute a major group of environmental pollutants. 4-Chloro-2-nitrophenol (4C2NP is an isomer of CNPs that has been detected in various industrial effluents. A number of physicochemical methods have been used for treatment of wastewater containing 4C2NP. These methods are not as effective as microbial degradation, however. Results A 4C2NP-degrading bacterium, Exiguobacterium sp. PMA, which uses 4C2NP as the sole carbon and energy source was isolated from a chemically-contaminated site in India. Exiguobacterium sp. PMA degraded 4C2NP with the release of stoichiometeric amounts of chloride and ammonium ions. The effects of different substrate concentrations and various inoculum sizes on degradation of 4C2NP were investigated. Exiguobacterium sp. PMA degraded 4C2NP up to a concentration of 0.6 mM. High performance liquid chromatography and gas chromatography–mass spectrometry identified 4-chloro-2-aminophenol (4C2AP and 2-aminophenol (2AP as possible metabolites of the 4C2NP degradation pathway. The crude extract of 4C2NP-induced PMA cells contained enzymatic activity for 4C2NP reductase and 4C2AP dehalogenase, suggesting the involvement of these enzymes in the degradation of 4C2NP. Microcosm studies using sterile and non-sterile soils spiked with 4C2NP were carried out to monitor the bioremediation potential of Exiguobacterium sp. PMA. The bioremediation of 4C2NP by Exiguobacterium sp. PMA was faster in non-sterilized soil than sterilized soil. Conclusions Our studies indicate that Exiguobacterium sp. PMA may be useful for the bioremediation of 4C2NP-contaminated sites. This is the first report of (i the formation of 2AP in the 4C2NP degradation pathway by any bacterium and (iii the bioremediation of 4C2NP by any bacterium.

  4. A turn-on near-infrared fluorescent chemosensor for selective detection of lead ions based on a fluorophore-gold nanoparticle assembly.

    Science.gov (United States)

    Wang, Shaozhen; Sun, Junyong; Gao, Feng

    2015-06-21

    A turn-on fluorescent chemosensor of Pb(2+) in the near-infrared (NIR) region, which is based on the Pb(2+)-tuned restored fluorescence of a weakly fluorescent fluorophore-gold nanoparticle (AuNPs) assembly, has been reported. In this fluorophore-AuNP assembly, NIR fluorescent dye brilliant cresyl blue (BCB) molecules act as fluorophores and are used for signal transduction of fluorescence, while AuNPs act as quenchers to quench the nearby fluorescent BCB molecules via electron transfer. In the presence of Pb(2+), fluorescent BCB molecules detached from AuNPs and restored their fluorescence due to the formation of a chelating complex between Pb(2+) and glutathione confined on AuNPs. Under the optimal conditions, the present BCB-AuNP assembly is capable of detecting Pb(2+) with a concentration ranging from 7.5 × 10(-10) to 1 × 10(-8) mol L(-1) (0.16-2.1 ng mL(-1)) and a detection limit of 0.51 nM (0.11 ng mL(-1)). The present BCB-AuNP assembly can be used in aqueous media for the determination of Pb(2+) unlike common organic fluorescent reagents, and also shows advantages of NIR fluorescence spectrophotometry such as less interference, lower detection limit, and higher sensitivity. Moreover, the present method was successfully applied for the detection of Pb(2+) in water samples with satisfactory results.

  5. Synthesis of 1-chloro-1-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization

    DEFF Research Database (Denmark)

    Ivan, Bela; Chen, Xianyi; Kops, Jørgen

    1998-01-01

    1-Chloro-1-phenylethyl-telechelic polyisobutylene (PIB) was synthesized by living carbocationic polymerization (LCCP). LCCP of isobutylene was induced by a difunctional initiator in conjunction with TiCl4 as coinitiator in the presence of N,N-dimethylacetamide in CH2Cl2/hexane (40:60 v/v) solvent...... terminal groups. The resulting telechelic polymer (Cl-PSt-PIB-PSt-Cl) is a potential new macroinitiator for atom transfer radical polymerization of a variety of vinyl monomers.......1-Chloro-1-phenylethyl-telechelic polyisobutylene (PIB) was synthesized by living carbocationic polymerization (LCCP). LCCP of isobutylene was induced by a difunctional initiator in conjunction with TiCl4 as coinitiator in the presence of N,N-dimethylacetamide in CH2Cl2/hexane (40:60 v/v) solvent...... mixture at -78 degrees C. After complete isobutylene conversion a small amount of styrene was added leading to a rapid crossover reaction and thus to the attachment of short outer polystyrene (PSt) blocks to the PIB segment. Quenching the living polymerization of styrene yielded 1-chloro-1-phenylethyl...

  6. ChloroSeq, an Optimized Chloroplast RNA-Seq Bioinformatic Pipeline, Reveals Remodeling of the Organellar Transcriptome Under Heat Stress

    Directory of Open Access Journals (Sweden)

    Benoît Castandet

    2016-09-01

    Full Text Available Although RNA-Seq has revolutionized transcript analysis, organellar transcriptomes are rarely assessed even when present in published datasets. Here, we describe the development and application of a rapid and convenient method, ChloroSeq, to delineate qualitative and quantitative features of chloroplast RNA metabolism from strand-specific RNA-Seq datasets, including processing, editing, splicing, and relative transcript abundance. The use of a single experiment to analyze systematically chloroplast transcript maturation and abundance is of particular interest due to frequent pleiotropic effects observed in mutants that affect chloroplast gene expression and/or photosynthesis. To illustrate its utility, ChloroSeq was applied to published RNA-Seq datasets derived from Arabidopsis thaliana grown under control and abiotic stress conditions, where the organellar transcriptome had not been examined. The most appreciable effects were found for heat stress, which induces a global reduction in splicing and editing efficiency, and leads to increased abundance of chloroplast transcripts, including genic, intergenic, and antisense transcripts. Moreover, by concomitantly analyzing nuclear transcripts that encode chloroplast gene expression regulators from the same libraries, we demonstrate the possibility of achieving a holistic understanding of the nucleus-organelle system. ChloroSeq thus represents a unique method for streamlining RNA-Seq data interpretation of the chloroplast transcriptome and its regulators.

  7. Improved synthetic route to quinoxyfen photometabolite 2-chloro-10-fluorochromeno[2,3,4-de]quinoline.

    Science.gov (United States)

    Johnson, Peter L; Kister, Jeremy; Thornburgh, Scott

    2017-08-01

    Quinoxyfen is a fungicide developed by Dow AgroSciences for the control of powdery mildew. Re-registration studies required gram quantities of 2-chloro-10-fluorochromeno[2,3,4-de]quinoline, a photometabolite of quinoxyfen. The only previous method of preparation of this photometabolite was by photolysis of quinoxyfen in less than 1% yield. Therefore, a new method allowing for the preparation of this photometabolite in gram quantities was required. Several different metal catalyzed intramolecular cyclization approaches were investigated for the synthesis of 2-chloro-10-fluorochromeno[2,3,4-de]quinoline. While most methods failed to provide the desired product from a 2-bromophenyl derivative of quinoxyfen, a novel one-pot two-step synthesis led to the desired material in good yield from quinoxyfen. A short and efficient synthetic route was developed to access 2-chloro-10-fluorochromeno[2,3,4-de]quinoline from readily available (4-fluoro-2-hydroxyphenyl)boronic acid and quinoxyfen and was found to be scalable, which enabled the preparation of the desired photometabolite in gram quantities thus meeting material requirements to complete regulatory studies for the re-registration of quinoxyfen. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  8. Synthesis and structure-activity relationship exploration of some potent anti-cancer phenyl amidrazone derivatives.

    Science.gov (United States)

    Habashneh, Almeqdad Y; El-Abadelah, Mustafa M; Bardaweel, Sanaa K; Taha, Mutasem O

    2017-12-04

    Amidrazones have been reported to have significant anti-tumor properties against several cancer cell lines. The current project aims to profile the structure-anticancer activity relationship of phenyl-amidrazons. Fifteen phenyl-amidrazone-piperazine derivatives were prepared and tested against four cancer cell lines (leukemia, prostate, breast and colon cancers). Six compounds illustrated low micromolar anticancer IC50 values, while the remaining compounds were either inactive or of moderate potencies. All compounds were virtually nontoxic against normal fibroblast cells. Docking into the oncogenic kinase bcr/abl illustrated the critical importance of (i) p-halogen substituent on the ligand's phenyl ring and (ii) the presence of positive ionizable moiety at the ligand's piperazine fragment for anticancer activity. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  9. Esterification of phenyl acetic acid withp-cresol using metal cation exchanged montmorillonite nanoclay catalysts.

    Science.gov (United States)

    Bhaskar, M; Surekha, M; Suma, N

    2018-02-01

    The liquid phase esterification of phenyl acetic acid with p -cresol over different metal cation exchanged montmorillonite nanoclays yields p -cresyl phenyl acetate. Different metal cation exchanged montmorillonite nanoclays (M n +  = Al 3+ , Zn 2+ , Mn 2+ , Fe 3+ , Cu 2+ ) were prepared and the catalytic activity was studied. The esterification reaction was conducted by varying molar ratio of the reactants, reaction time and catalyst amount on the yield of the ester. Among the different metal cation exchanged catalysts used, Al 3+ -montmorillonite nanoclay was found to be more active. The characterization of the material used was studied under different techniques, namely X-ray diffraction, scanning electron microscopy and thermogravimetric analysis. The product obtained, p -cresyl phenyl acetate, was identified by thin-layer chromotography and confirmed by Fourier transform infrared, 1 H NMR and 13 C NMR. The regeneration activity of used catalyst was also investigated up to fourth generation.

  10. Production of allyl phenyl carbinol (APC by biotrans-formation using Rhizopus arrhizus

    Directory of Open Access Journals (Sweden)

    Vilas B. Shukla

    2000-01-01

    Full Text Available The objective of the present work was to study the stereoselective synthesis of homo-allylic alcohol using stereoselective hydrolysis by Rhizopus arrhizus and also to study the stereoselective synthesis of allyl phenyl carbinol (APC or 1-Phenyl-3-butene-1-o by combination of chemical synthesis and biotransformation from cheap raw materials such as benzaldehyde and allyl bromide. Stereospecific synthesis of allyl phenyl carbinol (APC was achieved by acetate hydrolysis by R. arrhizus giving R (+ enantiomer. Maximum enantiomeric excess of APC was obtained at 16 h where as maximum yield of it was obtained at 48 h of biotransformation.O objetivo deste trabalho foi estudar a síntese estereo-seletiva do álcool homo-allylico usando hidrólise estereo-seletiva pelo Rhizopus arrhizus e também estudar a síntese estereo-seletiva do allyl phenyl carbinol (APC ou 1-Phenyl-3-butene- 1-o pela combinação da síntese química e biotransformação dos materiais brutos e baratos, tais como; benzaldehyde and allyl bromide. A síntese Stereospecifica do allyl phenyl carbinol (APC foi conseguida pela hidrólise de acetato pelo R. arrhizus fornecendo enantiomero R (+. O excesso máximo do enantiomérico do APC foi obtido em 16 h sendo que seu rendimento máximo foi obtido após 48 h de biotransformação.

  11. Studies on Novel N4-[4,6-Diaryl-2-pyrimidinyl]-7-chloro-4-quinolinamine and their Microbicidal Efficacy

    Directory of Open Access Journals (Sweden)

    Arvind G. Mehta

    2009-01-01

    Full Text Available The required chalcones 1a-h were prepared by reaction of substituted acetophenone with different aryl aldehyde, which in turn treated with guanidine nitrate, yielded 4-(substituted phenyl-6-(substituted phenyl-2-pyrimidinamine 2a-h. Novel pyrimidine quinoline clubbed molecules 3a-h have been prepared by reaction of 2a-h with 4,7-dichloroquinoline. All the compounds were characterized by elemental analysis and spectral studies. The newly synthesized compounds were evaluated for their antibacterial and antifungal activity.

  12. Synthesis of 3-{4-[4-(Benzylideneaminobenzenesulfonyl]- phenyl}-2-phenylquinazolin-4(3H-one

    Directory of Open Access Journals (Sweden)

    Sunil Manohar Babu

    2009-01-01

    Full Text Available The present work describes the synthesis of a Schiff base, 3-{4-[4-(benzylideneamino benzenesulfonyl]phenyl}-2-phenylquinazolin-4(3H-one from a novel quinazolinone, 3-[4-(4 aminobenzenesulfonylphenyl]-2-phenylquinazolin-4(3H-one. The quinazolinone was prepared by reacting 2-phenyl-4H-3,1 benzoxazin-4-one with dapsone. The structure of the synthesized Schiff base is confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis.-

  13. 5-(2,4-Dichlorophenoxy-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

    Directory of Open Access Journals (Sweden)

    S. Madan Kumar

    2016-07-01

    Full Text Available In the crystal structure of the title compound, C17H12Cl2N2O2, the pyrazole ring makes dihedral angles of 65.0 (2 and 43.9 (2° with the dichlorophenyl and phenyl rings, respectively. The dihedral angle between the chlorophenyl and phenyl rings is 59.1 (2°. In the crystal, the molecules are linked by C—H...O hydrogen bonds and weak C—Cl...π and C—H...π interactions, generating a three-dimensional network.

  14. 1-[3-(2-Nitrophenyl-5-phenyl-2-pyrazolin-1-yl]ethanone

    Directory of Open Access Journals (Sweden)

    Huan-Mei Guo

    2010-07-01

    Full Text Available The title compound, C17H15N3O3, was prepared from 1-(2-nitrophenyl-3-phenylprop-2-en-1-one and hydrazine. The dihedral angle between the benzene and phenyl rings is 74.55 (2°. The pyrazoline ring is in a slight envelope conformation with the C atom bonded to the phenyl ring forming the flap. In the crystal structure, weak intermolecular C—H...O hydrogen bonds connect molecules into chains along [100].

  15. Controlled switching of single-molecule junctions by mechanical motion of a phenyl ring

    Directory of Open Access Journals (Sweden)

    Yuya Kitaguchi

    2015-10-01

    Full Text Available Mechanical methods for single-molecule control have potential for wide application in nanodevices and machines. Here we demonstrate the operation of a single-molecule switch made functional by the motion of a phenyl ring, analogous to the lever in a conventional toggle switch. The switch can be actuated by dual triggers, either by a voltage pulse or by displacement of the electrode, and electronic manipulation of the ring by chemical substitution enables rational control of the on-state conductance. Owing to its simple mechanics, structural robustness, and chemical accessibility, we propose that phenyl rings are promising components in mechanical molecular devices.

  16. Degradation of 4-Chloro phenol by gamma radiation of {sup 137}Cs and X-rays

    Energy Technology Data Exchange (ETDEWEB)

    Gonzalez J, J. C. [Instituto Tecnologico de Toluca, Av. Tecnologico s/n, Ex-Rancho La Virgen, 52140 Metepec, Estado de Mexico (Mexico); Jimenez B, J.; Cejudo A, J., E-mail: jaime.jimenez@inin.gob.m [ININ, Carretera Mexico-Toluca s/n, 52750 Ocoyoacac, Estado de Mexico (Mexico)

    2010-07-01

    This paper presents results of radiolytic degradation of 4-chloro phenol in the presence of TiO{sub 2}, Al{sub 2}O{sub 3} and SiO{sub 2}, using different radiation sources than {sup 60}Co, which is so common in this type of experiment. The radiation sources used were X-rays with energy of 100 keV and radiation from {sup 137}Cs (662 keV). After irradiation with a dose of 50 c Gy X-ray and TiO{sub 2} obtained a degradation of about 5%, no degradation was obtained with {sup 137}Cs source and other oxides. This may be due to the fact that X-rays have a linear energy transfer greater value, and in the case of TiO{sub 2} present a crystalline structure, whereas the other two oxides are amorphous. Both characteristics result in better formation of a reactive species that allows the degradation of the compound. (Author)

  17. Kinetic evaluation of the solvolysis of isobutyl chloro- and chlorothioformate esters

    Directory of Open Access Journals (Sweden)

    Song Hee Choi

    2011-04-01

    Full Text Available The specific rates of solvolysis of isobutyl chloroformate (1 are reported at 40.0 °C and those for isobutyl chlorothioformate (2 are reported at 25.0 °C, in a variety of pure and binary aqueous organic mixtures with wide ranging nucleophilicity and ionizing power. For 1, we also report the first-order rate constants determined at different temperatures in pure ethanol (EtOH, methanol (MeOH, 80% EtOH, and in both 97% and 70% 2,2,2-trifluoroethanol (TFE. The enthalpy (ΔH≠ and entropy (ΔS≠ of activation values obtained from Arrhenius plots for 1 in these five solvents are reported. The specific rates of solvolysis were analyzed using the extended Grunwald–Winstein equation. Results obtained from correlation analysis using this linear free energy relationship (LFER reinforce our previous suggestion that side-by-side addition–elimination and ionization mechanisms operate, and the relative importance is dependent on the type of chloro- or chlorothioformate substrate and the solvent.

  18. Spectroscopic investigations of Nd3+ doped flouro- and chloro-borate glasses.

    Science.gov (United States)

    Mohan, Shaweta; Thind, Kulwant Singh; Sharma, Gopi; Gerward, Leif

    2008-10-01

    Spectroscopic and physical properties of Nd3+ doped sodium lead flouro- and chloro-borate glasses of the type 20NaX-30PbO-49.5B2O3-0.5Nd2O3 (X=F and Cl) have been investigated. Optical absorption spectra have been used to determine the Slater Condon (F2, F4, and F6), spin orbit xi4f and Racah parameters (E1, E2, and E3). The oscillator strengths and the intensity parameters Omega2, Omega4 and Omega6 have been determined by the Judd-Ofelt theory, which in turn provide the radiative transition probability (A), total transition probability (A(T)), radiative lifetime (tauR) and branching ratio (beta) for the fluorescent level 4F3/2. The lasing efficiency of the prepared glasses has been characterized by the spectroscopic quality factor (Omega4/Omega6), the value of which is in the range of 0.2-1.5, typical for Nd3+ in different laser hosts. Nephelauxetic effect results in a red shift in the energy levels of Nd3+ for chloroborate glass. The radiative transition probability of the potential lasing transition 4F3/2-->4I11/2 of Nd3+ ions is found to be higher for flouroborate as compared to chloroborate glass.

  19. Removal of 4-chloro-2-methyl phenoxy acetic acid pesticide using coffee wastes from aqueous solution

    Directory of Open Access Journals (Sweden)

    M.I. Al-Zaben

    2017-05-01

    Full Text Available The objective of this study is to investigate the use of coffee waste (CW to remove the 4-chloro-2-methyl phenoxy acetic acid (MCPA from aqueous solutions. To prepare CW, it was first washed and boiled to remove color and impurities then it was air dried at room temperature for 48 h. Afterward the particle size distribution and zeta potential of the CW ground were determined. The porous texture of coffee was proved by scanning and transition electron microscopy. Batch adsorption tests were performed at 298 K. The effects of contact time, MCPA concentration, and pH were investigated. It was observed that the adsorption of MCPA by using CW is independent of the solution pH level. The Langmuir isotherm provided the best correlation for MCPA adsorption onto CW, showing that the adsorption was favorable. The Langmuir adsorption capacity was found to be 0.34 g/g. The second-order model provided the best description of MCPA adsorption onto CW when compared with the first order model. Infrared spectral studies revealed that acidic groups carboxyl and hydroxyl, are predominant contributors to MPCA adsorption by coffee.

  20. Effect of the modification of a natural mexican zeolite in the sorption of cadmium and 4-chloro phenol

    International Nuclear Information System (INIS)

    Cortes M, R.

    2007-01-01

    Clinoptilolite type zeolite is a material of relative abundance in Mexico, which possess ion exchange properties and it can be used in the removal of metal ions from polluted waters. The external surface of zeolites can be modified with cationic surfactants. This modification could have a negative effect on the removal of metal ions and provides to the material the capacity to adsorb phenolic compounds. For this reason, it is important to know the capability of the modified material on the sorption of metal ions and phenolic compounds, simultaneously. The aim of this work was to evaluate the effect of the external surface modification with surfactant of a Mexican zeolite over its sorption capacity of cadmium and 4-chloro phenol, in batch and column systems. To accomplish that, a clinoptilolite type zeolitic rock from a deposit located in the state of Sonora, Mexico, was used. It was ground, sieved and characterized with different techniques; and its external surface area was modified with hexadecyltrimethylammonium bromide (HDTMA-Br). A grain size fraction was selected to carry out sorption kinetics and equilibrium experiments, as well as packed column tests with zeolitic material and solutions of cadmium and 4-chloro phenol. There are different models proposed in literature that are used to describe sorption kinetics and equilibrium. In this work, the sorption experimental results were adjusted to some of these models to identify controlling mechanisms on the kinetics and equilibrium of the studied systems. The results showed that the cadmium adsorption on natural and modified zeolite was similar in batch systems. For the case of 4-chloro phenol sorption, it was observed that natural zeolite does not retain this compound, while in modified zeolite the sorption is better than other comparable materials. The results also showed that for the case of cadmium sorption, the mechanism involved was ion exchange; while for sorption of 4-chloro phenol, a partition mechanism

  1. An Endogenous Vaccine Based on Fluorophores and Multivalent Immunoadjuvants Regulates Tumor Micro-Environment for Synergistic Photothermal and Immunotherapy.

    Science.gov (United States)

    Li, Ling; Yang, Suleixin; Song, Linjiang; Zeng, Yan; He, Tao; Wang, Ning; Yu, Chuan; Yin, Tao; Liu, Li; Wei, Xiawei; Wu, Qinjie; Wei, Yuquan; Yang, Li; Gong, Changyang

    2018-01-01

    Recently, near-infrared (NIR) light-based photothermal therapy (PTT) has been widely applied in cancer treatment. However, in most cases, the tissue penetration depth of NIR light is not sufficient and thus photothermal therapy is unable to completely eradicate deep, seated tumors inevitably leading to recurrence of the tumor. Due to this significant limitation of NIR, improved therapeutic strategies are urgently needed. Methods: We developed an endogenous vaccine based on a novel nanoparticle platform for combinatorial photothermal ablation and immunotherapy. The design was based on fluorophore-loaded liposomes (IR-7-lipo) coated with a multivalent immunoadjuvant (HA-CpG). In vitro PTT potency was assessed in cells by LIVE/DEAD and Annexin V-FITC/PI assays. The effect on bone marrow-derived dendritic cells (BMDC) maturation and antigen presentation was evaluated by flow cytometry (FCM) with specific antibodies. After treatment, the immune cell populations in tumor micro-environment and the cytokines in the serum were detected by FCM and Elisa assay, respectively. Finally, the therapeutic outcome was investigated in an animal model. Results: Upon irradiation with 808 nm laser, IR-7-lipo induced tumor cell necrosis and released tumor-associated antigens, while the multivalent immunoadjuvant improved the expression of co-stimulatory molecules on BMDC and promoted antigen presentation. The combination therapy of PTT and immunotherapy regulated the tumor micro-environment, decreased immunosuppression, and potentiated host antitumor immunity. Most significantly, due to an enhanced antitumor immune response, combined photothermal immunotherapy was effective in eradicating tumors in mice and inhibiting tumor metastasis. Conclusion: This endogenous vaccination strategy based on synergistic photothermal and immunotherapy may provide a potentially effective approach for treatment of cancers, especially those difficult to be surgically removed.

  2. Optical Sensing of Aromatic Amino Acids and Dipeptides by a Crown-Ether-Functionalized Perylene Bisimide Fluorophore.

    Science.gov (United States)

    Weißenstein, Annike; Saha-Möller, Chantu R; Würthner, Frank

    2018-03-25

    We have studied the host-guest binding properties of a crown ether equipped, fluorescent perylene bisimide (PBI) receptor with a series of aromatic amino acids and dipeptides by UV/Vis, fluorescence and NMR spectroscopy. Fluorescence titration experiments showed that electron-rich aromatic amino acids L-tryptophan (L-Trp) and L-tyrosine (L-Tyr) as well as dipeptides containing these amino acids strongly quench the fluorescence of the electron-poor PBI molecule. Benesi-Hildebrand plots of fluorescence titration data confirmed the formation of host-guest complexes with 1:2 stoichiometry. Binding constants determined by UV/Vis and fluorescence titration experiments revealed values of 10³ - 10⁵ M-¹ in acetonitrile/methanol (9:1) at 23 °C. These data showed that amino acid L-Trp having an electron-rich indole unit and dipeptides containing this amino acid bind to the PBI receptor more strongly than other amino acids and dipeptides investigated here. For dipeptides containing L-Trp or L-Tyr the binding strength depends on the distance between the ammonium group and the aromatic unit of the amino acids and dipeptides, leading to a strong sensitivity for Ala-Trp dipeptide. 1D and 2D NMR experiments also corroborated 1:2 host-guest complexation and indicated formation of two diastereomeric species of the complexes. Our studies have shown that a properly functionalized PBI fluorophore can be applied as a molecular probe for the optical sensing of aromatic amino acids and dipeptides. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  3. Rational Design of in Vivo Tau Tangle-Selective Near-Infrared Fluorophores: Expanding the BODIPY Universe.

    Science.gov (United States)

    Verwilst, Peter; Kim, Hye-Ri; Seo, Jinho; Sohn, Nak-Won; Cha, Seung-Yun; Kim, Yeongmin; Maeng, Sungho; Shin, Jung-Won; Kwak, Jong Hwan; Kang, Chulhun; Kim, Jong Seung

    2017-09-27

    The elucidation of the cause of Alzheimer's disease remains one of the greatest questions in neurodegenerative research. The lack of highly reliable low-cost sensors to study the structural changes in key proteins during the progression of the disease is a contributing factor to this lack of insight. In the current work, we describe the rational design and synthesis of two fluorescent BODIPY-based probes, named Tau 1 and Tau 2. The probes were evaluated on the molecular surface formed by a fibril of the PHF6 ( 306 VQIVYK 311 ) tau fragment using molecular docking studies to provide a potential molecular model to rationalize the selectivity of the new probes as compared to a homologous Aβ-selective probe. The probes were synthesized in a few steps from commercially available starting products and could thus prove to be highly cost-effective. We demonstrated the excellent photophysical properties of the dyes, such as a large Stokes shift and emission in the near-infrared window of the electromagnetic spectrum. The probes demonstrated a high selectivity for self-assembled microtubule-associated protein tau (Tau protein), in both solution and cell-based experiments. Moreover, the administration to an acute murine model of tauopathy clearly revealed the staining of self-assembled hyperphosphorylated tau protein in pathologically relevant hippocampal brain regions. Tau 1 demonstrated efficient blood-brain barrier penetrability and demonstrated a clear selectivity for tau tangles over Aβ plaques, as well as the capacity for in vivo imaging in a transgenic mouse model. The current work could open up avenues for the cost-effective monitoring of the tau protein aggregation state in animal models as well as tissue staining. Furthermore, these fluorophores could serve as the basis for the development of clinically relevant sensors, for example based on PET imaging.

  4. Excited-state intramolecular proton transfer (ESIPT) inspired azole-quinoline based fluorophores: Synthesis and photophysical properties study

    Energy Technology Data Exchange (ETDEWEB)

    Padalkar, Vikas S.; Sekar, Nagaiyan, E-mail: n.sekar@ictmumbai.edu.in

    2014-11-15

    7-Hydroxy-3-(4-nitrophenyl)quinoline-6-carboxylic acid was obtained by the condensation reaction of p-amino salicylic acid and 4-nitrophenylmalonadialdehyde which was obtained from phenylacetonitrile through nitration, hydrolysis and Vilsmeier reaction. 7-Hydroxy-3-(4-nitrophenyl) quinoline-6-carboxylic acid was condensed with different o-aminophenols or o-aminothiophenol in ethanol in the presence of phosphorustrichloride. Synthesized quinoline contained benzimidazole and benzothiazole moieties. Photophysical behaviors of these compounds in solvents of different polarities were studied using UV–vis and fluorescence spectroscopy. The compounds showed single absorption in all the studied solvents. The dual emissions (normal emission and ESIPT emission) as well as large Stokes' shift emission pattern were observed for the synthesized fluorophores. The photophysical study shows that the emission properties of the compounds depend on the solvent polarity. The photophysical properties of the compounds were compared with structurally analogous ESIPT quinoline. Thermal stability of the compounds was studied using thermogravimetric analysis and results show that compounds are thermally stable up to 300 °C. The synthesized quinoline derivatives were characterized using elemental analysis, FT-IR and {sup 1}H –NMR, {sup 13}C –NMR spectroscopy and mass spectral analysis. - Highlights: • First and unique study of quinoline derivatives contain ESIPT azole unit at 6-position and hydroxyl group at 7-position. • Compounds are fluorescent with considerable quantum yields. • All compounds showed absorption in ultraviolet region and emission in visible region with large Stokes' shift. • The photophysical properties of new compounds were compared with reported ESIPT quinoline analogous.

  5. UV-visible spectrum of the phenyl radical and kinetics of its reaction with NO in the gas phase

    DEFF Research Database (Denmark)

    Wallington, T.J.; Egsgaard, H.; Nielsen, O.J.

    1998-01-01

    Pulse radiolysis transient UV-visible absorption spectroscopy was used to study the UV-visible absorption spectrum (225-575 nm) of the phenyl radical, C6H5(.), and kinetics of its reaction with NO. Phenyl radicals have a strong broad featureless absorption in the region of 225-340 nm...

  6. Preconcentration of Zn(II from Sample Water by Phenyl-iminodiacetic Acid Grafted Multiwalled Carbon Nanotubes

    Directory of Open Access Journals (Sweden)

    A. Moghimi

    2012-11-01

    Full Text Available : phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes were prepared by grafted phenyl-iminodiacetic acid groups onto multi-walled carbon nanotubes via a diazotation reaction. The stability of chemically phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes in concentrated hydrochloric acid which was then used as a recycling and pre-concentration reagent for further uses of phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes. The application of this  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes for sorption of a series of metal ions was performed by using different controlling factors such as the pH of metal ion solution and the equilibration shaking time by the static technique. Zn(II was found to exhibit the highest affinity towards extraction by these  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes phases. The pronounced selectivity was also confirmed from the determined distribution coefficient (Kd of all the metal ions, showing the highest value reported for Zn(II to occur by  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes. The potential applications of  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes for selective extraction of Zn(II to occur from aqueous solution were successfully accomplished as well as pre- concentration of low concentration of Zn(II (60 pg ml-1 from natural tap water with a pre-concentration factor of 100 for Zn(II off-line analysis by flame atomic absorption analysis. 

  7. Synthesis and Characterization of Ti-Phenyl at SiO2 Core-Shell Nanoparticles Catalyst

    International Nuclear Information System (INIS)

    Syamsi Aini; Jon Efendi; Syamsi Aini; Jon Efendi

    2012-01-01

    This study highlights the potential use of Ti-Phenyl at SiO 2 core-shell nanoparticles as heterogeneous catalysis in oxidation reaction. The Ti-Phenyl at SiO 2 was synthesized by reduction of TiCl 4 and diazonium salt with sodium borohydride to produce phenyl titanium nanoparticles (Ti-Phenyl), followed by the silica shell coating using tetraethyl orthosilicate (TEOS). The Ti-Phenyl at SiO 2 nanoparticles were characterized by Fourier transform infrared (FTIR) spectrometer, diffuse reflectance (DR) UV-visible spectrometer, thermogravimetric analyzer (TGA), X-ray diffraction (XRD) spectrometer, field emission scanning electron microscope (FESEM) and transmission electron microscope (TEM). The core-shell size of Ti-Phenyl at SiO 2 was in the range of 40 to 100 nm with its core composed with an agglomeration of Ti-Phenyl. The Ti-Phenyl at SiO 2 was active as a catalyst in the liquid phase epoxidation of 1-octene with aqueous hydrogen peroxide as an oxidant. (author)

  8. Zinc(II) and chloroindium(III) phthalocyanines bearing ethyl 7-oxy-6-chloro-4-methylcoumarin-3-propanoate groups: Synthesis, characterization and investigation of their photophysicochemical properties

    Science.gov (United States)

    Kuruca, Halid; Köksoy, Baybars; Karapınar, Begümhan; Durmuş, Mahmut; Bulut, Mustafa

    In this study, ethyl 7-hydroxy-6-chloro-4-methylcoumarin-3-propanoate (1), ethyl 7-(2,3-dicyanophenoxy)-6-chloro-4-methylcoumarin-3-propanoate (2), ethyl 7-(3,4-dicyanophenoxy)-6-chloro-4-methylcoumarin-3-propanoate (3), ethyl 4-chloro-5-(7-oxy-6-chloro-4-methylcoumarin-3-propanoate)phthalonitrile (4) were synthesized. The phthalonitrile derivatives (2, 3 and 4) were converted to their peripheral tetra, non-peripheral tetra and peripheral chlorocta substituted zinc(II) and chloroindium phthalocyanine derivatives. All novel compounds were characterized by elemental analysis, FT-IR, 1H-NMR, MALDI-TOF mass spectrometry and UV-vis spectral data. Additionally, the spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of the resulting substituted phthalocyaninatozinc(II) and indium(III) chloride complexes (5-10) were investigated in DMF, and the obtained results were compared for determination of the effects of the substituents’ positions and the variety of the central metal atom on these properties. The fluorescence quenching behavior of these phthalocyanines (5-10) were also investigated using 1,4-benzoquinone as a quencher. The obtained ethyl 7-oxy-6-chloro-4-methylcoumarin-3-propanoate bearing phthalocyaninatozinc(II) (5, 7 and 9) and indium(III) chloride (6, 8 and 10) complexes showed excellent solubility in most organic solvents. They produced high singlet-oxygen and showed appropriate photodegradation which is very important for photodynamic therapy applications. The novel ethyl 7-oxy-6-chloro-4-methylcoumarin-3-propanoate substituted zinc(II) and cloroindium(III) phthalocyanines were synthesized and characterized by using different spectroscopic methods such as 1H NMR, FT-IR, UV-vis, mass spectroscopy. The photophysical and photochemical properties as fluorescence lifetime, fluorescence, singlet oxygen and photodegredation quantum yields were

  9. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide

    Energy Technology Data Exchange (ETDEWEB)

    Sharma, R. [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics (India); Nayak, P. S.; Narayana, B. [Mangalore University, Mangalagangotri, Department of Studies in Chemistry (India); Kant, R., E-mail: rkvk.paper11@gmail.com [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics (India)

    2015-12-15

    The title compound, C{sub 13}H{sub 14}O{sub 2}N{sub 3}Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P2{sub 1}/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R{sub 2}{sup 2} (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λ{sub max} = 298 nm was determined by UV-Vis spectrophotometer.

  10. In vivo evaluation of [{sup 11}C]N-(2-chloro-5-thiomethylphenyl)-N'- (3-methoxy-phenyl)-N'-methylguanidine ([{sup 11}C]GMOM) as a potential PET radiotracer for the PCP/NMDA receptor

    Energy Technology Data Exchange (ETDEWEB)

    Waterhouse, Rikki N. E-mail: rnw7@columbia.edu; Slifstein, Mark; Dumont, Filip; Zhao Jun; Chang, Raymond C.; Sudo, Yasuhiko; Sultana, Abida; Balter, Andrew; Laruelle, Marc

    2004-10-01

    The development of imaging methods to measure changes in NMDA ion channel activation would provide a powerful means to probe the mechanisms of drugs and device based treatments (e.g., ECT) thought to alter glutamate neurotransmission. To provide a potential NMDA/PCP receptor PET tracer, we synthesized the radioligand [{sup 11}C]GMOM (K{sub i} = 5.2 {+-}0.3 nM; log P = 2.34) and evaluated this ligand in vivo in awake male rats and isoflurane anesthetized baboons. In rats, the regional brain uptake of [{sup 11}C]GMOM ranged from 0.75{+-}0.13% ID/g in the medulla and pons to 1.15{+-}0.17% ID/g in the occipital cortex. MK801 (1 mg/kg i.v.) significantly reduced (24-28%) [{sup 11}C]GMOM uptake in all regions. D-serine (10 mg/kg i.v.) increased [{sup 11}C]GMOM %ID/g values in all regions (10-24%) reaching significance in the frontal cortex and cerebellum only. The NR2B ligand RO 25-6981 (10 mg/kg i.v.) reduced [{sup 11}C]GMOM uptake significantly (24-38%) in all regions except for the cerebellum and striatum. Blood activity was 0.11{+-}0.03 %ID/g in the controls group and did not vary significantly across groups. PET imaging in isoflurane-anesthetized baboons with high specific activity [{sup 11}C]GMOM provided fairly uniform regional brain distribution volume (V{sub T}) values (12.8-17.1 ml g{sup -1}). MK801 (0.5 mg/kg, i.v., n = 1, and 1.0 mg/kg, i.v., n = 1) did not significantly alter regional V{sub T} values, indicating a lack of saturable binding. However, the potential confounding effects associated with ketamine induction of anesthesia along with isoflurane maintenance must be considered because both agents are known to reduce NMDA ion channel activation. Future and carefully designed studies, presumably utilizing an optimized NMDA/PCP site tracer, will be carried out to further explore these hypotheses. We conclude that, even though [{sup 11}C]GMOM is not an optimized PCP site radiotracer, its binding is altered in vivo in awake rats as expected by modulation of NMDA ion channel activity by MK801, D-serine or RO 25-6981. The development of higher affinity NMDA/PCP site radioligands is in progress.

  11. [2-(2,4-dimethylphenylthio)phenyl] aniline and its amide derivatives ...

    Indian Academy of Sciences (India)

    YOGESH PATIL

    2018-02-15

    Feb 15, 2018 ... These derivatives could be considered as a precursor structure for further design of antituberculosis agent. Keywords. [2-(2,4-dimethylphenylthio)phenyl] aniline; antituberculosis activity; cytotoxicity. 1. Introduction. Tuberculosis (TB) is a contagious disease caused by the. Mycobacterium tuberculosis (MTB).

  12. (2E-3-(3-Methoxy-1-phenyl-1H-pyrazol-4-yl-2-propenal

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2009-12-01

    Full Text Available The palladium-catalyzed reaction of 4-bromo-3-methoxy-1-phenyl-1H-pyrazole with acrolein diethyl acetal gives the title compound in good yield. Detailed spectroscopic data (1H NMR, 13C NMR, 15N NMR, IR, MS are presented.

  13. Complexometric determination of lanthanides with 3-hydroxy-3-phenyl-1-p-sulfonato phenyltriazenes

    International Nuclear Information System (INIS)

    Purohit, D.N.; Cahuhan, R.S.

    1985-01-01

    The use of 3-hydroxy-3-phenyl-1-p-sulphonato phenyltriazene as metallocromic indicator for complexometric determination of fourteen lanthanides is reported. The preparation of this indicator is described as well as the effects of pH and temperature on quantitative titrations. (C.L.B.) [pt

  14. Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions

    CSIR Research Space (South Africa)

    Madala, NE

    2012-07-01

    Full Text Available Biotechnology Letters July 2012/ Vol. 34 No.7, pp 1351-1356 Biotransformation of isonitrosoacetophenone (2-keto-2- phenyl-acetaldoxime) in tobacco cell suspensions Ntakadzeni E. Madala 1 , P. A. Steenkamp 2 , L. A. Piater 1 and I. A. Dubery 1 1...

  15. Behaviour of phenyl-urea type herbicides and related chemical residues in soil-plant systems

    International Nuclear Information System (INIS)

    Suess, A.; Eben, C.

    1975-01-01

    Uniformly 14 C-labelled aniline derivatives were used to indicate the degradation of phenyl-urea type herbicides. The results suggested cleavage of the benzene ring when present as a soil residue, cleavage apparently being reduced by increased chlorination of the ring. (author)

  16. Bis[(5-phenyl-1,3,4-thiadiazol-2-ylsulfanyl]methane

    Directory of Open Access Journals (Sweden)

    He-wen Wang

    2010-12-01

    Full Text Available The asymmetric unit of the title compound, C17H12N4S4, contains one half-molecule situated on a twofold rotational axis. In the molecule, the thiadiazole and attached phenyl rings are twisted by 5.8 (3°.

  17. Triplet state spectroscopy of .sigma.-conjugated poly[methyl(phenyl)silylene

    Czech Academy of Sciences Publication Activity Database

    Skryshevski, Y.; Piryatinski, Y.; Vakhnin, A.; Blonsky, I.; Kadashchuk, A.; Nešpůrek, Stanislav

    2007-01-01

    Roč. 30, č. 3 (2007), s. 384-392 ISSN 0925-3467 R&D Projects: GA AV ČR IAA100100622; GA AV ČR KAN401770651 Institutional research plan: CEZ:AV0Z40500505 Keywords : poly[methyl(phenyl)silylene] * polysilane * photoluminescence Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 1.519, year: 2007

  18. Pharmacological Studies of p, N-(3, 4-Methylenedioxy phenyl Benzoic Acid (RRL-1364 - Part-I

    Directory of Open Access Journals (Sweden)

    Dahanukar Sharadini

    1978-01-01

    Full Text Available Detailed pharmacological investigations of p-N-(3, 4-methylene dioxy phenyl benzoic acid revealed marked hypotensive action which was dose dependent and most marked in cats; it was absent in rats. Atropine could block this hypotensive action, thus suggest-ing cholinomimetic mechanism. Further studies indicated that the hypotension produced was central and possibly medullary in origin.

  19. Synthesis of duloxetine intermediate (S)-3-Chloro-1-(2-thienyl)-1-propanol with liquid-core immobilized Candida pseudotropicalis 104.

    Science.gov (United States)

    Zhimin, Ou; Xingyuan, Sun; Hanbing, Shi; Hongxia, Bi

    2012-12-01

    (S) -3-Chloro-1-(2-thienyl)-1-propanol was synthesized by the asymmetric reduction of 3-chloro-1-(2-thienyl)propanone with liquid-core immobilized Candida pseudotropicalis 104. The optimum time was 28 h for the re-cultivation of immobilized cells. The optimum film solvent for the liquid-core capsule was 0.3 % chitosan (M (w) 1.0 × 10(5)). Conversion decreased with the increase of the liquid-core capsule diameter and with the addition of more substrates at the same reduction time. The immobilized cells show good reduction ability in a potassium phosphate buffer (pH 6.6~7.2). The material outside the spread speed of immobilized cells was not restricted when the shaking speed was higher than 160 r/min. Liquid-core immobilized cells can be reused 11 times. Compared with the batch reduction, the continuous reduction of 3-chloro-1-(2-thienyl)propanone in the membrane reactor with liquid-core immobilized cells as catalyst can relieve the inhibition from a high-concentration substrate. Conversion and enantiometric excess of (S)-3-chloro-1-(2-thienyl)-1-propanol reached 100 % and >99 % in a continuous reduction of 12 g/L 3-chloro-1-(2-thienyl)propanone for 10 days.

  20. Organoselenium group is critical for antioxidant activity of 7-chloro-4-phenylselenyl-quinoline.

    Science.gov (United States)

    Vogt, Ane G; Voss, Guilherme T; de Oliveira, Renata L; Paltian, Jaini J; Duarte, Luis F B; Alves, Diego; Jesse, Cristiano R; Roman, Silvane S; Roehrs, Juliano A; Wilhelm, Ethel A; Luchese, Cristiane

    2018-02-25

    The quinolone compounds have been reported for many biological properties, especially as potent antioxidants. This study investigated the antioxidant effect of 7-chloro-4-phenylselenyl-quinoline (PSQ), a quinolone derivative with organoselenium group, against oxidative stress induced by sodium nitroprusside (SNP) in brains of mice. A second objective was to verify the importance of phenylselenyl group presents at position 4 of the quinoline structure to antioxidant effect of compound. So, it was compared the antioxidant effect of PSQ with a quinoline without organoseleniun group (7-chloroquinoline [QN]). Swiss mice were used and received SNP (0.335 μmol/site, intracerebroventricular) 30 min after treatment with PSQ or QN, at the doses of 50 mg/kg (intragastrically). After 1 h, animals were sacrificed and the brains were removed to biochemistry analysis. Thiobarbituric acid reactive species (TBARS), protein carbonyl (PC) and non-protein thiol (NPSH) levels, as well as catalase (CAT), glutathione S transferase (GST) and δ -aminolevulinic acid (δ-ALA-D) activities were determined. SNP increased TBARS and PC levels, and reduced the enzymatic (CAT and GST activity) and non-enzymatic (NPSH levels) antioxidant defenses and inhibited the δ-ALA-D activity. PSQ avoided the increase in the lipid peroxidation and PC levels, as well as the decrease in the NPSH levels, CAT, GST and δ-ALA-D activities QN partially avoided the increase in lipid peroxidation, but it not protected against alterations induced by SNP. In conclusion, phenylselenyl group present in quinoline structure is critical for antioxidant activity of PSQ. Copyright © 2018 Elsevier B.V. All rights reserved.

  1. Pharmacokinetic and metabolic disposition of p-chloro-m-xylenol (PCMX) in dogs.

    Science.gov (United States)

    Dorantes, A; Stavchansky, S

    1992-05-01

    The pharmacokinetic and metabolic profile of p-chloro-m-xylenol (PCMX) was studied in healthy mongrel dogs after intravenous and oral administration of single doses of 200 and 2000 mg of PCMX, respectively. Calculation of pharmacokinetic parameters was based on compartmental and noncompartmental methods. The mean pharmacokinetic parameters of elimination half-life and mean residence time were 1.84 and 1.69 hr, respectively. The apparent volume of distribution at steady state was estimated to be 22.4 liters, and the plasma clearance was 14.6 liters/hr. The bioavailability of PCMX was 21%, indicating low absorption for this drug. PCMX's metabolite data show that a presystemic elimination process (first-pass effect) is also occurring. PCMX plasma concentrations after intravenous administration of 500-, 200-, and 100-mg doses were found to be proportional to the dose given, demonstrating that the pharmacokinetic profile of PCMX is linear over the dose range studied. Biotransformation studies showed that urinary excretion was not the major route for rapid elimination of unchanged PCMX and almost all material excreted in urine was associated with the conjugated species (glucuronides and sulfates). Statistical significant differences were not found (P greater than 0.05) between the percentages excreted in urine of PCMX and its conjugated metabolites after intravenous and oral administration. The percentages excreted in urine after iv and oral doses of unchanged PCMX were, respectively, 0.45 and 0.37; total conjugates, 46.3 and 43.3; sulfates, 38.1 and 33.2; and glucuronides, 8.2 and 10.2.

  2. Effects of diphenyl and p-chloro-diphenyl diselenides on feeding behavior of rats.

    Science.gov (United States)

    Bortolatto, Cristiani F; Heck, Suélen O; Gai, Bibiana M; Zborowski, Vanessa A; Neto, José S S; Nogueira, Cristina W

    2015-07-01

    The searching for safe and effective antiobesity drugs has been the subject of intense research. Previous studies have shown several pharmacological applications of organoselenium compounds; however, their possible anorectic-like actions have not been investigated. This study aims to investigate the effects of (PhSe)2 and (p-ClPhSe)2 on feeding behavior of rats and their potential as weight-reducing agents. The effects of intraperitoneal administration of diselenides were investigated through the microstructural pattern of feeding behavior, behavioral satiety sequence (BSS), hypothalamic serotonin (5-HT) uptake, body weight, and epididymal fat content of male rats. Our findings demonstrated that food intake of fasted rats was reduced by both diselenides (1 and 10 mg/kg). Diphenyl diselenide [(PhSe)2] (1 mg/kg) and p-chloro-diphenyl diselenide [(p-ClPhSe)2] (10 mg/kg) decreased the frequency, mean duration, and mean size of meals compared with the control treatment. The BSS structure was preserved when organoselenium compounds (1 mg/kg) were administered, and it was associated to a displacement to the left when the resting period started indicating a satiating action. Inhibition of 5-HT uptake in the hypothalamus (∼20 %) was also found in rats treated with low doses of (PhSe)2 and (p-ClPhSe)2 (1 mg/kg). Treatments with a high dose of both diselenides (10 mg/kg) carried out for 7 days induced weight loss and epididymal fat reduction in sated rats. This study suggests that diselenides caused a satiating action in rats that could be partially explained by the inhibition of hypothalamic 5-HT uptake. These organoselenium compounds were potential weight-reducing agents when repeatedly administered.

  3. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

    International Nuclear Information System (INIS)

    Elhadi, S. A.

    2004-09-01

    Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, 1 H-and 13 C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)

  4. Bis[5-chloro-2-(phenyldiazenyl-κN2pyridine-κN]bis(thiocyanato-κNiron(II

    Directory of Open Access Journals (Sweden)

    Luksamee Vittaya

    2012-05-01

    Full Text Available In the title complex, [Fe(NCS2(C11H8ClN32], the FeII atom is coordinated by two N atoms from the thiocyanate ligands and four N atoms from two chelating 5-chloro-2-(phenyldiazenylpyridine ligands, generating a fairly regular FeN6 octahedral coordination geometry. The thiocyanate ions are in a cis disposition and the pyridine N atoms are in a trans orientation. In the crystal, a short intermolecular Cl...S contact [3.366 (3 Å] is observed.

  5. Hybrid Molecules Containing a 7-Chloro-4-aminoquinoline Nucleus and a Substituted 2-Pyrazoline with Antiproliferative and Antifungal Activity

    Directory of Open Access Journals (Sweden)

    Alba Montoya

    2016-07-01

    Full Text Available Twenty-four new hybrid analogues (15–38 containing 7-chloro-4-aminoquinoline and 2-pyrazoline N-heterocyclic fragments were synthesized. Twelve of the new compounds were evaluated against 58 human cancer cell lines by the U.S. National Cancer Institute (NCI. Compounds 25, 30, 31, 36, and 37 showed significant cytostatic activity, with the most outstanding GI50 values ranging from 0.05 to 0.95 µM. The hybrid compounds (15–38 were also evaluated for antifungal activity against Candida albicans and Cryptococcus neoformans. From the obtained results some structure–activity relationships were outlined.

  6. Some Anilides of 2-Alkylthio- and 2-Chloro-6-Alkylthio-4-Pyridinecarboxylic Acids: Synthesis and Photosynthesis-Inhibiting Activity

    Directory of Open Access Journals (Sweden)

    Miloš Macháček

    2001-06-01

    Full Text Available Many compounds containing a -CONH- group display photosynthesis inhibiting activity. Based on this structural feature, a group of anilides of 2-alkylthio-(1b-4f or 2-chloro-6-alkylthio-4-pyridinecarboxylic acids (5a-6c was synthesised. The prepared compounds were tested for their inhibition of the oxygen evolution rate (OER in spinach chloroplasts. A quasi-parabolic dependence between photosynthesis-inhibiting activity and the lipophilicity of the compounds was determined for 1b-4f as well as for 5a-6c. The inhibitory activity of compounds 1b-4f was higher than that of 5a-6c for comparable lipophilicity values.

  7. Visible properties of Sm{sup 3+} ions in chloro-fluoro-borate glasses for reddish - orange emission

    Energy Technology Data Exchange (ETDEWEB)

    Rao, K. Venkata, E-mail: drvenkataraok@gmail.com [Department of Physics, S.B.V.R. Degree College, Badvel - 516227, A.P. (India); Babu, S.; Ratnakaram, Y. C. [Department of Physics, Sri Venkateswara University, Tirupati- 517502 (India); Rao, B. Venkata [Department of Physics, Loyola Degree College, Pulivendula- 516390, A.P. (India)

    2016-05-23

    Optical properties of different concentration (0.2, 0.4, 0.6, 0.8 and 1.0 mol %) of Sm{sup 3+} doped chloro-fluoro-borate glasses have been synthesized and discussed. Structural characterizations have been studied through XRD analysis. Spectroscopic analysis has done from absorption spectra, luminescence spectra and decay lifetime profiles. From the emission spectra, concentration quenching is observed, with increase of samarium concentration and discussed behind the phenomena. The nature of decay curve analysis was performed for the {sup 4}G{sub 5/2} level. These glasses are expected to give interesting application in the field of optics.

  8. 3,5-Bis(4-meth-oxy-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

    Science.gov (United States)

    Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S; Narayana, B; Yathirajan, H S

    2011-01-12

    In the title compound, C(23)H(22)N(2)O(2), the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth-oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C-H⋯π stacking inter-actions and weak π-π inter-actions [centriod-centroid distance = 3.891 (2) Å].

  9. Effective Biotransformation of Ethyl 4-Chloro-3-Oxobutanoate into Ethyl (S)-4-Chloro-3-Hydroxybutanoate by Recombinant E. coli CCZU-T15 Whole Cells in [ChCl][Gly]-Water Media.

    Science.gov (United States)

    Dai, Yong; Huan, Bin; Zhang, Hai-Sheng; He, Yu-Cai

    2017-04-01

    To increase the biocatalytic activity of Escherichia coli CCZU-T15 whole cells, choline chloride/glycerol ([ChCl][Gly]) was firstly used as biocompatible solvent for the effective biotransformation of ethyl 4-chloro-3-oxobutanoate (COBE) into ethyl (S)-4-chloro-3-hydroxybutanoate [(S)-CHBE]. Furthermore, L-glutamine (150 mM) was added into [ChCl][Gly]-water ([ChCl][Gly] 12.5 vol%, pH 6.5) media instead of NAD + for increasing the biocatalytic efficiency. To further improve the biosynthesis of (S)-CHBE (>99 % e.e.) by E. coli CCZU-T15 whole cells, Tween-80 (7.5 mM) was also added into this reaction media, and (S)-CHBE (>9 % e.e.) could be effectively synthesized from 2000 and 3000 mM COBE in the yields of 100 and 93.0 % by whole cells of recombinant E. coli CCZU-T15, respectively. TEM image indicated that the cell membrane was permeabilized and lost its integrity and when the cell was exposed to [ChCl][Gly]-water media with Tween-80. Clearly, this bioprocess has high potential for the effective biosynthesis of (S)-CHBE (>99 % e.e.).

  10. A general three-step one-pot synthesis of novel (E)-6-chloro-2-(aryl/hetarylvinyl)quinoline-3-carboxylic acids.

    Science.gov (United States)

    Li, Yang; Wang, Yang; Zou, Hongtao

    2017-05-01

    In this work, a facile and general three-step one-pot synthesis of structurally new (E)-6-chloro-2-(aryl/hetarylvinyl)quinoline-3-carboxylic acid derivatives has been achieved from easily available ethyl 6-chloro-2-(chloromethyl) quinoline-3-carboxylate and aromatic or heteroaromatic aldehydes. This strategy features simple one-pot operation, tolerance of a wide range of substituents, and good yields. Moreover, these newly synthesized compounds belong to a new class of quinoline derivatives and could be good candidates for the development of more complex quinoline compounds for use in medicinal chemistry.

  11. Biotransformation of trans-1-chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd).

    Science.gov (United States)

    Schmidt, Tobias; Bertermann, Rüdiger; Rusch, George M; Tveit, Ann; Dekant, Wolfgang

    2013-05-01

    trans-1-Chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd) is a novel foam blowing and precision cleaning agent with a very low impact for global warming and ozone depletion. trans-HCFO-1233zd also has a low potential for toxicity in rodents and is negative in genotoxicity testing. The biotransformation of trans-HCFO-1233zd and kinetics of metabolite excretion with urine were assessed in vitro and in animals after inhalation exposures. For in vitro characterization, liver microsomes from rats, rabbits and humans were incubated with trans-HCFO-1233zd. Male Sprague Dawley rats and female New Zealand White rabbits were exposed to 2,000, 5,000 and 10,000ppm for 6h and urine was collected for 48h after the end of the exposure. Study specimens were analyzed for metabolites using (19)F NMR, LC-MS/MS and GC/MS. S-(3,3,3-trifluoro-trans-propenyl)-glutathione was identified as predominant metabolite of trans-HCFO-1233zd in all microsomal incubation experiments in the presence of glutathione. Products of the oxidative biotransformation of trans-HCFO-1233zd were only minor metabolites when glutathione was present. In rats, both 3,3,3-trifluorolactic acid and N-acetyl-(3,3,3-trifluoro-trans-propenyl)-l-cysteine were observed as major urinary metabolites. 3,3,3-Trifluorolactic acid was not detected in the urine of rabbits. Quantitation showed rapid excretion of both metabolites in both species (t1/2trans-HCFO-1233zd was determined as approximately 0.01% of received dose in rabbits and approximately 0.002% in rats. trans-HCFO-1233zd undergoes both oxidative biotransformation and glutathione conjugation at very low rates. The low extent of biotransformation and the rapid excretion of metabolites formed are consistent with the very low potential for toxicity of trans-HCFO-1233zd in mammals. Copyright © 2013 Elsevier Inc. All rights reserved.

  12. Covalent modification of mutant rat P2X2 receptors with a thiol-reactive fluorophore allows channel activation by zinc or acidic pH without ATP.

    Directory of Open Access Journals (Sweden)

    Shlomo S Dellal

    Full Text Available Rat P2X2 receptors open at an undetectably low rate in the absence of ATP. Furthermore, two allosteric modulators, zinc and acidic pH, cannot by themselves open these channels. We describe here the properties of a mutant receptor, K69C, before and after treatment with the thiol-reactive fluorophore Alexa Fluor 546 C(5-maleimide (AM546. Xenopus oocytes expressing unmodified K69C were not activated under basal conditions nor by 1,000 µM ATP. AM546 treatment caused a small increase in the inward holding current which persisted on washout and control experiments demonstrated this current was due to ATP independent opening of the channels. Following AM546 treatment, zinc (100 µM or acidic external solution (pH 6.5 elicited inward currents when applied without any exogenous ATP. In the double mutant K69C/H319K, zinc elicited much larger inward currents, while acidic pH generated outward currents. Suramin, which is an antagonist of wild type receptors, behaved as an agonist at AM546-treated K69C receptors. Several other cysteine-reactive fluorophores tested on K69C did not cause these changes. These modified receptors show promise as a tool for studying the mechanisms of P2X receptor activation.

  13. Production of (R)-Ethyl-4-Chloro-3-Hydroxybutanoate Using Saccharomyces cerevisiae YOL151W Reductase Immobilized onto Magnetic Microparticles.

    Science.gov (United States)

    Choo, Jin Woo; Kim, Hyung Kwoun

    2015-11-01

    For the synthesis of various pharmaceuticals, chiral alcohols are useful intermediates. Among them, (R)-ethyl-4-chloro-3-hydroxybutanoate ((R)-ECHB) is an important building block for the synthesis of L-carnitine. (R)-ECHB is produced from ethyl-4-chloro-3-oxobutanoate (ECOB) by a reductase-mediated, enantioselective reduction reaction. The Saccharomyces cerevisiae YOL151W reductase that is expressed in Escherichia coli cells exhibited an enantioselective reduction reaction toward ECOB. By virtue of the C-terminal His-tag, the YOL151W reductase was purified from the cell-free extract using Ni(2+)-NTA column chromatography and immobilized onto Ni(2+)-magnetic microparticles. The physical properties of the immobilized reductase (Imm-Red) were measured using electron microscopy, a magnetic property measurement system, and a zeta potential system; the average size of the particles was approximately 1 μm and the saturated magnetic value was 31.76 emu/g. A neodymium magnet was used to recover the immobilized enzyme within 2 min. The Imm-Red showed an optimum temperature at 45°C and an optimum pH at 6.0. In addition, Bacillus megaterium glucose dehydrogenase (GDH) was produced in the E. coli cells and was used in the coupling reaction to regenerate the NADPH cofactor. The reduction/oxidation coupling reaction composed of the Imm-Red and GDH converted 20 mM ECOB exclusively into (R)- ECHB with an e.e.p value of 98%.

  14. Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride.

    Science.gov (United States)

    Vilhelmsen, Mie Højer; Ostergaard, Lars Frøsig; Nielsen, Mogens Brøndsted; Hammerum, Steen

    2008-05-21

    The reduction of 2-chloro-N-phenylpropanamide with LiAlH(4) has been re-examined. In contrast to previous findings, we obtain in almost equal quantities two amines from this reaction, namely N-propylaniline and the rearranged product N-isopropylaniline. 2-Methyl-N-phenylaziridine is an intermediate in the reduction and can be isolated from reactions with less LiAlH(4). Reduction of 2-methyl-N-phenylaziridine itself proceeds non-regioselectively to provide a mixture of propyl- and isopropylanilines. Formation of the amines by reduction of the aziridine is much slower than formation by reduction of the 2-chloropropanamide, which indicates that Lewis acid catalysis (by aluminium chlorohydrides) facilitates the reduction of the aziridine. In addition, Lewis acid catalysis increases the relative yield of the propylamine product. The reduction of 2-chloro-N-phenylpropanamide furnishes 2-phenylamino-1-propanol as a by-product, rather than the previously proposed 1-phenylamino-2-propanol.

  15. Synthesis and Physico-Chemical Properties of Zinc Layered Hydroxide-4-Chloro-2-Methylphenoxy Acetic Acid (ZMCPA) Nanocomposite

    Science.gov (United States)

    Salleh, N. M.; Mohsin, SM N.; Sarijo, S. H.; Ghazali, S. A. I. S. M.

    2017-05-01

    Hybrid nanocomposite zinc layered hydroxide-4-chloro-2-methylphenoxyacetic acid (ZMCPA) was successfully synthesized via direct reaction of 4-chloro-2-methylphenoxy acetic acid (MCPA) with zinc oxide (ZnO) under an aqueous environment. The pure phase and well-ordered ZMCPA was obtained when ZMCPA was synthesized at 0.3 M MCPA. The resulting nanocomposite, ZMCPA was characterized by powder X-ray diffraction (PXRD), fourier transform infrared(FTIR) spectroscopy, field emission scanning electron microscopy (FESEM), thermogravimetric and differential thermogravimetric analyses (TGA/DTG) and CHNS Analyzer. Basal spacing showed that the gallery height of zinc layered hydroxide (ZLH) expanded from 11.Å to 24.1 Å, indicating that the MCPA anions were successfully intercalated into the interlayer space of ZLH. The FTIR spectrum of the ZMCPA shows it resembles the spectra of ZnO and MCPA that confirms the intercalation of MCPA between the ZLH sheets. FESEM shows the ZnO precursor has granular structure and transformed into a flake-like structure when the nanohybrid is formed. Percentage loading of MCPA interleaved in the nanohybrid is 50.2%.

  16. Crystal structures of (E-3-(furan-2-yl-2-phenyl-N-tosylacrylamide and (E-3-phenyl-2-(m-tolyl-N-tosylacrylamide

    Directory of Open Access Journals (Sweden)

    Dong Cheng

    2016-06-01

    Full Text Available In the title N-tosylacrylamide compounds, C20H17NO4S, (I, and C23H21NO3S, (II, the conformation about the C=C bond is E. The acrylamide groups, [–NH—C(=O—C=C–], are almost planar, with the N—C—C=C torsion angle being −170.18 (14° in (I and −168.01 (17° in (II. In (I, the furan, phenyl and 4-methylbenzene rings are inclined to the acrylamide mean plane by 26.47 (11, 69.01 (8 and 82.49 (9°, respectively. In (II, the phenyl, 3-methylbenzene and 4-methylbenzene rings are inclined to the acrylamide mean plane by 11.61 (10, 78.44 (10 and 78.24 (10°, respectively. There is an intramolecular C—H...π interaction present in compound (II. In the crystals of both compounds, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(8 ring motif. In (I, the dimers are reinforced by C—H...O hydrogen bonds and linked by C—H...π interactions, forming chains along [011]. In the crystal of (II, the dimers are linked via C—H...O hydrogen bonds, forming chains along [100]. The chains are further linked by C—H...π interactions, forming layers parallel to (010.

  17. First principle evaluation of the chiroptical activity of the di-phenyl-diazene derivatives

    Science.gov (United States)

    Benassi, Enrico; Corni, Stefano

    2012-09-01

    Azobenzene (di-phenyl-diazene) is well-known as a photoisomerisable molecule and has been widely studied as a molecular photoswitcher. Molecular rods, where di-phenyl arms are bound to the diazene moiety, have been also synthesized. In this article we explore by first principle density functional theory calculations the chiroptical properties (electronic circular dichroism spectra, ECD) of azobenzene and its homologues with polyphenyl arms. In particular, we demonstrate that for molecules in the cis configuration the intrinsic chirality of the distorted cis diazene group dominates the ECD response, while for trans species the non-planarity of the polyphenyl arms induces peaks in the ECD spectrum. Finally, the possibility of obtaining a light-controlled chiral switch by proper functionalization is also speculated.

  18. Liquid Crystals Derived from 2-phenyl-isoindoles: Synthesis and Characterization

    Science.gov (United States)

    Jow, Kenny G.; Dingemans, Theo J.; Bushnell, Dennis M. (Technical Monitor)

    2001-01-01

    2-Phenyl-isoindole was investigated as the rigid core unit in a series of asymmetric mesogenic molecules. When the 2-phenyl-isoindole core was terminated with a hexyl tail, no mesophase formation could be observed. When 4-n-(tridecafluorohexyl) was used, however, we observed both monotropic and enantiotropic phase behavior. We found that most functionalities at the anhydride 5-position results in the formation of smectic A (SmA) phases in the temperature range of 70-180 C. Functionalities at the anhydride 4-position suppress mesophase formation. Large substituents (-Br, -NO2) and symmetric substitution patterns (5,6-dichloro, 4,7-dichloro and 4,5,6,7-tetrachloro) on the anhydride moiety increase the melting point and destabilize the mesophase. Temperature dependent X-ray diffraction experiments suggest an interdigitated SmA packing for this family of compounds.

  19. Synthesis and antifungal activities of N-aryl-4-phenyl-3-(4-phenoxyphenyl)butanamides.

    Science.gov (United States)

    Lee, S H; Kim, I O; Cheong, C S; Chung, B Y

    1999-10-01

    Various N-aryl-4-phenyl-3-(4-phenoxyphenyl)butanamides (2 and 3) were tested for fungicidal activities against Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea, Phytophthora infestans, Puccinia recondita, and Erysiphe graminis in vivo. Butanamides (2 and 3a) that have an electron withdrawing group (Cl, F) attached to the meta position of the phenyl ring showed good to excellent activities against Pyricularia oryzae, Puccinia recondita, and Erysiphe graminis in high concentration while those that have a strong electron withdrawing group (CN, NO2) or electron donating group (OCH3, CH3) attached to the meta position did not show good activities against all test fungi at 250 mg L-1. The antifungal activities of the compounds synthesized were compared with reference compounds such as Tricyclazole, Moncozeb, and Benomyl.

  20. (4E-1-Phenyl-4-{[(pyridin-2-ylamino]methylidene}pyrazolidine-3,5-dione

    Directory of Open Access Journals (Sweden)

    Shaaban K. Mohamed

    2016-06-01

    Full Text Available The title compound, C15H12N4O2, contains two independent molecules in the asymmetric unit. These differ in terms of dihedral angles that the phenyl and 2-pyridyl rings subtend with the central five-membered ring; 15.2 (2 and 2.9 (2°, respectively, in one molecule, 8.9 (2 and 5.1 (2°for the second. In the crystal, the independent molecules each self-associate to form layers through N—H...O and C—H...O hydrogen bonding. The layers associate through π–π interactions between the phenyl rings and isolated carbon–carbon double bonds [shortest midpoint–centroid distance = 3.347 (4 Å]. The crystal studied was refined as a two-component twin.

  1. Duplex and Triplex Formation of Mixed Pyrimidine Oligonucleotides with Stacking of Phenyl-triazole Moieties in the Major Groove

    DEFF Research Database (Denmark)

    Andersen, Nicolai Krog; Døssing, Holger; Jensen, Frank

    2011-01-01

    5-(1-Phenyl-1,2,3-triazol-4-yl)-2'-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine. With consecutive incorporations of the two modified...... nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π-π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal...... stability was found in between the uridine analogues or with the cytidine analogue placed in the 3' direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified...

  2. Photooxidation of poly[methyl(phenyl)silylene] and effect of photostabilizers

    Czech Academy of Sciences Publication Activity Database

    Meszároš, Oto; Schmidt, Pavel; Pospíšil, Jan; Nešpůrek, Stanislav

    2006-01-01

    Roč. 91, č. 3 (2006), s. 573-578 ISSN 0141-3910. [International Conference on Modification, Degradation , Stabilization Conference /3./. Lyon, 29.08.2004-02.09.2004] R&D Projects: GA MŠk ME 700; GA MŠk OC D14.30 Institutional research plan: CEZ:AV0Z40500505 Keywords : polysilane degradation * poly[methyl(phenyl)silylene] * photooxidation Subject RIV: CD - Macromolecular Chemistry Impact factor: 2.174, year: 2006

  3. Synthesis and properties of complexes of 1-phenyl-2,3-dimetylpyrazolone-5-thione with metals

    International Nuclear Information System (INIS)

    Bikkulova, A.T.; Kapina, A.P.; Medvedeva, E.A.

    1985-01-01

    Cadmium complexes with thiopyrine (1-phenyl-2.3-dimethylpyrazolone-5-thione) (R) of the composition CdR 2 X 2 are obtained by precipitation from hydrochloric acid solutions at pH=1 and at chloride and bromide (X) excess. The formation of coordination bond of a metal through the sulphur atom is established by the IR- and NMR-spectroscopy methods. Fungicidal activity of the compositions obtained is detected

  4. Dynamic changes of paraoxonase 1 activity towards paroxon and phenyl acetate during coronary artery surgery.

    Science.gov (United States)

    Wysocka, Anna; Cybulski, Marek; Berbeć, Henryk; Wysokiński, Andrzej; Stążka, Janusz; Daniluk, Jadwiga; Zapolski, Tomasz

    2017-04-04

    Serum paraoxonase 1 (PON1), an enzyme associated with high - density lipoproteins (HDL) particles, inhibits the oxidation of serum lipoproteins and cell membranes. PON1 activity is lower in patients with atherosclerosis and in inflammatory diseases. The systemic inflammatory response provoked during cardiopulmonary bypass grafting may contribute to the development of postoperative complications. The aim of the present study was to estimate the dynamic changes in paraoxonase 1 (PON1) activity towards paraoxon and phenyl acetate during and after coronary artery surgery. Twenty six patients with coronary heart disease undergoing coronary artery bypass grafting (CABG) were enrolled into the study. Venous blood samples were obtained preoperatively, after aortic clumping, after the end of operation, at 6, 18, 30 and 48 h after operation. Paraoxonase activity was measured spectrophotometrically in 50 mM glycine/NaOH buffer (pH 10.5) containing 1.0 mM paraoxon, and 1.0 mM CaCl 2 . Arylesterase activity was measured in 20 mM TrisCl buffer (pH 8.0) containing 1 mM phenyl acetate and 1 mM CaCl 2 . PON1 activity toward paraoxon and phenyl acetate significantly decreased after aorta cross clumping and increased directly after operation. PON1 activity towards paraoxon in preoperative period and PON1 activity towards phenyl acetate in seventh stage of experiment tended to inversely correlate with the occurrence of postoperative complications. The paraoxonase 1 plasma activity is markedly reduced during CABG surgery.

  5. Synthesis, Characterization and Chelating Properties of 4-Butyrylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one

    Directory of Open Access Journals (Sweden)

    J. D. Patel

    2010-01-01

    Full Text Available 4-Butyrylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one (BUMP-SC was prepared and its metal chelates of Cu2+, Ni2+, Co2+, Mn2+, Fe2+, Fe3+, Cr3+, UO2 and OV were prepared. The ligands and its chelates were characterized by elemental analysis, metal:ligand (M:L stoichiometry, IR-electronic spectral studies and magnetic properties. The compounds also were screened for their antimicrobial activity.

  6. Synthesis and Application of Phenyl Nitrone Derivatives as Acidic and Microbial Corrosion Inhibitors

    OpenAIRE

    Chen, Shijun; Zhao, Kang; Chen, Gang

    2015-01-01

    Nitrone has drawn great attention due to its wide applications as a 1,3-dipole in heterocyclic compounds synthesis and the bioactivities. With the special structure, nitrone can also be used as ligand in inorganic chemistry. Based on the current research, the nitrones are anticipated to be effective inhibitors against acidic and microbial corrosion. The aim of this work is to investigate the inhibitory action of nitrones. In this work, a series of phenyl nitrone derivatives (PN) was synthesiz...

  7. {2,6-Bis[(di-tert-butyl-phosphino)-methyl]-phenyl}chloridonickel(II).

    Science.gov (United States)

    Boro, Brian J; Dickie, Diane A; Goldberg, Karen I; Kemp, Richard A

    2008-09-20

    In the title compound, [Ni(C(24)H(43)P(2))Cl], the Ni atom adopts a distorted square-planar geometry, with the P atoms of the 2,6-bis-[(di-tert-butyl-phosphino)meth-yl]phenyl ligand trans to one another. The P-Ni-P plane is twisted out of the plane of the aromatic ring by 21.97 (6)°.

  8. Corrosion inhibition of alpha brass by 1-phenyl-3-methyl-pyrazol-5 ...

    African Journals Online (AJOL)

    Corrosion inhibition of alpha brass by 1-phenyl-3-methyl-pyrazol-5-one in acidic media at different temperatures. ... Global Journal of Engineering Research ... The corrosion inhibition efficiency (C.I.E.) of the alpha brass was 99.83%, using the condition of 3.0M HNO3 for the uninhibited experiment and 0.03M HPMP for the ...

  9. New phenyl-ethanediols from the culture broth of Boletus edulis.

    Science.gov (United States)

    Yang, Wan-Qiu; Qin, Xiang-Dong; Shao, Hong-Jun; Fang, Li-Zhen; Wang, Fei; Ding, Zhi-Hui; Dong, Ze-Jun; Liu, Ji-Kai

    2007-04-01

    A new phenyl-ethanediol, (1S)-(4-acetylphenyl)-1, 2-ethanediol (1), and a new natural product, (1S)-(3-ethenylphenyl)-1, 2-ethanediol (2), were isolated from the culture broth of the basidiomycete Boletus edulis together with three related known compounds, 1-(4-ethylphenyl)-1, 2-ethanediol (3), 1-(3-ethylphenyl)-1, 2-ethanediol (4) and 1-(3-formylphenyl)-ethanone (5). Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques.

  10. Synthesis and anti-HIV activity of novel phenyl branched cyclopropyl nucleosides.

    Science.gov (United States)

    Wu, Ying; Hong, Joon Hee

    2005-09-01

    Novel phenyl branched cyclopropyl nucleoside analogues were designed and synthesized as potential antiviral agents. Cyclopropanation was performed via classical Simmons-Smith reaction using Zn(Et)2 and CH2I2. Coupling of the mesylates 11 and 12 with natural bases (A,C,T,U) and desilylation afforded a series of novel cyclopropyl nucleosides 21-28. The synthesized compounds were evaluated for their antiviral and antitumor activity against various viruses such as HIV, HSV-1, HSV-2 and HCMV.

  11. Photoinduced metastability and degradation of poly[methyl(phenyl)silylene] as seen by thermoluminescence

    Czech Academy of Sciences Publication Activity Database

    Kadashchuk, A.; Nešpůrek, Stanislav; Ostapenko, N.; Skryshevskii, Yu.; Zaika, V.

    2001-01-01

    Roč. 35, special issue (2001), s. 413-428 ISSN 1058-725X R&D Projects: GA AV ČR IAA1050901; GA MŠk OC 518.10; GA AV ČR KSK4050111 Institutional research plan: CEZ:AV0Z4050913 Keywords : metastability * degradation * poly[methyl(phenyl)silylene] Subject RIV: BG - Nuclear, Atomic and Molecular Physics, Colliders Impact factor: 0.457, year: 2001

  12. High-spin chloro mononuclear MnIII complexes: a multifrequency high-field EPR study.

    Science.gov (United States)

    Mantel, Claire; Chen, Hongyu; Crabtree, Robert H; Brudvig, Gary W; Pécaut, Jacques; Collomb, Marie-Noëlle; Duboc, Carole

    2005-03-01

    The isolation, structural characterization, and electronic properties of two six-coordinated chloromanganese (III) complexes, [Mn(terpy)(Cl)3] (1) and [Mn(Phterpy)(Cl)3] (2), are reported (terpy = 2,2':6'2"-terpyridine, Phterpy = 4'-phenyl-2,2':6',2"-terpyridine). These complexes complement a series of mononuclear azide and fluoride Mn(lll) complexes synthesized with neutral N-tridentate ligands, [Mn(L)(X)3] (X = F- or N3 and L = terpy or bpea [N,N-bis(2-pyridylmethyl)-ethylamine)], previously described. Similar to these previous complexes, 1 and 2 exhibit a Jahn-Teller distortion of the octahedron, characteristic of a high-spin Mn(III) complex (S = 2). The analysis of the crystallographic data shows that, in both cases, the manganese ion lies in the center of a distorted octahedron characterized by an elongation along the tetragonal axis. Their electronic properties were investigated by multifrequency EPR (190-475 GHz) performed in the solid state at different temperatures (5-15 K). This study confirms our previous results and further shows that: i) the sign of D is correlated with the nature of the tetragonal distortion; ii) the magnitude of D is not sensitive to the nature of the anions in our series of rhombic complexes, contrary to the porphyrinic systems; iii) the [E/D] values (0.124 for 1 and 0.085 for 2) are smaller compared to those found for the [Mn(L)(X)3] complexes (in the range of 0.146 to 0.234); and iv) the E term increases when the ligand-field strength of the equatorial ligands decreases.

  13. Studies on thermal degradation kinetics of thermal and UV cured N-(4-hydroxy phenyl) maleimide derivatives

    International Nuclear Information System (INIS)

    Pitchaimari, G.; Vijayakumar, C.T.

    2014-01-01

    Graphical abstract: - Highlights: • UV cure materials are more thermally stable than the thermally cured materials. • Cyanate ester functionalization offers better thermal stability. • The Ea values for Poly NVPs are low compared to other materials investigated. • The UV cured materials showed higher Ea values than the thermally cured materials. - Abstract: The results of the studies concerning the thermal and photo initiated copolymerization of N-(4-acryloyloxy phenyl) maleimide (AX), N-(4-methacryloyloxy phenyl) maleimide (MAX) and N-(4-cyanato phenyl) maleimide (CNX) with N-vinyl-2-pyrrolidone (NVP) were presented. The structures of all the copolymers prepared were confirmed by FTIR studies. The thermogravimetric studies of both the thermal and UV cured materials indicated that the UV cured materials were comparatively thermally more stable than the thermally polymerized materials during thermal degradation. Of all the materials investigated, liquid composition having NVP and CNX cured by UV irradiation showed better thermal stability. The degradation kinetic studies using Flynn–Wall–Ozawa, Vyazovkin and Friedman methods showed that the activation energies (Ea) for the thermal degradation of polymeric materials cured by UV irradiation were slightly higher than the Ea values calculated for the thermally polymerized materials

  14. ED50 AP block predictions for phenyl substituted and unsubstituted n-alkanols.

    Science.gov (United States)

    Hahin, R; Kondratiev, A

    2001-03-15

    A series of n-alkanols and phenyl-substituted n-alkanols (phi-alkanols) of increasing chain length and phenol were characterized for their ability to block action potentials (APs) in frog sciatic nerves. APs were recorded using the single sucrose-gap method. The degree of AP attenuation when the nerve was exposed to different concentrations of an alcohol was used to construct dose-response curves. The reciprocals of the half-blocking doses (ED50s) were used to obtain a measure of the potency of the alcohols. For n-alkanols and phi-alkanols, increasing the chain length by the addition of a methylene group increased the potency on average by 3.1 for both groups of alkanols. The addition of a phenyl group caused a potency increase that ranged between the values of 77 and 122. The ED50 for both groups of alkanols could not be solely predicted by the log octanol-water partition coefficient (Kow). Using linear solvation energy relations (LSER), the log ED50 could be described as a linear combination of the intrinsic (van der Waals) molar volume (VI), polarity (P), and hydrogen bond acceptor basicity (beta) and donor acidity (alpha). Size alone could not predict the ED50 for both n-alkanols and phi-alkanols. The results are consistent with the hypothesis that alkanols bind to and interact with Na channels to cause AP block. Phenyl group addition to an alkanol markedly increases the molecule's potency.

  15. Optimization of lipase-catalyzed enantioselective production of 1-phenyl 1-propanol using response surface methodology.

    Science.gov (United States)

    Soyer, Asli; Bayraktar, Emine; Mehmetoglu, Ulku

    2010-01-01

    Optically active 1-phenyl 1-propanol is used as a chiral building block and synthetic intermediate in the pharmaceutical industries. In this study, the enantioselective production of 1-phenyl 1-propanol was investigated systematically using response surface methodology (RSM). Before RSM was applied, the effects of the enzyme source, the type of acyl donor, and the type of solvent on the kinetic resolution of 1-phenyl 1-propanol were studied. The best results were obtained with Candida antartica lipase (commercially available as Novozym 435), vinyl laurate as the acyl donor, and isooctane as the solvent. In the RSM, substrate concentration, molar ratio of acyl donor to the substrate, amount of enzyme, temperature, and stirring rate were chosen as independent variables. The predicted optimum conditions for a higher enantiomeric excess (ee) were as follows: substrate concentration, 233 mM; molar ratio of acyl donor to substrate, 1.5; enzyme amount, 116 mg; temperature, 47 °C; and stirring rate, 161 rpm. A verification experiment conducted at these optimized conditions for maximum ee yielded 91% for 3 hr, which is higher than the predicted value of 83%. The effect of microwave on the ee was also investigated and ee reached 87% at only 5 min.

  16. On the molecular conformation of bisaromatic systems the case of 2-phenyl-2H-benzotriazoles

    International Nuclear Information System (INIS)

    Catalan, Javier; Perez, Pilar; Claramunt, Rosa Maria; Maria, Dolores Santa; Bobosik, Vladimir

    2007-01-01

    2-Phenyl-2H-benzotriazole exhibits a planar molecular conformation both in its ground electronic state (S 0 ) and its first excited singlet (S 1 ) and triplet state (T 1 ). However, introducing one or two methyl groups in the ortho positions of the phenyl ring causes the aromatic systems in the compound to lose their coplanarity in both S 0 and T 1 electronic states. On the other hand, 2-(2-methylphenyl)-2H-benzotriazole regains such coplanarity in its first excited singlet state S 1 , giving rise to population inversion that could be used to generate stimulated radiation around 350 nm. As shown in this work, the effectiveness of the ISC process in these compounds is markedly dependent on the twisting angle, θ, of the structure; accordingly, ISC occurs to a negligible extent in a planar compound such as 2-phenyl-2H-benzotriazole, where θ = 0 o . This evidence supports the assumption that planar molecular forms of the TIN-P photoprotectors are more photostable than non-planar ones due to the non effective generation via ISC of their triplet states

  17. Novel organic dyes based on phenyl-substituted benzimidazole for dye sensitized solar cells

    Energy Technology Data Exchange (ETDEWEB)

    Saltan, Gözde Murat [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Dinçalp, Haluk, E-mail: haluk.dincalp@cbu.edu.tr [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Kıran, Merve; Zafer, Ceylan [Solar Energy Institute, Ege University, Bornova, 35100 Izmir (Turkey); Erbaş, Seçil Çelik [Celal Bayar University, Materials Engineering Department, Faculty of Engineering, Yunus Emre, 45140 Manisa (Turkey)

    2015-08-01

    Two new sensitizers derived from benzimidazole core for dye-sensitized solar cell (DSSC) applications were designed and synthesized as D–π–A structures, in which two phenyl-substituted benzimidazole group, a phenyl ring and a cyanoacrylic acid were used as the electron donor, π-conjugated linkage and the electron acceptor, respectively. Effect of methoxy- and N,N-dimetylamino- moieties attached to the phenyl groups of benzimidazole were investigated by means of optical and photovoltaic measurements. The compounds exhibit broad absorption maximum at 387 nm with the tail extending up to 500 nm on TiO{sub 2}-coated thin film. The longer wavelength absorption band around 360 nm and the much longer decay components could be attributed to the existence of charge transfer state of the dyes in solutions. DSSC device fabricated by using methoxy substituted dye (BI5a) as a sensitizer shows much better incident photon-to-current conversion efficiency (IPCE) of 64% giving cell efficiency of 2.68%. - Graphical abstract: Display Omitted - Highlights: • Long decay times suggest the delayed fluorescence caused by the existence of ICT. • The best solar energy conversion efficiency was obtained for BI5a dye (2.68%). • More fluorescent BI5a dye gives higher photocurrent generation.

  18. Click functionalization of phenyl-capped bithiophene on azide-terminated self-assembled monolayers

    International Nuclear Information System (INIS)

    Zheng, Yijun; Cui, Jiaxi; Ikeda, Taichi

    2015-01-01

    Graphical abstract: - Highlights: • Electrochemically-active self-assembled monolayers with phenyl-capped bithiophene were prepared. • Post-functionalization method based on click chemistry solved the solubility issue of phenyl-capped thiophene alkanethiol. • The capture and release of the counter anions during the redox reaction were detectable by E-QCM. - Abstract: We immobilized tetra(ethylene glycol)-substituted phenyl-capped bithiophene with alkyne terminals (Ph2TPh-alkyne) on azide-terminated self-assembled monolayers (N 3 -SAMs) by Cu-catalyzed azide-alkyne cycloaddition reaction. Ph2TPh-functionalized SAMs on a gold substrate showed reversible electrochemical response. The surface densities of the azide groups in N 3 -SAMs and Ph2TPh units in Ph2TPh-functionalized SAMs were estimated to be 7.3 ± 0.3 × 10 −10 mol cm −2 and 4.6 ± 0.3 × 10 −10 mol cm −2 , respectively, by quartz crystal microbalance (QCM). Most of Ph2TPh-alkynes are considered to be anchored on N 3 -SAMs via both terminal groups. Ph2TPh-functionalized SAMs exhibited reversible redox peaks in cyclic voltammetry (CV). In redox reaction, reversible capture and release of the counter anion could be monitored by electrochemical QCM (E-QCM).

  19. Click functionalization of phenyl-capped bithiophene on azide-terminated self-assembled monolayers

    Energy Technology Data Exchange (ETDEWEB)

    Zheng, Yijun; Cui, Jiaxi [Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, Mainz 55128 (Germany); Ikeda, Taichi, E-mail: IKEDA.Taichi@nims.go.jp [Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, Mainz 55128 (Germany); Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044 (Japan)

    2015-11-15

    Graphical abstract: - Highlights: • Electrochemically-active self-assembled monolayers with phenyl-capped bithiophene were prepared. • Post-functionalization method based on click chemistry solved the solubility issue of phenyl-capped thiophene alkanethiol. • The capture and release of the counter anions during the redox reaction were detectable by E-QCM. - Abstract: We immobilized tetra(ethylene glycol)-substituted phenyl-capped bithiophene with alkyne terminals (Ph2TPh-alkyne) on azide-terminated self-assembled monolayers (N{sub 3}-SAMs) by Cu-catalyzed azide-alkyne cycloaddition reaction. Ph2TPh-functionalized SAMs on a gold substrate showed reversible electrochemical response. The surface densities of the azide groups in N{sub 3}-SAMs and Ph2TPh units in Ph2TPh-functionalized SAMs were estimated to be 7.3 ± 0.3 × 10{sup −10} mol cm{sup −2} and 4.6 ± 0.3 × 10{sup −10} mol cm{sup −2}, respectively, by quartz crystal microbalance (QCM). Most of Ph2TPh-alkynes are considered to be anchored on N{sub 3}-SAMs via both terminal groups. Ph2TPh-functionalized SAMs exhibited reversible redox peaks in cyclic voltammetry (CV). In redox reaction, reversible capture and release of the counter anion could be monitored by electrochemical QCM (E-QCM).

  20. Neurotoxicological and thyroid evaluations of rats developmentally exposed to tris(1,3-dichloro-2-propyl)phosphate (TDICPP) and tris(2-chloro-2-ethyl)phosphate(TCEP)

    Science.gov (United States)

    ABSTRACT: Tris(1,3-dichloro-2-propyl)phosphate (TDICPP) and tris(2-chloro-2-ethyl)phosphate (TCEP) are organophosphorous flame retardants with widespread usage and human exposures through food, inhalation, and dust ingestion. They have been detected in human tissues including ur...

  1. Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride

    DEFF Research Database (Denmark)

    Vilhelmsen, Mie Højer; Østergaard, Lars Frøsig; Nielsen, Mogens Brøndsted

    2008-01-01

    -chloropropanamide, which indicates that Lewis acid catalysis (by aluminium chlorohydrides) facilitates the reduction of the aziridine. In addition, Lewis acid catalysis increases the relative yield of the propylamine product. The reduction of 2-chloro-N-phenylpropanamide furnishes 2-phenylamino-1-propanol as a by......-product, rather than the previously proposed 1-phenylamino-2-propanol....

  2. Thermodynamic study of solubility for 2-amino-4-chloro-6-methoxypyrimidine in twelve organic solvents at temperatures from 273.15 K to 323.15 K

    International Nuclear Information System (INIS)

    Yao, Ganbing; Xia, Zhanxiang; Li, Zhihui

    2017-01-01

    Highlights: • 2-Amino-4-chloro-6-methoxypyrimidine solubility in twelve solvents were determined. • The solubility were correlated with four models. • The mixing properties were derived. - Abstract: The solubility of 2-amino-4-chloro-6-methoxypyrimidine in methanol, ethanol, chloroform, toluene, ethyl acetate, acetonitrile, n-propanol, acetone, N,N-dimethylformamide, isopropanol, 1,4-dioxane and ethyl benzene was obtained experimentally using the high-performance liquid chromatography analysis at temperatures ranging from (273.15 to 323.15) K under atmospheric pressure. The solubility of 2-amino-4-chloro-6-methoxypyrimidine in a fixed solvent increased with an increase in temperature. At a certain temperature, the mole fraction solubility in different solvents decreased according to the following order: N,N-dimethylformamide > dioxane > acetone > ethyl acetate > chloroform > (acetonitrile, n-propanol) > (ethanol, isopropanol) > methanol > toluene > ethyl benzene. Four models, modified Apelblat equation, λh equation, Wilson model and NRTL model were applied to correlate of the experimental solubility results. The largest values of relative average deviation and root-mean-square deviation acquired by the four models are 1.21% and 10.71 × 10 −4 , respectively. The modified Apelblat model is regarded as the best one for describing the experimental values. Furthermore, the mixing Gibbs energy, mixing enthalpy, and mixing entropy, activity coefficient and reduced excess enthalpy at infinitesimal concentration were obtained based on the mole fraction solubility. The mixing process of 2-amino-4-chloro-6-methoxypyrimidine in the selected solvents is discussed.

  3. Catalytic aziridination of electron-deficient olefins with an N-chloro-N-sodio carbamate and application of this novel method to asymmetric synthesis.

    Science.gov (United States)

    Minakata, Satoshi; Murakami, Yuta; Tsuruoka, Ryoji; Kitanaka, Shinsuke; Komatsu, Mitsuo

    2008-12-21

    A new method for the aziridination of electron-deficient olefins using an N-chloro-N-sodio carbamate is described; the reaction was promoted by phase-transfer catalysis (solid-liquid) and afforded aziridines from alpha,beta-unsaturated ketones, esters, sulfones and amides.

  4. CHARACTERISTICS AND TOXICITY OF THE DRINKING WATER DISINFECTION BY-PRODUCT 3-CHLORO-4(DICHLOROMETHYL)-5-HYDROXY-2[5H]-FURANONE (MX) TO MEDAKA (ORYZIAS LATIPES)

    Science.gov (United States)

    The compound 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone, also known as MX, is a by-product of wood pulp manufacture and a contaminant of chlorinated drinking and sewage water. MX has recently been shown to be carcinogenic to rodents. However, no data exist for its effec...

  5. Bioactivation mechanism of the cytotoxic and nephrotoxic S-conjugate S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine.

    Science.gov (United States)

    Dekant, W; Lash, L H; Anders, M W

    1987-11-01

    The bioactivation of S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine (CTFC) was studied with purified bovine kidney cysteine conjugate beta-lyase and with N-dodecylpyridoxal bromide in cetyltrimethylammonium bromide micelles as a pyridoxal model system. The beta-lyase and the pyridoxal model system converted CTFC to chlorofluoroacetic acid and inorganic fluoride, which were identified by 19F NMR spectrometry. 2-Chloro-1,1,2-trifluoroethanethiol and chlorofluorothionoacetyl fluoride were formed as metabolites of CTFC and were trapped with benzyl bromide and diethylamine, respectively, to yield benzyl 2-chloro-1,1,2-trifluoroethyl sulfide and N,N-diethyl chlorofluorothioacetamide, which were identified by gas chromatography/mass spectrometry. The bioactivation mechanism of CTFC therefore involves the initial formation of the unstable thiol 2-chloro-1,1,2-trifluoroethanethiol, which loses hydrogen fluoride to form the acylating agent chlorofluorothionoacetyl fluoride; hydrolysis of the thionoacyl fluoride affords the stable, terminal metabolites chlorofluoroacetic acid and inorganic fluoride. The intermediate acylating agent and chlorofluoroacetic acid may contribute to the cytotoxic effects of CTFC.

  6. Iodine catalyzed one-pot synthesis of chloro-substituted linear and angular indoloquinolines and in vitro antiproliferative activity study of different indoloquinolines

    Digital Repository Service at National Institute of Oceanography (India)

    Parvatkar, P.T.; Ajay, A.K.; Bhat, M.K.; Parameswaran, P.S.; Tilve, S.G.

    -substituted 6H-indolo[2,3-b]quinoline 3c to be the most active and the parent 6H-indolo[2,3-b]quinoline 3a to be the least active, while the other compounds including the different chloro derivatives exhibited only intermediate activity....

  7. 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino-N-substituted benzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies

    Directory of Open Access Journals (Sweden)

    Mahesh Kumar

    2014-09-01

    Full Text Available A series of 4-(1-aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino-N-substituted benzenesulfonamide derivatives (1–20 was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial results indicated that compounds N-(4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino phenylsulfonyl-4-isopropoxy benzamide (9 and N-(4-(5-chloro-1-(2-chlorobenzoyl-2-oxoindolin-3-ylideneamino phenylsulfonyl-4-isopropoxybenzamide (19 were found to be the most effective ones. The anticancer results indicated that almost all the synthesized compounds were more active than the standard drug carboplatin but less active than the standard drug 5-fluorouracil (5-FU against both the cell lines (HCT116 and RAW 264.7. 4-(1-Benzoyl-5-chloro-2-oxoindolin-3-ylideneamino-N-(pyrimidin-2-yl benzenesulfonamide (3 was found to be most potent and exhibited selectivity toward HCT 116. QSAR studies indicated that antimicrobial activity of isatin derivatives against different microbial strains was governed by lipophilic parameter, log P and topological parameters valance zero and third order molecular connectivity indices (0χv and 3χv.

  8. 8-Chloro-dGTP, a hypochlorous acid-modified nucleotide, is hydrolyzed by hMTH1, the human MutT homolog.

    Science.gov (United States)

    Fujikawa, Katsuyoshi; Yakushiji, Hiroyuki; Nakabeppu, Yusaku; Suzuki, Toshinori; Masuda, Mitsuharu; Ohshima, Hiroshi; Kasai, Hiroshi

    2002-02-13

    The human mutT homolog, hMTH1, suppresses spontaneous mutations by degrading the endogeneous mutagen, 8-hydroxy-dGTP. We previously reported the broad substrate specificity of hMTH1, which also degrades the oxidatively damaged purine nucleotides, 2-hydroxy-dATP, 8-hydroxy-dATP, 2-hydroxy-ATP, and 8-hydroxy-GTP, in addition to 8-hydroxy-dGTP. In this paper, we describe the hMTH1 activity for 8-chloro-dGTP, which could be formed in inflamed tissue by the reaction of dGTP with hypochlorous acid, a product of myeloperoxidase from activated human neutrophils. The hMTH1 protein was mixed with 1-20 microM of 8-chloro-dGTP and 8-hydroxy-dGTP, and the reaction products were quantified by anion-exchange HPLC to measure the pyrophosphatase reaction rate. The kinetic parameters revealed that 8-chloro-dGTP was degraded by hMTH1 with 50% efficiency as compared with that of 8-hydroxy-dGTP. This result suggests that 8-chloro-dGTP is an intrinsic substrate for hMTH1.

  9. Effect of H4R antagonist N-(2-aminoethyl)-5-chloro-1H-indol-2-carboxamides and 5-chloro-2-(piperazin-1-ylmethyl)-1H-benzimidazole on histamine and 4-methylhistamine-induced mast cell response.

    Science.gov (United States)

    Nagarajan, Gomathi; Mariappanadar, Vairamani; Tamizh, Muthu; Kaliappan, Ilango; Elden, Berla Thangam

    2017-06-01

    The histamine plays a decisive role in acute and chronic inflammatory responses and is regulated through its four types of distinct receptors designated from H1 to H4. Recently histamine 4 receptor (H4R) antagonists have been reported to possess various pharmacological effects against various allergic diseases. To investigate the inhibitory effect of N-(2-aminoethyl)-5-chloro-1H-indol-2-carboxamide (Compound A) and 5-chloro-2-(piperazin-1-ylmethyl)-1H-benzimidazole (Compound L) on H4R-mediated calcium mobilization, cytokine IL-13 production, ERK1/2, Akt and NF-κB activation in human mastocytoma cells-1 (HMC-1). Compounds A and L were synthesized chemically and their inhibitory effect on intracellular calcium release was analyzed by Fluo-4 calcium assay, cytokine measurement through ELISA and activation of signaling molecules by western blot. Pre-treatment with compounds A and L significantly reduced the H4R-mediated intracellular calcium release. Histamine and 4-methylhistamine (4-MH) induced Th2 cytokine IL-13 production in HMC-1 cells, was inhibited by compound A (77.61%, 74.25% at 1 μM concentration) and compound L (79.63%, 81.70% at 1 μM concentration). Furthermore, histamine induced the phosphorylation of ERK1/2, Akt and NF-κB was suppressed by compounds A and L at varying levels, ERK1/2 (88%, 86%), Akt (88%, 89%) and NF-κB (89%, 87%) in HMC-1 cells. Taken together these data demonstrate that compound A and compound L may block H4R-mediated downstream signaling events.

  10. Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ- butyro lactones: Key intermediates in the synthesis of β-phenyl-Gaba and baclofene

    International Nuclear Information System (INIS)

    Gomez G, J.; Melendez R, M.; Suarez C, O. R.; Castelan D, L. E.; Fragoso V, M. J.; Lopez V, E.; Sanchez Z, M.

    2014-01-01

    the preparation of β-phenyl- and β-(4-chlorophenyl)-γ-butyro lactones (±)-4 and their resolution to the corresponding (+)-(S)-3, (-)-(R)-3 and (+)-(S)-4, (-)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of dia stereoisomeric 4-hydroxybutyramide s (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6. (Author)

  11. Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ- butyro lactones: Key intermediates in the synthesis of β-phenyl-Gaba and baclofene

    Energy Technology Data Exchange (ETDEWEB)

    Gomez G, J.; Melendez R, M.; Suarez C, O. R.; Castelan D, L. E.; Fragoso V, M. J.; Lopez V, E.; Sanchez Z, M., E-mail: melendez@uaeh.edu.mx [Universidad Autonoma del Estado de Hidalgo, Area Academica de Quimica, Carretera Pachuca-Tulancingo Km. 4.5, Mineral de la Reforma 42184, Hidalgo (Mexico)

    2014-07-01

    the preparation of β-phenyl- and β-(4-chlorophenyl)-γ-butyro lactones (±)-4 and their resolution to the corresponding (+)-(S)-3, (-)-(R)-3 and (+)-(S)-4, (-)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of dia stereoisomeric 4-hydroxybutyramide s (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6. (Author)

  12. Acquisition of a potent and selective TC-PTP inhibitor via a stepwise fluorophore-tagged combinatorial synthesis and screening strategy.

    Science.gov (United States)

    Zhang, Sheng; Chen, Lan; Luo, Yong; Gunawan, Andrea; Lawrence, David S; Zhang, Zhong-Yin

    2009-09-16

    Protein tyrosine phosphatases (PTPs) regulate a broad range of cellular processes including proliferation, differentiation, migration, apoptosis, and immune responses. Dysfunction of PTP activity is associated with cancers, metabolic syndromes, and autoimmune disorders. Consequently, small molecule PTP inhibitors should serve not only as powerful tools to delineate the physiological roles of these enzymes in vivo but also as lead compounds for therapeutic development. We describe a novel stepwise fluorophore-tagged combinatorial library synthesis and competitive fluorescence polarization screening approach that transforms a weak and general PTP inhibitor into an extremely potent and selective TC-PTP inhibitor with highly efficacious cellular activity. The result serves as a proof-of-concept in PTP inhibitor development, as it demonstrates the feasibility of acquiring potent, yet highly selective, cell permeable PTP inhibitory agents. Given the general nature of the approach, this strategy should be applicable to other PTP targets.

  13. Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S-1-Chloro-3-(1-naphthyloxy-2-propanol

    Directory of Open Access Journals (Sweden)

    Zhi Wang

    2012-09-01

    Full Text Available (R-1-Chloro-3-(1-naphthyloxy-2-propanol (3, which is the key intermediate of (S-propranolol, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically increased under ultrasound exposure. Effects of various reaction conditions on the synthetic activity of enzyme as well as enantioselectivity, including the type of enzyme, ultrasound power, solvent, acyl donor, temperature and substrate molar ratio, were investigated. Pseudomonas sp. lipase (PSL showed an excellent catalytic performance under optimum conditions (enzyme activity: 78.3 ± 3.2 μmol·g−1·min−1, E value: 98 ± 6.

  14. Effect of DDT and MCPA (4-chloro-2-methylphenoxyacetic acid) on reproduction of the pond snail, Lymnaea stagnalis L

    Energy Technology Data Exchange (ETDEWEB)

    Woin, P.; Broenmark, C. (Univ. of Lund (Sweden))

    1992-01-01

    Reproduction is the single most important function in the life cycle of an organism. Successful reproduction determines fitness of organisms. The inability of an organism to complete any one stage of the reproductive process severely reduces its lifetime reproductive success. Disruptions in the reproduction will ultimately affect the abundance and distribution of the species. Therefore, laboratory tests of long-term impact of sublethal pollutant concentrations on organisms preferably is done on the reproductive success. Pollutants of diverse structure may affect the reproductive system which is sensitive to toxic agents. Certain pollutants, notably the organochlorine compounds, have been shown to affect the male and female reproductive systems. The authors have studied the effect of sublethal concentrations of DDT and the herbicide 4-chloro-2-methylphenoxyacetic acid (MCPA) on the reproductive output of the pulmonate snail Lymnaea stagnalis under a 2-mon exposure period.

  15. Electrochemical oxidation of 4-chloro phenol over a carbon paste electrode modified with Zn Al layered double hydroxides

    Energy Technology Data Exchange (ETDEWEB)

    Hernandez F, D.; Palomar P, M.; Licona S, T. de J.; Romero R, M. [Universidad Autonoma Metropolitana, Unidad Azcapotzalco, Departamento de Materiales, Av. San Pablo 180, Col. Reynosa-Tamaulipas, 02200 Mexico D. F. (Mexico); Valente, Jaime S., E-mail: mepp@correo.azc.uam.mx [Instituto Mexicano del Petroleo, Eje Central No. 152, 07730 Mexico D. F. (Mexico)

    2014-07-01

    A study is presented on the electrochemical oxidation of 4-chloro phenol (4cp) in aqueous solution using a bare carbon paste electrode, Cpe, and another one that was modified with Zn Al layered double hydroxides (Cpe/Zn Al-LDH). The electro-oxidation was effected at ph values ranging from 3 up to 11. It was found through cyclic voltammetry that this process was irreversible, namely, there were no reduction peaks, and that depending on the nature of the electrode, the anodic current was limited either by adsorption (Cpe) or diffusion (Cpe/Zn Al-LDH). The energy required and the oxidation reaction rate depended on the ph and on the nature of the electrode, such that the greater rates were obtained when the Cpe/Zn Al-LDH electrode and acid ph were used. The Zn Al-LDH was characterized by means of X-ray diffraction. (Author)

  16. Theoretical Study of Chloro-N-(4-methoxybenzylideneaniline Derivatives as Corrosion Inhibitors for Zinc in Hydrochloric Acid

    Directory of Open Access Journals (Sweden)

    S. Kumar

    2013-01-01

    Full Text Available The density functional theory (DFT was used to investigate the corrosion inhibition of three inhibitors on zinc. Quantum chemical parameters such as the energy of highest occupied molecular orbital (EHOMO, the energy of lowest unoccupied molecular orbital (ELUMO, energy gap (ΔE, hardness (η, softness (σ, electrophilicity index (ω, the fraction of electrons transferred (ΔN from inhibitor molecule to the metal surface, energy change when both processes occur, namely, charge transfer to the molecule and backdonation from the molecule (ΔEbackdonation, natural charge (qN, and Fukui functions have been calculated by using B3LYP/6-31+G(d basis set. The relation between the inhibition efficiency and quantum chemical parameters has been discussed in order to elucidate the inhibition mechanism of the chloro-N-(4-methoxybenzylideneaniline derivatives.

  17. In vitro phenotypic screening of 7-chloro-4-amino(oxy)quinoline derivatives as putative anti-Trypanosoma cruzi agents.

    Science.gov (United States)

    Fonseca-Berzal, Cristina; Rojas Ruiz, Fernando A; Escario, José A; Kouznetsov, Vladimir V; Gómez-Barrio, Alicia

    2014-02-15

    In this study, a series of 22 pre-synthesized 7-chloro-4-amino(oxy)quinoline derivatives was assayed in vitro as potential antichagasic agents. A primary screening against Trypanosoma cruzi epimastigotes and a non-specific cytotoxicity assay on murine fibroblasts were simultaneously performed, resulting quinolines 3, 7 and 12 with great selectivity (SI) on the extracellular parasite (SI7, SI3, SI12 and SIBZ >9.44). Therefore, the activity of these derivatives was evaluated on intracellular amastigotes, achieving derivative 7 the best SI (SI=12.73). These results, supported by the in silico prediction of a good oral bioavailability and a suitable risk profile, propose the 4-amino-7-chloroquinoline scaffold as a potential template for designing trypanocidal prototypes. Copyright © 2014 Elsevier Ltd. All rights reserved.

  18. Synthesis of N-(2-chloro purin-6-yl) aza-18-crown-6 and its interaction with human serum albumin.

    Science.gov (United States)

    Li, Cui; Cui, Fengling; Mao, Runze; Huo, Ruina; Qu, Guirong

    2012-01-28

    The synthesis of novel purine nucleosides-linked azacrown ethers in the C6 position, N-(2-chloro purin-6-yl) aza-18-crown-6 (NCPAC), was described. This new nucleoside analogue can be prepared from a series of N9-modified nucleosides and the method allows for new and easy modification of the nucleosides. The interaction between NCPAC and human serum albumin (HSA) was studied using molecular docking and fluorescence techniques. Thermodynamics revealed that the interaction was entropy driven with predominantly hydrophobic forces. From the observed Föster's-type fluorescence resonance energy transfer, the donor (Trp 214 in HSA) to acceptor (NCPAC) distance was calculated to be 3.6 nm. The conformational changes of HSA due to the interaction were investigated qualitatively from synchronous fluorescence spectra. Molecular docking studies were performed to obtain information on the possible residues involved in the interaction process.

  19. Selected alkyl(phenyl)-N,N-dialkylcarbamoylmethylphosphine oxides as extractants for Am(III) from nitric acid media

    International Nuclear Information System (INIS)

    Horwitz, E.P.; Kalina, D.G.; Kaplan, L.; Mason, G.W.; Diamond, H.

    1982-01-01

    A new series of neutral bifunctional extractants, alkyl(phenyl)-N,N-dialkyl-carbamoylmethylphosphine oxides, has been prepared and studied as extractants for Am(III) from nitric acid media. Two types of alkyl(phenyl)-N,N-dialkyl CMPO compounds were prepared, one containing N,N-diethyl groups and the other containing N,N-diisobutyl groups. The N,N-diethyl series contained hexyl(phenyl) and 6-methylheptyl(phenyl) derivatives, abbreviated H phi DECMPO and 6-MH phi DECMPO, respectively. The N,N-diisobutyl series contained the n-octyl(phenyl), 6-methylheptyl(phenyl), and the 2-ethylhexyl(phenyl) derivatives, abbreviated O phi D[IB]CMPO, 6-MH phi D[IB]CMPO, and 2-EH phi D[IB]CMPO, respectively. Third power extractant dependencies for the extraction of Am(III) from 0.5 and 3 M HNO 3 were obtained at low ( 3 . The H phi DECMPO, 6-MH phi DECMPO, 6-MH phi D[IB]CMPO, and O phi D[IB]CMPO [all 0.5 M in diethylbenzene (DEB)] are significantly better extractants than DHDECMPO for Am(III) from 1 to 6 M HNO 3 . These same extractants have lower D/sub Am/ values than DHDECMPO at low acidities. H phi DECMPO and O phi D[IB]CMPO also have better selectivity for Am(III) over Fe(III) than DHDECMPO. H phi DECMPO in DEB has a strong tendency toward the formation of a second liquid organic phase on extracting macroconcentrations of Nd(III) and U(VI) from 3 M HNO 3 ; however, this behavior is substantially diminished with the O phi D[IB]CMPO and 6-MH phi D[IB]CMPO compounds

  20. In vivo subcellular imaging of tumors in mouse models using a fluorophore-conjugated anti-carcinoembryonic antigen antibody in two-photon excitation microscopy.

    Science.gov (United States)

    Koga, Shigehiro; Oshima, Yusuke; Honkura, Naoki; Iimura, Tadahiro; Kameda, Kenji; Sato, Koichi; Yoshida, Motohira; Yamamoto, Yuji; Watanabe, Yuji; Hikita, Atsuhiko; Imamura, Takeshi

    2014-10-01

    Recently, there has been growing interest in applying fluorescence imaging techniques to the study of various disease processes and complex biological phenomena in vivo. To apply these methods to clinical settings, several groups have developed protocols for fluorescence imaging using antibodies against tumor markers conjugated to fluorescent substances. Although these probes have been useful in macroscopic imaging, the specificity and sensitivity of these methods must be improved to enable them to detect micro-lesions in the early phases of cancer, resulting in better treatment outcomes. To establish a sensitive and highly specific imaging method, we used a fluorophore-conjugated anti-carcinoembryonic antigen (CEA) antibody to perform macroscopic and microscopic in vivo imaging of inoculated cancer cells expressing GFP with or without CEA. Macroscopic imaging by fluorescence zoom microscopy revealed that bio-conjugation of Alexa Fluor 594 to the anti-CEA antibody allowed visualization of tumor mass consisting of CEA-expressing human cancer cells, but the background levels were unacceptably high. In contrast, microscopic imaging using a two-photon excitation microscope and the same fluorescent antibody resulted in subcellular-resolution imaging that was more specific and sensitive than conventional imaging using a fluorescence zoom microscope. These results suggest that two-photon excitation microscopy in conjunction with fluorophore-conjugated antibodies could be widely adapted to detection of cancer-specific cell-surface molecules, both in cancer research and in clinical applications. © 2014 The Authors. Cancer Science published by Wiley Publishing Asia Pty Ltd on behalf of Japanese Cancer Association.

  1. The periplasmic transaminase PtaA of Pseudomonas fluorescens converts the glutamic acid residue at the pyoverdine fluorophore to α-ketoglutaric acid.

    Science.gov (United States)

    Ringel, Michael T; Dräger, Gerald; Brüser, Thomas

    2017-11-10

    The periplasmic conversion of ferribactin to pyoverdine is essential for siderophore biogenesis in fluorescent pseudomonads, such as pathogenic Pseudomonas aeruginosa or plant growth-promoting Pseudomonas fluorescens The non-ribosomal peptide ferribactin undergoes cyclizations and oxidations that result in the fluorophore, and a strictly conserved fluorophore-bound glutamic acid residue is converted to a range of variants, including succinamide, succinic acid, and α-ketoglutaric acid residues. We recently discovered that the pyridoxal phosphate-containing enzyme PvdN is responsible for the generation of the succinamide, which can be hydrolyzed to succinic acid. Based on this, a distinct unknown enzyme was postulated to be responsible for the conversion of the glutamic acid to α-ketoglutaric acid. Here we report the identification and characterization of this enzyme in P. fluorescens strain A506. In silico analyses indicated a periplasmic transaminase in fluorescent pseudomonads and other proteobacteria that we termed PtaA for " p eriplasmic t ransaminase A " An in-frame-deleted ptaA mutant selectively lacked the α-ketoglutaric acid form of pyoverdine, and recombinant PtaA complemented this phenotype. The ptaA / pvdN double mutant produced exclusively the glutamic acid form of pyoverdine. PtaA is homodimeric and contains a pyridoxal phosphate cofactor. Mutation of the active-site lysine abolished PtaA activity and affected folding as well as Tat-dependent transport of the enzyme. In pseudomonads, the occurrence of ptaA correlates with the occurrence of α-ketoglutaric acid forms of pyoverdines. As this enzyme is not restricted to pyoverdine-producing bacteria, its catalysis of periplasmic transaminations is most likely a general tool for specific biosynthetic pathways. © 2017 by The American Society for Biochemistry and Molecular Biology, Inc.

  2. Photophysics of a solvent sensitive keto-tetrahydrocarbazole based fluorophore and its interaction with triethylamine: A spectroscopic inquest under surfactant and β-CD confinement

    Science.gov (United States)

    Mitra, Amrit Krishna; Ghosh, Sujay; Sarangi, Manas Kumar; Chakraborty, Suchandra; Saha, Chandan; Basu, Samita

    2014-09-01

    In this communication, we wish to report solution phase photophysics of 6,7-dimethoxy-3-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (DMMTCO) and its interaction with a simple aliphatic organic donor, triethylamine (TEA) in different environments using absorption, steady-state and time-resolved fluorescence techniques. We have chosen ten solvents of varied nature and have observed that the fluorescence emission maximum of the compound is sensitive to the ET(30) value of the solvent. Quantum yield of the fluorophore is found to be higher in polar aprotic solvents like DMSO, DMF and ACN. When the fluorophore interacts with an anionic surfactant solution of sodium dodecyl sulphate (SDS), a hypsochromic shift of 17 nm is observed with respect to pure aqueous medium as the concentration of the surfactant increases. On switching over to the neutral surfactant of Triton X-100, a hypsochromic shift of 29 nm with respect to pure aqueous medium is witnessed as the concentration surges. Likewise, with the increase in concentration of β-cyclodextrin, we have noted a hypsochromic shift of 26 nm. In all of the above mentioned occasions, we have perceived hypsochromic shifts along with concomitant increase in fluorescence intensity. These observations regarding the organised media indicate that the immediate surrounding around the probe gets modified with the increase in surfactant and β-cyclodextrin concentration. TEA is a simple organic molecule that interacts with DMMTCO in a differing manner when we change the atmosphere from purely homogeneous to surfactant environment. In the confined medium, we observe the formation of a ground state complex, which is not that much appreciable in the case of homogeneous solvents.

  3. Antifungal Effect of Novel 2-bromo-2-chloro-2-(4-chlorophenylsulfonyl-1-phenylethanone against Candida strains

    Directory of Open Access Journals (Sweden)

    Monika Staniszewska

    2016-08-01

    Full Text Available We investigated the antifungal activity of novel a 2-bromo-2-chloro-2-(4-chlorophenylsulfonyl-1-phenylethanone (compound 4. The synthesis of compound 4 was commenced from sodium 4-chlorobenzene sulfinate and the final product was obtained by treatment of β-chloro β-keto-sulfone with sodium hypobromite. The sensitivity of sixty three clinical isolates belonging to the most relevant Candida species towards compound 4 using the method M27-A3 was evaluated. We observed among most of the clinical strains of C. albicans MIC ranging from 0.00195 to 0.0078 µg/mL. Compound 4 at 32 μg/mL exhibited fungicidal activity against nine Candida strains tested using the MFC assay. Compound 4 displayed anti-Candida activity (with clear endpoint against 22% of clinical strains of Candida. Under compound 4, Candida susceptibility and tolerance, namely paradoxical effect (PG, was found for only two clinical isolates (C. glabrata and C. parapsilosis and reference strain 14053 using both M27-A3 and MFC method. We found that compound 4 does not induce toxicity in vivo against larvae of Galleria mellonella (≥97% survival and it displays reduced toxicity on mammalian cells in vitro (

  4. 1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl-3-(3-methoxyphenylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Wan-Sin Loh

    2010-01-01

    Full Text Available In the title compound, C26H20ClNO2, the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2 Å and forms a dihedral angle of 73.84 (5° with the phenyl ring. Two neighbouring molecules are arranged into a centrosymmetric dimer through a pair of intermolecular C—H...Cl interactions. A pair of intermolecular C—H...O hydrogen bonds link two methoxyphenyl groups into another centrosymmetric dimer, generating an R22(8 ring motif. The structure is further stabilized by C—H...π interactions.

  5. Toward the Oxidation of the Phenyl Radical and Prevention of PAH Formation in Combustion Systems.

    Science.gov (United States)

    Parker, Dorian S N; Kaiser, Ralf I; Troy, Tyler P; Kostko, Oleg; Ahmed, Musahid; Mebel, Alexander M

    2015-07-16

    The reaction of the phenyl radical (C6H5) with molecular oxygen (O2) plays a central role in the degradation of poly- and monocyclic aromatic radicals in combustion systems which would otherwise react with fuel components to form polycyclic aromatic hydrocarbons (PAHs) and eventually soot. Despite intense theoretical and experimental scrutiny over half a century, the overall reaction channels have not all been experimentally identified. Tunable vacuum ultraviolet photoionization in conjunction with a combustion simulating chemical reactor uniquely provides the complete isomer specific product spectrum and branching ratios of this prototype reaction. In the reaction of phenyl radicals and molecular oxygen at 873 K and 1003 K, ortho-benzoquinone (o-C6H4O2), the phenoxy radical (C6H5O), and cyclopentadienyl radical (C5H5) were identified as primary products formed through emission of atomic hydrogen, atomic oxygen and carbon dioxide. Furan (C4H4O), acrolein (C3H4O), and ketene (C2H2O) were also identified as primary products formed through ring opening and fragmentation of the 7-membered ring 2-oxepinoxy radical. Secondary reaction products para-benzoquinone (p-C6H4O2), phenol (C6H5OH), cyclopentadiene (C5H6), 2,4-cyclopentadienone (C5H4O), vinylacetylene (C4H4), and acetylene (C2H2) were also identified. The pyranyl radical (C5H5O) was not detected; however, electronic structure calculations show that it is formed and isomerizes to 2,4-cyclopentadienone through atomic hydrogen emission. In combustion systems, barrierless phenyl-type radical oxidation reactions could even degrade more complex aromatic radicals. An understanding of these elementary processes is expected to lead to a better understanding toward the elimination of carcinogenic, mutagenic, and environmentally hazardous byproducts of combustion systems such as PAHs.

  6. Synthesis and fuel cell characterization of blend membranes from phenyl phosphine oxide containing flourinated novel polymers

    Science.gov (United States)

    Gürtekin Seden, Merve; Baştürk, Emre; Inan, Tülay Y.; Kayaman Apohan, Nilhan; Güngör, Atilla

    2014-12-01

    Novel fluorinated poly(arylene ether)'s are synthesized from polycondensation of bis (p-hydroxy-tetrafluoro) phenyl) phenyl phosphine oxide (PFPPO-OH) with 4,4‧-dichlorodiphenyl sulfone (DCDPS) and 2,2-bis(4-hydroxyphenyl)propane (Bisfenol A) (Copolymer 1a) or 2,2-bis(4-hydroxyphenyl) hexafluoropropane (Bisphenol AF) (Copolymer 1b). The fluorinated copolymers have been blended with sulphonated poly(ether ether ketone)-SPEEK by solvent casting method. The water uptake and proton conductivity of the blend membranes decreases with the increase of copolymer content as expected, but proton conductivity values are still comparable to that of Nafion117® membrane. Addition of hydrophobic copolymer 1b to the SPEEK caused increase in water vapor transmission. Methanol permeability of the membranes is decreased to 8.2 × 10-8 cm2 s-1 and 1.3 × 10-9 cm2 s-1 by addition of Copolymer 1a and 1b, respectively and they are much lower than that of Nafion® 117 (1.21E-06 (cm2 s-1). The blend membranes endure up to 6.5 h before it starts to dissolve. Hydrogen and oxygen permeability of the blend membranes is one-hundredth of the Nafion®. Fluorinated polymer improved chemical, mechanical, and hydrolytic stability and also phenyl phosphine oxide structure in the ionomer increased the thermal stability, gas and methanol permeability and overcomed the drawbacks of the Nafion® type membranes.

  7. Diazido{(S-1-phenyl-N,N-bis[(2-pyridylmethyl]ethanamine}copper(II

    Directory of Open Access Journals (Sweden)

    Sankara Rao Rowthu

    2011-07-01

    Full Text Available In the title compound, [Cu(N32(C20H21N3], the CuII ion is coordinated by the three N atoms of the (S-1-phenyl-N,N-bis[(2-pyridylmethyl]ethanamine ligand and two N atoms from two azide anions, resulting in a distorted square-pyramidal environment. A weak intermolecular C—H...N hydrogen-bonding interaction between one pyridine group of the ligand and an azide N atom of an adjacent complex unit gives a one-dimensional chain structure parallel to the c axis.

  8. ED50 G(Na) block predictions for phenyl substituted and unsubstituted n-alkanols.

    Science.gov (United States)

    Kondratiev, A; Hahin, R

    2001-03-15

    To study the role the phenyl group plays in producing local anesthetic block, a sequence of n-alkanols and phenyl-substituted alkanols (phi)-alkanols) were characterized in their ability to block Na channels. The sequence of n-alkanols studied possess 3-5 carbons (propanol-pentanol). The action of phenol and 3-phi-alkanols (benzyl alcohol, phenethyl alcohol, 3-phenyl-1-propanol) were also studied. Na currents (INa) were recorded from single frog skeletal muscle fibers using the Vaseline-gap voltage clamp technique. INas were recorded prior to, during, and following the removal of the solutes in Ringer's solution. All alkanols and phenol acted to block INa in a dose-dependent manner. Effective doses to produce half block (ED50) of INa or Na conductance (GNa) were obtained from dose-response relations for all solutes used. The block of GNa depended on voltage, and could be separated into voltage-dependent and -independent components. Each solute acted to shift GNa-V relations in a depolarized direction and reduce the maximum GNa and slope of the relation. All solutes acted to speed up INa kinetics and cause hyperpolarizing shifts in steady-state inactivation. The magnitude of the kinetic changes increased with dose. Size was an important variable in determining the magnitude of the changes in INa; however, size alone was not sufficient to predict the changes in INa. ED50s for GNa and AP block could be predicted as a function of intrinsic molar volume, hydrogen bond acceptor basicity (beta) and donor acidity (alpha), and polarity (P) of the solutes. The equivalency of ED50 predictions for AP and GNa block can be explained by the fact that AP block arises from channel block and solute-induced changes in INa kinetics. phi-Alkanols were more effective at blocking and inactivating Na channels than their unsubstituted counterparts. Phenyl-substituted alkanols are more likely to interact with the channel than their unsubstituted counterparts.

  9. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    International Nuclear Information System (INIS)

    Cirpan, A.; Guner, Y.; Toppare, L.

    2004-01-01

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique

  10. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    Energy Technology Data Exchange (ETDEWEB)

    Cirpan, A.; Guner, Y.; Toppare, L

    2004-05-15

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique.

  11. 3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile

    Directory of Open Access Journals (Sweden)

    Sabry H. H. Younes

    2013-03-01

    Full Text Available In the title compound, C20H14N2O, the phenyl ring is almost normal to the naphthalene ring system with a dihedral angle of 86.72 (9°. The 4H-pyran ring fused with the naphthalene ring system has a boat conformation. In the crystal, molecules are linked into a helical supramolecular chain along the b axis via N—H...N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H...π interactions.

  12. Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

    Directory of Open Access Journals (Sweden)

    Krzysztof M. Borys

    2012-02-01

    Full Text Available A halogenmethylsulfonyl moiety is incorporated in numerous active herbicides and fungicides. The synthesis of tribromomethyl phenyl sulfone derivatives as novel potential pesticides is reported. The title sulfone was obtained by following three different synthetic routes, starting from 4-chlorothiophenol or 4-halogenphenyl methyl sulfone. Products of its subsequent nitration were subjected to the SNAr reactions with ammonia, amines, hydrazines and phenolates to give 2-nitroaniline, 2-nitrophenylhydrazine and diphenyl ether derivatives. Reduction of the nitro group of 4-tribromomethylsulfonyl-2-nitroaniline yielded the corresponding o-phenylenediamine substrate for preparation of structurally varied benzimidazoles.

  13. Crystal structure of a diaryl carbonate: 1,3-phenylene bis(phenyl carbonate

    Directory of Open Access Journals (Sweden)

    Marina A. Solomos

    2017-12-01

    Full Text Available The whole molecule of the title compound, C20H14O6, is generated by mirror symmetry, the mirror bisecting the central benzene ring. The carbonate groups adopt an s-cis-s-cis conformation, with torsion angles of 58.7 (2 and 116.32 (15°. The crystal structure of 1,3-phenylene bis(phenyl carbonate contains no strong hydrogen bonds, though weak C—H...O and offset π–π interactions are observed, forming layers parallel to the ac plane.

  14. Tris(phenyl 2-pyridyl ketone oxime-κ2N,N′cadmium(II dinitrate

    Directory of Open Access Journals (Sweden)

    Juan Yan

    2009-06-01

    Full Text Available The Cd atom in the title compound, [Cd(C12H10N2O3](NO32, adopts a distorted octahedral geometry, being ligated by six N atoms from three different phenyl-2-pyridyl ketone oxime ligands. In the crystal structure, intermolecular O—H...O and C—H...O hydrogen bonds link the molecules into a chain structure propagating along [100]. The chains are further linked into a three-dimensional supramolecular structure via van der Waals forces.

  15. Dichloridobis(phenyl 2-pyridyl ketone oximenickel(II acetone solvate

    Directory of Open Access Journals (Sweden)

    Guang-Xiang Liu

    2009-02-01

    Full Text Available The Ni atom in the title compound, [NiCl2(C12H10N2O2]·C3H6O, adopts a distorted octahedral geometry, being ligated by four N atoms from two different phenyl 2-pyridyl ketone oxime ligands and two Cl atoms. In the crystal structure, intermolecular O—H...Cl hydrogen bonds link the molecules into a chain structure along [010]. There is a π–π contact between the pyridine rings [centroid–centroid distance = 3.824 (5 Å].

  16. Study of methyl- and phenyl-substituted thermostable polysiloxane-silarylene motionless phases for capillary gas chromatography

    Science.gov (United States)

    Komarova, A. O.; Shashkov, M. V.; Sidel'nikov, V. N.

    2017-11-01

    Capillary columns based on a number of thermostable polysiloxane-silarylene motionless phases are prepared and their properties are studied. Three polymers with different contents of methyl and phenyl groups are synthesized: dimethylsiloxanesilarylene (DMS), methylphenylsiloxanesilarylene (MPhS), and diphenylsiloxanesilarylene (DPhS). Studies of their thermostability show that the level of the background current of these columns upon heating to 350°C is several times lower than that of a column based on polydimethylsiloxane. Based on McReynolds' studies of polarity and Abraham's studies of the selectivity of prepared columns according to the parameters of intermolecular interactions, it is found that silarylene MLPs are more affected by the contributions from specific interactions (especially for dipole-dipole, π-π-, and n-π-interactions) than MLPs with no phenylene inserts. The effect on the selectivity of a phenyl group inside a chain differs from the one produced by the phenyl groups in side MLP chains. The effect on the selectivity of a phenyl group inside a chain differs from the one produced by the phenyl groups in side MLP chains. Examples of the separation of test mixtures of aromatic and oxygen-containing compounds are obtained, along with an extract of thistle oil containing tocopherols and phytosterols at a final temperature of analysis of 350°C.

  17. Design, synthesis and inhibitory activities of 8-(substituted styrol-formamido)phenyl-xanthine derivatives on monoamine oxidase B.

    Science.gov (United States)

    Hu, Suwen; Nian, Siyun; Qin, Kuiyou; Xiao, Tong; Li, Lingna; Qi, Xiaolu; Ye, Faqing; Liang, Guang; Hu, Guoxin; He, Jincai; Yu, Yinfei; Song, Bo

    2012-01-01

    The design and synthesis of two series of 8-(substituted styrol-formamido)phenyl-xanthine derivatives are described. Their in vitro monoamine oxidase B (MAO-B) inhibition were tested and the effect of substituents on the N-7, phenyl and the substituted positions are discussed. It was observed that compound 9b displayed significant MAO-B inhibition activity and selectivity, fluorine substitution plays a key role in the selectivity of MAO-B inhibition, and the styrol-formamido group at position-3' may enhance the activity and selectivity of 8-phenyl-xanthine analogues. These results suggest that such compounds may be utilized for the development of new candidate MAO-B inhibitors for treatment of Parkinson's disease.

  18. 4-Phenyl quinoline derivatives as potential serotonin receptor ligands with antiproliferative activity.

    Science.gov (United States)

    Joshi, Pranaya V; Sayed, Alim A; RaviKumar, Ameeta; Puranik, Vedavati G; Zinjarde, Smita S

    2017-08-18

    Antagonists of signaling receptors are often effective non-toxic therapeutic agents. Over the years, there have been evidences describing the role of serotonin or 5-hydroxytryptamine (5-HT) in development of cancer. Although there are reports on the antiproliferative effects of some serotonin receptor antagonists, there are very few investigations related to understanding their structure-activity relationships. In this study, we report the screening of a library of 4-phenyl quinoline derivatives for their antiproliferative activities. Preliminary docking studies indicated that these ligands had the ability to bind to two of the serotonin receptors, 5-HT 1B and 5-HT 2B . The results of the in silico experiments were validated by performing in vitro studies on MCF-7 breast cancer cell line. The ethylpiperazine derivatives showed maximum toxicity against this cancer cell line. The compounds inhibited Calcium ion efflux (induced by serotonin) and ERK activation. One of the most active 4-phenyl quinoline derivatives (H3a) also induced apoptosis, thereby, suggesting the use of this scaffold as a potential anticancer drug. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  19. Photochemical oxidation processes for the elimination of phenyl-urea herbicides in waters

    Energy Technology Data Exchange (ETDEWEB)

    Benitez, F. Javier [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain)]. E-mail: javben@unex.es; Real, Francisco J. [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain); Acero, Juan L. [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain); Garcia, Carolina [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain)

    2006-11-16

    Four phenyl-urea herbicides (linuron, chlorotoluron, diuron, and isoproturon) were individually photooxidized by monochromatic UV radiation in ultra-pure aqueous solutions. The influence of pH and temperature on the photodegradation process was established, and the first-order rate constants and quantum yields were evaluated. The sequence of photodecomposition rates was: linuron > chlorotoluron > diuron > isoproturon. The simultaneous photooxidation of mixtures of the selected herbicides in several types of waters was then performed by means of UV radiation alone, and by UV radiation combined with hydrogen peroxide. The types of waters used were: ultra-pure water, a commercial mineral water, a groundwater, and a lake water. The influence of the independent variables in these processes - the presence or absence of tert-butyl alcohol, types of herbicide and waters, and concentration of hydrogen peroxide - were established and discussed. A kinetic study was performed using a competitive kinetic model that allowed various rate constants to be evaluated for each herbicide. This kinetic model allows one to predict the elimination of these phenyl-urea herbicides in contaminated waters by the oxidation systems used (UV alone and combined UV/H{sub 2}O{sub 2}). The herbicide concentrations predicted by this model agree well with the experimental results that were obtained.

  20. Photochemical oxidation processes for the elimination of phenyl-urea herbicides in waters

    International Nuclear Information System (INIS)

    Benitez, F. Javier; Real, Francisco J.; Acero, Juan L.; Garcia, Carolina

    2006-01-01

    Four phenyl-urea herbicides (linuron, chlorotoluron, diuron, and isoproturon) were individually photooxidized by monochromatic UV radiation in ultra-pure aqueous solutions. The influence of pH and temperature on the photodegradation process was established, and the first-order rate constants and quantum yields were evaluated. The sequence of photodecomposition rates was: linuron > chlorotoluron > diuron > isoproturon. The simultaneous photooxidation of mixtures of the selected herbicides in several types of waters was then performed by means of UV radiation alone, and by UV radiation combined with hydrogen peroxide. The types of waters used were: ultra-pure water, a commercial mineral water, a groundwater, and a lake water. The influence of the independent variables in these processes - the presence or absence of tert-butyl alcohol, types of herbicide and waters, and concentration of hydrogen peroxide - were established and discussed. A kinetic study was performed using a competitive kinetic model that allowed various rate constants to be evaluated for each herbicide. This kinetic model allows one to predict the elimination of these phenyl-urea herbicides in contaminated waters by the oxidation systems used (UV alone and combined UV/H 2 O 2 ). The herbicide concentrations predicted by this model agree well with the experimental results that were obtained

  1. Microwave Assisted Enzymatic Kinetic Resolution of (±-1-Phenyl-2-propyn-1-ol in Nonaqueous Media

    Directory of Open Access Journals (Sweden)

    Saravanan Devendran

    2014-01-01

    Full Text Available Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis. Lipases from different microbial origins were employed for the kinetic resolution of (R/S-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435, was found to be the best catalyst in n-hexane as solvent. Vinyl acetate was the most effective among different acyl esters studied. The effect of various parameters was studied in a systematic manner. Definite synergism between microwave and enzyme was observed. The initial rate was improved around 1.28 times under microwave irradiation than conventional heating. Under optimum conditions, maximum conversion (48.78% and high enantiomeric excess (93.25% were obtained in 2 h. From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is green, clean, and easily scalable as compared to the chemical process.

  2. Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids

    Energy Technology Data Exchange (ETDEWEB)

    Geiger, H.C.; Perlstein, J.; Lachicotte, R.J.; Wyrozebski, K.; Whitten, D.G. [Univ. of Rochester, NY (United States)]|[Los Alamos National Lab., NM (United States). Chemical Science and Technology Div.

    1999-08-17

    This paper reports the synthesis of a series of amphiphiles (fatty acids and phosphatidylcholine derivatives) containing phenyl, biphenyl, and terphenyl chromophores inserted in the hydrocarbon chain and a study of their self-assembly in Langmuir-Blodgett films and aqueous dispersions. As observed and reported earlier for amphiphiles containing trans-stilbene, styrylthiophene, or azobenzene chromophores, several of the biphenyl and terphenyl derivatives show strong evidence of ground state association to form H aggregates characterized by a blue shift in absorption and a structured, red-shifted fluorescence. The phenyl amphiphiles show different behavior, suggesting that, even for pure films or bilayers, there is very little or no ground state association. For the biphenyl and terphenyl phospholipids, aqueous suspensions obtained by sonication are closed bilayer vesicles similar in size to those formed from the corresponding saturated phospholipids. The overall results of the present study indicate that biphenyl and terphenyl amphiphiles undergo aggregation processes to form compact arrays formally similar to those observed with stilbenen tolan, azobenzene, and squaraine derivatives but that the aromatic-aromatic interactions are considerably weaker than those for the more extended aromatics and lead to less distortion of the assembly structure.

  3. Kinetic α secondary deuterium isotope effects for O-ethyl S-phenyl benzaldehyde acetal hydrolysis

    International Nuclear Information System (INIS)

    Ferraz, J.P.; Cordes, E.H.

    1979-01-01

    The rate of hydrolysis of O-ethyl S-phenyl benzaldehyde acetal at 25 0 C in 20% dioxane--80% water is independent of pH over the range pH6-12; k/sub obsd/ = 1.9 x 10 -7 s -1 . Under more acidic conditions, the rate increases linearly with the activity of the hydrated proton; k 2 = 2.95 x 10 -2 M -1 s -1 . The kinetic α secondary deuterium isotope effect for acid-catalyzed hydrolysis of O-ethyl S-phenyl benzaldehyde acetal, measured at 25 0 C in 20% aqueous dioxane containing 0.05 M HCl, is k/sub H//k/sub D/ = 1.038 +- 0.008, a value consistent with a transition state in which the C--S bond is stretched rather little. In contrast, the corresponding isotope effect for the pH-independent hydrolysis of this substrate, measured at 42.5 0 C in 20% dioxane, is 1.13 +- 0.02, a value consistent with complete C--S bond cleavage in the transition state and rate-determining diffusion apart of the ion-pair formed as the initial intermediate, in accord with the suggestion of Jensen and Jencks. 1 figure, 4 tables

  4. 4-Methyl-5-phenyl-1H-pyrazol-3(2H-one

    Directory of Open Access Journals (Sweden)

    V. Vijayakumar

    2011-01-01

    Full Text Available The asymmetric unit of the title compound, C10H10N2O, contains two crystallographically independent molecules with similar geometries, which exist in the keto form. The C=O bond lengths are 1.2878 (12 Å in molecule A and 1.2890 (12 Å in molecule B, indicating that the compound undergoes enol-to-keto tautomerism during the crystallization process. In molecule A, the pyrazole ring is approximately planar [maximum deviation = 0.007 (1 Å] and forms a dihedral angle of 36.67 (6° with the attached phenyl ring. In molecule B, the dihedral angle formed between the pyrazole ring [maximum deviation = 0.017 (1 Å] and the phenyl ring is 41.19 (6°. In the crystal, intermolecular N—H...O hydrogen bonds link neighbouring molecules into dimers generating R22(8 ring motifs. These dimers are linked into ribbons along [101] via intermolecular N—H...O hydrogen bonds, forming R42(10 ring motifs.

  5. Enhanced dispersion of multiwall carbon nanotubes in natural rubber latex nanocomposites by surfactants bearing phenyl groups.

    Science.gov (United States)

    Mohamed, Azmi; Anas, Argo Khoirul; Bakar, Suriani Abu; Ardyani, Tretya; Zin, Wan Manshol W; Ibrahim, Sofian; Sagisaka, Masanobu; Brown, Paul; Eastoe, Julian

    2015-10-01

    Here is presented a systematic study of the dispersibility of multiwall carbon nanotubes (MWCNTs) in natural rubber latex (NR-latex) assisted by a series of single-, double-, and triple-sulfosuccinate anionic surfactants containing phenyl ring moieties. Optical polarising microscopy, field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), and Raman spectroscopy have been performed to obtain the dispersion-level profiles of the MWCNTs in the nanocomposites. Interestingly, a triple-chain, phenyl-containing surfactant, namely sodium 1,5-dioxo-1,5-bis(3-phenylpropoxy)-3-((3-phenylpropoxy)carbonyl) pentane-2-sulfonate (TCPh), has a greater capacity the stabilisation of MWCNTs than a commercially available single-chain sodium dodecylbenzenesulfonate (SDBS) surfactant. TCPh provides significant enhancements in the electrical conductivity of nanocomposites, up to ∼10(-2) S cm(-1), as measured by a four-point probe instrument. These results have allowed compilation of a road map for the design of surfactant architectures capable of providing the homogeneous dispersion of MWCNTs required for the next generation of polymer-carbon-nanotube materials, specifically those used in aerospace technology. Copyright © 2015 Elsevier Inc. All rights reserved.

  6. Preparation of nanosheet by exfoliation of layered iron phenyl phosphate under ultrasonic irradiation

    International Nuclear Information System (INIS)

    Tanaka, Hidekazu; Okumiya, Takeshi; Ueda, Shun-kichi; Taketani, Yukihiko; Murakami, Masahiko

    2009-01-01

    Synthetic layered iron phenyl phosphate (Fe(OH)(C 6 H 5 PO 4 H) 1.6 (H 2 PO 4 ) 0.4 .5.1H 2 O: FePP), which is composed of a multilayer alternating bilayer of phenyl groups of the phosphates and amorphous iron phosphate phase, was exfoliated in ethanol under ultrasonic irradiation. The exfoliation of FePP was recognized at 10-10,000 ppm of FePP concentration. No reaggregation and reprecipitation of the nanosheets took place for at least 6 months of standing at room temperature. The UV-vis measurements indicated that the nanosheet dispersing solution possessed a UV absorption property which would be due to the charge transfer transition of Fe-O. The FePP nanosheet-doped silica gel with UV absorption property could be prepared by sol-gel process. The Beer's plot and EDX elemental mapping analysis for Fe and P revealed that the nanosheets are homogeneously dispersed in the silica gels

  7. The Influence of Alkoxy Substitutions on the Properties of Diketopyrrolopyrrole-Phenyl Copolymers for Solar Cells

    Directory of Open Access Journals (Sweden)

    Paul Heremans

    2013-07-01

    Full Text Available A previously reported diketopyrrolopyrrole (DPP-phenyl copolymer is modified by adding methoxy or octyloxy side chains on the phenyl spacer. The influence of these alkoxy substitutions on the physical, opto-electronic properties, and photovoltaic performance were investigated. It was found that the altered physical properties correlated with an increase in chain flexibility. Well-defined oligomers were synthesized to verify the observed structure-property relationship. Surprisingly, methoxy substitution on the benzene spacer resulted in higher melting and crystallization temperatures in the synthesized oligomers. This trend is not observed in the polymers, where the improved interactions are most likely counteracted by the larger conformational possibilities in the polymer chain upon alkoxy substitution. The best photovoltaic performance was obtained for the parent polymer: fullerene blends whereas the modifications on the other two polymers result in reduced open-circuit voltage and varying current densities under similar processing conditions. The current densities could be related to different polymer: fullerene blend morphologies. These results show that supposed small structural alterations such as methoxy substitution already significantly altered the physical properties of the parent polymer and also that oligomers and polymers respond divergent to structural alterations made on a parent structure.

  8. Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues.

    Science.gov (United States)

    Ozaki, Hitomi; Sugihara, Kazumi; Tamura, Yuki; Fujino, Chieri; Watanabe, Yoko; Uramaru, Naoto; Sone, Tomomichi; Ohta, Shigeru; Kitamura, Shigeyuki

    2015-12-01

    Salicylates are used as fragrance and flavor ingredients for foods, as UV absorbers and as medicines. Here, we examined the hydrolytic metabolism of phenyl and benzyl salicylates by various tissue microsomes and plasma of rats, and by human liver and small-intestinal microsomes. Both salicylates were readily hydrolyzed by tissue microsomes, predominantly in small intestine, followed by liver, although phenyl salicylate was much more rapidly hydrolyzed than benzyl salicylate. The liver and small-intestinal microsomal hydrolase activities were completely inhibited by bis(4-nitrophenyl)phosphate, and could be extracted with Triton X-100. Phenyl salicylate-hydrolyzing activity was co-eluted with carboxylesterase activity by anion exchange column chromatography of the Triton X-100 extracts of liver and small-intestinal microsomes. Expression of rat liver and small-intestinal isoforms of carboxylesterase, Ces1e and Ces2c (AB010632), in COS cells resulted in significant phenyl salicylate-hydrolyzing activities with the same specific activities as those of liver and small-intestinal microsomes, respectively. Human small-intestinal microsomes also exhibited higher hydrolyzing activity than liver microsomes towards these salicylates. Human CES1 and CES2 isozymes expressed in COS cells both readily hydrolyzed phenyl salicylate, but the activity of CES2 was higher than that of CES1. These results indicate that significant amounts of salicylic acid might be formed by microsomal hydrolysis of phenyl and benzyl salicylates in vivo. The possible pharmacological and toxicological effects of salicylic acid released from salicylates present in commercial products should be considered. Copyright © 2015. Published by Elsevier Ltd.

  9. Synthesis, Characterization, and Biological Activity of 5-Phenyl-1,3,4-thiadiazole-2-amine Incorporated Azo Dye Derivatives

    OpenAIRE

    Chinnagiri T. Keerthi Kumar; Jathi Keshavayya; Tantry N. Rajesh; Sanehalli K. Peethambar; Angadi R. Shoukat Ali

    2013-01-01

    5-Phenyl-1,3,4-thiadiazole-2-amine has been synthesized by single step reaction. A series of heterocyclic azodyes were synthesized by diazotisation of 5-phenyl-1,3,4-thiadiazole-2-amine by nitrosyl sulphuric acid followed by coupling with different coupling compounds such as 8-hydroxyquinoline, 2,6-diaminopyridine, 2-naphthol, N,N-dimethyl aniline, resorcinol, and 4,6-dihydroxypyrimidine. The dyes were characterized by UV-Vis, IR, 1H-NMR, 13C NMR, and elemental analysis. The synthesized compo...

  10. Substituted piperazines as nootropic agents: 2- or 3-phenyl derivatives structurally related to the cognition-enhancer DM235.

    Science.gov (United States)

    Guandalini, Luca; Martino, Maria Vittoria; Di Cesare Mannelli, Lorenzo; Bartolucci, Gianluca; Melani, Fabrizio; Malik, Ruchi; Dei, Silvia; Floriddia, Elisa; Manetti, Dina; Orlandi, Francesca; Teodori, Elisabetta; Ghelardini, Carla; Romanelli, Maria Novella

    2015-04-15

    A series of 2-phenyl- or 3-phenyl piperazines, structurally related to DM235 and DM232, two potent nootropic agents, have been prepared and tested in the mouse passive-avoidance test, to assess their ability to revert scopolamine-induced amnesia. Although the newly synthesized molecules were less potent than the parent compounds, some useful information has been obtained from structure-activity relationships. A small but significant enantioselectivity has been found for the most potent compound 5a. Copyright © 2015 Elsevier Ltd. All rights reserved.

  11. Synthesis, Characterization, and Biological Activity of 5-Phenyl-1,3,4-thiadiazole-2-amine Incorporated Azo Dye Derivatives

    Directory of Open Access Journals (Sweden)

    Chinnagiri T. Keerthi Kumar

    2013-01-01

    Full Text Available 5-Phenyl-1,3,4-thiadiazole-2-amine has been synthesized by single step reaction. A series of heterocyclic azodyes were synthesized by diazotisation of 5-phenyl-1,3,4-thiadiazole-2-amine by nitrosyl sulphuric acid followed by coupling with different coupling compounds such as 8-hydroxyquinoline, 2,6-diaminopyridine, 2-naphthol, N,N-dimethyl aniline, resorcinol, and 4,6-dihydroxypyrimidine. The dyes were characterized by UV-Vis, IR, 1H-NMR, 13C NMR, and elemental analysis. The synthesized compounds were also screened for biological activity.

  12. 4-[(Z-(n-Butylamino(phenylmethylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H-one

    Directory of Open Access Journals (Sweden)

    Hai-Wen Wang

    2012-04-01

    Full Text Available The title compound, C21H23N3O, exists in an enamine–keto form with the amino group involved in an intramolecular N—H...O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7 Å, and makes dihedral angles of 4.81 (6 and 69.81 (5° wth the phenyl rings. In the crystal, pairs of weak C—H...O interactions link the molecules into centrosymmetric dimers.

  13. Crystal structure of 3-({[(morpholin-4-yl)carbono-thio-yl]sulfan-yl}acet-yl)phenyl benzoate.

    Science.gov (United States)

    Ambekar, Sachin P; Mahesh Kumar, K; Shirahatti, Arun Kumar M; Kotresh, O; Anil Kumar, G N

    2014-11-01

    In the title compound, C20H19NO4S2, the morpholine ring adopts the expected chair conformation. The central phenyl ring makes dihedral angles of 67.97 (4) and 7.74 (3)°, respectively, with the benzoate phenyl ring and the morpholine mean plane. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions link centrosymmetrically related mol-ecules, reinforcing the three-dimensional structure.

  14. Magnetic isotopic effect and mechanisms of chemical reactions. Photolysis of dimethylphenylsilyl phenyl ketone and of its carbon analog in micelles

    International Nuclear Information System (INIS)

    Step, E.N.; Tarasov, V.F.; Buchachenko, A.L.

    1986-01-01

    In the photolysis of cumyl phenyl ketone in micelles, for which photodecomposition occurs with the formation of a triplet geminal radical pair (Norrish type-I breakdown), with high efficiency the separation of carbon isotopes, induced by the magnetic isotopic effect, occurs for the original ketone. The isotopic composition of dimethylphenylsilyl phenyl ketone, either with respect to carbon or with respect to silicon, does not change in photolysis, i.e., in the primary act of the photolysis the separation of isotopes does not occur. It follows that the primary act of the photolysis of the ketone is not the formation of a radical pair, but is probably isomerization into a carbene

  15. Magnetic, thermal and spectroscopic properties of 5-chloro-2-methoxybenzoates of Mn(II, Co(II, Ni(II, Cu(II and Zn(II

    Directory of Open Access Journals (Sweden)

    BEATA BOCIAN

    2002-09-01

    Full Text Available The 5-chloro-2-methoxybenzoates of Mn(II, Co(II, Ni(II, Cu(II and Zn(II were synthesized as solids and their magnetic, spectral and thermal properties studied. The complexes possess colours typical of the M(II ions. The thermal stabilities were examined in air and nitrogen atmospheres and the products of decompositions were also identified. The magnetic susceptibilities of the complexes were measured over the temperature range 4.4–300 K and the magnetic moments were calculated. The results show that the 5-chloro-2-methoxybenzoates of Mn(II, Co(II and Ni(II are octahedral, high-spin complexes.

  16. Investigating Spectrum of Biological Activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino-1-alkyl-2-oxoethyl]benzamides

    Directory of Open Access Journals (Sweden)

    Jirina Stolarikova

    2011-03-01

    Full Text Available In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET in spinach (Spinacia oleracea L. chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed.

  17. High- and low-temperature phases in isostructural 4-chloro-3-nitro­aniline and 4-iodo-3-nitro­aniline

    Czech Academy of Sciences Publication Activity Database

    Fábry, Jan; Dušek, Michal; Vaněk, Přemysl; Rafalovskyi, Iegor; Hlinka, Jiří; Urban, Jiří

    2014-01-01

    Roč. 70, Part 12 (2014), s. 1153-1160 ISSN 2053-2296 R&D Projects: GA ČR GA203/09/0878 Grant - others:AVČR(CZ) Praemium Academiae Institutional support: RVO:68378271 ; RVO:61388955 Keywords : crystal structure * geometric constraints * 4-chloro-3-nitro­aniline * 4-iodo-3-nitro­aniline * phase transitions * Raman Subject RIV: BM - Solid Matter Physics ; Magnetism

  18. Experimental and In-Silico Investigation of Anti-Microbial Activity of 1-Chloro-2-Isocyanatoethane Derivatives of Thiomorpholine, Piperazine and Morpholine

    OpenAIRE

    Nwuche, Charles O.; Ujam, Oguejiofo T.; Ibezim, Akachukwu; Ujam, Ifeoma B.

    2017-01-01

    The Antibiogram properties of 1-chloro-2-isocyanatoethane derivatives of thiomorpholine (CTC), piperazine (CPC) and morpholine (CMC) were evaluated by the approved agar well diffusion, the minimum inhibitory concentration (MIC) and in silico techniques. A total of fourteen microbial cultures consisting of ten bacteria and four yeast strains were used in the biological study while affinity of the compounds for DNA gyrase, a validated antibacterial drug target, was investigated by docking metho...

  19. Thermal Decomposition Reaction of cis-6-Phenyl-5,6-(2-phenylpropilydene-3,3-tetramethylene-1,2,4-trioxacyclohexane in Different Solvents

    Directory of Open Access Journals (Sweden)

    L. F. R. Cafferata

    2000-03-01

    Full Text Available The kinetics of the thermal decomposition reaction of cis-6-phenyl-5,6-(2-phenyl-propilydene-3,3-tetramethylene-1,2,4-trioxacyclohexane (I was investigated in the temperature range of 100-130°C in selected solvents of different physicochemical properties to evaluate a solvent effect on the reaction.

  20. Techniques in gas-phase thermolyses - Part 7. Direct surface participation in gas-phase Curie-point pyrolysis: The pyrolysis of phenyl azide

    DEFF Research Database (Denmark)

    Egsgaard, Helge; Carlsen, Lars

    1986-01-01

    The possible direct participation of the hot reactor surface in the formation of pyrolysis products was elucidated through the pyrolytic decomposition of phenyl azide. It is demonstrated that the intermediate phenyl nitrene generated reacts with elemental carbon at the filament surface, leading...

  1. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Science.gov (United States)

    2010-07-01

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721...]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. (a) Chemical substance and significant new uses... alpha-[2,4,6-tris(1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate (PMN P-98-185...

  2. Synthesis of 2,3-epoxy-1-phenyl-3-aryl-1-propanone by combination of phase transfer catalyst and ultrasound irradiation

    Directory of Open Access Journals (Sweden)

    Ji-Tai Li

    2009-03-01

    Full Text Available Seven 2,3-epoxy-1-phenyl-3-aryl-1-propanones were synthesized via epoxidation of thecorresponding 1-phenyl-3-aryl-2-propen-1-ones with 30% aqueous hydrogen peroxide in 74-99% yields usingbenzyldimethyltetradecylammonium chloride as phase transfer catalyst under ultrasound irradiation.

  3. In-vitro antimicrobial screening and molecular docking studies of synthesized 2-chloro-N-(4-phenylthiazol-2-ylacetamide derivatives

    Directory of Open Access Journals (Sweden)

    Rahmat Ali

    2015-01-01

    Full Text Available Introduction: Glucosamine-6-phosphate (GlcN6P synthase biosynthetic pathway has been identified as potential targets for the development of new antimicrobial agents. Aim: A series of 2-chloro-N-(42-phenylthiazol-25-ylacetamide derivatives (3a-r was synthesized and evaluated their antimicrobial activity. Materials and Methods: The 2-chloro-N-(Para substituted phenylthiazol-25-yl acetamide (2a-c were synthesized by stirring intermediates (1a-c with 2-chloroacetylchloride in dichloromethane in the presence of K2CO3. The intermediate (2a-c were further reacted with different secondary amine such as pyrrolidine, N-methyl piperazine, N-ethyl piperazine, thiomorpholine, morpholine, piperidine etc in ethanol in presence of TEA Triethylamine (TEA to get desired compounds (3a-r. Compounds were characterized by a spectroscopic technique such as Fourier transform infraredFTIR, 1 H-NMR, 13 C-NMR, and mass spectrometry. The synthesized thiazole derivatives (3a-r were screened for anti-bacterial and anti-fungal activity against Escherichia coli, Staphylococcus aureus NCTC 6571, Pseudomonas aeruginosa NCTC 10662, CandidaC. albicans (MTCC-183, AspergillusA. niger (MTCC 281 NCTC 10418 and AspergillusA. flavus (MTCC 277. Result and Conclusion: The results of anti-bacterial screening revealed that among all the screened compounds, eight compounds viz. 3b, 3c, 3d, 3e, 3i, 3j, 3k, and 3p showed moderate to good anti-bacterial and antifungal activity having minimum inhibitory concentration (MIC between 6.25- and 25 µg/ml. While compound 3d showed the most promising antibacterial activity against E. coli and S. aureus, while the compound 3j showed promising antifungal activity with MIC value 6.25 µg/ml against C. albicans, A. niger and A. flavus. In addition, all these eight potential molecules were also examined for possible binding on enzyme GlcN6Pglucosamine-6-phosphate synthase by molecular docking studies on (PDB ID 1JXA.

  4. Catalytic combustion of chloro-benzene on lanthanum perovskites systems; Combustion catalytique du chlorobenzene sur des perovskites a base de La

    Energy Technology Data Exchange (ETDEWEB)

    Elhachimi, A.; Nguyen, T.B.; Giraudon, J.M.; Leclercq, G. [Universite des Sciences et Technologies de Lille, Lab. de Catalyse, UMR 8010, 59 - Villeneuve d' Ascq (France)

    2004-07-01

    The aim of this work is to study the potentialities of the lanthanum perovskites systems for the deep oxidation of chloro-benzene into CO{sub 2}, H{sub 2}O and HCl. The LaMO{sub 3} solids have been synthesized and characterized by XRD, FTIR, and BET. In all the cases the final product has been calcined at 700 C (Mn, Fe) or 800 C (Co, Ni) during 5 hours ({beta}=2 C.min{sup -1}). The oxidation of chloro-benzene has been carried out in a fixed bed tubular reactor. According to the light-off temperatures T{sub 50}, the activity of the catalysts decreases as the following: LaMnO{sub 3} (378 C) {>=} LaCoO{sub 3} (406 C) {>=} LaNiO{sub 3} (456 C) {>=} LaFeO{sub 3} (492 C). In fact, the substitution of the cation in B site has a great influence on the deep decomposition of chloro-benzene, Mn and Co leading to the best results. (O.M.)

  5. N-[2-chloro-9H-purin-6-yl]-N-cyclopropylglycylamino acids and derivatives: synthesis, evaluation as a class of novel analgesics, and 3D QSAR analysis.

    Science.gov (United States)

    Zhao, Jinghua; Kang, Guifeng; Wang, Wei; Zhao, Ming; Zhang, Xiaoyi; Lu, Chunbo; Mao, Wei; Chang, Heng Wei; Ye, Weidong; Peng, Shiqi

    2009-09-01

    Via a five-step-reaction procedure for the preparation of 19 known N-[2-chloro-9-(tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters (6a-s) and successive removal of 9-(tetrahydropyran-2-yl) and benzylester groups 19 novel N-[2-chloro-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters (7a-s) and 19 novel N-[2-chloro-9H-purin-6-yl]-N-cyclopropylglycylamino acids (8a-s) were provided. On tail-flick mouse model the in vivo analgesic activities of these 38 novel compounds were measured and most of them were defined as good analgesics. Based on Molecular Field Analysis of the pain threshold variations of the mice receiving 48 compounds in terms of the descriptors proton and methyl an equation was established. The data points (n), correlation coefficient (r), and square correlation coefficient (r(2)) of this equation were 48, 0.923, and 0.852, respectively. Using this equation pain threshold variations of 9 compounds were predicted and the errors ranged from 1.71 to 8.92.

  6. Preparation of lanthanide arylphosphonates and crystal structures of lanthanum phenyl- and benzylphosphonates

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Ren-Chang; Zhang, Y.; Hu, Hengliang; Frausto, R.R.; Clearfield, A. (Texas A M Univ., College Station, TX (United States))

    A series of phenyl- and benzylphosphonates of the lanthanide elements has been prepared. In the lanthanum system single crystals have been obtained and the crystal structures determined. Lanthanum phenylphosphate, La(O[sub 3]PC[sub 6]H[sub 5])(HO[sub 3]PC[sub 6]H[sub 5]), triclinic, space group. The structure is a layered one in which the lanthanum atoms are eight-coordinate. Both phosphonate groups chelate the metal atom. One oxygen of each chelate ring then bridges to an adjacent La atom, while the third oxygen bridges to lanthanum at right angles to the bridging of the chelating oxygens. The phenyl rings protrude into the interlamellar space but are disordered. This disorder arises because the true unit cell has a doubled c axis. Thus, the phenyl rings in any one row are parallel to each other in the a-axis direction but are inclined to each other in adjacent rows in the c-axis direction at angle of 58[degrees]. A short hydrogen bond (2.41 [angstrom] O-O distance) is present within the layers. La(O[sub 3]PCH[sub 2]C[sub 6]H[sub 5])(HO[sub 3]PCH[sub 2]C[sub 6]HJ[sub 5])[center dot]2H[sub 2]O is orthorhombic, space group Pbcn. This structure is also a layered one with 8-fold coordination about the lanthanum atom. There are six phosphonate and two water oxygens in the La coordination sphere in a distorted dodecahedral arrangement. One phosphonate group chelates the lanthanum, while the remaining oxygen bridges to an adjacent La atom. One of the chelating oxygens also bonds to an adjacent lanthanum atom. The second phosphonate group bridges across two La atoms with two of its oxygens, while the third bonds to hydrogen. This acid proton and the water molecules form an extensive system of intralayer hydrogen bonds. A second type of rare-earth phosphonate of composition Ln[sub 2](O[sub 3]PC[sub 6]H[sub 5])[sub 3] was prepared in slightly alkaline media. 35 refs., 6 figs., 8 tabs.

  7. Preparation of new fluorophore lanthanide complexes-Cloisite nanohybrids using the tricationic Pr(III), Gd(III) and Dy(III) complexes with 9,10-phenanthrenequinone

    Science.gov (United States)

    Mallakpour, Shadpour; Behnamfar, Mohammad Taghi; Dinari, Mohammad; Hadadzadeh, Hassan

    2015-02-01

    New fluorophore lanthanide complexes-Cloisite (LCs-C) nanohybrids have been prepared by the intercalation reaction of Cloisite Na+ with the tricationic lanthanide complexes (1-3), [M(PQ)3(DMF)2(H2O)2]3+ (M = Pr(III) (1), Gd(III) (2), and Dy(III) (3); PQ = 9,10-phenanthrenequinone), in aqueous solutions. The X-ray diffraction analysis of the modified clays (LCs-C) showed an increase in the interlayer distance (d) as compared to the pure Cloisite Na+. Field-emission scanning electron microscopy (FE-SEM) was used to study the morphology of the modified clays and the results were demonstrated a homogeneous morphology for the nanohybrids. The thermal behavior of the LCs-C nanohybrids was investigated using thermogravimetric analysis. Solid-state fluorescence properties of the LCs-C nanohybrids were also investigated. The results show that all tricationic complexes have a significant fluorescence at room temperature when the complexes are adsorbed onto Cloisite.

  8. Preparation of new fluorophore lanthanide complexes-Cloisite nanohybrids using the tricationic Pr(III), Gd(III) and Dy(III) complexes with 9,10-phenanthrenequinone.

    Science.gov (United States)

    Mallakpour, Shadpour; Behnamfar, Mohammad Taghi; Dinari, Mohammad; Hadadzadeh, Hassan

    2015-02-25

    New fluorophore lanthanide complexes-Cloisite (LCs-C) nanohybrids have been prepared by the intercalation reaction of Cloisite Na(+) with the tricationic lanthanide complexes (1-3), [M(PQ)3(DMF)2(H2O)2](3+) (M=Pr(III) (1), Gd(III) (2), and Dy(III) (3); PQ=9,10-phenanthrenequinone), in aqueous solutions. The X-ray diffraction analysis of the modified clays (LCs-C) showed an increase in the interlayer distance (d) as compared to the pure Cloisite Na(+). Field-emission scanning electron microscopy (FE-SEM) was used to study the morphology of the modified clays and the results were demonstrated a homogeneous morphology for the nanohybrids. The thermal behavior of the LCs-C nanohybrids was investigated using thermogravimetric analysis. Solid-state fluorescence properties of the LCs-C nanohybrids were also investigated. The results show that all tricationic complexes have a significant fluorescence at room temperature when the complexes are adsorbed onto Cloisite. Copyright © 2014 Elsevier B.V. All rights reserved.

  9. In Vivo Imaging of Xenograft Tumors Using an Epidermal Growth Factor Receptor-Specific Affibody Molecule Labeled with a Near-infrared Fluorophore

    Directory of Open Access Journals (Sweden)

    Haibiao Gong

    2010-02-01

    Full Text Available Overexpression of epidermal growth factor receptor (EGFR is associated with many types of cancers. It is of great interest to noninvasively image the EGFR expression in vivo. In this study, we labeled an EGFR-specific Affibody molecule (Eaff with a near-infrared (NIR dye IRDye800CW maleimide and tested the binding of this labeled molecule (Eaff800 in cell culture and xenograft mouse tumor models. Unlike EGF, Eaff did not activate the EGFR signaling pathway. Results showed that Eaff800 was bound and taken up specifically by EGFR-overexpressing A431 cells. When Eaff800 was intravenously injected into nude mice bearing A431 xenograft tumors, the tumor could be identified 1 hour after injection and it became most prominent after 1 day. Images of dissected tissue sections demonstrated that the accumulation of Eaff800 was highest in the liver, followed by the tumor and kidney. Moreover, in combination with a human EGFR type 2 (HER2-specific probe Haff682, Eaff800 could be used to distinguish between EGFR- and HER2-overexpressing tumors. Interestingly, the organ distribution pattern and the clearance rate of Eaff800 were different from those of Haff682. In conclusion, Eaff molecule labeled with a NIR fluorophore is a promising molecular imaging agent for EGFR-overexpressing tumors.

  10. Cranial nerve contrast using nerve-specific fluorophores improved by paired-agent imaging with indocyanine green as a control agent

    Science.gov (United States)

    Torres, Veronica C.; Vuong, Victoria D.; Wilson, Todd; Wewel, Joshua; Byrne, Richard W.; Tichauer, Kenneth M.

    2017-09-01

    Nerve preservation during surgery is critical because damage can result in significant morbidity. This remains a challenge especially for skull base surgeries where cranial nerves (CNs) are involved because visualization and access are particularly poor in that location. We present a paired-agent imaging method to enhance identification of CNs using nerve-specific fluorophores. Two myelin-targeting imaging agents were evaluated, Oxazine 4 and Rhodamine 800, and coadministered with a control agent, indocyanine green, either intravenously or topically in rats. Fluorescence imaging was performed on excised brains ex vivo, and nerve contrast was evaluated via paired-agent ratiometric data analysis. Although contrast was improved among all experimental groups using paired-agent imaging compared to conventional, solely targeted imaging, Oxazine 4 applied directly exhibited the greatest enhancement, with a minimum 3 times improvement in CNs delineation. This work highlights the importance of accounting for nonspecific signal of targeted agents, and demonstrates that paired-agent imaging is one method capable of doing so. Although staining, rinsing, and imaging protocols need to be optimized, these findings serve as a demonstration for the potential use of paired-agent imaging to improve contrast of CNs, and consequently, surgical outcome.

  11. Development of a real-time PCR assay with fluorophore-labelled hybridization probes for detection of Schistosoma mekongi in infected snails and rat feces.

    Science.gov (United States)

    Sanpool, O; Intapan, P M; Thanchomnang, T; Sri-Aroon, P; Lulitanond, V; Sadaow, L; Maleewong, W

    2012-09-01

    Schistosoma mekongi, a blood-dwelling fluke, is a water-borne parasite that is found in communities along the lower Mekong River basin, i.e. Cambodia and Lao People's Democratic Republic. This study developed a real-time PCR assay combined with melting-curve analysis to detect S. mekongi in laboratory setting conditions, in experimentally infected snails, and in fecal samples of infected rats. The procedure is based on melting-curve analysis of a hybrid between an amplicon from S. mekongi mitochondrion sequence, the 260 bp sequence specific to S. mekongi, and specific fluorophore-labelled probes. This method could detect as little as a single cercaria artificially introduced into a pool of 10 non-infected snails, a single cercaria in filtered paper, and 2 eggs inoculated in 100 mg of non-infected rat feces. All S. mekongi-infected snails and fecal samples from infected rats were positive. Non-infected snails, non-infected rat feces, and genomic DNA of other parasites were negative. The method gave high sensitivity and specificity, and could be applied as a fast and reliable tool for cercarial location in water environments in endemic areas and for epidemiological studies and eradication programmes for intermediate hosts.

  12. Diacetonitriletetrakis{μ2-3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyldiazenyl]-2-naphtholato}tetraaquadiiron(IIIdisodium(I dihydrate

    Directory of Open Access Journals (Sweden)

    Sato Yohei

    2008-01-01

    Full Text Available The title compound, [Fe2Na2(C23H14ClN3O34(C2H3N2(H2O4]·2H2O, is a hydrated Fe–azo complex dimer that is used as a charge-control agent in electrophotography. The molecule is a centrosymmetric dimer with two octahedral FeIII units linked by two bridging five-coordinate NaI cations. Each FeIII atom is chelated by the N and two O atoms from two 3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyldiazenyl]-2-naphtholate ligands. The Na+ cation is coordinated by a carbonyl O atom from the two ligands of each octahedral FeIII unit, two water molecules and the N atom of an acetonitrile molecule. Two solvent water molecules complete the structure. In the crystal structure, the dimeric molecules are bridged by a pair of discrete intermolecular O—H...O hydrogen bonds, one of which involves a sodium-bound water molecule and a hydrate water, and the other a 5-chlorophenolate O atom and a water molecule to form an extended chain along b.

  13. Chiral analysis of chloro intermediates of methylamphetamine by one-dimensional and multidimentional NMR and GC/MS.

    Science.gov (United States)

    Płotka, Justyna M; Morrison, Calum; Adam, David; Biziuk, Marek

    2012-07-03

    Impurity profiling and classification of abused drugs using chiral analytical techniques is of particular interest and importance because of the additional information obtained from this approach. When these methods are applied to the synthesis of illicitly used substances, they can supply valuable information about the conditions/chemicals used in the synthesis. We have applied GC and NMR methods to the study of intermediates found in methylamphetamine manufacture with the aim of linking the intermediates to the ephedrine/pseudoephedrine starting materials. Therefore, determination of the stereochemical makeup within samples of forensic interest is important giving further specific information to the analyst. This study investigates the stereochemical course of the Emde synthesis of methylamphetamine with particular focus on intermediate formation via the chlorination of ephedrine and pseudoephedrine enantiomers. The configurations of these chloro-phenethylamines were determined by 1D and 2D NMR analysis, and thereafter, the GC/MS analysis was carried out. We have shown here that chlorination of the ephedrine/pseudoephedrine compounds occurs via inversion (S(N)2) and retention (S(N)i) of configuration around the α carbon and mixture of diastereoisomers (chloroephedrine and chloropseudoephedrine) were formed, with the ratio of the resulting compounds dependent on the precursors used. The preparation and analytical properties of these intermediate standards provide data for laboratories interested in the stereochemical analysis of methylamphetamine intermediates such as forensic/law enforcement, and illustrate the value of using a combination of analytical methodology.

  14. Synthesis, growth, optical and anisotropic mechanical behaviour of organic nonlinear optical imidazolium 2-chloro-4-nitrobenzoate single crystals

    Science.gov (United States)

    Krishnakumar, Varadharajan; Jayaprakash, Jeyaram; Boobas, Singaram; Komathi, Muniraj

    2016-10-01

    The title compound, imidazolium 2-chloro-4-nitrobenzoate (I2C4NB), has been synthesized and optical quality single crystals were grown with a dimension of 4 × 2 × 1 mm3 using an ethanol and acetone (1:1) mixed solvent by slow evaporation solution growth technique. The powder XRD analysis confirmed the crystal structure and found that it is crystallized in the non-centrosymmetric space group P21 with the monoclinic system. The symmetries of molecular vibrations were confirmed by FT-IR spectrum. The CHN(S) analysis confirmed the stoichiometric composition of the grown crystal. It also exhibits a good transparency in the entire visible region (300-800nm) and it was thermally stable up to 131.1 °C. The microhardness measurement shows the anisotropic nature of I2C4NB and also that it belongs to a soft material category. Photoconductivity studies reveal a linear increase of the photocurrent with respect to the applied electric field. HOMO LUMO studies were carried out for the crystal. The second harmonic generation test by the Kurtz powder method shows that the crystal exhibits phase matching and a conversion efficiency which is 2 times that of KDP.

  15. The infrared, Raman, NMR and UV spectra, ab initio calculations and spectral assignments of 2-amino-4-chloro-6-methoxypyrimidine.

    Science.gov (United States)

    Cinar, Z; Karabacak, M; Cinar, M; Kurt, M; Chinna Babu, P; Sundaraganesan, N

    2013-12-01

    The 2-amino-4-chloro-6-methoxypyrimidine abbreviated as ACMP have been investigated by both the experimental and theoretical methods; through this work we provide the essential fact about the structural and vibrational insights. The optimized molecular structure, atomic charges, vibrational frequencies and ultraviolet spectral interpretation of ACMP have been studied by performing DFT/B3LYP/6-311++G(df,pd) level of theory. The FT-IR, FT-Raman spectra were recorded in the region 4000-400 cm(-1) and 4000-50 cm(-1) respectively. The UV absorption spectrum of the compound that dissolved in ethanol and water solution were recorded in the range of 200-400 nm. The scaled wavenumbers are compared with the experimental values. The difference between the observed and scaled wavenumber values of most of the fundamentals is very small. Based on the UV spectrum and TD-DFT calculations, the electronic structure and the assignments of the absorption bands were carried out. The (1)H, (13)C and DEPT 135 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated using with the Gauge Including Atomic Orbital (GIAO) method and compared with experimental results. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis were investigated using theoretical calculations. Copyright © 2013 Elsevier B.V. All rights reserved.

  16. Methylene blue and 4-chloro phenol degradation by photo catalysis with ultraviolet light, using TiO2 as catalyst

    International Nuclear Information System (INIS)

    Martinez H, A.

    2010-01-01

    Within the decontamination and remediation processes of the contaminated waters, as the refining or tertiary processes are the Advanced Oxidation Technologies. Among this technology is the heterogeneous photo catalysis, which is the object of this work to de grate 4-chloro phenol and methylene blue, using as semiconductor commercial titanium dioxide (TiO 2 ). On the degradation the combination is exposed in the use of TiO 2 under gamma irradiation of 60 Co at different doses 400, 500, 800, 1000 and 1500 kGy. The organic compounds degradation was determined and the results show that to more radiation dose, the material is modified in such way that shows a major absorption of the organic compound, in the same way it is determined that to more dose which undergoes the TiO 2 generally a major degradation is observed, but also it is has to give a more time of previous stabilization, for that the degradation is observed of better way. (Author)

  17. Photodynamic therapy using chloro-aluminum phthalocyanine decreases inflammatory response in an experimental rat periodontal disease model.

    Science.gov (United States)

    de Moraes, Maiara; Vasconcelos, Roseane Carvalho; Longo, João Paulo Figueiró; Muehlmann, Luis Alexandre; de Azevedo, Ricardo Bentes; de Araújo Júnior, Raimundo Fernandes; Araujo, Aurigena Antunes; de Lisboa Lopes Costa, Antonio

    2017-02-01

    Emerging evidence suggests that photodynamic therapy (PDT) can exhibit immunomodulatory activity. The purpose of the present study was to analyse cytokine profiles after application of PDT in gingival tissues of rats with ligature-induced periodontal disease (PD). Periodontal disease was induced through the introduction of a cotton thread around the first left mandibular molar, while the right side molars did not receive ligatures. After 7days of PD evolution, ligatures were removed from the left side, and the animals were randomically divided into the following treatment groups: I, rats without treatment; II, rats received chloro-aluminum phthalocyanine (AlClPc); III, rats received low-level laser alone; and IV, rats received AlClPc associated with low-level laser (PDT). The animals were killed 7days after the treatments, and the mandibles were histologically processed to assess morphological and immunohistochemical profile, while gingival tissues were removed for quantification of tumor necrosis factor (TNF)-α, interleukin (IL-)1β and IL-10 expression (by ELISA). Histomorphological analysis of periodontal tissues demonstrated that PDT-treated animals show tissue necrosis, as well as lower TNF- α expression, compared to ligatured animals treated with AlClPc alone. It was concluded that PDT using AlClPc entrapped in a lipid nanoemulsion may be useful in therapies, because of immunomodulatory effects that decreased the inflammatory response and cause tissue destruction. Copyright © 2016 Elsevier B.V. All rights reserved.

  18. Migration studies of 3-chloro-1,2-propanediol (3-MCPD) in polyethylene extrusion-coated paperboard food packaging.

    Science.gov (United States)

    Pace, Gregory V; Hartman, Thomas G

    2010-06-01

    The manufacturing process of paperboard food packaging can produce small quantities of 3-chloro-1,2-propanediol (3-MCPD or 3-monochloropropane-1,2-diol) when wet-strength resins containing epichlorohydrin are used. 3-MCPD is from the same family as 1,3-dichloro-2-propanol (1,3-DCP), which is known to cause cancer in animals. 3-MCPD has been found in acid hydrolyzed vegetable protein, Asian sauces and paperboard for food contact. In this investigation, we conducted extraction studies to measure 3-MCPD migration into food simulant solvents from the food contact side of polyethylene extrusion-coated paperboard beverage cartons and aqueous extractions of cut pieces from the entire paperboard. We demonstrate that 3-MCPD confirmed present at concentrations up to 9.9 mg kg(-1) within the paperboard matrix does not migrate through the polyethylene-coated food contact surface. The aqueous extraction of the entire paperboard and food contact side extractions with aqueous/acidic food simulants were performed using US Food and Drug Administration (FDA) and European Commission (EU) migration testing protocols. We also show that no significant amount of 3-MCPD migrates through the unskived edges on the inside seam of the paperboard structure. The methodology for the aqueous and migration cell extractions using GC-MS analyses was validated with a limit of quantification (LOQ) of 0.009 mg kg(-1) and a limit of detection (LOD) of 0.005 mg kg(-1).

  19. [Study on elimination of 3-chloro-1,2-propanediol in hydrolyzed vegetable protein by capillary electrophoresis with electrochemical detection].

    Science.gov (United States)

    Xing, Xiaoping; Cao, Yuhua

    2006-03-01

    A method was developed to estimate 3-chloro-1,2-propanediol (3-MCPD) in hydrolyzed vegetable protein (HVP) by capillary electrophoresis with electrochemical detection. The optimum conditions were investigated to determine 3-MCPD in hydrolyzed vegetable protein. In 30 mmol/L borax (pH 9.24) running buffer, separation of 3-MCPD from glycerol was achieved. A 328 microm copper-disk electrode used as the working electrode exhibited a good response at + 0.65 V (vs. saturated calomel electrode (SCE)) in 0.05 mol/L sodium hydroxide solution. The effects of pH value, temperature and hydrolysis time on the elimination of 3-MCPD in hydrolyzed vegetable protein were studied. By adjusting hydrolyzed vegetable protein to pH value of 8.0 and heating up for 1 h at 90 degrees C, the content of 3-MCPD in hydrolyzed vegetable protein could be controlled under the level of 1.0 mg/kg, which coincides with the criterion of food safety in China.

  20. Synthesis and in-vitro antibacterial activity of N-piperazinyl quinolone derivatives with 5-chloro-2-thienyl group

    Directory of Open Access Journals (Sweden)

    2008-08-01

    Full Text Available Background and the purpose of the study: Fluoroquinolones are an important group of antimicrobial agents that are used widely in the treatment of various infectious diseases. The purpose of the present study was to synthesize new N-piperazinyl quinolone derivatives with 5-chloro-2-theinyl group having possible antimicrobial activity. Methods: Reaction of ciprofloxacin (1, norfloxacin (2 and enoxacin (3 with α-bromoketone 10 or α-bromooxime derivatives 11a-c in DMF, in the presence of NaHCO3 at room temperature, afforded corresponding ketones 4a-c or oxime derivatives 5-7(a-c, respectively. Results and major conclusion: The synthesized compounds were tested against a series of Gram-positive and Gram-negative bacteria. The results of MIC tests against both Gram-positive and Gram-negative bacteria revealed that ciprofloxacin derivatives (compounds 4a, 5a, 6a and 7a were more active than norfloxacin and enoxacin analogues. Compound 5a, containing N-[2-(5-chlorothiophen-2-yl-2-hydroxyiminoethyl] residue provided a high in vitro antibacterial activity against Gram-positive bacteria, with MIC of 0.06, 0.125, 0.5 and 0.125 μg/mL against S. aureus, S. epidermidis, E. feacalis and B. subtilis, respectively. Its activity was found to be 4 to 8 times better than reference drug (ciprofloxacin against all Gram-positive bacteria with the exception of E. feacalis.

  1. Nano silver-embedded electrospun nanofiber of poly(4-chloro-3-methylphenyl methacrylate): use as water sanitizer.

    Science.gov (United States)

    Shekh, Mehdihasan I; Patel, Nirmal N; Patel, Kaushal P; Patel, Rajnikant M; Ray, Arabinda

    2017-02-01

    Water contaminated with microorganisms causes numerous diseases and is a major concern for public health. In search of a simple material which can provide clean water free from pathogens, nanofibers of poly(4-chloro-3-methylphenyl methacrylate, abbreviated as CMPMA, and nano Ag-doped poly(CMPMA) composite nanofibers were used to decontaminate water from microorganisms such as Escherichia coli and Bacillus subtilis. Nanofibers were prepared by electrospinning. X-ray diffraction (XRD) and transmission electron microscopy (TEM) provide the diameters of the Ag nanoparticles which are in the range 18-21 and 13-18 nm. The diameter of the poly(CMPMA) and nano Ag-doped poly(CMPMA) composite nanofiber is seen to vary between 400 and 700 nm with the change of the processing parameters. Optimum parameters for uniform nanofibers have been obtained. The morphology of the fibers is derived from scanning electron microscopy (SEM). The superiority of the nano Ag-doped poly(CMPMA) composite nanofiber was established.

  2. Comparison of 4-chloro-2-nitrophenol adsorption on single-walled and multi-walled carbon nanotubes

    Directory of Open Access Journals (Sweden)

    Mehrizad Ali

    2012-09-01

    Full Text Available Abstract The adsorption characteristics of 4-chloro-2-nitrophenol (4C2NP onto single-walled and multi-walled carbon nanotubes (SWCNTs and MWCNTs from aqueous solution were investigated with respect to the changes in the contact time, pH of solution, carbon nanotubes dosage and initial 4C2NP concentration. Experimental results showed that the adsorption efficiency of 4C2NP by carbon nanotubes (both of SWCNTs and MWCNTs increased with increasing the initial 4C2NP concentration. The maximum adsorption took place in the pH range of 2–6. The linear correlation coefficients of different isotherm models were obtained. Results revealed that the Langmuir isotherm fitted the experimental data better than the others and based on the Langmuir model equation, maximum adsorption capacity of 4C2NP onto SWCNTs and MWCNTs were 1.44 and 4.42 mg/g, respectively. The observed changes in the standard Gibbs free energy, standard enthalpy and standard entropy showed that the adsorption of 4C2NP onto SWCNTs and MWCNTs is spontaneous and exothermic in the temperature range of 298–328 K.

  3. Effects of Acupuncture on 1-chloro-2,4-dinitrochlorobenzene-induced Allergic Contact Dermatitis in Mice

    Directory of Open Access Journals (Sweden)

    Cuicui Chen

    2017-08-01

    Full Text Available Allergic contact dermatitis (ACD is a chronic inflammatory skin disease. Topical corticosteroids are the first-line therapy for ACD despite their significant adverse effects. Acupuncture has been widely used in the treatment of various skin diseases, but its underlying mechanism remains unrevealed. In this study, we investigated the characteristics of acupuncture treatment based on effectiveness and mechanism. BALB/c mice received 1-chloro-2,4-dinitrobenzene (DNCB application to build AD-like model. Results showed that acupuncture was an effective treatment method in inhibiting inflammatory conditions, serum IgE levels, and expression of proinflammatory cytokine Th2 (IL-4, IL-6, and Th2 (IL-1β, TNF-α mRNA compared with DNCB treatment. Acupuncture treatment also inhibited nuclear factor-κB p65, phosphorylation of IκBα, and phosphorylation of occludin proteins expression. Furthermore, it could improve the expression of epidermal growth factor in both mRNA and protein levels. These results suggest that acupuncture, as an alternative therapy treatment for its no significant side effects, was effective in alleviating ACD by reducing proinflammatory cytokines and changing proteins' expression.

  4. Exposure of Human Lung Cancer Cells to 8-Chloro-Adenosine Induces G2/M Arrest and Mitotic Catastrophe

    Directory of Open Access Journals (Sweden)

    Hong-Yu Zhang

    2004-11-01

    Full Text Available 8-Chloro-adenosine (8-CI-Ado is a potent chemotherapeutic agent whose cytotoxicity in a variety of tumor cell lines has been widely investigated. However, the molecular mechanisms are uncertain. In this study, we found that exposure of human lung cancer cell lines A549 (p53-wt and H1299 (p53-depleted to 8-CI-Ado induced cell arrest in the G2/M phase, which was accompanied by accumulation of binucleated and polymorphonucleated cells resulting from aberrant mitosis and failed cytokinesis. Western blotting showed the loss of phosphorylated forms of Cdc2 and Cdc25C that allowed progression into mitosis. Furthermore, the increase in Ser10-phosphorylated histone H3-positive cells revealed by fluorescence-activated cell sorting suggested that the agent-targeted cells were able to exit the G2 phase and enter the M phase. Immunocytochemistry showed that microtubule and microfilament arrays were changed in exposed cells, indicating that the dynamic instability of microtubules and microfilaments was lost, which may correlate with mitotic dividing failure. Aberrant mitosis resulted in mitotic catastrophe followed by varying degrees of apoptosis, depending on the cell lines. Thus, 8-CI-Ado appears to exert its cytotoxicity toward cells in culture by inducing mitotic catastrophe.

  5. Spectrophotometric methods for the determination of ampicillin by potassium permanganate and 1-chloro-2,4-dinitrobenzene in pharmaceutical preparations

    Directory of Open Access Journals (Sweden)

    Aftab Aslam Parwaz Khan

    2015-03-01

    Full Text Available Two simple and sensitive kinetic methods for the determination of ampicillin (AMP are described. The first method is based on kinetic investigation of the oxidation reaction of the drug with alkaline potassium permanganate at room temperature for a fixed time of 25 min. The absorbance of the colored manganate ions is measured at 610 nm. The second method is based on the reaction of AMP with 1-chloro-2,4-dinitrobenzene (CDNB in the presence of 0.1 mol L−1 sodium bicarbonate. Spectrophotometric measurement was achieved by recording the absorbance at 490 nm for a fixed time of 60 min. All variables affecting the development of the color were investigated and the conditions were optimized. Plots of absorbance against concentration in both procedures were rectilinear over the ranges 5–30 and 50–260 μg mL−1, with mean recoveries 99.80 and 99.91, respectively. The proposed methods were successfully applied for the determination of AMP in bulk powder and in capsule dosage form. The determination of AMP by the fixed concentration method is feasible with the calibration equations obtained, but the fixed time method proves to be more applicable.

  6. Investigation of antimicrobial activities, DNA interaction, structural and spectroscopic properties of 2-chloro-6-(trifluoromethyl)pyridine

    Science.gov (United States)

    Evecen, Meryem; Kara, Mehmet; Idil, Onder; Tanak, Hasan

    2017-06-01

    2-Chloro-6-(trifluoromethyl)pyridine has been characterized by FT-IR, 1H and 13C NMR experiment. FT-IR spectra of the molecule has been recorded in the 4000-400 cm-1 region. The molecular structural parameters and vibrational frequencies were computed using the HF and DFT (B3LYP, B3PW91) methods with the 6-31+G(d,p) and 6-311++G(d,p) basis sets. 1H and 13C NMR Gauge Including Atomic Orbital (GIAO) chemical shifts of the compound were calculated using the density functional method (B3LYP) with the 6-311++G(d,p) basis set. The vibrational wavenumbers and chemical shifts were compared with the experimental data of the compound. Using the TD-DFT methodology, electronic absorption spectra of the compound have been computed. Besides, solvent effects on the excitation energies and chemical shifts were carried out using the integral equation formalism of the polarisable continuum model (IEF-PCM). DFT calculations of the compound, Mulliken's charges, molecular electrostatic potential (MEP), natural bond orbital (NBO) and thermodynamic properties were also obtained theoretically. In addition, the antimicrobial activities were tested by using minimal inhibitory concentration method (MIC) and also the effect of the molecule on pBR322 plasmid DNA was monitored byagarose gel electrophoresis experiments.

  7. (3RS,4SR-Methyl 4-(2-chloro-5,8-dimethoxyquinolin-3-yl-1-phenylpyrrolidine-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Saida Benzerka

    2008-11-01

    Full Text Available The molecule of the title compound, C23H23ClN2O4, contains a quinolyl unit linked to a functionalized pyrrolidine system with a 3,4-trans arrangement of the substituents. The unit cell contains two stereoisomers that have the absolute stereochemistry 3S,4R and 3R,4S. The pyrrolidine ring adopts a twist conformation with pseudo-rotation parameters P = 258.2 (3° and τ(M = 35.3 (1°. The packing is stabilized by C—H...π interactions and offset π–π stacking (centroid-to-centroid distance = 3.849 Å, interplanar distance = 3.293 Å and slippage = 1.994 Å between phenyl rings, leading to a two-dimensional network.

  8. 4-{[(1-Phenyl-1H-pyrazol-3-yloxy]methyl}-1,3-dioxolan-2-one

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2012-11-01

    Full Text Available The title compound was obtained by the reaction of tosylated glycerol carbonate with 1-phenyl-1H-pyrazol-3-ol in a good 71% yield. Detailed spectroscopic data (1H-NMR, 13C-NMR, 15N-NMR, IR, MS are presented.

  9. Methyl 6-Methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Haiping Wang

    2012-04-01

    Full Text Available Methyl 6-methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate has been synthesized via the modified Biginelli reaction from benzaldehyde, p-tolylurea, and methyl acetoacetate, promoted with microwave irradiation and catalyzed by TsOH under solvent-free conditions in high yield.

  10. 4-(3,5-Dibromo-4-hydroxyphenyl-3-butoxycarbonyl-5-ethoxycarbonyl-2-methyl-6-phenyl-1,4-dihydropyridine

    Directory of Open Access Journals (Sweden)

    Zhen Wang

    2011-04-01

    Full Text Available One-pot two-step Hantzsch synthesis of 4-(3,5-dibromo-4-hydroxyphenyl-3- butoxycarbonyl-5-ethoxycarbonyl-2-methyl-6-phenyl-1,4-dihydropyridine under solvent- and catalyst-free conditions promoted with microwave irradiation is presented.

  11. Annulation Reactions of Donor-Acceptor Cyclopropanes with (1-Azidovinyl)benzene and 3-Phenyl-2H-azirine.

    Science.gov (United States)

    Curiel Tejeda, Joanne E; Irwin, Lauren C; Kerr, Michael A

    2016-09-16

    Under the influence of heat and Lewis acid, donor/acceptor cyclopropanes underwent annulation reactions with (1-azidovinyl)benzene and 3-phenyl-2H-azirine to form an unusual azabicyclic scaffold with an imbedded aziridine. The mechanism of reaction is believed to proceed via a vinyl nitrene intermediate.

  12. Bis{2-[(dimethylamino)methyl]phenyl}silverlithium. A tetranuclear organometallic compound with bridging aryl groups between silver and lithium

    NARCIS (Netherlands)

    Koten, G. van; Leusink, A.J.; Marsman, J.W.; Noltes, J.G.

    1973-01-01

    Bis{2-[(dimethylamino)methyl]phenyl}silverlithium has been prepared and characterized. Molecular weight determinations, and }1{}3{C NMR and }1{H NMR spectra reveal that the compound exists (in benzene) as a tetranuclear mixed metal cluster containing aryl groups bridging the silver and lithium

  13. Synthesis and 99Tcm labelling of three kinds of derivatives of β-methyl-15-phenyl pentadecanoic acid

    International Nuclear Information System (INIS)

    Lu Chunxiong; Ji Shuren; Wu Chunying; Fang Ping

    2002-01-01

    Three kinds of derivatives of β-methyl-15-phenyl pentadecanoic acid (BMPPA) are synthesized. These derivatives are characterized by IR, MS and elementary analysis. These derivatives are labelled with 99 Tc m , the labelling yields are higher than 70% confirmed by TLC and HPLC and the radiochemical purity are more than 95% after extraction

  14. Separation of hexabromocyclododecane diastereomers: Application of C18 and phenyl-hexyl ultra-performance liquid chromatography columns.

    Science.gov (United States)

    Baek, Song-Yee; Lee, Sunyoung; Kim, Byungjoo

    2017-03-10

    This study was performed to establish the proper liquid chromatographic conditions for the separation of hexabromocyclododecane (HBCD) diastereomers. Column selectivity towards HBCD diastereomers was evaluated for C18 and phenyl-hexyl stationary phases. First, the baseline separation of the primary HBCDs (α-, β-, and γ-HBCD) was obtained using the ultra-performance liquid chromatography (UPLC) column with C18 stationary phase chosen in most previous studies for HBCD analysis; however, co-elution of δ- and ε-HBCD with the primary HBCD diastereomers was observed. To prevent the interference from δ- and ε-HBCD, we adopted a phenyl-hexyl UPLC column to resolve the HBCD diastereomers. The phenyl-hexyl UPLC column showed significantly different selectivity for the HBCD diastereomers compared with the C18 column, which allowed the clear isolation of δ-HBCD and ε-HBCD from the primary HBCD diastereomers. In addition, by checking the retention times of all HBCD diastereomers using both C18 and phenyl-hexyl columns, we confirmed the presence of δ-, ε-, η-, and θ-HBCDs in two technical HBCD mixtures. Copyright © 2017 Elsevier B.V. All rights reserved.

  15. Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea

    KAUST Repository

    Wang, Chao-Yi

    2016-10-26

    Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13–15) exhibited potent anti-larval settlement activity with the EC50 values lower than 3.05 μM and the LC50/EC50 ratios higher than 15. The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2′, 4′, 6′-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents.

  16. New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius.

    Science.gov (United States)

    Bai, Zhi-Qiang; Lin, Xiuping; Wang, Yizhu; Wang, Junfeng; Zhou, Xuefeng; Yang, Bin; Liu, Juan; Yang, Xianwen; Wang, Yi; Liu, Yonghong

    2014-06-01

    Two new aromatic butyrolactones, flavipesins A (1) and B (2), two new natural products (3 and 4), and a known phenyl dioxolanone (5) were isolated from marine-derived endophytic fungus Aspergillus flavipes. The structures of compounds 1-5 were elucidated by 1D- and 2D-NMR and MS analysis, the absolute configurations were assigned by optical rotation and CD data, and the stereochemistry of 1 was determined by X-ray crystallography analysis. 1 demonstrated lower MIC values against Staphylococcus aureus (8.0 μg/mL) and Bacillus subtillis (0.25 μg/mL). 1 also showed the unique antibiofilm activity of penetration through the biofilm matrix and kills live bacteria inside mature S. aureus biofilm. Copyright © 2014 Elsevier B.V. All rights reserved.

  17. Block-Localized Wavefunction (BLW) Based Two-State Approach for Charge Transfers between Phenyl Rings.

    Science.gov (United States)

    Mo, Yirong; Song, Lingchun; Lin, Yuchun; Liu, Minghong; Cao, Zexing; Wu, Wei

    2012-03-13

    The block-localized wave function (BLW) method is the simplest and most efficient variant of ab initio valence bond (VB) theory which defines electron-localized resonance states following the conventional VB concepts. Here, a BLW-based two-state approach is proposed to probe the charge/hole transfer reactions within the Marcus-Hush model. With this approach, both the electronic coupling and reorganization energies can be derived at the ab initio level. Pilot applications to the electron/hole transfers between two phenyl rings are presented. Good exponential correlation between the electronic coupling energy and the donor-acceptor distance is shown, whereas the inner-sphere reorganization shows little geometric dependency. Computations also support the assumption in Marcus theory that the thermal electron transfer barrier (ΔG*), which is a sum of the reaction barrier (ΔEa) for electron/hole transfer and the coupling energy (VAB), is a quarter of the reorganization energy (λ).

  18. Photovoltaic Properties of Solar Cells Based on Poly(methyl phenyl silane) and C60

    Science.gov (United States)

    Mizuno, Toya; Akasaka, Yumeno; Tachibana, Hiroaki

    2012-10-01

    Photovoltaic (PV) devices using blend films of poly(methyl phenyl silane) (PMPS) and fullerene (C60) are fabricated, and the effects of various technical parameters during device fabrication on the PV characteristics under AM 1.5G simulated solar light illumination of 100 mW/cm2 intensity are investigated. The PV performance of the devices depends on the mixing ratio of PMPS:C60, the kind of buffer layer, the thickness of the buffer layer, and the thermal annealing temperature of the devices. The devices optimized for the mixing ratio, kind of buffer layer, and thermal annealing temperature exhibit a short-circuit current density (JSC) of 2.26 mA/cm2, an open circuit voltage (VOC) of 0.71 V, a fill factor (FF) of 0.35, and a power conversion efficiency (PCE) of 0.57%.

  19. 3-Benzyl-3-hydroxy-2-phenyl-3H-indole 1-oxide

    Directory of Open Access Journals (Sweden)

    Corrado Rizzoli

    2010-08-01

    Full Text Available The asymmetric unit of the title compound, C21H17NO2, contains two crystallographically independent molecules of similar geometry. The indole ring systems form dihedral angles of 8.30 (5 and 9.58 (5° with the attached phenyl rings, and 56.96 (5 and 57.68 (5° with the aromatic rings of the respective benzyl groups. The molecular conformations are stabilized by intramolecular C—H...O hydrogen bonds. In the crystal structure, centrosymmetrically related pairs of molecules are linked into dimers through pairs of intermolecular O—H...O hydrogen bonds, generating 12-membered rings with R22(12 motifs. The dimers are further linked into a three-dimensional network by C—H...O interactions.

  20. Kinetics and Mechanism of Nanoparticles-Catalyzed Piperidinolysis of Anionic Phenyl Salicylate

    Directory of Open Access Journals (Sweden)

    Norazizah Abd. Razak

    2014-01-01

    Full Text Available The values of the relative counterion (X binding constant RXBr (=KX/KBr, where KX and KBr represent cetyltrimethylammonium bromide, CTABr, micellar binding constants of Xv- (in non-spherical micelles, v=1,2, and Br− (in spherical micelles are 58, 68, 127, and 125 for Xv−=1−, 12−, 2−, and 22-, respectively. The values of 15 mM CTABr/[NavX] nanoparticles-catalyzed apparent second-order rate constants for piperidinolysis of ionized phenyl salicylate at 35°C are 0.417, 0.488, 0.926, and 0.891 M−1 s−1 for NavX = Na1, Na21, Na2, and Na22, respectively. Almost entire catalytic effect of nanoparticles catalyst is due to the ability of nonreactive counterions, Xv-, to expel reactive counterions, 3−, from nanoparticles to the bulk water phase.

  1. Nucleophilic reactions of hydrazido(2-) complexes of molybdenum and tungsten with succinyl dichloride and phenyl isocyanate

    International Nuclear Information System (INIS)

    Iwanami, Kiyotaka; Mizobe, Yasushi; Takahashi, Tamotsu; Kodama, Teruyuki; Uchida, Yasuzo

    1981-01-01

    Nucleophilic attack of the WNNH 2 group in the hydrazido(2-) complex [WF(NNH 2 )(dpe) 2 ][BF 4 ] (dpe = Ph 2 PCH 2 CH 2 PPh 2 ) on succinyl dichloride gives a novel ethanedioylhydrazido(2-) complex, [WF(NNCOCH 2 CH 2 CO)(dpe) 2 ][BF 4 ]. X-Ray structural analysis shows that the carbon, nitrogen, and oxygen atoms of the ethanedioylhydrazido(2-) ligand lie nearly in the same plane, indicating sp 2 character of the nitrogen atom bearing the two carbonyl groups. Phenyl isocyanate also undergoes nucleophilic attack by the hydrazido(2-) complex [MBr(NNH 2 )(dpe) 2 ]Br (M = Mo or W) to yield the phenylsemicarbazido(2-) type complex, [MBr(NNHCONHPh)(dpe) 2 ]Br. Treatment of the semicarbazido(2-) complex with triethylamine gives a new diazenido complex [MBr(NNCONHPh)(dpe) 2 ]. (author)

  2. Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors.

    Science.gov (United States)

    Paul, R; Hallett, W A; Hanifin, J W; Reich, M F; Johnson, B D; Lenhard, R H; Dusza, J P; Kerwar, S S; Lin, Y; Pickett, W C

    1993-09-17

    The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2- pyrimidinamine (1-27) was chosen for toxicological evaluation.

  3. Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response.

    Science.gov (United States)

    Barbosa, Maria Letícia de Castro; Ramos, Thiago José Figueira; de Arantes, Ana Carolina Santos; Martins, Marco Aurélio; Silva, Patrícia Machado Rodrigues E; Barreiro, Eliezer J; Lima, Lídia Moreira

    2012-12-10

    In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439 (2e) stands out showing an in vitro anti-TNF-α effect similar to the standard thalidomide. The relevance of tetrafluorination of the phthalimide nucleus was also confirmed by the anti-inflammatory profile of 2e, through oral administration, in a murine model of pulmonary inflammation. The corresponding tetrafluorocarboxyamide metabolite LASSBio-1454 (15), generated from partial hydrolysis of the derivative 2e, presented a significant in vitro effect and a pronounced anti-inflammatory activity in vivo.

  4. Donor-substituted phenyl-pi-chromones: electrochemiluminescence and intriguing electronic properties.

    Science.gov (United States)

    Yang, Shu-Wen; Elangovan, Arumugasamy; Ho, Tong-Ing

    2005-04-01

    Phenylethynylchromones bearing different donor groups at the phenyl moiety have been prepared and their photophysical and electrogenerated chemiluminescence (ECL) properties have been studied with respect to their structural features. Intriguingly, the presence and variation of donor groups do not much influence the absorption spectra, which can be compared with the spectrum of unsubstituted chromone, whereas the photoluminescence (PL) spectra show pronounced changes. Density functional theory (DFT) calculations indicate enhancement of HOMO energy levels upon increasing the donor strength. The photophysical properties have also been studied in various solvents, and the PL spectra in particular show the anticipated trend. The introduction of pi-extension imparts ECL to the new molecules and the electronic coupling between the donor and the acceptor moieties through C-C triple bond influences ECL emission maxima. Weaker donors impart excimer ECL while stronger donors impart monomeric intramolecular charge transfer (ICT) ECL.

  5. Hybrid Detectors for Neutrons Combining Phenyl- Polysiloxanes with 3D Silicon Detectors

    International Nuclear Information System (INIS)

    Dalla Palma, Matteo; Quaranta, Alberto; Collazuol, Gianmaria; Carturan, Sara; Cinausero, Marco; Gramegna, Fabiana; Marchi, Tommaso; Dalla Betta, Gian-Franco; Mendicino, Roberto; Povoli, Marco; Boscardin, Maurizio; Giacomini, Gabriele; Ronchin, Sabina; Zorzi, Nicola

    2013-06-01

    We report on the initial results of a research project aimed at the development hybrid detectors for fast neutrons by combining a phenyl-polysiloxane-based converter with a 3D silicon detector. To this purpose, new 3D sensor structures have been designed, fabricated and electrically tested, showing low depletion voltage and good leakage current. Moreover, the radiation detection capability of 3D sensors was tested by measuring the signals recorded from alpha particles, gamma rays, and pulsed lasers. The converter has been poured into the 3D cavities with excellent coupling, as confirmed by cross-section SEM analyses. Preliminary tests with neutrons have been carried out on the first hybrid detector prototypes at the CN accelerator of INFN LNL. The device design and technology are discussed, along with the first results from the electrical and functional characterization. (authors)

  6. 1-Phenyl-5-{[2-(trimethylsilylethyl]sulfonyl}-1H-tetrazole

    Directory of Open Access Journals (Sweden)

    David Tymann

    2011-09-01

    Full Text Available The title compound, C12H18N4O2SSi, was synthesized to be employed in a Julia–Kocieński olefination. In the molecule, the dihedral angle between the phenyl ring and the tetrazole ring is 41.50 (5°. The significantly longer Si—C(methylene bond [1.8786 (13 Å] and the shortened adjacent C—C bond [1.5172 (18 Å], as well as the significant deviation of the corresponding Si—C—C angle [114.16 (9°] from the ideal tetrahedral angle, can be attributed to the β-effect of silicon. In the crystal, molecules are held together by van der Waals interactions.

  7. Synergistic extraction of trivalent lanthanoids with 3-phenyl-4-benzoyl-5-isoxazolone and various sulphoxides

    International Nuclear Information System (INIS)

    Sahu, S.K.; Chakravortty, V.; Reddy, M.L.P.; Ramamohan, T.R.

    1999-01-01

    Synergistic extraction of trivalent lanthanoids Nd, Tb and Tm with mixtures of 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and dioctyl sulphoxide (DOSO), bis-2-ethylhexyl sulphoxide (B2EHSO) or diphenyl sulphoxide (DPhSO) in xylene from perchlorate solution was investigated. Lanthanoids were found to be extracted as Ln(PBI) 3 with HPBI alone. In the presence of sulphoxides, Nd(III) was found to be extracted as Nd(PBI) 3 . S and Nd(PBI) 3 . 2 S (where S = sulphoxide). On the other hand, Tb(III) and Tm(III) were extracted as Tb(PBI) 3 . S and Tm(PBI) 3 . S respectively. The equilibrium constants of the synergistic species were found to increase monotonically with decreasing ionic radii of these metal ions. The addition of a sulphoxide to the metal chelate system not only enhances the extraction efficiency but also improves the selectivities among these trivalent lanthanoids. (orig.)

  8. [Removal of oral Prevotella intermedia Endotoxin by octyl phenyl polyoxyethylene ether extraction method].

    Science.gov (United States)

    Wang, Ai-wu; Liu, Yan; Hu, Kong-xin; Cheng, Qian

    2012-12-01

    To investigate an effective purification method for removing endotoxin from Prevotella intermedia. The main protein ingredients of bacteria prepared from ammonium sulfate precipitation were further treated with octyl phenyl polyoxyethylene ether (Triton X-114), and then processed at 4°C, 37°C and 25°C. The obtained aqueous phase after at least two more cycle repeated operations was assayed for endotoxin by Western blotting, LAL-clotting method, in vitro cell stimulation and in vivo animal experiments. Western blotting and LAL-clotting method demonstrated that the reduction in endotoxin level was greater than 99.99% and recovery of the proteins after endotoxin removal was greater than 90% with Triton X-114 treatment for 3 cycles. The cytokines expression level was lower in both in vitro cell stimulation and in vivo animal experiments than in untreated group (P Prevotella intermedia.

  9. Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine.

    Science.gov (United States)

    Papadopoulou, Christina; Geronikaki, Athina; Hadjipavlou-Litina, Dimitra

    2005-01-01

    A series of thiazolyl-N-phenyl piperazines has been synthesised and tested for anti-inflammatory activity. Their R(M) values were determined as an expression of their lipophilicity. Theoretical calculation of their lipophilicity, as clog P and logPsk also performed. The effect of the synthesised compounds on inflammation, using the carrageenin induced mouse paw oedema model was studied. In general, the studied compounds were found to be potent anti-inflammatory agents (44-74.1%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesised compounds. An attempt was made to correlate their biological activity with some physicochemical parameters using a quantitative structure-activity relationship approach (QSAR).

  10. 5-(4-Methoxyphenyl-4-methyl-1-phenyl-3-p-tolyl-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Yahya Ben Soumane

    2017-11-01

    Full Text Available The title compound, C24H22N2O, crystallizes with two independent molecules (A and B in the asymmetric unit. The phenyl, p-tolyl and p-methoxyphenyl rings are inclined to the pyrazole ring by 42.5 (2, 17.68 (19 and 52.20 (19°, respectively, in molecule A, and by 39.5 (2, 40.77 (19 and 59.76 (18°, respectively, in molecule B. In the asymmetric unit, the pyrarole ring of molecule A makes a dihedral angle of 3.7 (2° with that of molecule B. In the crystal, the two independent molecules are linked to each other by a C—H...O hydrogen bond.

  11. 3-Phenyl-6-(2-pyridyl-1,2,4,5-tetrazine

    Directory of Open Access Journals (Sweden)

    Daniel Chartrand

    2008-01-01

    Full Text Available The title compound, C13H9N5, is the first asymmetric diaryl-1,2,4,5-tetrazine to be crystallographically characterized. We have been interested in this motif for incorporation into supramolecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric molecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The molecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed is very common in diaryltetrazines and is dominated by π stacking [centroid-to-centroid distance between the tetrazine ring and the aromatic ring of an adjacent molecule is 3.6 Å, perpendicular (centroid-to-plane distance of about 3.3 Å].

  12. Molecular pharmacology and ligand docking studies reveal a single amino acid difference between mouse and human serotonin 5-HT2A receptors that impacts behavioral translation of novel 4-phenyl-2-dimethylaminotetralin ligands.

    Science.gov (United States)

    Canal, Clinton E; Cordova-Sintjago, Tania; Liu, Yue; Kim, Myong S; Morgan, Drake; Booth, Raymond G

    2013-12-01

    During translational studies to develop 4-phenyl-2-dimethylaminotetralin (PAT) compounds for neuropsychiatric disorders, the (2R,4S)-trans-(+)- and (2S,4R)-trans-(-)-enantiomers of the analog 6-hydroxy-7-chloro-PAT (6-OH-7-Cl-PAT) demonstrated unusual pharmacology at serotonin (5-HT) 5-HT2 G protein-coupled receptors (GPCRs). The enantiomers had similar affinities (Ki) at human (h) 5-HT2A receptors (≈ 70 nM). In an in vivo mouse model of 5-HT2A receptor activation [(±)-(2,5)-dimethoxy-4-iodoamphetamine (DOI)-elicited head twitch], however, (-)-6-OH-7-Cl-PAT was about 5-fold more potent than the (+)-enantiomer at attenuating the DOI-elicited response. It was discovered that (+)-6-OH-7-Cl-PAT (only) had ≈ 40-fold-lower affinity at mouse (m) compared with h5-HT2A receptors. Molecular modeling and computational ligand docking studies indicated that the 6-OH moiety of (+)- but not (-)-6-OH-7-Cl-PAT could form a hydrogen bond with serine residue 5.46 of the h5-HT2A receptor. The m5-HT2A as well as m5-HT2B, h5-HT2B, m5-HT2C, and h5-HT2C receptors have alanine at position 5.46, obviating this interaction; (+)-6-OH-7-Cl-PAT also showed ≈ 50-fold lower affinity than (-)-6-OH-7-Cl-PAT at m5-HT2C and h5-HT2C receptors. Mutagenesis studies confirmed that 5-HT2A S5.46 is critical for (+)- but not (-)-6-OH-7-Cl-PAT binding, as well as function. The (+)-6-OH-7-Cl-PAT enantiomer showed partial agonist effects at h5-HT2A wild-type (WT) and m5-HT2A A5.46S point-mutated receptors but did not activate m5-HT2A WT and h5-HT2A S5.46A point-mutated receptors, or h5-HT2B, h5-HT2C, and m5-HT2C receptors; (-)-6-OH-7-Cl-PAT did not activate any of the 5-HT2 receptors. Experiments also included the (2R,4S)-trans-(+)- and (2S,4R)-trans-(-)-enantiomers of 6-methoxy-7-chloro-PAT to validate hydrogen bonding interactions proposed for the corresponding 6-OH analogs. Results indicate that PAT ligand three-dimensional structure impacts target receptor binding and translational outcomes

  13. Novel Scintillating Materials Based on Phenyl-Polysiloxane for Neutron Detection and Monitoring

    Science.gov (United States)

    Degerlier, M.; Carturan, S.; Gramegna, F.; Marchi, T.; Palma, M. Dalla; Cinausero, M.; Maggioni, G.; Quaranta, A.; Collazuol, G.; Bermudez, J.

    Neutron detectors are extensively used at many nuclear research facilities across Europe. Their application range covers many topics in basic and applied nuclear research: in nuclear structure and reaction dynamics (reaction reconstruction and decay studies); in nuclear astrophysics (neutron emission probabilities); in nuclear technology (nuclear data measurements and in-core/off-core monitors); in nuclear medicine (radiation monitors, dosimeters); in materials science (neutron imaging techniques); in homeland security applications (fissile materials investigation and cargo inspection). Liquid scintillators, widely used at present, have however some drawbacks given by toxicity, flammability, volatility and sensitivity to oxygen that limit their duration and quality. Even plastic scintillators are not satisfactory because they have low radiation hardness and low thermal stability. Moreover organic solvents may affect their optical properties due to crazing. In order to overcome these problems, phenyl-polysiloxane based scintillators have been recently developed at Legnaro National Laboratory. This new solution showed very good chemical and thermal stability and high radiation hardness. The results on the different samples performance will be presented, paying special attention to a characterization comparison between synthesized phenyl containing polysiloxane resins where a Pt catalyst has been used and a scintillating material obtained by condensation reaction, where tin based compounds are used as catalysts. Different structural arrangements as a result of different substituents on the main chain have been investigated by High Resolution X-Ray Diffraction, while the effect of improved optical transmittance on the scintillation yield has been elucidated by a combination of excitation/fluorescence measurements and scintillation yield under exposure to alpha and γ-rays.

  14. Combination Phenyl Propionate/Pheromone Traps for Monitoring Navel Orangeworm (Lepidoptera: Pyralidae) in Almonds in the Vicinity of Mating Disruption.

    Science.gov (United States)

    Burks, Charles S

    2017-04-01

    Aerosol mating disruption is used for management of navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), in an increasing portion of California almonds and pistachios. This formulation suppresses pheromone monitoring traps far beyond the treatment block, potentially complicating monitoring and management of this key pest. Phenyl propionate is an attractant used to capture adults in the presence of mating disruption, completely suppressing pheromone traps, and lures combining phenyl propionate with a pheromone lure (PPO-combo lure) synergize trap capture in the presence of mating disruption. In this study, laboratory and field trials of different phenyl propionate dispensers indicate a useful life of six weeks. Controlled experiments found similar numbers of adults captured in phenyl propionate and PPO-combo lures in the presence of varying levels of mating disruption intensity. A subsequent trial compared monitoring of field plots at various distances from fields under commercial mating disruption for much of the growing season with pheromone and PPO-combo lures. Although there was some evidence of partial suppression of capture in PPO-combo traps closer to mating disruption compared with lures farther away, there was no failure of detection as occurred with pheromone lures. The ratio of adults in pheromone and PPO-combo traps varied with proximity from treated fields. These results indicate that, in addition to monitoring in mating disruption plots, phenyl propionate lures can be useful for insuring against failure of detection of navel orangeworm pressure in areas where mating disruption is widely used. Published by Oxford University Press on behalf of Entomological Society of America 2017. This work is written by a US Government employee and is in the public domain in the US.

  15. Effective biosynthesis of ethyl (R)-4-chloro-3-hydroxybutanoate by supplementation of l-glutamine, d-xylose and β-cyclodextrin in n-butyl acetate-water media.

    Science.gov (United States)

    He, Yu-Cai; Tao, Zhi-Cheng; Ding, Yun; Zhang, Dan-Ping; Wu, Yin-Qin; Lu, Yun; Liu, Feng; Xue, Yu-Feng; Wang, Cheng; Xu, Jian-He

    2015-06-10

    To avoid adding NAD(+) and effectively transform ethyl 4-chloro-3-oxobutanoate, the mixture of l-glutamine (200mM) and d-xylose (250mM) was added into in n-butyl acetate-water (10:90, v/v) biphasic system instead of NAD(+) for increasing the biocatalytic efficiency. To further improve the synthesis of optically pure ethyl (R)-4-chloro-3-hydroxybutanoate (>99% ee), β-cyclodextrin was also added into this reaction media, and ethyl (R)-4-chloro-3-hydroxybutanoate (>99% ee) could be effectively synthesized from 800mM ethyl 4-chloro-3-oxobutanoate in the yield of 100% by whole-cells of recombinant E. coli CCZU-A13. Finally, the possible mechanism for improving the reductase activity by supplementation of l-glutamine, d-xylose and β-CD was proposed. In conclusion, this strategy has high potential for the effective biosynthesis of ethyl (R)-4-chloro-3-hydroxybutanoate (>99% ee). Copyright © 2015 Elsevier B.V. All rights reserved.

  16. 3,5-Bis(4-meth­oxy­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

    OpenAIRE

    Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S.; Narayana, B.; Yathirajan, H. S.

    2011-01-01

    In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [cen...

  17. A Fluorophore Fusion Construct of Human Profilin I with Non-Compromised Poly(L-Proline) Binding Capacity Suitable for Imaging.

    Science.gov (United States)

    Nejedla, Michaela; Li, Zhilun; Masser, Anna E; Biancospino, Matteo; Spiess, Matthias; Mackowiak, Sebastian D; Friedländer, Marc R; Karlsson, Roger

    2017-04-07

    Profilin is vital for actin organisation in eukaryotic cells. It controls actin filament formation by binding monomeric actin and numerous proteins involved in polarised actin assembly. Important for the latter is the interaction surface formed by the N- and C-terminal helices, which pack close to each other on one side of the molecule at a distance from the actin site and mediate binding to poly-proline sequences present in many of the targeted proteins. Via these interactions, profilin contributes to the spatiotemporal control of actin filament growth. Studies of profilin dynamics in living cells by imaging techniques have been hampered by problems to generate fusion constructs with fluorophore proteins without negatively impacting on its poly-proline binding. With the object to circumvent this problem, we have generated an internal fusion of profilin with the green fluorescent variant citrine, here referred to as citrine-profilin. The characterisation of citrine-profilin (CIT-Pfn) demonstrates that it has full capacity to interact with poly-proline and also binds phosphatidylinositol lipids and actin, albeit with 10 times reduced affinity for the latter. Imaging of living cells expressing CIT-Pfn showed a distribution of the fusion protein similar to endogenous profilin. Furthermore, CIT-Pfn rescued the phenotypes observed after the Crispr/Cas9 knockout of the profilin 1 gene, including the lost migratory capacity characterising the knockout cells. Based on this, we conclude that the CIT-Pfn construct will be useful as a tool for displaying profilin localisation in living cells and obtaining information on its dynamic organisation under different conditions and activations of the actin microfilament and microtubule systems. Copyright © 2017 Elsevier Ltd. All rights reserved.

  18. Sunlight-induced changes in chromophores and fluorophores of wastewater-derived organic matter in receiving waters--the role of salinity.

    Science.gov (United States)

    Yang, Xiaofang; Meng, Fangang; Huang, Guocheng; Sun, Li; Lin, Zheng

    2014-10-01

    Wastewater-derived organic matter (WOM) is an important constituent of discharge to urban rivers and is suspected of altering the naturally occurring dissolved organic matter (DOM) in water systems. This study investigated sunlight-induced changes in chromophores and fluorophores of WOM with different salinities (S = 0, 10, 20 and 30) that were collected from two wastewater treatment plants (WWTP-A and WWTP-B). The results showed that exposure to sunlight for 5.3 × 10(5) J/m(2) caused significant decreases in UV254-absorbing WOM (45-59% loss) compared to gross dissolved organic carbon (WOM and natural DOM. In addition, irradiated WOM at a higher salinity had a larger molecular size than that at a lower salinity. However, natural DOM did not display such behavior. Parallel factor analysis of the excitation-emission matrix determined the presence of two humic-like components (C1 and C2) and two protein-like components (C3 and C4). All the components in WOM followed second-order kinetics, except for the C4 component in WWTP-A, which fit zero-order photoreaction kinetics. The photo-degradation of the C1 component in both WWTPs appeared to be independent of salinity; however, the photo-degradation rates of the C2 and C3 components in both WWTPs and C4 in WWTP-B increased significantly with increasing salinity. In comparison, the photo-degradation of the C1 component was significantly facilitated by increased salinity in natural DOM, fitting first-order photoreaction kinetics. As such, the current knowledge concerning the photo-degradation of naturally occurring DOM cannot be extrapolated for the understanding of WOM photo-degradation. Copyright © 2014 Elsevier Ltd. All rights reserved.

  19. Increased Structural Flexibility at the Active Site of a Fluorophore-conjugated β-Lactamase Distinctively Impacts Its Binding toward Diverse Cephalosporin Antibiotics*

    Science.gov (United States)

    Wong, Wai-Ting; Chan, Kwok-Chu; So, Pui-Kin; Yap, Hong-Kin; Chung, Wai-Hong; Leung, Yun-Chung; Wong, Kwok-Yin; Zhao, Yanxiang

    2011-01-01

    The Ω-loop at the active site of β-lactamases exerts significant impact on the kinetics and substrate profile of these enzymes by forming part of the substrate binding site and posing as steric hindrance toward bulky substrates. Mutating certain residues on the Ω-loop has been a general strategy for molecular evolution of β-lactamases to expand their hydrolytic activity toward extended-spectrum antibiotics through a mechanism believed to involve enhanced structural flexibility of the Ω-loop. Yet no structural information is available that demonstrates such flexibility or its relation to substrate profile and enzyme kinetics. Here we report an engineered β-lactamase that contains an environment-sensitive fluorophore conjugated near its active site to probe the structural dynamics of the Ω-loop and to detect the binding of diverse substrates. Our results show that this engineered β-lactamase has improved binding kinetics and positive fluorescence signal toward oxyimino-cephalosporins, but shows little such effect to non-oxyimino-cephalosporins. Structural studies reveal that the Ω-loop adopts a less stabilized structure, and readily undergoes conformational change to accommodate the binding of bulky oxyimino-cephalosporins while no such change is observed for non-oxyimino-cephalosporins. Mutational studies further confirm that this substrate-induced structural change is directly responsible for the positive fluorescence signal specific to oxyimino-cephalosporins. Our data provide mechanistic evidence to support the long-standing model that the evolutionary strategy of mutating the Ω-loop leads to increased structural flexibility of this region, which in turn facilitates the binding of extended spectrum β-lactam antibiotics. The oxyimino-cephalosporin-specific fluorescence profile of our engineered β-lactamase also demonstrates the possibility of designing substrate-selective biosensing systems. PMID:21705325

  20. Nitrosation of glycine ethyl ester and ethyl diazoacetate to give the alkylating agent and mutagen ethyl chloro(hydroximino)acetate.

    Science.gov (United States)

    Zhou, Lin; Haorah, James; Chen, Sheng C; Wang, Xiaojie; Kolar, Carol; Lawson, Terence A; Mirvish, Sidney S

    2004-03-01

    Whereas nitrosation of secondary amines produces nitrosamines, amino acids with primary amino groups and glycine ethyl ester were reported to react with nitrite to give unidentified agents that alkylated 4-(p-nitrobenzyl)pyridine to produce purple dyes and be direct mutagens in the Ames test. We report here that treatment of glycine ethyl ester at 37 degrees C with excess nitrite acidified with HCl, followed by ether extraction, gave 30-40% yields of a product identified as ethyl chloro(hydroximino)acetate [ClC(=NOH)COOEt, ECHA] and a 9% yield of ethyl chloroacetate. The ECHA was identical to that synthesized by a known method from ethyl acetoacetate, strongly alkylated nitrobenzylpyridine, and may have arisen by N-nitrosation of glycine ethyl ester to give ethyl diazoacetate, which was C-nitrosated and reacted with chloride to give ECHA. Nitrosation of ethyl diazoacetate also yielded ECHA. Ethyl nitroacetate was not an intermediate as its nitrosation did not produce ECHA. ECHA reacted with aniline to give ethyl (hydroxamino)(phenylimino)acetate [PhN=C(NHOH)CO2Et]. This product was different from ethyl [(phenylamino)carbonyl]carbamate [PhNHC(=O)NHCO2Et], which was synthesized by reacting ethyl isocyanatoformate (OCN.CO2Et) with aniline. ECHA reacted with guanosine to give a derivative, which may have been a guanine-C(=NOH)CO2Et derivative. ECHA showed moderate toxicity and weak but significant mutagenicity without activation in Salmonella typhimurium TA-100 (mean, 1.31 x control value for 12-18 microg/plats) and for V79 mammalian cells (1.5-1.7 x control value for 60-100 microM). In conclusion, gastric nitrosation of glycine derivatives such as peptides with a N-terminal glycine might produce ECHA analogues that alkylate bases of gastric mucosal DNA and thereby initiate gastric cancer.

  1. A VUV photoionization study of the multichannel reaction of phenyl radicals with 1,3-butadiene under combustion relevant conditions.

    Science.gov (United States)

    Golan, Amir; Ahmed, Musahid; Mebel, Alexander M; Kaiser, Ralf I

    2013-01-07

    We studied the reaction of phenyl radicals (C(6)H(5)) with 1,3-butadiene (H(2)CCHCHCH(2)) exploiting a high temperature chemical reactor under combustion-like conditions (300 Torr, 873 K). The reaction products were probed in a supersonic beam by utilizing VUV radiation from the Advanced Light Source and by recording the experimental PIE curves at mass-to-charge ratios of m/z = 130 (C(10)H(10)(+)), 116 (C(9)H(8)(+)), and 104 (C(8)H(8)(+)). Our data suggest that the atomic hydrogen (H), methyl (CH(3)), and vinyl (C(2)H(3)) losses are open with estimated branching ratios of about 86 ± 4%, 8 ± 2%, and 6 ± 2%, respectively. The isomer distributions were probed further by fitting the experimentally recorded PIE curves with a linear combination of the PIE curves of individual C(10)H(10), C(9)H(8), and C(8)H(8) isomers. These fits indicate the formation of three C(10)H(10) isomers (trans-1,3-butadienylbenzene, 1,4-dihydronaphthalene, 1-methylindene), three C(9)H(8) isomers (indene, phenylallene, 1-phenyl-1-methylacetylene), and a C(8)H(8) isomer (styrene). A comparison with results from recent crossed molecular beam studies of the 1,3-butadiene-phenyl radical reaction and electronic structure calculations suggests that trans-1,3-butadienylbenzene (130 amu), 1,4-dihydronaphthalene (130 amu), and styrene (104 amu) are reaction products formed as a consequence of a bimolecular reaction between the phenyl radical and 1,3-butadiene. 1-Methylindene (130 amu), indene (116 amu), phenylallene (116 amu), and 1-phenyl-1-methylacetylene (116 amu) are synthesized upon reaction of the phenyl radical with three C(4)H(6) isomers: 1,2-butadiene (H(2)CCCH(CH(3))), 1-butyne (HCCC(2)H(5)), and 2-butyne (CH(3)CCCH(3)); these C(4)H(6) isomers can be formed from 1,3-butadiene via hydrogen atom assisted isomerization reactions or via thermal rearrangements of 1,3-butadiene involving hydrogen shifts in the high temperature chemical reactor.

  2. Synthesis and electropolymerization properties of [(4-{3-[3-(dimethylamino)phenoxy]propoxy}phenyl)metoxy] and [(4-{3-[3-(diethylamino)phenoxy]propoxy}phenyl)metoxy] substituted silicon naphthalocyanines

    Science.gov (United States)

    Biyiklioglu, Zekeriya; Sofuoğlu, Ayşenur

    2017-11-01

    In this study, the first synthesis of axially disubstituted silicon naphthalocyanines bearing electropolymerizable bis[(4-{3-[3-(dimethylamino)phenoxy]propoxy}phenyl)metoxy], bis[(4-{3-[3-(diethylamino)phenoxy]propoxy}phenyl)metoxy] units has been reported. Aggregation behavior of silicon naphthalocyanines were examined in different solvents and concentrations. In all studied solvents and concentrations, silicon naphthalocyanines were non-aggregated. Electrochemical and electropolymerization properties of the silicon naphthalocyanines were studied by cyclic and square wave voltammetry. Electrochemical studies reveal that axially disubstituted silicon naphthalocyanines gave only naphthalocyanine based reduction process during the cathodic potential scans, but they were electropolymerized on the working electrode during the anodic potential scan because of the oxidative electropolymerization of dimethylamino and diethylamino groups on the substituents of the complexes. Therefore, this study is the first example of electropolymerization of axially disubstituted silicon naphthalocyanines.

  3. Ruthenium(II carbonyl compounds with the 4′-chloro-2,2′:6′,2′′-terpyridine ligand

    Directory of Open Access Journals (Sweden)

    Rajendhraprasad Tatikonda

    2017-04-01

    Full Text Available Two ruthenium carbonyl complexes with the 4′-chloro-2,2′:6′,2′′-terpyridine ligand (tpy-Cl, C15H10ClN3, i.e. [RuCl(tpy-Cl(CO2][RuCl3(CO3] (I [systematic name: cis-dicarbonylchlorido(4′-chloro-2,2′:6′,2′′-terpyridine-κ3Nruthenium(II fac-tricarbonyltrichloridoruthenate(II], and [RuCl2(tpy-Cl(CO2] (II [cis-dicarbonyl-trans-dichlorido(4′-chloro-2,2′:6′,2′′-terpyridine-κ2N1,N1′ruthenium(II], were synthesized and characterized by single-crystal X-ray diffraction. The RuII atoms in both centrosymmetric structures (I and (II display similar, slightly distorted octahedral coordination spheres. The coordination sphere in the complex cation in compound (I is defined by three N atoms of the tridentate tpy-Cl ligand, two carbonyl carbon atoms and one chlorido ligand; the charge is balanced by an octahedral [Ru(CO3Cl3]− counter-anion. In the neutral compound (II, the tpy-Cl ligand coordinates to the metal only through two of its N atoms. The coordination sphere of the RuII atom is completed by two carbonyl and two chlorido ligands. In the crystal structures of both (I and (II, weak C—H...Cl interactions are observed.

  4. Characterization of the effects of 2-methylthio-ATP and 2-chloro-ATP on brain capillary endothelial cells: similarities to ADP and differences from ATP.

    OpenAIRE

    Vigne, P.; Feolde, E.; Breittmayer, J. P.; Frelin, C.

    1994-01-01

    1. Brain capillary endothelial cells responded to 2-methylthio-ATP (2MeSATP) by large increases in [Ca2+]i (EC50 = 27 nM) that were partially dependent on the presence of extracellular Ca2+ and that were not associated with a measurable production of inositol phosphates. 2. 2-chloro-ATP (2ClATP) raised [Ca2+]i in a biphasic manner. At low concentrations, intracellular Ca2+ mobilization was not associated with a measurable production of inositol phosphates. At concentrations > 30 microM, 2ClAT...

  5. Kinetics and Mechanism of Electron Transfer Reaction: Oxidation of Sulfanilic Acid by N-Chloro-p-Toluene Sulfonamide in Acid Perchlorate Medium

    International Nuclear Information System (INIS)

    Sailani, Riya; Bhasin, Meneka; Khandelwal, C. L.; Sharma, P. D.

    2014-01-01

    The kinetics and mechanism of oxidation of sulfanilic acid by N-chloro-p-toluene sulfonamide (chloramine-T) have been studied in acid medium. The species of chloramine-T were analysed on the basis of experimental observations and predominantly reactive species was taken into account for proposition of most plausible reaction mechanism. The derived rate law (1) conforms to such a mechanism. All kinetic parameters were evaluated. Activation parameters such as energy and entropy of activation were calculated to be (61.67 ± 0.47) kJ mol -1 and (-62.71 ± 2.48) JK -1 mol -1 respectively employing Eyring equation

  6. Design, Synthesis, and Acetylcholinesterase Inhibition Assay of Novel 9-(1-(Substituted-benzylpiperidin-4-yl-2-chloro-9H-purin-6-amine Derivatives

    Directory of Open Access Journals (Sweden)

    Dongwei Kang

    2013-01-01

    Full Text Available A new series of 9-(1-(substituted-benzylpiperidin-4-yl-2-chloro-9H-purin-6-amine derivatives were designed, synthesized, and characterized on the basis of 1H-NMR, 13C-NMR, and mass spectra. The newly synthesized compounds were evaluated for the inhibition activity against acetylcholinesterase (AChE. Biological results revealed that four compounds among them showed moderate activities against AChE with inhibitory percentage more than 10% at 100 μM. Further pharmacology investigation towards other pathological routes in AD is currently underway.

  7. Synthesis and Fungicidal Activity of Novel Chloro-Containing 1-Aryl-3-oxypyrazoles with an Oximino Ester or Oximino Amide Moiety

    Directory of Open Access Journals (Sweden)

    Yuanyuan Liu

    2014-06-01

    Full Text Available Six novel chloro-containing 1-aryl-3-oxypyrazoles TMa–TMf with an oximino ester or an oximino amide moiety were prepared by the reaction of 1-aryl-1H-pyrazol-3-ols with benzyl bromide. Their structures were characterized by 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. A preliminary in vitro bioassay indicated that compounds TMa, TMe and TMf displayed excellent fungicidal activity against Rhizoctonia solani and could be used as potential lead compounds for further development of novel fungicides.

  8. Synthesis of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives and evaluation of their anticancer activity

    Directory of Open Access Journals (Sweden)

    Nitin Kumar

    2017-05-01

    Full Text Available A novel series of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives were synthesized. In the first step salicylaldehyde was reacted with ethylacetoacetate at room temperature by stirring which gives compound (I. Compound (I when refluxed with substituted benzaldehyde and diethylamine in the presence of n-butanol for 4–5 h gives substituted derivatives (IIa–d. Compounds synthesized in step 2 when refluxed with phenyl hydrazine in the presence of pyridine for 6–7 h gives the title compounds (IIIa–d. All the synthesized compounds were sent to NCI for anticancer activity. Synthesized compounds were tested for anticancer activity against 60 different cell lines. From the data thus obtained it was observed that simple coumarin ring derivatives were more effective in inhibiting the growth of cancerous cell lines, than coumarin-pyrazoline derivatives. Among all the synthesized compounds, irrespective of compounds having simple coumarin ring and coumarin-pyrazoline combination, compounds IIa–c, IIIb and IIId were potent anticancer agents. Compounds were active for the single dose therapeutic program at the dose of 1.00E-5 molar concentration. The main anti cancer activity is assumed to be due to the presence of the lactone structure in coumarin moiety.

  9. Oxidative alkylation of azoles. 6. Generation of active alkylating agents at oxidation of 1-iodo- and 1-bromo-adamantane by 3-nitro-1-chloro-1,2,4-triazole and chlorine

    International Nuclear Information System (INIS)

    Tsypin, V.G.; Pevzner, M.S.

    2000-01-01

    Reactions of N-chloro-triazole with iodo-adamantane were carried out in chloroform at 15-20 Deg C with varied excess of iodine-derivative, up to 200 mol. %. 1-chloro-adamantane, 1-iodo-adamantane, adamantanol-1,3-nitro-1,2,4-triazole, 1-(1-adamantyl)-5-nitro-1,2,4-triazole, 1-(1-adamantyl)-3-nitro-1,2,4-triazole, I 2 , ICl and non-identification impurities are discovered in the reaction mass. Dosing of iodo-derivatives in the excess of oxidative gave rise to separation of I 2 , which was then as a reductant in the reaction with N-chloro-triazole. On further dosing of iodo-derivative steady iodine coloring appeared and unsubstituted triazole was the main product of the reaction. It is supposed that using chlorine for oxidation of iodo-derivative trends to formation of unstable intermediate AdICl 2 [ru

  10. Spectral Properties of Novel 1,3-oxazol-5(4H)-ones With Substituted Benzylidene and Phenyl Rings

    DEFF Research Database (Denmark)

    Palcut, Marián

    2009-01-01

    In the present work, five novel (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) were investigated by the infra-red (IR) and nuclear magnetic resonance spectroscopy (NMR) of the 1H and 13C nuclei. The spectral properties of the oxazolone ring were monitored with respect to the subst......In the present work, five novel (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) were investigated by the infra-red (IR) and nuclear magnetic resonance spectroscopy (NMR) of the 1H and 13C nuclei. The spectral properties of the oxazolone ring were monitored with respect...

  11. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine inhibits proton motive force in energized liver mitochondria

    International Nuclear Information System (INIS)

    Singh, Y.; Bhatnagar, R.; Sidhu, G.S.; Batra, J.K.; Krishna, G.

    1989-01-01

    It is known that 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), which induces Parkinson's-like disease in primates and humans, depletes hepatocytes of ATP and subsequently causes cell death. Incubation of rat liver mitochondria with MPTP and 1-methyl-4-phenyl pyridinium ion (MPP+) significantly inhibited incorporation of 32 Pi into ATP. MPTP and MPP+ inhibited the development of membrane potential and pH gradient in energized rat liver mitochondria, suggesting that reduction of the proton motive force may have reduced ATP synthesis. Since deprenyl, an inhibitor of monoamine oxidase, prevented the formation of MPP+ and inhibited the decrease in membrane potential caused by MPTP, but not that caused by MPP+, these effects of MPTP, as well as cell death, probably were mediated by MPP+. This mechanism may play a role in the specific loss of dopaminergic neurons resulting in MPTP-induced Parkinson's disease

  12. 2-(2,4-Dichlorophenyl-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline

    Directory of Open Access Journals (Sweden)

    K. Balamurugan

    2009-08-01

    Full Text Available In the title compound, C23H15Cl2NS, the quinoline system is almost planar [r.m.s. deviation = 0.013 (2 Å]. The phenyl group is disordered over two positions with site occupancies of 0.55 and 0.45, and is oriented in a nearly perpendicular configuration to the quinoline ring [the dihedral angles between the quinoline ring and the major and minor disordered components of the phenyl ring are 81.8 (2 and 71.6 (2°, respectively]. The dihydrothiene ring adopts an envelope conformation. The dihedral angle between the chlorophenyl ring and the quinoline system is 79.32 (1°. In the crystal weak C—H...π interactions occur.

  13. Purification of di-nonyl phenyl phosphoric acid (DNPPA) for synergistic extraction of uranium from strong phosphoric acid

    International Nuclear Information System (INIS)

    Singh, D.K.; Vijayalakshmi, R.; Singh, H.; Sharma, J.N.; Ruhela, R.

    2009-01-01

    Di-nonyl phenyl phosphoric acid (DNPPA) obtained from various synthesis methods is always associated with impurities such as mono-nonyl phenyl phosphoric acid and nonyl phenol which need to be separated for its effective use in the extraction of uranium from strong phosphoric acid. Two methods of purification namely liquid-solid separation method using neodymium salt and liquid-liquid separation method using methylene glycol have been described. In the liquid solid separation method the purity of DNPPA obtained was about 95% with less than 1.0% monoester, however it heavily suffers in the recovery aspect which is of the order of 50-60%. The methylene glycol treatment method, results in high purity and recovery of the product. Purity obtained was about 95.0% diester and less than 0.5% monoester and recovery was more than 90%. Analysis of DNPPA was done by potentiometric titration method using autotitrator. (author)

  14. Crystal structures and hydrogen bonding in the isotypic series of hydrated alkali metal (K, Rb and Cs) complexes with 4-amino?phenyl?arsonic acid

    OpenAIRE

    Smith, Graham; Wermuth, Urs D.

    2017-01-01

    The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino?phenyl?arsonic acid (p-arsanilic acid) manifest an isotypic series with the general formula [M 2(C6H7AsNO3)2(H2O)3], with M = K {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dipotassium], [K2(C6H7AsNO3)2(H2O)3], (I)}, Rb {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dirubidium], [Rb2(C6H7AsNO3)2(H2O)3], (II)}, and Cs {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dirubidium], [Cs2(C6H7AsNO3)2(H2O)3], (III)}, in ...

  15. Synthesis of poly[methyl(phenyl)silanediyl] containing 1,3,4-oxadiazole electron-transporting moieties

    Czech Academy of Sciences Publication Activity Database

    Kotva, Rudolf; Cimrová, Věra; Výprachtický, Drahomír

    2003-01-01

    Roč. 50, č. 4 (2003), s. 227-234 ISSN 0170-0839 R&D Projects: GA ČR GA102/98/0696; GA ČR GA203/01/0512 Institutional research plan: CEZ:AV0Z4050913 Keywords : oxadiazole derivative * poly[methyl(phenyl)silanediyl] * modified polysilanes Subject RIV: CD - Macromolecular Chemistry Impact factor: 0.795, year: 2003

  16. IR Laser Ablative and Conventional Decomposition of Poly(vinyl phenyl ketone) : Different Processes and Different Products.

    Czech Academy of Sciences Publication Activity Database

    Pokorná, Dana; Šubrt, Jan; Galíková, Anna; Pola, Josef

    2007-01-01

    Roč. 92, 3 (2007) , s. 352-358 ISSN 0141-3910 R&D Projects: GA ČR(CZ) GA104/04/2028 Institutional research plan: CEZ:AV0Z40720504; CEZ:AV0Z40320502 Keywords : laser ablation * poly(vinyl phenyl ketone ) * laser degradation Subject RIV: CC - Organic Chemistry Impact factor: 2.073, year: 2007

  17. 3-Phenyl-6-(2-pyrid­yl)-1,2,4,5-tetra­zine

    OpenAIRE

    Chartrand, Daniel; Laverdière, François; Hanan, Garry

    2007-01-01

    The title compound, C13H9N5, is the first asymmetric diaryl-1,2,4,5-tetrazine to be crystallographically characterized. We have been interested in this motif for incorporation into supramolecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric molecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The molecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed...

  18. Design, synthesis, docking and biological evaluation of 4-phenyl-thiazole derivatives as autotaxin (ATX) inhibitors.

    Science.gov (United States)

    Balupuri, Anand; Lee, Dae-Yon; Lee, Myeong Hwi; Chae, Sangeun; Jung, Eunmi; Kim, Yunki; Ryu, Jeonghee; Kang, Nam Sook

    2017-09-01

    The autotaxin-lysophophatidic acid (ATX-LPA) signaling pathway is involved in several human diseases such as cancer, autoimmune diseases, inflammatory diseases neurodegenerative diseases and fibrotic diseases. Herein, a series of 4-phenyl-thiazole based compounds was designed and synthesized. Compounds were evaluated for their ATX inhibitory activity using FS-3 and human plasma assays. In the FS-3 assay, compounds 20 and 21 significantly inhibited the ATX at low nanomolar level (IC 50 =2.99 and 2.19nM, respectively). Inhibitory activity of 21 was found to be slightly better than PF-8380 (IC 50 =2.80nM), which is one of the most potent ATX inhibitors reported till date. Furthermore, 21 displayed higher potency (IC 50 =14.99nM) than the first clinical ATX inhibitor, GLPG1690 (IC 50 =242.00nM) in the human plasma assay. Molecular docking studies were carried out to explore the binding pattern of newly synthesized compounds within active site of ATX. Docking studies suggested the putative binding mode of the novel compounds. Good ATX inhibitory activity of 21 was attributed to the hydrogen bonding interactions with Asn230, Trp275 and active site water molecules; electrostatic interaction with catalytic zinc ion and hydrophobic interactions with amino acids of the hydrophobic pocket. Copyright © 2017 Elsevier Ltd. All rights reserved.

  19. Potential Activity of 3-(2-Chlorophenyl)-1-phenyl-propenonein Accelerating Wound Healing in Rats

    Science.gov (United States)

    Dhiyaaldeen, Summaya M.; Alshawsh, Mohammed A.; Salama, Suzy M.; Alwajeeh, Nahla S. I.

    2014-01-01

    Wound healing involves inflammation followed by granular tissue development and scar formation. In this study, synthetic chalcone 3-(2-Chlorophenyl)-1-phenyl-propenone (CPPP) was investigated for a potential role in enhancing wound healing and closure. Twenty-four male rats were divided randomly into 4 groups: carboxymethyl cellulose (CMC) (0.2 mL), Intrasite gel, and CPPP (25 or 50 mg/mL). Gross morphology, wounds treatment with the CPPP, and Intrasite gel accelerate the rate of wound healing compared to CMC group. Ten days after surgery, the animals were sacrificed. Histological assessment revealed that the wounds treated with CPPP showed that wound closure site contained little amount of scar and the granulation tissue contained more collagen and less inflammatory cells than wound treated with CMC. This finding was confirmed with Masson's trichrome staining. The antioxidant defence enzymes catalase (CAT) and superoxide dismutase (SOD) were significantly increased in the wound homogenates treated with CPPP (P healing. PMID:24587992

  20. Negative polarity of phenyl-C61 butyric acid methyl ester adjacent to donor macromolecule domains

    International Nuclear Information System (INIS)

    Alley, Olivia J.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Katz, Howard E.; Wu, Meng-Yin; Johns, Gary L.; Markovic, Nina; Arnold, Michael S.

    2015-01-01

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (V oc ) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the V oc , which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C 61 butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased V oc , but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions

  1. Synthesis and Application of Phenyl Nitrone Derivatives as Acidic and Microbial Corrosion Inhibitors

    Directory of Open Access Journals (Sweden)

    Shijun Chen

    2015-01-01

    Full Text Available Nitrone has drawn great attention due to its wide applications as a 1,3-dipole in heterocyclic compounds synthesis and the bioactivities. With the special structure, nitrone can also be used as ligand in inorganic chemistry. Based on the current research, the nitrones are anticipated to be effective inhibitors against acidic and microbial corrosion. The aim of this work is to investigate the inhibitory action of nitrones. In this work, a series of phenyl nitrone derivatives (PN was synthesized and used as acidic and microbial corrosion inhibitors. The results indicate that several compounds show moderate to high inhibition efficiency (IE in 3% HCl. Accompanied with HMTA or BOZ, the IEs greatly increase, and the highest efficiency of 98.5% was obtained by using PN4 + BOZ. Investigation of the antibacterial activity against oilfield microorganism shows that the nitrone derivatives can inhibit SRB, IB, and TGB with moderate to high efficiency under 1,000 mg/L, which makes them potential to be used as bifunctional oilfield chemicals.

  2. Inactivation of acetylcholinesterase by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride.

    Science.gov (United States)

    Zang, Lun-Yi; Misra, Hara P

    2003-12-01

    The neurotoxicant 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) has been shown to reversibly inhibit the activity of acetylcholinesterase. The inactivation of the enzyme was detected by monitoring the accumulation of yellow color produced from the reaction between thiocholine and dithiobisnitrobenzoate ion. The kinetic parameter, Km for the substrate (acetylthiocholine), was found to be 0.216 mM and Ki for MPTP inactivation of acetylcholinesterase was found to be 2.14 mM. The inactivation of enzyme by MPTP was found to be dose-dependent. It was found that MPTP is neither a substrate of AChE nor the time-dependent inactivator. The studies of reaction kinetics indicate the inactivation of AChE to be a linear mixed-type inhibition. The dilution assays indicate that MPTP is a reversible inhibitor for AChE. These data suggest that once MPTP enters the basal ganglia of the brain, it can inactivate the acetylcholinesterase enzyme and thereby increase the acetylcholine level in the basal ganglia of brain, leading to potential cell dysfunction. It appears that the nigrostriatal toxicity by MPTP leading to Parkinson's disease-like syndrome may, in part, be mediated via the acetylcholinesterase inactivation.

  3. Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases

    Energy Technology Data Exchange (ETDEWEB)

    He, Jiayue; Lu, Lu; Zhao, Chen; Mei, Donghai; Lercher, Johannes A.

    2014-03-01

    Catalytic pathways for the cleavage of ether bonds in benzyl phenyl ether (BPE) in liquid phase using Ni- and zeolite-based catalysts are explored. In the absence of catalysts, the C-O bond is selectively cleaved in water by hydrolysis, forming phenol and benzyl alcohol as intermediates, followed by alkylation. The hydronium ions catalyzing the reactions are provided by the dissociation of water at 523 K. Upon addition of HZSM-5, rates of hydrolysis and alkylation are markedly increased in relation to proton concentrations. In the presence of Ni/SiO2, the selective hydrogenolysis dominates for cleaving the Caliphatic-O bond. Catalyzed by the dual-functional Ni/HZSM-5, hydrogenolysis occurs as the major route rather than hydrolysis (minor route). In apolar undecane, the non-catalytic thermal pyrolysis route dominates. Hydrogenolysis of BPE appears to be the major reaction pathway in undecane in the presence of Ni/SiO2 or Ni/HZSM-5, almost completely suppressing radical reactions. Density functional theory (DFT) calculations strongly support the proposed C-O bond cleavage mechanisms on BPE in aqueous and apolar phases. These calculations show that BPE is initially protonated and subsequently hydrolyzed in the aqueous phase. Finally, DFT calculations suggest that the radical reactions in non-polar solvents lead to primary benzyl and phenoxy radicals in undecane, which leads to heavier condensation products as long as metals are absent for providing dissociated hydrogen.

  4. Observation of the a_1 CH Stretching Modes of Phenyl Radical

    Science.gov (United States)

    Chang, Chih-Hsuan; Buckingham, Grant T.; Nesbitt, David J.

    2013-06-01

    High resolution spectroscopy for infrared rovibrational transitions in the CH stretching manifold of phenyl radical (C_6H_5) has been investigated in the slit-jet supersonic expansion at sub-Doppler resolution (60 MHz). Two new fundamental modes are observed and analyzed in this present study, corresponding to b-type structure originating from excitation of the fundamentals v_1 and v_2 mode. The band origins are determined to be 3073.96850(8) cm^{-1} and 3062.26480(7) cm^{-1}, respectively, which agree well with theoretical anharmonic scaling prediction within 5 cm^{-1} based on the B3LYP/6-311g++(3df,3dp) basis set, but shifted by 11 cm^{-1} from the corresponding experimental Ar-matrix's results of Ellison and coworkers. Intensities for the three bands are also analyzed, with the relative intensities between these three agreeing well with theoretical calculation. The physical interpretation of the inertia defect and perturbations of the band positions to explain the experimental observation and the frequencies shift. Anders. V. Friderichsen, Juliusz G. Radziszewski, Mark R. Nimols, Paul R. Winter, David C. Dayton, Donald E. David, and G. Barney Ellison, J. Am. Chem. Soc. 123, 1977 (2001)

  5. Synthesis and molecular modelling studies of phenyl linked oxadiazole-phenylhydrazone hybrids as potent antileishmanial agents.

    Science.gov (United States)

    Taha, Muhammad; Ismail, Nor Hadiani; Imran, Syahrul; Anouar, El Hassane; Selvaraj, Manikandan; Jamil, Waqas; Ali, Muhammad; Kashif, Syed Muhammad; Rahim, Fazal; Khan, Khalid Mohammed; Adenan, Mohd Ilham

    2017-01-27

    Molecular hybridization yielded phenyl linked oxadiazole-benzohydrazones hybrids 6-35 and were evaluated for their antileishmanial potentials. Compound 10, a 3,4-dihydroxy analog with IC 50 value of 0.95 ± 0.01 μM, was found to be the most potent antileishmanial agent (7 times more active) than the standard drug pentamidine (IC 50  = 7.02 ± 0.09 μM). The current series 6-35 conceded in the identification of thirteen (13) potent antileishmanial compounds with the IC 50 values ranging between 0.95 ± 0.01-78.6 ± 1.78 μM. Molecular docking analysis against pteridine reductase (PTR1) were also performed to probe the mode of action. Selectivity index showed that compounds with higher number of hydroxyl groups have low selectivity index. Theoretical stereochemical assignment was also done for certain derivatives by using density functional calculations. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  6. Methyl 6-methoxycarbonylmethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Lucia Veizerová

    2008-09-01

    Full Text Available The title compound, C15H16N2O5, belongs to the class of monastrol-type anti-cancer agents and was selected for crystal structure determination in order to determine the conformational details needed for subsequent structure–activity relationship studies. The central tetrahydropyrimidine ring has a flat-envelope conformation. The 4-phenyl group occupies a pseudo-axial position and is inclined at an angle of ca 90° to the mean plane of the heterocyclic ring. Of the two methyl ester groups, one (in the 5-position is in a coplanar and the other (in the 6-position in a perpendicular orientation with respect to the heterocyclic plane. The coplanar 5-ester group has its carbonyl bond oriented cis with respect to the pyrimidine C=C double bond. By comparison of the structural results for the present compound with those determined previously for its diethyl analogue, we have identified the molecular factors which control the dual course of the Biginelli reaction with salicylaldehyde. The crystal structure is dominated by two hydrogen bonds which link the molecules into chains of dimers.

  7. Synthesis of Highly Branched Polyolefins Using Phenyl Substituted α-Diimine Ni(II Catalysts

    Directory of Open Access Journals (Sweden)

    Fuzhou Wang

    2016-04-01

    Full Text Available A series of α-diimine Ni(II complexes containing bulky phenyl groups, [ArN = C(NaphthC = NAr]NiBr2 (Naphth: 1,8-naphthdiyl, Ar = 2,6-Me2-4-PhC6H2 (C1; Ar = 2,4-Me2-6-PhC6H2 (C2; Ar = 2-Me-4,6-Ph2C6H2 (C3; Ar = 4-Me-2,6-Ph2C6H2 (C4; Ar = 4-Me-2-PhC6H3 (C5; Ar = 2,4,6-Ph3C6H2 (C6, were synthesized and characterized. Upon activation with either diethylaluminum chloride (Et2AlCl or modified methylaluminoxane (MMAO, all Ni(II complexes showed high activities in ethylene polymerization and produced highly branched amorphous polyethylene (up to 145 branches/1000 carbons. Interestingly, the sec-butyl branches were observed in polyethylene depending on polymerization temperature. Polymerization of 1-alkene (1-hexene, 1-octene, 1-decene and 1-hexadecene with C1-MMAO at room temperature resulted in branched polyolefins with narrow Mw/Mn values (ca. 1.2, which suggested a living polymerization. The polymerization results indicated the possibility of precise microstructure control, depending on the polymerization temperature and types of monomers.

  8. Thermolysis of phenethyl phenyl ether: A model of ether linkages in low rank coal

    Energy Technology Data Exchange (ETDEWEB)

    Britt, P.F.; Buchanan, A.C. III; Malcolm, E.A.

    1994-09-01

    Currently, an area of interest and frustration for coal chemists has been the direct liquefaction of low rank coal. Although low rank coals are more reactive than bituminous coals, they are more difficult to liquefy and offer lower liquefaction yields under conditions optimized for bituminous coals. Solomon, Serio, and co-workers have shown that: in the pyrolysis and liquefaction of low rank coals, a low temperature cross-linking reaction associated with oxygen functional groups occurs before tar evolution. A variety of pretreatments (demineralization, alkylation, and ion-exchange) have been shown to reduce these retrogressive reactions and increase tar yields, but the actual chemical reactions responsible for these processes have not been defined. In order to gain insight into the thermochemical reactions leading to cross-linking in low rank coal, we have undertaken a study of the pyrolysis of oxygen containing coal model compounds. Solid state NMR studies suggest that the alkyl aryl ether linkage may be present in modest amounts in low rank coal. Therefore, in this paper, we will investigate the thermolysis of phenethyl phenyl ether (PPE) as a model of 0-aryl ether linkages found in low rank coal, lignites, and lignin, an evolutionary precursor of coal. Our results have uncovered a new reaction channel that can account for 25% of the products formed. The impact of reaction conditions, including restricted mass transport, on this new reaction pathway and the role of oxygen functional groups in cross-linking reactions will be investigated.

  9. Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes

    Directory of Open Access Journals (Sweden)

    Andrew Levitz

    2018-01-01

    Full Text Available Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.

  10. Synthesis, characterization and corrosion inhibition efficiency of N-(4-(Morpholinomethyl Carbamoyl Phenyl Furan-2-Carboxamide

    Directory of Open Access Journals (Sweden)

    N. Zulfareen

    2016-01-01

    Full Text Available A mannich base namely N-(4-(Morpholinomethyl Carbamoyl Phenyl Furan-2-Carboxamide (MFC was synthesized and characterized by FT-IR, 1H NMR, and 13C NMR. The molecular weight of MFC was confirmed by LC-MS. The inhibition effect of MFC on brass in 1 M HCl medium has been investigated by weight loss measurement, potentiodynamic polarization, electrochemical impedance spectroscopy (EIS and cyclic voltametry (CV. Thermodynamic parameters such as free energy, entropy and enthalpy were calculated to describe the mechanism of corrosion inhibitor. The inhibition efficiency of MFC increases with increase in concentration and temperature ranges from 30 °C to 60 °C. Polarization measurements indicated that MFC acts as a mixed type corrosion inhibitor. AC impedance indicates that Rct value increases with increase in the concentration of inhibitor. CV reveals that the oxidation of the copper is controlled by the addition of inhibitor on the brass metal. Surface analysis using scanning electron microscope (SEM shows a significant morphological improvement on the brass surface with the addition of the inhibitor. The adsorption of MFC on brass obeys Langmuir adsorption isotherm. The molecular structure of MFC was distorted to quantum chemical indices using density functional theory (DFT which indicates that the inhibition efficiency of MFC is closely related to quantum parameters.

  11. Mg(II Selective PVC Membrane Electrode Based on Methyl Phenyl Semicarbazone as an Ionophore

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2013-01-01

    Full Text Available A PVC-membrane-based Mg(II selective electrode was constructed using methyl phenyl semicarbazone (MPS as a neutral carrier. The sensor exhibits a Nernstian response for Mg(II ion over a wide concentration range 1.0×10-8  to  1.0×10-1 M with the slope of 28.4 mV/per decade having detection limit 1.7×10-9 M. It was relatively a fast response time (<10 s for concentration ≥1.0×10-3 and <15 s for concentration of ≥1.0×10-6 M and can be used for 8 months without any considerable divergence in potentials. The proposed sensor revealed relatively good selectivity and high sensitivity for Mg(II over a mono-, di-, and trivalent cation and can be used in a pH range of 1.0–9.5. It was also successfully used as an indicator electrode in potentiometer titration and in the analysis of concentration of magnesium in various real samples.

  12. Incorporating Methyl and Phenyl Substituted Stannylene Units into Oligosilanes. The Influence on Optical Absorption Properties.

    Science.gov (United States)

    Stella, Filippo; Marschner, Christoph; Baumgartner, Judith

    2017-12-12

    Molecules containing catenated heavy group 14 atoms are known to exhibit the interesting property of σ-bond electron delocalization. While this is well studied for oligo- and polysilanes the current paper addresses the UV-absorption properties of small tin containing oligosilanes in order to evaluate the effects of Sn-Si and Sn-Sn bonds as well as the results of substituent exchange from methyl to phenyl groups. The new stannasilanes were compared to previously investigated oligosilanes of equal chain lengths and substituent pattern. Replacing the central SiMe₂ group in a pentasilane by a SnMe₂ unit caused a bathochromic shift of the low-energy band (λ max = 260 nm) of 14 nm in the UV spectrum. If, instead of a SnMe 2, a SnPh₂ unit is incorporated, the bathochromic shift of 33 nm is substantially larger. Keeping the SnMe₂ unit and replacing the two central silicon with tin atoms causes shift of the respective band (λ = 286 nm) some 26 nm to the red. A similar approach for hexasilanes where the model oligosilane [(Me₃Si)₃Si]₂(SiMe₂)₂ (λ max = 253 nm) was modified in a way that the central tetramethyldisilanylene unit was exchanged for a tetraphenyldistannanylene caused a 50 nm bathochromic shift to a low-energy band with λ max = 303 nm.

  13. In vitro photosensitization initiated by camphorquinone and phenyl propanedione in dental polymeric materials.

    Science.gov (United States)

    Christensen, Terje; Morisbak, Else; Tønnesen, Hanne Hjorth; Bruzell, Ellen M

    2010-09-02

    Documentation is scarce on the photobiological effects of photoinitiators present in dental light curable materials. The aim of this study was to determine cellular effects of the photoinitiators camphorquinone (CQ) and phenyl propanedione (PPD) and to investigate whether these substances produced reactive oxygen species after low and high doses of optical radiation (between 0 and 17J/cm(2)). Rat salivary gland cells in vitro were exposed to visible blue light and/or UVA. Hematoporphyrin (HP), a photosensitizer used in medicine, and the UVA-filter 2-methoxy-4-hydroxy-benzophenone (B-3) were used as reference substances. It was found that PPD produced hydrogen peroxide, but not singlet oxygen, upon light irradiation. CQ produced neither hydrogen peroxide nor singlet oxygen. Cell death by necrosis and apoptosis was induced by irradiation in the presence of CQ, PPD and HP. Doses higher than 6J/cm(2) UVA and blue visible light from a source similar to clinically applied sources, induced apoptosis even in the absence of photosensitizers added. A reciprocity relationship was found between radiant exposure (at constant irradiance) and concentration of photoinitiators. In conclusion, the oral cells under investigation were light sensitive, and the sensitivity increased in presence of photoinitiators. PPD acted by mechanisms that included reactive oxygen species and CQ probably by formation of free radicals. Copyright (c) 2010 Elsevier B.V. All rights reserved.

  14. 2-Acetylpyridine N4-Phenyl- Thiosemicarbazone as a new tool for tumour diagnosis

    International Nuclear Information System (INIS)

    Soares, Marcella Araugio; Pesquero, Jorge Luiz

    2009-01-01

    The aim of this work was to determine in vivo biodistribution of radiolabelled 2-acetylpyridine N4 phenyl thiosemicarbazone (Ph) and to evaluate its applicability for tumour diagnosis. Ph was labelled with 125 I using lactoperoxidase method and radiochemical analysis was performed by chromatography. 125 I-Ph production was successful with 86 ± 9.2% of radiochemical purity and high specific activity (17.6 TBq /mmol). 125 I-Ph was used for biodistribution and pharmacokinetics studies on Swiss mice bearing Ehrlich solid tumour. 125 I-Ph presented a rapid blood clearance (T 1/2 = 97.2 min.) and the kidneys were the main excretion pathway (CL0.01 mL/min). 125 I-Ph uptake was significant in tumour (2.5%ID/g) and tumour-to-normal tissue uptake was more than 20-fold higher depending on the organ. The uptake by the organs like heart, lungs, stomach and liver followed the blood perfusion. Our results suggest that 125 I-Ph possess indispensable characteristics for an efficient radiopharmaceutical for tumour diagnosis. The next step will be to evaluate the quality of tumour SPECT images provided by 131 I-Ph. (author)

  15. Efficient kinetic resolution of phenyl glycidyl ether by a novel epoxide hydrolase from Tsukamurella paurometabola.

    Science.gov (United States)

    Wu, Kai; Wang, Hualei; Sun, Huihui; Wei, Dongzhi

    2015-11-01

    Enantioselective hydrolysis of racemic epoxides mediated by epoxide hydrolases (EHs) is one of the most promising approaches to obtain enantiopure epoxides. In this study, we identified and characterized a novel EH (TpEH1) from Tsukamurella paurometabola by analyzing the conserved catalytic residues of EH. TpEH1 was overexpressed and purified, and its catalytic properties were studied using racemic phenyl glycidyl ether (PGE) and its derivatives as substrates. TpEH1 showed excellent enantioselectivity to the substrates PGE, 3-methylPGE, and 3-nitroPGE. The highest enantioselectivity (E > 100) was achieved when 3-nitroPGE was used as the substrate. The recombinant Escherichia coli TpEH1 demonstrated high substrate tolerance toward PGE and could hydrolyze PGE at concentrations of up to 400 mM (60 g/L) with high enantioselectivity (E = 65), giving (R)-PGE with enantiomeric excess of more than 99 % ee and 45 % yield within 1 h. This concentration of PGE is the highest reported concentration catalyzed by native EHs to date. Thus, the easily available and highly active E. coli TpEH1 showed great potential for the practical preparation of optically pure (R)-PGE.

  16. Bioimaging of peroxynitrite in MCF-7 cells by a new fluorescent probe rhodamine B phenyl hydrazide.

    Science.gov (United States)

    Ambikapathi, Gopi; Kempahanumakkagari, Suresh Kumar; Ramappa Lamani, Babu; Kuramkote Shivanna, Devaraju; Bodagur Maregowda, Harish; Gupta, Anushree; Malingappa, Pandurangappa

    2013-07-01

    Peroxynitrite is a potent oxidizing and nitrating agent which has detrimental effects on cells by altering the structure and function of biomolecules present within. A fluorescent probe rhodamine B phenyl hydrazide (RBPH) has been proposed for peroxynitrite (ONOO(-)) imaging in MCF-7 cells based on its oxidation property, which converts RBPH to pink colored and highly fluorescent rhodamine B. The fluorescence emission intensity of the rhodamine B produced in the above process is linearly related to the concentration of peroxynitrite. The method obeys Beer's law in the concentration range 2-20 nM and the detection limit has been found to be 1.4 nM. The possible reaction mechanism of peroxynitrite with RBPH to produce rhodamine B has been discussed with spectroscopic evidence. The Probe is selective to the peroxynitrite in the pH range 6-8 which is near physiological pH. Fluorescence microscopic studies suggest that the probe is cell permeable and hence peroxynitrite was imaged in MCF-7 cells.

  17. Electronic Structures and Optical Properties of Phenyl C71 Butyric Acid Methyl Esters

    Directory of Open Access Journals (Sweden)

    Cai-Rong Zhang

    2013-01-01

    Full Text Available Phenyl C71 butyric acid methyl ester (PC71BM has been adopted as electron acceptor materials in bulk heterojunction solar cells with relatively higher power conversion efficiency. The understanding of the mechanism and performance for the devices based upon PC71BM requires the information of conformations, electronic structures, optical properties, and so forth. Here, the geometries, IR and Raman, electronic structures, polarizabilities, and hyperpolarizabilities of PC71BM isomers are studied by using density functional theory (DFT; the absorption and excitation properties are investigated via time-dependent DFT with B3LYP, PBE0, and CAM-B3LYP functionals. The calculated results show that [6,6]PC71BM is more stable than [5,6]PC71BM due to the lower total energy. The vibrational modes of the isomers at IR and Raman peaks are quite similar. As to absorption properties, CAM-B3LYP functional is the suitable functional for describing the excitations of PC71BM because the calculated results with CAM-B3LYP functional agree well with that of the experiment. The analysis of transition configurations and molecular orbitals demonstrated that the transitions at the absorption maxima in UV/Vis region are localized π-π* transitions in fullerenes cages. Furthermore, the larger isotropic polarizability of PC71BM indicates that the response of PC71BM to applied external electric field is stronger than that of PC61BM, and therefore resulting into better nonlinear optical properties.

  18. Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

    Directory of Open Access Journals (Sweden)

    Minlong Wang

    2017-05-01

    Full Text Available Sulfonyl-containing compounds, which exhibit a broad spectrum of biological activities, comprise a substantial proportion of and play a vital role, not only in medicines but also in agrochemicals. As a result increasing attention has been paid to the research and development of sulfonyl derivatives. A series of thirty-eight 2-substituted phenyl-2-oxo- III, 2-hydroxy- IV and 2-acyloxyethylsulfonamides V were obtained and their structures confirmed by IR, 1H-NMR, and elemental analysis. The in vitro and in vivo bioactivities against two Botrytis cinerea strains, DL-11 and HLD-15, which differ in their sensitivity to procymidone, were evaluated. The in vitro activity results showed that the EC50 values of compounds V-1 and V-9 were 0.10, 0.01 mg L−1 against the sensitive strain DL-11 and 3.32, 7.72 mg L−1 against the resistant strain HLD-15, respectively. For in vivo activity against B. cinerea, compound V-13 and V-14 showed better control effect than the commercial fungicides procymidone and pyrimethanil. The further in vitro bioassay showed that compounds III, IV and V had broad fungicidal spectra against different phytopathogenic fungi. Most of the title compounds showed high fungicidal activities, which could be used as lead compounds for further developing novel fungicidal compounds against Botrytis cinerea.

  19. Photochemistry of phenyl alkyl ketones. The lifetime of the intermediate biradicals

    International Nuclear Information System (INIS)

    Small, R.D. Jr.; Scalano, J.C.

    1977-01-01

    The lifetimes of a number of biradicals produced in the photochemical Norrish type II reaction of phenyl alkyl ketones have been measured. The decay of the biradicals was followed by monitoring the competition with electron transfer to paraquat dications using nanosecond laser techniques. The lifetimes are rather insensitive to changes in temperature, substitution, and solvent, and are typically in the neighborhood of 100 ns. It is concluded that intersystem crossing is the main factor determining the biradical lifetimes. The rate constant for electron transfer to paraquat dications is 3.7 x 10 9 M -1 s -1 in methanol at room temperature for 1,4-ketyl--alkyl biradicals, and considerably higher for diketyl biradicals, apparently reflecting a change in path degeneracy. Oxygen behaves as a biradical scavenger with a rate constant of 6.2 x 10 9 M -1 s -1 in methanol. The lifetimes of the excited ketone triplets have also been determined at room temperature under the experimental conditions employed; this is an important parameter in determining the viability of the measurements of biradical lifetimes by this technique

  20. Entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine into the rat brain

    International Nuclear Information System (INIS)

    Riachi, N.J.; LaManna, J.C.; Harik, S.I.

    1989-01-01

    We studied blood-to-brain entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 1-methyl-4-phenylpyridinium (MPP+) and butanol in anesthetized rats using the indicator-fractionation method with right atrial bolus injection. Minimal amounts of MPP+, which has low octanol/water partition coefficient, crossed the blood-brain barrier. MPTP and butanol, both of which have high octanol/water partition coefficients, were almost completely extracted by all regions of the brain on the first pass. The main difference between the MPTP and butanol tracers is that butanol rapidly left the brain with an exponential rate constant of 1.24 min-1, whereas MPTP was avidly retained by the brain with a washout rate constant of 0.10 min-1 (mean values for the four brain regions that we studied). Early retention of MPTP by the brain was not due to its rapid metabolism by monoamine oxidase because pargyline pretreatment did not affect this rate constant. However, 30 min after [ 3 H]MPTP injection, brain retention of the 3H tracer was reduced significantly by pargyline treatment, and the ratio of brain MPTP/MPP+ was increased markedly

  1. Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform.

    Science.gov (United States)

    Kudryavtsev, Konstantin V; Bentley, Matthew L; McCafferty, Dewey G

    2009-04-01

    cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.

  2. Synthesis of 2-iodo- and 2-phenyl-[11C]melatonin: potential PET tracers for melatonin binding sites

    International Nuclear Information System (INIS)

    Chen Jiajun; Fiehn-Schulze, Brita; Firnau, Guenter; Brough, Paul A.; Snieckus, Victor

    1998-01-01

    Two 11 C-labelled melatonin derivatives, 2-iodo-[ 11 C]melatonin (2-iodo-5-methoxy-N[ 11 C-acetyl]-tryptamine, an agonist) and 2-phenyl-[ 11 C]melatonin (2-phenyl-5-methoxy-N[ 11 C-acetyl]tryptamine, a putative antagonist) were synthesized from [ 11 C]carbon dioxide. The reaction sequence was common to both compounds and consisted of three steps: (i) carbonylation of methyl magnesium bromide with [ 11 C]carbon dioxide, (ii) conversion of the adduct to [ 11 C]acetyl chloride, (iii) acetylation of the amine precursors (2-iodo-5-methoxy-tryptamine or 2-phenyl-5-methoxy-tryptamine) with [ 11 C]acetyl chloride. The precursors were especially prepared. The radiochemical yield was 19% for 2-iodomelatonin and 32% for 2-phenymelatonin, based on [ 11 C]carbon dioxide; the specific activity ranged from 300 to 600 mCi/μmol. Both labelled 2-substituted-melatonins are intended to be used as radiotracers to study melatonin binding sites in man with positron emission tomography

  3. Isothermal (vapour + liquid) equilibrium (VLE) for binary mixtures containing diethyl carbonate, phenyl acetate, diphenyl carbonate, or ethyl acetate

    International Nuclear Information System (INIS)

    Ho, Hsiao-Yun; Shu, So-Siou; Wang, San-Jang; Lee, Ming-Jer

    2015-01-01

    Highlights: • Isothermal (vapour + liquid) equilibrium (VLE) data were measured. • Binary mixtures contain ethyl acetate, diethyl carbonate, phenyl acetate, diphenyl carbonate. • No azeotrope formed in the systems investigated. • The VLE data were correlated well with Wilson-HOC, NRTL-HOC, UNIQUAC-HOC models. - Abstract: The isothermal (vapour + liquid) equilibrium (VLE) (P–T–x i –y i ) was determined the binary systems of (ethyl acetate + diethyl carbonate) from T = (373.2 to 453.2) K, (ethyl acetate + phenyl acetate) at T = 373.2 K, and (diethyl carbonate + phenyl acetate) at T = 373.2 K, while the VLE (P–T–x i ) of three diphenyl carbonate-containing binary systems was also determined experimentally at temperatures from (373.2 to 453.2) K. The experimental results show no azeotrope formation and near ideal solution behaviour for each binary system. These new VLE (P–T–x i –y i ) data have been passed by the point, area, and infinite dilution thermodynamic consistency tests. The Wilson-HOC, the NRTL-HOC, and the UNIQUAC-HOC models were applied to correlate the VLE results and the optimal values of the model parameters have been determined through data reduction. Comparable results were obtained from these three models.

  4. Separation of flavonoids on different phenyl-bonded stationary phases-the influence of polar groups in stationary phase structure.

    Science.gov (United States)

    Janas, Petr; Bocian, Szymon; Jandera, Pavel; Kowalkowski, Tomasz; Buszewski, Bogusław

    2016-01-15

    Four phenyl-bonded stationary phases, differing in polar embedded group between spacer and phenyl ring, were used for the separation of flavonoids in reversed-phase conditions. In addition, the work was focused on the comparison of these stationary phases in terms of retention and nature of interactions between flavonoid solutes and both, mobile and stationary phases. The differences and similarities between the columns and between individual flavonoids were evaluated by a statistical analysis. The retention over the wider range of mobile phase composition was described using well known model suggested for partition chromatographic systems. Due to differences in polarity of flavonoids, gradient elution had to be applied to achieve appropriate conditions for the successful separation. A chromatographic optimization software was employed for establish the appropriate profiles of gradient separations using UV detection at 275 nm. The most appropriate conditions for the separation of flavonoids were apparent on the phenyl and phenoxy columns. Copyright © 2015 Elsevier B.V. All rights reserved.

  5. Synthesis and Antiplasmodial Activity of 2-(4-Methoxyphenyl-4-Phenyl-1,10-Phenanthroline Derivative Compounds

    Directory of Open Access Journals (Sweden)

    Nazudin

    2012-08-01

    Full Text Available A unique of synthetic methods was employed to prepare 2-(4-methoxyphenyl-4-phenyl-1,10-phenanthroline (5 derivatives from 4-methoxy-benzaldehyde (1, acetophenone (2, and 8-aminoquinoline (4 with aldol condensation and cyclization reactions. The derivatives were tested through antiplasmodial test. The synthesis of derivatives compound 5 was conducted in three steps. The 3-(4-methoxyphenyl-1-phenylpropenone 3 was synthesized through aldol condensation of 1 and 2 which has a yield of 96.42%. The compound 5 was synthesized through cyclization of compound 4 and 3 with 84.55% yield. The derivative of compound 5 was synthesized from compound 5 using DMS and DES reagents which refluxed for 21 and 22 h, to produce (1-N-methyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (6 and (1-N-ethyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (7 with 91.42 and 86.36% yields, respectively. Results of in vitro testing of antiplasmodial activity of compound 5 derivatives (i.e., compound 6 and 7 against chloroquine-resistant P. falciparum FCR3 strain showed that compound 7 had higher antimalarial activity than compounds 5 and 6. Whereas, results of in vitro testing against chloroquine-sensitive P. falciparum D10 strain showed that compound 6 has higher antimalarial activity than compounds 5 and 7.

  6. Synthesis, studies and in-vitro antibacterial activity of N-substituted 5-(furan-2-yl-phenyl pyrazolines

    Directory of Open Access Journals (Sweden)

    Mamta Rani

    2015-03-01

    Full Text Available Novel compounds with antibacterial properties: pyrazoline derivatives were synthesized by the cyclization of various -1-[2-(alkoxyphenyl]-3-(furan-2-yl prop-2-en-1-one 1a–1d with N-substituted phenyl hydrazine in the presence of CH3COOH in ethanol. The structures of these compounds were elucidated by, IR, 1H NMR, 13C NMR, ESI-MS spectral data and their purities were confirmed by elemental analyses. The in vitro antibacterial activity of these compounds was evaluated against two Gram-positive and two Gram-negative bacteria Aeromonas hydrophila, Yersinia enterocolitica, Listeria monocytogenes, and Staphylococcus aureus by microdilution method and then the minimum inhibitory concentration (MIC of compounds were determined. The results showed that compounds (5R-5-(furan-2-yl-1-phenyl-3-[2-(benzyloxyphenyl]-4, 5-dihydro-1H-pyrazole (2b and (5R-5-(furan-2-yl-1-phenyl-3-[2-(naphthalen-2-ylmethoxy prop-2-en-1-yloxyphenyl]-4,5-dihydro-1H-pyrazole (2d showing most promising antibacterial activities as compared to Gentamicin and Tetracycline are given.

  7. Electrochemical and Spin-Trapping Properties of para-substituted α-Phenyl-N-tert-butyl Nitrones

    International Nuclear Information System (INIS)

    Rosselin, Marie; Tuccio, Béatrice; Pério, Pierre; Villamena, Frederick A.; Fabre, Paul-Louis; Durand, Grégory

    2016-01-01

    Nitrones are known both as therapeutic antioxidants and efficient spin-traps. In this work, the redox behavior of various para-substituted α-phenyl-N-tert-butyl nitrones (PBN) was studied by cyclic voltammetry. The polar effect of the substituents was found to correlate with the electrochemical properties of the nitronyl function. Compounds bearing an electron-withdrawing group were more easily reduced than those having an electron-donating group and an opposite trend was observed for the oxidation. Ease of oxidation was also computationally rationalized using DFT approach showing increased ease of oxidation with electron donating functionalities. Since electrochemical properties of nitrones are known to correlate with biological properties, this work provides insights in the design of potent nitrone antioxidants. Using cyclic voltammetry the relative rate of superoxide trapping by nitrones was investigated and compared to the classical antioxidant BHT. The determination of the relative rate of phenyl radical trapping was also carried out but showed no clear correlation with the nature of the substituents. This indicates the absence of a polar effect in agreement with previous data and further supports the intermediate nature, that is, non- or weakly nucleophile, of phenyl radical. On the contrary kinetics of hydroxymethyl radical trapping was found to correlate with the nature of the substituents, demonstrating the nucleophilic nature of its addition onto nitrones.

  8. SYNTHESIS OF 1,4-BIS [(1-HYDROXY-4-T-BUTYL-PHENYL METHYL]PIPERAZINE AS ANTIOXIDANTS

    Directory of Open Access Journals (Sweden)

    Susy Yunita Prabawati

    2016-11-01

    Full Text Available A study has been conducted to synthesize 1,4-bis [(1-hydroxy-4-t-butyl-phenyl-methyl]piperazin using phenol derivate and investigate the capability of that compound, as an antioxidant. The synthesis was carried out through Mannich reaction using p-t-butylphenol, paraformaldehyde, and piperazine. The product was characterized by IR and 1H NMR spectroscopic. Testing of antioxidant activity was done with the immersion of DPPH (1,1-diphenyl-2 picrylhydrazyl free radical method. The product was obtained as a white solid, with a point of 252,7-254,7 ºC and a yield of 65.76%. The test of antioxidant activity with DPPH method showed that 1,4-bis [(1-hydroxy-4-t-butyl-phenyl-methyl]piperazin had the IC50 values was 0.84 nM. It means that the 1,4- bis[(1-hydroxy-4-t-butyl-phenyl methyl]piperazine has potential as antioxidants.

  9. 1,1′-{1,4-Phenylene bis[3-(6-chloro-2-methyl-4-phenylquinolin-3-yl-4,5-dihydro-1H-pyrazole-5,1-diyl]}dibutan-1-one

    Directory of Open Access Journals (Sweden)

    Allaoua Kedjadja

    2015-10-01

    Full Text Available A new polycyclic compound, 1,1′-{1,4-phenylene bis[3-(6-chloro-2-methyl-4-phenylquinolin-3-yl-4,5-dihydro-1H-pyrazole-5,1-diyl]}dibutan-1-one (3 has been synthesized by cyclocondensation of (2E,2′E-1,1′-bis(6-chloro-2-methyl-4-phenylquinolin-3-yl-3,3′-(1,4-phenylenediprop-2-en-1-one (2 and hydrazine hydrate in butanoic acid. The structure of this compound was established by elemental analysis, 1H-NMR, 13C-NMR, mass and IR spectroscopy.

  10. Characterization of changes in IgG associated oligosaccharide profiles in rheumatoid arthritis, psoriatic arthritis, and ankylosing spondylitis using fluorophore linked carbohydrate electrophoresis.

    Science.gov (United States)

    Martin, K; Talukder, R; Hay, F C; Axford, J S

    2001-07-01

    To investigate fluorophore linked carbohydrate electrophoresis (FCE) as a method of analyzing serum immunoglobulin G (IgG) oligosaccharides in healthy individuals and those with rheumatic disease and compare with lectin binding assays of carbohydrate composition. IgG was isolated from patients with rheumatoid arthritis (RA) (n = 21), ankylosing spondylitis (AS) (n = 20), psoriatic arthritis (PsA) (n = 20), and healthy adults (n = 36). IgG oligosaccharides were released enzymatically, fluorescently labelled using 8 aminonaphthalene-136 trisulfonic acid; and identification of the oligosaccharide bands was by stepwise enzymatic degradation. Comparison of FCE was made with lectin binding analysis in which the lectins Ricinus communis (RCA1) and Bandeiraea simplicifolia (BSII) were used to detect galactose (Gal) and N-acetylglucosamine (GlcNAc), respectively. Each disease could be differentiated from healthy adults on the basis of Band 1 asialodigalacto core fucosylated oligosaccharide (gf2) intensity (p = 0.001), but not from each other. Reduced levels of different sugars were associated with specific diseases: reduced gf2 with RA (p < 0.001), PsA (p < 0.001) and AS (p < 0.02), reduced Band 5 disialo-digalacto core fucosylated (a2f) oligosaccharide with AS (p < 0.001), reduced Band 6 disialo-digalacto (a2) oligosaccharide with AS (p < 0.001) and PsA (p = 0.021). All diseases were associated with a significant increase in Band 4 asialo-agalacto core fucosylated oligosaccharide (g0f) (p < 0.001). In RA, FCE band intensities correlated with sugar quantity when identified using lectin binding analysis (p < 0.003). In contrast, there was no correlation between the same bands in healthy individuals. FCE is an accurate method of analyzing IgG associated oligosaccharides and reveals unique band patterns or sugar prints associated with healthy adults and patients with RA, PsA, and AS, and comparison with lectin binding analysis suggests undetected RA glycoprotein structural

  11. Orthogonal Electric Field Measurements near the Green Fluorescent Protein Fluorophore through Stark Effect Spectroscopy and pKa Shifts Provide a Unique Benchmark for Electrostatics Models.

    Science.gov (United States)

    Slocum, Joshua D; First, Jeremy T; Webb, Lauren J

    2017-07-20

    Measurement of the magnitude, direction, and functional importance of electric fields in biomolecules has been a long-standing experimental challenge. pK a shifts of titratable residues have been the most widely implemented measurements of the local electrostatic environment around the labile proton, and experimental data sets of pK a shifts in a variety of systems have been used to test and refine computational prediction capabilities of protein electrostatic fields. A more direct and increasingly popular technique to measure electric fields in proteins is Stark effect spectroscopy, where the change in absorption energy of a chromophore relative to a reference state is related to the change in electric field felt by the chromophore. While there are merits to both of these methods and they are both reporters of local electrostatic environment, they are fundamentally different measurements, and to our knowledge there has been no direct comparison of these two approaches in a single protein. We have recently demonstrated that green fluorescent protein (GFP) is an ideal model system for measuring changes in electric fields in a protein interior caused by amino acid mutations using both electronic and vibrational Stark effect chromophores. Here we report the changes in pK a of the GFP fluorophore in response to the same mutations and show that they are in excellent agreement with Stark effect measurements. This agreement in the results of orthogonal experiments reinforces our confidence in the experimental results of both Stark effect and pK a measurements and provides an excellent target data set to benchmark diverse protein electrostatics calculations. We used this experimental data set to test the pK a prediction ability of the adaptive Poisson-Boltzmann solver (APBS) and found that a simple continuum dielectric model of the GFP interior is insufficient to accurately capture the measured pK a and Stark effect shifts. We discuss some of the limitations of this

  12. Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol.

    Science.gov (United States)

    Andersen, Alan

    2006-01-01

    Sodium p-Chloro-m-Cresol, p-Chloro-m-Cresol (PCMC), Mixed Cresols, m-Cresol, o-Cresol, p-Cresol, Isopropyl Cresols, Thymol, Chlorothymol, o-Cymen-5-ol, and Carvacrol are substituted phenols used as cosmetic biocides/preservatives and/or fragrance ingredients. Only PCMC, Thymol, and o-Cymen-5-ol are reported to be in current use, with the highest concentration of use at 0.5% for o-Cymen-5-ol in perfumes. The use of PCMC in cosmetics is restricted in Europe and Japan. Cresols can be absorbed through skin, the respiratory tract, and the digestive tract; metabolized by the liver; and excreted by the kidney as glucuronide and sulfate metabolites. Several of these cresols increase the dermal penetration of other agents, including azidothymidine. In acute oral toxicity studies, LD50 values were in the 200 to 5000 mg/kg day-1 range across several species. In short-term studies in rats and mice, an o-Cresol, m-Cresol, p-Cresol or m-Cresol/p-Cresol mixture at 30,000 ppm in the diet produced increases in liver and kidney weights, deficits in liver function, bone marrow hypocellularity, irritation to the gastrointestinal tract and nasal epithelia, and atrophy of female reproductive organs. The no observed effect levels (NOEL) of o-Cresol was 240 mg/kg in mink and 778 mg/kg in ferrets in short-term feeding studies, with no significant dose-related toxicity (excluding body weight parameters). In mice, 0.5% p-Cresol, but neither m-Cresol nor o-Cresol, caused loss of pigmentation. Short-term and subchronic oral toxicity tests performed with various cresols using mice, rats, hamsters, and rabbits resulted in no observed adverse effect levels (NOAELs) for mice of 625 ppm and rats of 50 mg/kg day-1, although the NOEL was 2000 ppm in a chronic study using rats. In rabbits, 20 mg/m(3) for o-Cresol to >583 mg/m(3) for PCMC. No deaths were recorded in mice given o-Cresol at 50 mg/m(3). Cats exposed (short-term) to 9 to 50 mg/m(3) of o-Cresol developed inflammation and irritation of the

  13. Determination by high resolution liquid chromatography of 5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside (Xgal) and intermediates of its synthesis

    International Nuclear Information System (INIS)

    Fernandez Villalobo, Anais; Nuevas Paz, Lauro; Rodriguez Dominguez, Juan C

    2010-01-01

    In microbiology, microorganisms markers have been found to be useful in the quality control of different products such as water and food, in which the presence of coliforms, especially E. coli has been identified. Several methods for detection and quantification of enterobacteria have been developed by using chromogenic substrates. Among them, indole derivatives such as 5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside (Xgal), have come out. This indole derivative is widely employed as a constituent of microbiological diagnostic media because in the presence of coliforms (β-galactosidase producers), it forms a blue-indigo color. In this paper, the development and the validation, of an HPLC method for the quality control of Xgal in the presence of its intermediates obtained in each step of the synthesis is reported. These compounds were separated by using a RP-18 column and gradient elution with a mobile phase consisting of triethylammonium phosphate solution at pH 3(A) and acetonitrile (B). The detection and quantitation limits of the method was between 0.2- 0.5 % and 1.0 - 2.0 % respectively, which is acceptable if we consider that Xgal is not used as a drug. The proposed method is simple, selective, linear, precise and accurate and it can be used for the quality control of each of the intermediates and the final product, 5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside

  14. Drug-induced protein free radical formation is attenuated by unsaturated fatty acids by scavenging drug-derived phenyl radical metabolites.

    Science.gov (United States)

    Narwaley, Malyaj; Michail, Karim; Arvadia, Pratik; Siraki, Arno G

    2011-07-18

    Aromatic amine drugs like aminoglutethimide (AG) and related congeners have been shown to produce phenyl radicals through metabolism by myeloperoxidase (MPO)/H(2)O(2), which has been proposed to play a role in drug-induced agranulocytosis. AG has also been shown to induce MPO protein radical formation, but the ultimate fate of these metabolically generated phenyl radicals is still unknown. We tested the reactivity of linoleic acid (LA) and GSH with aniline-based compounds in the presence of horseradish peroxidase (HRP)/H(2)O(2) by measuring oxygen consumption. We found a qualitative correlation between drugs or xenobiotics that formed phenyl radical metabolites with the cooxidation of LA. Most compounds that reacted with LA did not react with GSH. Furthermore, an AG-derived phenyl radical was detected by EPR spin-trapping with MNP (2-methyl-2-nitrosopropane), in a reaction containing AG and HRP/H(2)O(2); these spectra were attenuated in the presence of LA and docosahexaenoic acid (DHA) indicating that phenyl radical scavenging occurred. Since it has been proposed that the phenyl radical metabolite leads to protein radical formation on MPO, we investigated the effect of LA and DHA in immuno-spin trapping experiments with MPO-containing HL-60 cell lysate. Using anti-DMPO, a protein radical was detected on a putative MPO fragment from the reaction of DMPO, AG, and glucose/glucose oxidase. When LA or DHA was included in this reaction, protein radical formation was significantly inhibited. Our results show that certain polyunsaturated fatty acids (PUFAs) act as scavengers of aromatic amine drug-derived phenyl radicals which in turn prevent protein radical formation. However, the interaction of phenyl radical drug metabolites with PUFAs will be dictated by their relative concentrations compared to those of other targets. Most importantly, it is possible to differentiate peroxidase substrates that generate phenyl radical metabolites from N-centered radicals on the basis

  15. An excited-state intramolecular photon transfer fluorescence probe for localizable live cell imaging of cysteine

    Science.gov (United States)

    Liu, Wei; Chen, Wen; Liu, Si-Jia; Jiang, Jian-Hui

    2017-03-01

    Small molecule probes suitable for selective and specific fluorescence imaging of some important but low-concentration intracellular reactive sulfur species such as cysteine (Cys) pose a challenge in chemical biology. We present a readily available, fast-response fluorescence probe CHCQ-Ac, with 2-(5‧-chloro-2-hydroxyl-phenyl)-6-chloro-4(3 H)-quinazolinone (CHCQ) as the fluorophore and acrylate group as the functional moiety, that enables high-selectivity and high-sensitivity for detecting Cys in both solution and biological system. After specifically reacted with Cys, the probe undergoes a seven-membered intramolecular cyclization and released the fluorophore CHCQ with excited-state intramolecular photon transfer effect. A highly fluorescent, insoluble aggregate was then formed to facilitate high-sensitivity and high-resolution imaging. The results showed that probe CHCQ-Ac affords a remarkably large Stokes shift and can detect Cys under physiological pH condition with no interference from other analytes. Moreover, this probe was proved to have excellent chemical stability, low cytotoxicity and good cell permeability. Our design of this probe provides a novel potential tool to visualize and localize cysteine in bioimaging of live cells that would greatly help to explore various Cys-related physiological and pathological cellular processes in cell biology and diagnostics.

  16. Dimethyl phenyl piperazine iodide (DMPP) induces glioma regression by inhibiting angiogenesis

    Energy Technology Data Exchange (ETDEWEB)

    He, Yan-qing; Li, Yan; Wang, Xiao-yu [Key Laboratory for Regenerative Medicine of the Ministry of Education, Division of Histology and Embryology, Medical College, Jinan University, Guangzhou 510632 (China); He, Xiao-dong [Institute of Vascular Biological Sciences, Guangdong Pharmaceutical University, Guangzhou 510006 (China); Jun, Li [Guangdong Provincial Key Laboratory of Bioengineering Medicine, National Engineering Research Centre of Genetic Medicine, College of Life Science and Technology, Jinan University, Guangzhou 510632 (China); Chuai, Manli [Division of Cell and Developmental Biology, University of Dundee, Dundee, DD1 5EH (United Kingdom); Lee, Kenneth Ka Ho [Key Laboratory for Regenerative Medicine of the Ministry of Education, School of Biomedical Sciences, Chinese University of Hong Kong, Shatin (Hong Kong); Wang, Ju [Guangdong Provincial Key Laboratory of Bioengineering Medicine, National Engineering Research Centre of Genetic Medicine, College of Life Science and Technology, Jinan University, Guangzhou 510632 (China); Wang, Li-jing, E-mail: wanglijing62@163.com [Institute of Vascular Biological Sciences, Guangdong Pharmaceutical University, Guangzhou 510006 (China); Yang, Xuesong, E-mail: yang_xuesong@126.com [Key Laboratory for Regenerative Medicine of the Ministry of Education, Division of Histology and Embryology, Medical College, Jinan University, Guangzhou 510632 (China)

    2014-01-15

    1,1-Dimethyl-4-phenyl piperazine iodide (DMPP) is a synthetic nicotinic acetylcholine receptor (nAChR) agonist that could reduce airway inflammation. In this study, we demonstrated that DMPP could dramatically inhibit glioma size maintained on the chick embryonic chorioallantoic membrane (CAM). We first performed MTT and BrdU incorporation experiments on U87 glioma cells in vitro to understand the mechanism involved. We established that DMPP did not significantly affect U87 cell proliferation and survival. We speculated that DMPP directly caused the tumor to regress by affecting the vasculature in and around the implanted tumor on our chick CAM model. Hence, we conducted detailed analysis of DMPP's inhibitory effects on angiogenesis. Three vasculogenesis and angiogenesis in vivo models were used in the study which included (1) early chick blood islands formation, (2) chick yolk-sac membrane (YSW) and (3) CAM models. The results revealed that DMPP directly suppressed all developmental stages involved in vasculogenesis and angiogenesis – possibly by acting through Ang-1 and HIF-2α signaling. In sum, our results show that DMPP could induce glioma regression grown on CAM by inhibiting vasculogenesis and angiogenesis. - Highlights: ●We demonstrated that DMPP inhibited the growth of glioma cells on chick CAM. ●DMPP did not significantly affect the proliferation and survival of U87 cells. ●We revealed that DMPP suppressed vasculogenesis and angiogenesis in chick embryo. ●Angiogenesis in chick CAM was inhibited by DMPP via most probably Ang-1 and HIF-2α. ●DMPP could be potentially developed as an anti-tumor drug in the future.

  17. 2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine (ADAM): an improved serotonin transporter ligand

    Energy Technology Data Exchange (ETDEWEB)

    Oya, Shunichi; Choi, S.-R.; Hou, Catherine; Mu Mu; Kung, M.-P.; Acton, Paul D.; Siciliano, Michael; Kung, Hank F. E-mail: kunghf@sunmac.spect.upenn.edu

    2000-04-01

    Serotonin transporters (SERT) are target-sites for commonly used antidepressants, such as fluoxetine, paroxetine, sertraline, and so on. Imaging of these sites in the living human brain may provide an important tool to evaluate the mechanisms of action as well as to monitor the treatment of depressed patients. Synthesis and characterization of an improved SERT imaging agent, ADAM (2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine)(7) was achieved. The new compound, ADAM(7), displayed an extremely potent binding affinity toward SERT (K{sub i}=0.013 nM, in membrane preparations of LLC-PK{sub 1}-cloned cell lines expressing the specific monoamine transporter). ADAM(7) also showed more than 1,000-fold selectivity for SERT over norepinephrine transporter (NET) and dopamine transporter (DAT) (K{sub i}=699 and 840 nM, for NET and DAT, respectively). The radiolabeled compound [{sup 125}I]ADAM(7) showed an excellent brain uptake in rats (1.41% dose at 2 min post intravenous [IV] injection), and consistently displayed the highest uptake (between 60-240 min post IV injection) in hypothalamus, a region with the highest density of SERT. The specific uptake of [{sup 125}I]ADAM(7) in the hypothalamus exhibited the highest target-to-nontarget ratio ([hypothalamus - cerebellum]/cerebellum was 3.97 at 120 min post IV injection). The preliminary imaging study of [{sup 123}I]ADAM in the brain of a baboon by single photon emission computed tomography (SPECT) at 180-240 min post IV injection indicated a specific uptake in midbrain region rich in SERT. These data suggest that the new ligand [{sup 123}I]ADAM(7) may be useful for SPECT imaging of SERT binding sites in the human brain.

  18. Studies on the Synthesis, Photophysical and Biological Evaluation of Some Unsymmetrical Meso-Tetrasubstituted Phenyl Porphyrins

    Directory of Open Access Journals (Sweden)

    Rica Boscencu

    2017-10-01

    Full Text Available Abstract: We designed three unsymmetrical meso-tetrasubstituted phenyl porphyrins for further development as theranostic agents for cancer photodynamic therapy (PDT: 5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (P2.2, Zn(II-5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (Zn(II2.2 and Cu(II-5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (Cu(II2.2. The porphyrinic compounds were synthesized and their structures were confirmed by elemental analysis, FT-IR, UV-Vis, EPR and NMR. The compounds had a good solubility in polar/nonpolar media. P2.2 and, to a lesser extent, Zn(II2.2 were fluorescent, albeit with low fluoresence quantum yields. P2.2 and Zn(II2.2 exhibited PDT-acceptable values of singlet oxygen generation. A “dark” cytotoxicity study was performed using cells that are relevant for the tumor niche (HT-29 colon carcinoma cells and L929 fibroblasts and for blood (peripheral mononuclear cells. Cellular uptake of fluorescent compounds, cell viability/proliferation and death were evaluated. P2.2 was highlighted as a promising theranostic agent for PDT in solid tumors considering that P2.2 generated PDT-acceptable singlet oxygen yields, accumulated into tumor cells and less in blood cells, exhibited good fluorescence within cells for imagistic detection, and had no significant cytotoxicity in vitro against tumor and normal cells. Complexing of P2.2 with Zn(II or Cu(II altered several of its PDT-relevant properties. These are consistent arguments for further developing P2.2 in animal models of solid tumors for in vivo PDT.

  19. Controllable sulfonation of aromatic poly(arylene ether ketone)s containing different pendant phenyl rings

    Energy Technology Data Exchange (ETDEWEB)

    Li, Zhiliang; Liu, Xincai; Chao, Danming; Zhang, Wanjin [Alan G. MacDiarmid Institute, Jilin University, Qianjin Street 2699, Changchun 130012 (China)

    2009-09-05

    The sulfonation selectivity of various pendant phenyl groups in poly(arylene ether ketone) (Ph-3F-PAEK) is invested via the postsulfonation approach. The sulfonated Ph-3F-PAEKs with different degrees of sulfonation (DS) are quantitatively synthesized by controlling the length of the segments that cannot be sulfonated. In this study, {sup 1}H NMR and FT-IR are used to confirmed the structures of the polymers and the experimentally DS values were calculated by {sup 1}H NMR. The experimentally observed DSs are corresponding to the theoretical values expected from the monomer ratios. All the sulfonated membranes have excellent mechanical properties (with a Young's modulus >1.3 GPa, a tensile strength >55 MPa and the elongation >10%). Thermogravimetric analysis (TGA) is used to characterized the thermal stability of these polymers, and all the polymers show excellent thermal properties at high temperatures. The methanol permeability values of Ph-3F-SPAEKs in the range of 0.37 x 10{sup -7} cm{sup 2} s{sup -1} to 4.12 x 10{sup -7} cm{sup 2} s{sup -1} are much lower than that of Nafion {sup registered} 117 (1.55 x 10{sup -6} cm{sup 2} s{sup -1}). It should be noted that the polymer with highest DS, Ph-3F-SPAEK-100 with an ion exchange capacity of 2.16 mequiv. g{sup -1}, exhibits high proton conductivity of 0.187 S cm{sup -1} at 80 C, which is also higher than that of Nafion {sup registered} 117. (author)

  20. Phenyl vs Alkyl Polythiophene: A Solar Cell Comparison Using a Vinazene Derivative as Acceptor

    KAUST Repository

    Woo, Claire H.

    2010-03-09

    The solar cell performance of poly[3-(4-n-octyl)-phenylthiophene] (POPT) and poly(3hexylthiophene) (P3HT) are compared in devices using 4,7-bis(2-(l-(2-ethylhexyl)-4,5-dicyanoimidazol-2-yl)vinyi)benzo[c][l,2,5] -thiadiazole (EV-BT) as the electron acceptor. Despite their reduced light absorption, POPT:EV-BT devices generate higher photocurrents in both bilayer and bulk heterojunction (BHJ) architectures than analogous P3HT:EV-BT devices. Optimized POPT:EV-BT BHJ devices achieve 1.4% average efficiency, whereas the analogous P3HT devices only reach 1.1%. Morphology does not account for the large difference in performance as AFM studies of the active layer suggest, comparable levels of phase separation in the two systems. Reverse bias analysis demonstrates that P3HT devices have a higher maximum potential than POPT devices, but P3HT devices appear to be more severely limited by recombination losses under standard operating conditions. A possible explanation for the superior performance in POPT devices is that the pendant phenyl ring in POPT can twist out-of-plane and increase the separation distance with the acceptor molecule. A larger donor/acceptor separation distance can destabilize the geminate pair and lead to more efficient charge separation in POPT:EV-BT devices. Our results emphasize the importance of donor/acceptor pair interactions and its effect on charge separation, processes in polymer solar cells. © 2010 American Chemical Society.