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Sample records for acetanilides

  1. Deuteration of acetanilides

    Chin, S.K.; Collier, R.; Hutchinson, D.W. (Warwick Univ., Coventry (UK). Dept. of Chemistry and Molecular Sciences)

    1982-09-01

    The base-catalysed exchange of a proton of the methyl groups in acetanilides can be used to incorporate deuterium into these amides. 4'-Hydroxyl-2(/sup 2/H)acetanilide (acetaminophen, paracetamol) can be prepared by the demethylation with boron tribromide of 4'-methoxy-2(/sup 2/H) acetamide obtained by this base-catalysed exchange.

  2. The deuteration of acetanilides

    The base-catalysed exchange of a proton of the methyl groups in acetanilides can be used to incorporate deuterium into these amides. 4'-Hydroxyl-2[2H]acetanilide (acetaminophen, paracetamol) can be prepared by the demethylation with boron tribromide of 4'-methoxy-2[2H] acetamide obtained by this base-catalysed exchange. (author)

  3. Palladium-catalysed ortho arylation of acetanilides

    Guo-zhen zhang; Cheng-Qun Chen; Xin-Hua Feng; Guo-Sheng Huang

    2010-03-01

    The palladium-catalysed direct arylation of acetanilides by using C-H activation methodology has been demonstrated. Several acetanilides were coupled with aryl iodides in the presence of 10 mol% of Pd(OAc)2, 1.0 equiv of Cu(OTf)2, and 0.6 equiv of Ag2O to afford the corresponding products in moderate to excellent yields. The results showed that the amount of Ag2O was important for this protocol.

  4. Infrared Absorption in Acetanilide by Solitons

    Careri, G.; Buontempo, U.; Carta, F.;

    1983-01-01

    The infrared spectrum of acetanilide shows a new band that is red shifted from the main amide-I maximum by about 15 cm-1, the intensity of which increases at low temperature. It is suggested that this band may arise from the creation of amide-I solitons that are similar (but not identical) to those...

  5. Biodegradation of Para Amino Acetanilide by Halomonas sp. TBZ3

    Hajizadeh, Nader; Sefidi Heris, Youssof; Zununi Vahed, Sepideh; Vallipour, Javad; Hejazi, Mohammad Amin; Golabi, Sayyed Mahdi; Asadpour-Zeynali, Karim; Hejazi, Mohammad Saeid

    2015-01-01

    Background: Aromatic compounds are known as a group of highly persistent environmental pollutants. Halomonas sp. TBZ3 was isolated from the highly salty Urmia Lake of Iran. In this study, characterization of a new Halomonas isolate called Halomonas sp. TBZ3 and its employment for biodegradation of para-amino acetanilide (PAA), as an aromatic environmental pollutant, is described. Objectives: This study aimed to characterize the TBZ3 isolate and to elucidate its ability as a biodegradative age...

  6. Spectroscopy of the amide-I modes of acetanilide

    Raman measurements were made on acetanilide (N-phenyl-acetamide). Data are presented of the integrated intensity of the 1650 cm-1 band as a function of temperature. The experimental procedures and data reduction were highly rigorous and are believed to be to most reliable data available. A concise theory of polaron states is presented and used to interpret the data. 22 refs., 4 figs., 1 tab

  7. The temperature dependent amide I band of crystalline acetanilide

    The temperature dependent anomalous peak in the amide I band of crystalline acetanilide is thought to be due to self-trapped states. On the contrary, according to the present model, the anomalous peak comes from the fraction of ACN molecules strongly hydrogen-bonded to a neighboring ACN molecule, and its intensity decreases because, on average, this fraction decreases as temperature increases. This model provides, for the first time, an integrated and theoretically consistent view of the temperature dependence of the full amide I band and a qualitative explanation of some of the features of nonlinear pump–probe experiments.

  8. Biodegradation of acetanilide herbicides acetochlor and butachlor in soil.

    Ye, Chang-ming; Wang, Xing-jun; Zheng, He-hui

    2002-10-01

    The biodegradation of two acetanilide herbicides, acetochlor and butachlor in soil after other environmental organic matter addition were measured during 35 days laboratory incubations. The herbicides were applied to soil alone, soil-SDBS (sodium dodecylbenzene sulfonate) mixtures and soil-HA (humic acid) mixtures. Herbicide biodegradation kinetics were compared in the different treatment. Biodegradation products of herbicides in soil alone samples were identified by GC/MS at the end of incubation. Addition of SDBS and HA to soil decreased acetochlor biodegradation, but increased butachlor biodegradation. The biodegradation half-life of acetochlor and butachlor in soil alone, soil-SDBS mixtures and soil-HA mixtures were 4.6 d, 6.1 d and 5.4 d and 5.3 d, 4.9 d and 5.3 d respectively. The biodegradation products were hydroxyacetochlor and 2-methyl-6-ethylaniline for acetochlor, and hydroxybutachlor and 2,6-diethylaniline for butachlor. PMID:12491727

  9. Kinetics and mechanism of oxidation of acetanilide by quinquevalent vanadium in acid medium

    The kinetics of the oxidation of acetanilide with vanadium(V) in sulphuric acid medium at constant ionic strength has been studied. The reaction is first order with oxidant. The order of reaction in acetanilide varies from one to zero. The reaction follows an acid catalyzed independent path, exhibiting square dependence in H+. A Bunnett plot indicates that the water acts as a nucleophile. The thermodynamic parameters have been computed. A probable reaction mechanism and rate law consistent with these data are given. (Author)

  10. Adsorption of Acetanilide Herbicides on Soil and Its Components: IV. Sorption of Acetanilide Herbicides on Soils and Its Correlation with Soil Properties

    2001-01-01

    Sorption of acetanilide herbicides, metolachlor, acetochlor, pretilachlor and butachlor on eight soils with various physical and chemical properties was studied. The adsorption isotherms could fit Freundlich equation well (r2 >= 0.91) and the adsorption extents increased in the order: metolachlor < acetochlor < pretilachlor < butachlor. The product of Freundlich adsorption constants, Kf (1/n), showed to have a good correlation with organic matter content (OM) of soils for each of these herbicides, suggesting that OM is the primary factor dominating in the adsorption process of these acetanilide herbicides. Multivariant correlation regression between Kf(i/n) and two factors, water solubility (Sw) of herbicides and OM, was also performed. Kf(1/n) correlated with 1/Sw and OM/Sw well, showing that high Sw corresponds to a weak tendency to adsorb on soils. Infrared (IR) spectra and electron spin resonance (ESR) parameters confirmed that multifunctional H-bonds and charge-transfer bonds were the main adsorption mechanisms of these acetanilide herbicides. The abilities of herbicides to form these adsorption bonds with HA increased in the same order as the extent of adsorption.

  11. Adsorption of Acetanilide Herbicides on Soil and Its COmponents: Ⅳ.Sorption of Acetanilide Herbicides on Soils and Its Correlation with Soil Properties

    LIUWEIPING; WANGQIQUAN; 等

    2001-01-01

    Sorption of acetanilide herbicides,metolachlor,acetochlor,pretilachlor and butachlor on eight soils with various physical and chemical properties was studied,The adsporption isotherms could fit Freundlich equation well(r2≥0.91) and the adsorption extents increased in the order:metolachloracetanilide herbicides.Multivariant orrelation regression between Kf(1/n) and two factors,water solubility(Sw) of herbicides and OM,was also performed,Kf(1/n) correlated with 1/Sw and OM/Sw well showing that high Sw corresponds to a weak tendency to adsorb on soils.Infrared(IR) spectra and electron pin resonance(ESR) parameters confirmed that multifunctional H-bonds and charge-transfer bonds were the mian adsorption mechanismes of these acetanilitde herbicides,The abilities of herbicides to form these adsorption bonds with HA increased in the same order as the extent of adsorption.

  12. Anomalous vibrational modes in acetanilide: A F.D.S. incoherent inelastic neutron scattering study

    The origin of the anomalous infra-red and Raman modes in acetanilide (C6H5NHCOCH3, or ACN), remains a subject of considerable controversy. One family of theoretical models involves Davydov-like solitons nonlinear vibrational coupling, or ''polaronic'' localized modes. An alternative interpretation of the extra-bands in terms of a Fermi resonance was proposed and recently the existence of slightly non-degenerate hydrogen atom configurations in the H-bond was suggested as an explanation for the anomalies. In this paper we report some new results on the anomalous vibrational modes in ACN that were obtained by inelastic incoherent neutron scattering (INS)

  13. Research strategies for design and development of NSAIDs: clue to balance potency and toxicity of acetanilide compounds.

    Pal, A K; Sen, S; Ghosh, S; Bera, A K; Bhattacharya, S; Chakraborty, S; Banerjee, A

    2001-08-01

    Despite the fact that many modern drug therapies are based on the concept of enzyme inhibition, inhibition of several enzymes leads to pathological disorders. Clinically used nonsteroidal anti-inflammatory drugs (NSAIDs) bind to the active site of the membrane protein, cyclooxygenase (COX) and inhibit the synthesis of prostaglandins, the mediators for causing inflammation. At the same time, inhibition of hepatic cysteine proteases by some NSAID metabolites like NAPQI is implicated in the pathogenesis of hepatotoxicity. As a part of our efforts to develop new effective NSAIDs, a comprehensive investigation starting from synthesis to the study of the final metabolism of acetanilide group of compound has been envisaged with appropriate feedback from kinetic studies to enhance our knowledge and technical competency to feed the know-how to the medicinal chemist to screen out and design new acetanilide derivatives of high potency and low toxicity. Structure-function relationship based on the interaction of acetanilide with its cognate enzyme, cyclooxygenase has been studied critically with adequate comparison with several other available crystal structures of COX-NSAID complexes. Furthermore, to make the receptor based drug design strategy a novel and comprehensive one, both the mechanism of metabolism of acetanilide and structural basis of inhibition of cysteine proteases by the reactive metabolite (NAPQI) formed by cytochrome P450 oxidation of acetanilide have been incorporated in the study. It is hoped that this synergistic approach and the results obtained from such consorted structural investigation at atomic level may guide to dictate synthetic modification with judicious balance between cyclooxygenase inhibition and hepatic cysteine protease inhibition to enhance the potential of such molecular medicine to relieve inflammation on one hand and low hepatic toxicity on the other. PMID:11565854

  14. BINDING EFFICACY AND ELUCIDATION OF QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP OF ACETANILIDE AND ITS DERIVATIVES WITH BOVINE SERUM ALBUMIN AND THEIR INHIBITION AGAINST COX1

    Dr. Violet Dhayabaran et al

    2012-09-01

    Full Text Available Serum albumins are the most abundant proteins in plasma with many physiological functions. Among them, BSA has a wide range of functions involving the binding, transport and delivery of fatty acids, porphyrins, bilirubin, steroids, etc and it is home to specific binding sites for metals, pharmaceuticals and dyes. Recently, nanotechnology has become a popular term in the current science and technology. Nanotechnology has been introduced for the food and drug industry, including encapsulations and delivery systems. BSA nanoparticles were prepared and their binding efficacy with the available analgesics such as acetanilide and its derivatives were studied. The value of apparent rate constant Kapp from the interaction between acetanilide and BSA by UV visible spectroscopic and fluorescence technique was found to be 2.294X106. The quenching rate constant of BSA-Acetanilide was found to be 1.0345X1015M-1 S-1. There are two binding sites in BSA for acetanilide. A QSAR study was performed for the different analgesics. Inhibition of Acetanilide and its derivatives with the Cyclooxygenase (COX 1 was studied using docking mechanism. The electro chemical behavior of acetanilide is studied and it is found to be reversible.

  15. Fast thermal cycling of acetanilide and magnesium chloride hexahydrate for indoor solar cooking

    Solar cookers are broadly divided into a direct or focusing type, indirect or box-type and advanced solar cookers. The focusing and box-type solar cookers are for outdoor applications. The advanced solar cookers have the advantage of being usable indoors and thus solve one of the problems, which impede the social acceptance of solar cookers. The advanced type solar cookers are employing additional solar units that increase the cost. Therefore, the solar cooker must contain a heat storage medium to store thermal energy for use during off-sunshine hours. The main aim of this study is to investigate the influence of the melting/solidification fast cycling of the commercial grade acetanilide C8H9NO (Tm = 116 deg. C) and magnesium chloride hexahydrate MgCl2.6H2O (Tm = 116.7 deg. C) on their thermo-physical properties; such as melting point and latent heat of fusion, to be used as storage media inside solar cookers. Five hundred cycles have been performed. The thermo-physical properties are measured using the differential scanning calorimetric technique. The compatibility of the selected phase change materials (PCMs) with the containing material is also studied via the surface investigation, using the SIM technique, of aluminum and stainless steel samples embedded in the PCM during cycling. It is inferred that acetanilide is a promising PCM for cooking indoors and during law intensity solar radiation periods with good compatibility with aluminum as a containing material. However, MgCl2.6H2O is not stable during its thermal cycling (even with the extra water principle) due to the phase segregation problem; therefore, it is not recommended as a storage material inside solar cookers for cooking indoors. It is also indicated that MgCl2.6H2O is not compatible with either aluminum or stainless steel.

  16. Drug delivery system prepared by ionizing radiation of the N,N-dimethyl acrylamide with acryloyloxy-acetanilide copolymerization

    Radiation induced polymerization has been used in biomaterials used in systems which such as drug delivery (DDS). This work describes the copolymerization of the monomers by gamma rays N,N-dimethyl acrylamide (DMAA) and acryloyloxy-acetanilide (AOA) for the immobilization of paracetamol, an analgesic and anti thermic drug. Dimethylformamide solutions were used in two concentrations of DMAA and AOA (FDMAA/AOA = 0,85/015 and 0,70/0,30, where F = molar fraction in the monomer feed). The samples were irradiated in the dose range of 30-800 Gy. The copolymer poly(DMAA-co-AOA) characterization was carried out by FTIR and 1HRMN. The hydrolysis was studied considering the formation of sodium salts of 4-hydroxy acetanilide at different times of treatment using colorimetric assay. (author). 6 refs., 5 figs

  17. Fast thermal cycling of acetanilide and magnesium chloride hexahydrate for indoor solar cooking

    El-Sebaii, A.A.; Al-Amir, S.; Al-Marzouki, F.M.; Faidah, Adel S.; Al-Ghamdi, A.A.; Al-Heniti, S. [Physics Dept., Faculty of Science, King Abdul Aziz Univ., P.O. Box 80203, Jeddah 21589 (Saudi Arabia)

    2009-12-15

    Solar cookers are broadly divided into a direct or focusing type, indirect or box-type and advanced solar cookers. The focusing and box-type solar cookers are for outdoor applications. The advanced solar cookers have the advantage of being usable indoors and thus solve one of the problems, which impede the social acceptance of solar cookers. The advanced type solar cookers are employing additional solar units that increase the cost. Therefore, the solar cooker must contain a heat storage medium to store thermal energy for use during off-sunshine hours. The main aim of this study is to investigate the influence of the melting/solidification fast cycling of the commercial grade acetanilide C{sub 8}H{sub 9}NO (T{sub m} = 116 C) and magnesium chloride hexahydrate MgCl{sub 2}.6H{sub 2}O (T{sub m} = 116.7 C) on their thermo-physical properties; such as melting point and latent heat of fusion, to be used as storage media inside solar cookers. Five hundred cycles have been performed. The thermo-physical properties are measured using the differential scanning calorimetric technique. The compatibility of the selected phase change materials (PCMs) with the containing material is also studied via the surface investigation, using the SIM technique, of aluminum and stainless steel samples embedded in the PCM during cycling. It is inferred that acetanilide is a promising PCM for cooking indoors and during low intensity solar radiation periods with good compatibility with aluminum as a containing material. However, MgCl{sub 2}.6H{sub 2}O is not stable during its thermal cycling (even with the extra water principle) due to the phase segregation problem; therefore, it is not recommended as a storage material inside solar cookers for cooking indoors. It is also indicated that MgCl{sub 2}.6H{sub 2}O is not compatible with either aluminum or stainless steel. (author)

  18. Design, synthesis, and evaluation of conformationally restricted acetanilides as potent and selective β3 adrenergic receptor agonists for the treatment of overactive bladder.

    Moyes, Christopher R; Berger, Richard; Goble, Stephen D; Harper, Bart; Shen, Dong-Ming; Wang, Liping; Bansal, Alka; Brown, Patricia N; Chen, Airu S; Dingley, Karen H; Di Salvo, Jerry; Fitzmaurice, Aileen; Gichuru, Loise N; Hurley, Amanda L; Jochnowitz, Nina; Miller, Randall R; Mistry, Shruty; Nagabukuro, Hiroshi; Salituro, Gino M; Sanfiz, Anthony; Stevenson, Andra S; Villa, Katherine; Zamlynny, Beata; Struthers, Mary; Weber, Ann E; Edmondson, Scott D

    2014-02-27

    A series of conformationally restricted acetanilides were synthesized and evaluated as β3-adrenergic receptor agonists (β3-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine β3-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent β3-AR mediated responses in a rat bladder hyperactivity model. PMID:24437735

  19. Theoretical studies on the mechanism of palladium(II)-catalysed ortho-carboxylation of acetanilide with CO

    Xing Hui Zhang; Zhi Yuan Geng; Ke Tai Wang

    2014-01-01

    The mechanism of palladium(II)-catalysed carboxylation of acetanilide with CO has been investigated using density functional theory calculation done at the B3LYP/6-31G(d, p)(SDD for Pd) level of theory. Solvent effects on these reactions have been explored by calculation that included a polarizable continuum model (PCM) for the solvent. Two plausible pathways which led to the formation of anhydride or benzoxazinone intermediate structure were proposed. Our calculated results suggested that the steps of forming the anhydride or benzoxazinone intermediate became the rate-determining one in the whole catalytic cycle. The process of forming benzoxazinone is more favoured kinetically with a barrier of 16.6 kcal/mol versus 22.9 kcal/mol for the pathway of forming anhydride structure. Subsequent hydrolysis process of these intermediates then provide the corresponding product ortho-acetaminobenzoic acid. The computational results are consistent with the experimental observations of Yu et al. for palladium(II)-catalysed synthesis of acetanilide based on carbon monoxide.

  20. Modulational instabilities in acetanilide taking into account both the N-H and the C=O vibrational self-trappings

    A model of crystalline acetanilide, ACN accounting for the C=O and N-H vibrational self-trappings is presented. We develop a fully discrete version of ACN. We show that acetanilide can be described by a set of two coupled discrete nonlinear Schroedinger (DNLS) equations. Modulational instabilities (MI) are studied both theoretically and numerically. Dispersion laws for the wave numbers and frequencies of the linear modulation waves are determined. We also derived the criterion for the existence of MI. Numerical simulations are carried out for a variety of selected wave amplitudes in the unstable zone. It is shown that instabilities grow as the wave numbers and amplitudes of the modulated waves increase. MI grow faster in the N-H mode than in the C=O mode. Temporal evolution of the density probabilities of the vibrational excitons are obtained by the numerical integration of the coupled DNLS equations governing the ACN molecule. These investigations confirm the generation of localized modes by the phenomenon of MI and the predominance of the N-H vibrational mode in the MI process of the acetanilide. (author)

  1. Nicotine, acetanilide and urea multi-level2H-,13C- and15N-abundance reference materials for continuous-flow isotope ratio mass spectrometry

    Schimmelmann, A.; Albertino, A.; Sauer, P.E.; Qi, H.; Molinie, R.; Mesnard, F.

    2009-01-01

    Accurate determinations of stable isotope ratios require a calibration using at least two reference materials with different isotopic compositions to anchor the isotopic scale and compensate for differences in machine slope. Ideally, the S values of these reference materials should bracket the isotopic range of samples with unknown S values. While the practice of analyzing two isotopically distinct reference materials is common for water (VSMOW-SLAP) and carbonates (NBS 19 and L-SVEC), the lack of widely available organic reference materials with distinct isotopic composition has hindered the practice when analyzing organic materials by elemental analysis/isotope ratio mass spectrometry (EA-IRMS). At present only L-glutamic acids USGS40 and USGS41 satisfy these requirements for ??13C and ??13N, with the limitation that L-glutamic acid is not suitable for analysis by gas chromatography (GC). We describe the development and quality testing of (i) four nicotine laboratory reference materials for on-line (i.e. continuous flow) hydrogen reductive gas chromatography-isotope ratio mass-spectrometry (GC-IRMS), (ii) five nicotines for oxidative C, N gas chromatography-combustion-isotope ratio mass-spectrometry (GC-C-IRMS, or GC-IRMS), and (iii) also three acetanilide and three urea reference materials for on-line oxidative EA-IRMS for C and N. Isotopic off-line calibration against international stable isotope measurement standards at Indiana University adhered to the 'principle of identical treatment'. The new reference materials cover the following isotopic ranges: ??2Hnicotine -162 to -45%o, ??13Cnicotine -30.05 to +7.72%, ?? 15Nnicotine -6.03 to +33.62%; ??15N acetanilide +1-18 to +40.57%; ??13Curea -34.13 to +11.71%, ??15Nurea +0.26 to +40.61% (recommended ?? values refer to calibration with NBS 19, L-SVEC, IAEA-N-1, and IAEA-N-2). Nicotines fill a gap as the first organic nitrogen stable isotope reference materials for GC-IRMS that are available with different ??13N

  2. Drug delivery system prepared by ionizing radiation of the N,N-dimethyl acrylamide with acryloyloxy-acetanilide copolymerization; Sistema de liberacao de droga obtido via radiacao ionizante pela copolimerizacao do N,N-dimetilacrilamida com 4-acriloiloxiacetanilida

    Martellini, Flavia; Higa, Olga Z. [Instituto de Pesquisas Energeticas e Nucleares (IPEN), Sao Paulo, SP (Brazil); Queiroz, Alvaro A.A. de [Escola Federal de Engenharia de Itajuba, MG (Brazil); Rodighiero, Paolo [Universidade de Padova (Italy). Inst. de Ciencias Farmaceuticas

    1995-12-31

    Radiation induced polymerization has been used in biomaterials used in systems which such as drug delivery (DDS). This work describes the copolymerization of the monomers by gamma rays N,N-dimethyl acrylamide (DMAA) and acryloyloxy-acetanilide (AOA) for the immobilization of paracetamol, an analgesic and anti thermic drug. Dimethylformamide solutions were used in two concentrations of DMAA and AOA (F{sub DMAA/AOA} = 0,85/015 and 0,70/0,30, where F = molar fraction in the monomer feed). The samples were irradiated in the dose range of 30-800 Gy. The copolymer poly(DMAA-co-AOA) characterization was carried out by FTIR and {sup 1}HRMN. The hydrolysis was studied considering the formation of sodium salts of 4-hydroxy acetanilide at different times of treatment using colorimetric assay. (author). 6 refs., 5 figs.

  3. Metabolite kinetics: formation of acetaminophen from deuterated and nondeuterated phenacetin and acetanilide on acetaminophen sulfation kinetics in the perfused rat liver preparation

    The role of hepatic intrinsic clearance for metabolite formation from various precursors on subsequent metabolite elimination was was investigated in the once-through perfused rat liver preparation. Two pairs of acetaminophen precursors: [14C] phenacetin-d5 and [3H] phenacetin-do, [14C] acetanilide and [3H] phenacetin were delivered by constant flow (10 ml/min/liver) either by normal or retrograde perfusion to the rat liver preparations. The extents of acetaminophen sulfation were compared within the same preparation. The data showed that the higher the hepatocellular activity (intrinsic clearance) for acetaminophen formation, the greater the extent of subsequent acetaminophen sulfation. The findings were explained on the basis of blood transit time and metabolite duration time. Because of blood having only a finite transit time in liver, the longer the drug requires for metabolite formation, the less time will remain for metabolite sulfation and the less will be the degree of subsequent sulfation. Conversely, when the drug forms the primary metabolite rapidly, a longer time will remain for the metabolite to be sulfated in liver to result in a greater degree of metabolite sulfation. Finally, the effects of hepatic intrinsic clearances for metabolite formation and zonal distribution of enzyme systems for metabolite formation and elimination in liver are discussed

  4. Modulational instabilities in acetanilide taking into account both the N-H and the C=O vibrational self-trappings

    A model of crystalline acetanilide, ACN accounting for the C=O and N-H vibrational self-trappings is presented. We develop a fully discrete version of ACN. We show that ACN can be described by a set of two coupled discrete nonlinear Schroedinger (DNLS) equations. Modulational instabilities (MI) are studied both theoretically and numerically. Dispersion laws for the wavenumbers and frequencies of the linear modulation waves are determined. We also derived the criterion for the existence of MI. Numerical simulations are carried out for a variety of selected wave amplitudes in the unstable zone. It is shown that instabilities grow as the wavenumbers and amplitudes of the modulated waves increase. MI grow faster in the N-H mode than in the C=O mode. Temporal evolution of the density probabilities of the vibrational excitons are obtained by the numerical integration of the coupled DNLS equations governing the ACN molecule. These investigations confirm the generation of localized modes by the phenomenon of MI and the predominance of the N-H vibrational mode in the MI process of the ACN

  5. AN ECONOMICAL AND ECOFRIENDLY REGIOSELECTIVE BROMINATION OF ACETANILIDES USING POTASSIUM BROMIDE AND CERIC AMMONIUM NITRATE IN POLYETHYLENE GLYCOL Eine wirtschaftliche und umweltfreundliche regioselektive Bromierung von Acetanilide unter Verwendung von Kaliumbromid UND CERIC AMMONIUM NITRATE in Polyethylenglykol

    Ritu Gupta and Lata

    2012-07-01

    Full Text Available A fast, economically, eco-friendly and highly chemo-regioselective method for the bromination of electron rich aromatic molecules has been developed by electrophilic substitution of Br+, which is generated in situ from KBr using ceric ammonium nitrate as the lewis acid catalyst in PEG-400 and the products are produced in highly excellent isolated yields and crude products do not require any further purification. Free aromatic amines remained unaffected under the reaction conditions.

  6. Estimation of the aqueous solubility of some acetanilide derivatives from octanol-water partition coefficients and entropies of fusion

    Baena, Yolima; Barbosa, Helber J.; Pinzón, Jorge A.; Martínez, Fleming

    2004-01-01

    Se utilizaron algunas ecuaciones empíricas desarrolladas por Yalkowsky et al. para la estimación de la solubilidad en medios acuosos (SW), del acetaminofén, la fenacetina y la acetanilida, utilizando valores experimentales de coeficiente de reparto (PC) y, de temperaturas (tm) y entropías de fusión (ΔSf). Las solubilidades calculadas fueron comparadas con las determinadas experimen...

  7. Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity

    Mistry, Rakesh N.; K. R. Desai

    2005-01-01

    1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid g...

  8. Proposal of an Amide-Directed Carbocupration Mechanism for Copper-Catalyzed meta-Selective C-H Arylation of Acetanilides by Diaryliodonium Salts

    Song-lin Zhang; Yu-qiang Ding

    2011-01-01

    We examined the puzzling mechanism for Cu-catalyzed meta-C-H arylation reaction of anilides by diaryliodonium salts through systematic theoretical analysis.The previously proposed anti-oxy-cupration mechanism featuring anti- 1,2- or anti- 1,4-addition of cuprate and oxygen to the phenyl ring generating a meta-cuprated intermediate was excluded due to the large activation barriers.Alternatively,a new amide-directed carbocupration mechanism was proposed which involves a critical rate- and regio-determining step of amide-directed addition of the Cu(III)-aryl bond across the phenyl C2=C3 double bond to form an orthocuprated,meta-arylated intermediate.This mechanism is kinetically the most favored among several possible mechanisms such as ortho- or para-cupration/migration mechanism,direct meta C-H bond cleavage mediated by Cu(III) or Cu(I),and Cu(III)-catalyzed ortho-directed C-H bond activation mechanism.Furthermore,the predicted regioselectivity based on this mechanism has been shown to favor the meta-arylation that is consistent with the experimental observations.

  9. Unidirectional circulation in a prebiotic photochemical cycle

    Careri, Giorgio; Wyman, Jeffries

    1985-01-01

    In this brief note, we suggest the possibility that a soliton-assisted unidirectional photochemical cycle has played a role in prebiotic evolution. This suggestion is based on a model calculation which is itself based on the detection of Davydov-type soliton overtones in acetanilide.

  10. Oceurrence of fungi degrading aniline and its derivatives in biocenoses of wastewater treatment systems

    Tomasz Słomczyński

    2014-08-01

    Full Text Available It has been found that numerous yeast-like microorganisms from the genera Geotrichum, Trichmporon, Candida, Rhodotorula and Sporobolomyces occurring in wastewater treatment systems biocenoses arę able to utilize aniline, p-nitroaniline and acetanilide as a sole C-source. High active in this respect were strains belonging to the species of Geoirichum candidum, G. sericeum and Candida boidinii.

  11. Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.).

    Chakraborty, Kajal; Devakumar, C

    2006-09-01

    Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4'-fluoroacetoacetanilide (7) and ethyl 4'-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4'-fluoro (23) and 4'-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion. PMID:16939342

  12. Dimethyl (E-2-(N-phenylacetamidobut-2-enedioate

    Ting Bin Wen

    2011-01-01

    Full Text Available The title compound, C14H15NO5, was obtained from the reaction of acetanilide with dimethyl acetylenedicarboxylate in the presence of potassium carbonate. The C=C double bond adopts an E configuration and the geometry around the amide N atom is almost planar rather than pyramidal (mean deviation of 0.0032 Å from the C3N plane. The packing of the molecules in the crystal structure is stabilized by intermolecular C—H...O hydrogen bonds.

  13. Highly Efficient N-Monomethylation of Primary Aryl Amines

    PENG, Yiyuan; LIU, Hanliang; TANG, Min; CAI, Lisheng; PIKE, Victor

    2009-01-01

    A highly efficient method for specific synthesis of N-monomethylarylamines is presented. Anilines were treated with acetic anhydride and triethylamine in dry CH2Cl2 to give the corresponding acetamides. The subsequent N-monomethylation of acetyl aryl amines with methyl iodide and Nail in THF introduced methyl group. Acid hy- drolysis of the N-methyl acetanilides in ethylene glycol generated the corresponding N-methyl-N-aryi amines in high yields. This method was also used to synthesize (E)-2-bromo-5-(4-methylaminostyryl)pyridine that may be useful as an amyloid imaging agent for Alzheimer's disease.

  14. AN EFFICIENT CLAY CATALYZED CYCLIZATION OF SUBSTITUTED PROPENAMIDE TO ISOXAZOLINE AN EFFICIENT CLAY Cyclisierung SUBSTITUIERTER Propenamid TO Isoxazolin

    Sonal D. Bajaj, Om A. Mahodaya, Pradip V. Tekade

    2013-04-01

    Full Text Available A series of newly substituted isoxazoline derivatives (3a-g have been synthesized by conventional as well as microwave assisted technology by the reaction of acetanilide, aromatic aldehydes (1a-g and hydroxylamine hydrochloride in two steps by using K10 Montmorillonite clay as a catalyst. It was found that some compounds show the better yield with K-10 Montmorillonite catalyst under microwave irradiation than conventional synthesis. The newly synthesized products were characterized by IR, 1HNMR and 13CNMR.

  15. Human metabolism and excretion kinetics of aniline after a single oral dose.

    Modick, Hendrik; Weiss, Tobias; Dierkes, Georg; Koslitz, Stephan; Käfferlein, Heiko Udo; Brüning, Thomas; Koch, Holger Martin

    2016-06-01

    Aniline is an important source material in the chemical industry (e.g., rubber, pesticides, and pharmaceuticals). The general population is known to be ubiquitously exposed to aniline. Thus, assessment of aniline exposure is of both occupational and environmental relevance. Knowledge on human metabolism of aniline is scarce. We orally dosed four healthy male volunteers (two fast and two slow acetylators) with 5 mg isotope-labeled aniline, consecutively collected all urine samples over a period of 2 days, and investigated the renal excretion of aniline and its metabolites by LS-MS/MS and GC-MS. After enzymatic hydrolysis of glucuronide and sulfate conjugates, N-acetyl-4-aminophenol was the predominant urinary aniline metabolite representing 55.7-68.9 % of the oral dose, followed by the mercapturic acid conjugate of N-acetyl-4-aminophenol accounting for 2.5-6.1 %. Acetanilide and free aniline were found only in minor amounts accounting for 0.14-0.36 % of the dose. Overall, these four biomarkers excreted in urine over 48 h post-dose represented 62.4-72.1 % of the oral aniline dose. Elimination half-times were 3.4-4.3 h for N-acetyl-4-aminophenol, 4.1-5.5 h for the mercapturic acid conjugate, and 1.3-1.6 and 0.6-1.2 h for acetanilide and free aniline, respectively. Urinary maximum concentrations of N-acetyl-4-aminophenol were reached after about 4 h and maximum concentrations of the mercapturic acid conjugate after about 6 h, whereas concentrations of acetanilide and free aniline peaked after about 1 h. The present study is one of the first to provide reliable urinary excretion factors for aniline and its metabolites in humans after oral dosage, including data on the predominant urinary metabolite N-acetyl-4-aminophenol, also known as an analgesic under the name paracetamol/acetaminophen. PMID:26233686

  16. A semi-micro combustion assembly for the determination of carbon and hydrogen in actinide compounds

    A rapid combustion unit (Baird and Tatlock) incorporating a combustion chamber provided with baffle plates for complete combustion of the sample without the use of a catalyst has been assembled in a glove box for the determination of carbon and hydrogen in actinide complexes. The unit has been modified employing a movable electric furnace and a proportional temperature controller, for decomposition of the sample at desired heating rates. The set-up was standardised employing various reference materials such as benzoic acid, acetanilide, sulphanilamide and 1-chloro 2:4 dinitrobenzene and the standard deviation in the measurements evaluated. It has also been used successfully for the determination of carbon in uranium carbide and carbon and hydrogen in some uranyl-β-diketone-amine N-oxide complexes and in plutonium(IV) oxalate. (auth.)

  17. Spectroscopic investigations of the chiral interactions of metolachlor and its (S)-isomer with lipase and phosphatase.

    Wen, Yue Z; Yuan, Yu L; Chen, Hui; Wang, He L; Liu, Hui J; Kang, Xiao D; Fu, Liu S

    2010-04-01

    Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] is a chiral acetanilide herbicide. We investigated its enantioselective interactions, and that of its (S)-isomer, with Penicillium expansum alkaline lipase and phosphatase. UV differential spectroscopy and fluorescence spectrophotometry studies were conducted in phosphate buffered solution at pH 7. Chiral differences in the UV absorption and fluorescence spectra of lipase and phosphatase with metolachlor and its (S)-isomer were detected. The results showed that the interactions of metolachlor and its (S)-isomer with lipase and phosphatase occur statically through complex formation, and enantioselectivity was clearly observed. In addition, both UV absorption and fluorescence spectrophotometry showed that the (S)-isomer interacted more strongly with lipase and phosphatase than metolachlor. PMID:20390958

  18. Influence of electropolishing and anodic oxidation on morphology, chemical composition and corrosion resistance of niobium

    The work presents results of the studies performed on electropolishing of pure niobium in a bath that contained: sulphuric acid, hydrofluoric acid, ethylene glycol and acetanilide. After the electropolishing, the specimens were subjected to anodic passivation in a 1 mol dm−3 phosphoric acid solution at various voltages. The surface morphology, thickness, roughness and chemical composition of the resulting oxide layers were analysed. Thusly prepared niobium samples were additionally investigated in terms of their corrosion resistance in Ringer's solution. The electropolished niobium surface was determined to be smooth and lustrous. The anodisation led to the growth of barrier-like oxide layers, which were enriched in phosphorus species. - Highlights: • Pure niobium was electropolished and subsequently anodised in a H3PO4 solution. • Phosphorus was successfully introduced into the oxide layers after the treatment. • Corrosion resistance of niobium in Ringer's solution was improved after anodising

  19. Evaluation of butachlor for control of some submerged macrophytes along with its impact on biotic components of freshwater system

    A. Chattopadhyay, S. Adhikari, S. P. Adhikary, S. Ayyappan

    2006-04-01

    Full Text Available In this investigation, the efficacy of the herbicide butachlor, (N-butoxymethyl-2 chloro-21, 61 diethyl acetanilide was tested against few common submerged macrophytes namely Hydrilla (Hydrilla verticillata (L. Royale, Najas (Najas minor All., Nechamandra (Nechamandra alternifolia (Roxb. Thwaites and Ottelia (Ottelia alismoides (L. Pers. of freshwater fish ponds. Almost complete decay of Hydrilla, Nechamandra and Ottelia was achieved at 7.5 L of active ingredient/ha/m butachlor within 15 days while the herbicide showed no negative effect on Najas. However at the same concentration of butachlor, total mortality of zooplankton and water fern Azolla (Azolla caroliniana Lamarck occurred within seven days. In case of few freshwater fish species like Rohu (Labeo rohita, Channa (Channa punctatus, Anabas (Anabas testitudineus and Heteropneustes (Heteropneustes fossilis, total mortality occurred upto 90 days after application of the same dose of butachlor but fish survived beyond 120 days of herbicide application indicating degradation of the herbicides.

  20. Semi-microdetermination of nitrogen in actinide compounds by Dumas method

    This report describes the application of the Dumas method for the semi-micro determination of nitrogen in actinide compounds and actinide complexes with organic ligands. The usual set up has been modified to make it adaptable for glove box operations. The carbon dioxide generator and nitrometer assemblies were located outside the glove box while the reaction tube and combustion furnaces were housed inside. The nitrogen gas collected in the nitrometer was read with the help of a travelling microscope with a vernier attachment fitted in front of the nitrometer burette. The set up was standardised using acetanilide and employed for the determination of nirtogen in various substances such as uranium nitride, and a variety of substituted quinoline and pyrazolone derivatives of actinides as well as some ternary uranium-PMBR-sulphoxide complexes. Full details of the technique and the analytical data obtained are contained in this report. (author)

  1. Influence of electropolishing and anodic oxidation on morphology, chemical composition and corrosion resistance of niobium

    Sowa, Maciej; Greń, Katarzyna [Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego Street 6, 44-100 Gliwice (Poland); Kukharenko, Andrey I. [Institute of Metal Physics, Russian Academy of Sciences-Ural Division, S. Kovalevskoi Street 18, 620990 Yekaterinburg (Russian Federation); Ural Federal University, Mira Street 19, 620002 Yekaterinburg, Mira str. 19 (Russian Federation); Korotin, Danila M. [Institute of Metal Physics, Russian Academy of Sciences-Ural Division, S. Kovalevskoi Street 18, 620990 Yekaterinburg (Russian Federation); Michalska, Joanna [Faculty of Materials Engineering and Metallurgy, Silesian University of Technology, Krasińskiego Street 8, 40-019 Katowice (Poland); Szyk-Warszyńska, Lilianna; Mosiałek, Michał [Jerzy Haber Institute of Catalysis and Surface Chemistry PAS, Niezapominajek Street 8, 30-239 Kraków (Poland); Żak, Jerzy [Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego Street 6, 44-100 Gliwice (Poland); Pamuła, Elżbieta [AGH University of Science and Technology, Faculty of Materials Science and Ceramics, Mickiewicza Avenue 30, 30-059 Kraków (Poland); Kurmaev, Ernst Z. [Institute of Metal Physics, Russian Academy of Sciences-Ural Division, S. Kovalevskoi Street 18, 620990 Yekaterinburg (Russian Federation); Cholakh, Seif O. [Ural Federal University, Mira Street 19, 620002 Yekaterinburg, Mira str. 19 (Russian Federation); Simka, Wojciech, E-mail: wojciech.simka@polsl.pl [Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego Street 6, 44-100 Gliwice (Poland)

    2014-09-01

    The work presents results of the studies performed on electropolishing of pure niobium in a bath that contained: sulphuric acid, hydrofluoric acid, ethylene glycol and acetanilide. After the electropolishing, the specimens were subjected to anodic passivation in a 1 mol dm{sup −3} phosphoric acid solution at various voltages. The surface morphology, thickness, roughness and chemical composition of the resulting oxide layers were analysed. Thusly prepared niobium samples were additionally investigated in terms of their corrosion resistance in Ringer's solution. The electropolished niobium surface was determined to be smooth and lustrous. The anodisation led to the growth of barrier-like oxide layers, which were enriched in phosphorus species. - Highlights: • Pure niobium was electropolished and subsequently anodised in a H{sub 3}PO{sub 4} solution. • Phosphorus was successfully introduced into the oxide layers after the treatment. • Corrosion resistance of niobium in Ringer's solution was improved after anodising.

  2. Synthesis of 14C- and 3H-labelled 4-(4-nitrophenyl)aminophenylisothiocyanate (Go 9333/CGP 4540; amoscanate)

    Amoscanate, a broad spectrum anthelmintic, labelled with carbon-14 on the isothiocyanate carbon atom was prepared in an overall yield of 13% at a specific activity of 4.13 μCi/mg from potassium [14C]thiocyanate. The 4-nitro[U-14C]phenyl ring labelled compound was synthesized in 20.4% overall yield from [U-14C]aniline at a specific activity of 12.2 μCi/mg. The corresponding tritiated compound was prepared from 4-amino[2-3H]acetanilide at 112 μCi/mg. Labelling with tritium in the aromatic ring bearing the isothiocyanate group was achieved by catalysed halogen-tritium replacement. However, for pharmacokinetic and metabolism studies in experimental animals, the 14C- and 3H-labels associated with the phenylisothiocyanate moiety subsequently proved disadvantageous because of the instability of the labels in vivo. (author)

  3. A combined liquid chromatography-triple-quadrupole mass spectrometry method for the residual detection of veterinary drugs in porcine muscle, milk, and eggs.

    Zhang, Dan; Park, Zee-Yong; Park, Jin-A; Kim, Seong-Kwan; Jeong, Daun; Cho, Sang-Hyun; Shim, Jae-Han; Kim, Jin-Suk; Abd El-Aty, A M; Shin, Ho-Chul

    2016-06-01

    A liquid chromatography-electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) method was developed for monitoring and detection of four different drugs, namely acetanilide, pentylenetetrazole, phenacetin, and tetramethrin in porcine muscle, pasteurized milk, and table egg samples. For acetanilide and pentylenetetrazole, the samples were extracted with 0.1 % formic acid in acetonitrile, followed by defatting with n-hexane, partitioning at -20 °C for 1 h, centrifugation, and filtration, whereas the quick, easy, cheap, effective, rugged, and safe "QuEChERS" method was used for phenacetin and tetramethrin. The final extracts were combined and analyzed in a single chromatographic run using an XBridge(TM) analytical column and 0.1 % formic acid and 10 mM ammonium formate in ultrapure water (A) and 0.1 % formic acid and 10 mM ammonium formate in methanol (B) as the mobile phase. Owing to the unavailability of internal standards, matrix-matched calibrations were used for analyte quantification with coefficients of determination (R (2)) ≥ 0.9865. The intra- and inter-day accuracies ranged from 60.75 to 90.90 % and from 63.75 to 89.30 %, respectively, while the respective analytical precisions were 1.48-17.44 % (23.3 % for porcine sample spiked with phenacetin) and 1.97-15.78 %. The limits of quantification (LOQ) were between 0.5 and 2.5 ng/g in the matrices tested. Food samples purchased from local markets in Seoul were analyzed using the developed method and none of the tested drugs was detected. PMID:27178050

  4. Comparative sensitivity of Selenastrum capricornutum and Lemna minor to sixteen herbicides

    Fairchild, J.F.; Ruessler, D.S.; Haverland, P.S.; Carlson, A.R.

    1997-01-01

    Aquatic plant toxicity tests are frequently conducted in environmental risk assessments to determine the potential impacts of contaminants on primary producers. An examination of published plant toxicity data demonstrates that wide differences in sensitivity can occur across phylogenetic groups of plants. Yet relatively few studies have been conducted with the specific intent to compare the relative sensitivity of various aquatic plant species to contaminants. We compared the relative sensitivity of the algae Selenestrum capricornutum and the floating vascular plant Lemna minor to 16 herbicides (atrazine, metribuzin, simazine, cyanazine, alachlor, metolachlor, chlorsulfuron, metsulfuron, triallate, EPTC, trifluralin, diquat, paraquat, dicamba, bromoxynil, and 2,4-D). The herbicides studied represented nine chemical classes and several modes of action and were chosen to represent major current uses in the United States. Both plant species were generally sensitive to the triazines (atrazine, metribuzin, simazine, and cyanazine), sulfonureas (metsulfuron and chlorsulfuron), pyridines (diquat and paraquat), dinitroaniline (trifluralin), and acetanilide (alachlor and metolachlor) herbicides. Neither plant species was uniformly more sensitive than the other across the broad range of herbicides tested. Lemna was more sensitive to the sulfonureas (metsulfuron and chlorsulfuron) and the pyridines (diquat and parequat) than Selenastrum. However Selenastrum was more sensitive than Lemna to one of two thiocarbamates (triallate) and one of the triazines (cyanazine). Neither species was sensitive to selective broadleaf herbicides including bromoxynil, EPTC, dicamba, or 2,4-D. Results were not always predictable in spite of obvious differences in herbicide modes of action and plant phylogeny. Major departures in sensitivity of Selenastrum occurred between chemicals within individual classes of the triazine, acetanilide, and thiocarbamate herbicides. Results indicate that neither

  5. Effects of alachlor on the early development and induction of estrogen-responsive genes in Medaka, Oryzias latipes

    Lee, C.; Ryu, J.; Park, S.Y.; Choi, K.; Jeon, S.H.; Na, J.G.; Rhee, D.G. [National Inst. of Environmental Research, Incheon (Korea)

    2004-09-15

    Alachlor is an acetanilide herbicide used to control annual grasses and weeds in field corn, soybeans, and peanuts. It is a selective systemic herbicide, absorbed by germinating shoots and by roots. Although the specific pathways are not exactly understood, the acetanilide herbicides apparently interfere with several physiological processes including biosynthesis of lipids, proteins and flavonoids. These herbicides are widely used in agriculture and are commonly detected in surface water and groundwater. Alachlor has a relatively low acute toxicity, however, repeated exposure has been reported to cause hepatotoxicity, irreversible uveal degeneration and tumour formation in some animals. Besides alachlor is one of the herbicides reported to have endocrine disrupting effects. 2,4-D, 2,4,5-T, amitrole and atrazine also belong to these types of herbicides. Alachlor is a strongly suspected endocrine disruptor in that it is listed by EPA and the World Wildlife Fund [WWF] as a potential endocrine disrupting chemical. Many mammalian and aquatic toxicological studies with alachlor were performed under the conditions of acute, subacute and chronic experiment. However, not many studies using fish have been carried out with the purpose of screening and testing of endocrine disrupting effects of alachlor. The purpose of this study was to determine the effects of alachlor on the early morphological development of medaka (Oryzias latipes). Embryonic growth, deformation and hatching success were determined to see the effects of this chemical. Also, we tried to measure the estrogenic activity of alachlor using the ELISA and RT-PCR methods. By using these techniques, we evaluated the induction of the estrogen-responsive genes, vitellogenin (precursor of yolk protein) and choriogenin (precursor of egg envelope protein) in male medaka exposed to alachlor.

  6. The effect of lycopene on the total cytochrome P450, CYP1A2 and CYP2E1

    Melva Louisa

    2009-12-01

    Full Text Available Aim: Some carotenoids such as canthaxantin, astaxanthin and beta apo-8’-carotenal were reported to have modulatoryeffect on the cytochrome P450. The present study was conducted to investigate the effects of lycopene, a nonprovitamin A carotenoid, on microsomal cytochrome P450, CYP1A2 and CYP2E1.Methods: Total cytochrome P450 levels, CYP1A2 and CYP2E1-catalyzed reactions (acetanilide 4-hydroxylation and p-nitrophenol hydroxylation were studied in the liver microsomes of male Sprague Dawley rats. Microsomes were prepared using differential centrifugation combined with calcium aggregation method. Lycopene was orally administered in the dosages of 0, 25, 50 or 100 mg/kgBW/day for 14 days in a repeated fashion. Data were analyzed using ANOVA test.Results: Total cytochrome P450 level and acetanilide 4-hydroxylase activity were unaffected by any of the treatments. The CYP2E1 probe enzyme (p-nitrophenol hydroxylase was significantly reduced by repeated administration of 100mg/ kgBW/day lycopene (7.88 + 2.04 vs 12.26 + 2.77 n mol/min/mg prot.Conclusion: The present results suggest that lycopene does not affect the total cytochrome P450 or CYP1A2 activity but it inhibits the activity of CYP2E1 (p-nitrophenol hydroxylase in the rat. (Med J Indones 2009; 18: 233-8Keywords: lycopene, cytochrome P450, CYP1A2, CYP2E1

  7. Partial molar volumes of some drug and pro-drug substances in 1-octanol at T = 298.15 K

    Manin, Alex N.; Shmukler, Liudmila E.; Safonova, Liubov P. [Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo (Russian Federation); Perlovich, German L., E-mail: glp@isc-ras.r [Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo (Russian Federation)

    2010-03-15

    The article deals with measuring the densities of phenol, acetanilide, benzamide, benzoic acid, phenacetin, i-(acetylamino)-benzoic acid, i-hydroxy-benzamide, and i-acetaminophen (where i = 1, 2, 3) in 1-octanol in the wide concentration interval at T = 298.15 K. It also concerns the evaluation of apparent molar volumes and partial molar volumes at infinite dilution, V{sub 2}{sup 0}-bar as well as comparative analysis of the free volumes per molecule in the octanolic solutions, V{sub 2}{sup free}, and in the crystal lattices, V{sub 2}{sup free} (cr), from the nature and position of the substitutes. Also described is the evaluation of the increments of V{sub 2}{sup 0}-bar andV{sub 2}{sup free} for the unsubstituted molecules and isomers and the methods to obtain partial molar volumes for various functional groups at infinite dilution in 1-octanol at T = 298.15 K. Also considered is the limiting partial molar volume of the solutes in terms of the scaled particle theory.

  8. Study On The Synthesis Of Disida Derivatives For Labeling With 99mTc

    This study describes the synthesis method and characterization of 2,6-Diisopropyl acetanilide iminodiacetic acid (DISIDA). DISIDA is synthesized by replacement reaction of two Clo atoms in chloroacetyl chloride molecule. The synthesis process has two steps. Step1: The synthesis of 2,6-diisopropylacetanilide; Step 2: The synthesis of DISIDA. The good result obtained in the step 1 reaction, it was carried out in the low pH i.e acid medium. The synthesis reaction achieved high performance at room temperature for 2 hours. The product was crystallized completely while adding in mixture reaction amount sodium acetate by drop wise and stir slowly. The step 2 reaction was carried out in medium of alkali (pH = 10-12), reaction temperature was 50 oC - 60 oC, reaction time during 8 hours. After that EtOH was evaporated by vacuum and compound was crystallized with pH = 2-3, in cool medium (oC ). Raw material was recrystallized many time by cool EtOH. Pure product (DISIDA ) was characterized by IR, LC/MS, HPLC spectroscopy, melting point, crystal picture. Synthesized DISIDA, when tagged with diagnostic radionuclides such as 99mTc are quite good, 99mTc-DISIDA Complexes with RC purity and labeling efficiency >98% and above could be prepared by ordinary reaction condition, that reason can apply for valuation of possibility and reality on different purposes. (author)

  9. Adsorption of chloroacetanilide herbicides on soil I. Structural influence of chloroacetanilide herbicide for their adsorption on soils and its components

    2001-01-01

    Adsorption of chloroacetanilide herbicide acetochlor,alachlor, metolachlor and propachlor on soils and soil components was determined, and the structural differences of these herbicides were used to explain the order of sorptivity. Adsorption isotherms for all herbicide-soil combinations conformed to the Freundlich equation, and Kf increased with increasing soil organic carbon content. Kd on soil humic acid was greater than that on clay, but association of humic acid with clay reduced the overall adsorption. On all soils and soil humic acids, herbicide adsorption decreased in the order: metolachlor > acetochlor > propachlor > alachlor. On Ca2+-montmorrilonite, the order changed to metolachlor > acetochlor > alachlor > propachlor. FT-IR spectra of herbicide-clay or herbicide-humic acid-clay mixtures showed that H-bonding and charge transfer were the primary interaction pathways between these compounds and the surface of clay or humic acids. The different moieties attached to 2-chloro-acetanilide and their unique arrangement may have influenced the binding mechanisms and thus the sorptivity of these herbicides. This study indicates that the structural difference of pesticides in the same classes may be used as a molecular probe to obtain a better understanding of sorption mechanisms of pesticides on soil.

  10. Formation of Carbamate Anions by the Gas-phase Reaction of Anilide Ions with CO2

    Liu, Chongming; Nishshanka, Upul; Attygalle, Athula B.

    2016-05-01

    The anilide anion ( m/z 92) generated directly from aniline, or indirectly as a fragmentation product of deprotonated acetanilide, captures CO2 readily to form the carbamate anion ( m/z 136) in the collision cell, when CO2 is used as the collision gas in a tandem-quadrupole mass spectrometer. The gas-phase affinity of the anilide ion to CO2 is significantly higher than that of the phenoxide anion ( m/z 93), which adds to CO2 only very sluggishly. Our results suggest that the efficacy of CO2 capture depends on the natural charge density on the nitrogen atom, and relative nucleophilicity of the anilide anion. Generally, conjugate bases generated from aniline derivatives with proton affinities (PA) less than 350 kcal/mol do not tend to add CO2 to form gaseous carbamate ions. For example, the anion generated from p-methoxyaniline (PA = 367 kcal/mol) reacts significantly faster than that obtained from p-nitroaniline (PA = 343 kcal/mol). Although deprotonated p-aminobenzoic acid adds very poorly because the negative charge is now located primarily on the carboxylate group, it reacts more efficiently with CO2 if the carboxyl group is esterified. Moreover, mixture of CO2 and He as the collision gas was found to afford more efficient adduct formation than CO2 alone, or as mixtures made with nitrogen or argon, because helium acts as an effective "cooling" gas and reduces the internal energy of reactant ions.

  11. N-(3-Cyanophenyl)-2-phenylacetamide, an effective inhibitor of morbillivirus-induced membrane fusion with low cytotoxicity.

    Singethan, K; Hiltensperger, G; Kendl, S; Wohlfahrt, J; Plattet, P; Holzgrabe, U; Schneider-Schaulies, J

    2010-11-01

    Based on the structural similarity of viral fusion proteins within the family Paramyxoviridae, we tested recently described and newly synthesized acetanilide derivatives for their capacity to inhibit measles virus (MV)-, canine distemper virus (CDV)- and Nipah virus (NiV)-induced membrane fusion. We found that N-(3-cyanophenyl)-2-phenylacetamide (compound 1) has a high capacity to inhibit MV- and CDV-induced (IC(50) μM), but not NiV-induced, membrane fusion. This compound is of outstanding interest because it can be easily synthesized and its cytotoxicity is low [50 % cytotoxic concentration (CC(50)) ≥ 300 μM], leading to a CC(50)/IC(50) ratio of approximately 100. In addition, primary human peripheral blood lymphocytes and primary dog brain cell cultures (DBC) also tolerate high concentrations of compound 1. Infection of human PBMC with recombinant wild-type MV is inhibited by an IC(50) of approximately 20 μM. The cell-to-cell spread of recombinant wild-type CDV in persistently infected DBC can be nearly completely inhibited by compound 1 at 50 μM, indicating that the virus spread between brain cells is dependent on the activity of the viral fusion protein. Our findings demonstrate that this compound is a most applicable inhibitor of morbillivirus-induced membrane fusion in tissue culture experiments including highly sensitive primary cells. PMID:20685931

  12. Dielectric behaviour of some amides and formamides dissolved in nonpolar solvents under static electric field

    S Sahoo; S K Sit

    2011-08-01

    Structural and associational aspects of polar amides () like formamide, acetamide, Nmethyl acetamide (NMA), N,N-dimethyl formamide (DMF), N,N-dimethyl acetamide (DMA) and acetanilide dissolved in the nonpolar solvent () benzene or 1,4-dioxan have been estimated from the measured static relative permittivity 0 and high-frequency permittivity ∞ at different weight fractions s of polar solute at 35°C under static electric field using Debye model of polar liquid molecule. The static dipole moments s are compared with s reported from conductivity method and theoretical theos to get exact cal $\\cdot$ theos of the molecules are predicted from the available bond angles and bond moments where difference in electron affinity exists between two adjacent atoms of a polar group due to inductive, mesomeric and electromeric effects in them. Solute–solute molecular association for NMA in benzene and solute–solvent association for other amides are ascertained to arrive at their conformational structures.

  13. Diagnostic value of ultrasonography, infusion tomography of the gall-bladder and sup(99m)Tc-DIDA hepatobiliary scanning in cases of suspected acute cholecystitis

    Holst Pedersen, J.; Hancke, S.; Christensen, B.; Gammelgaard, J.; Haubek, A.; Ingemann Jensen, L.; Munck, O.; Wied, U. (Koebenhavns amts sygehus i Herlev, kirurgisk gastroenterologisk afd., Herlev, Denmark)

    1982-01-01

    Ultrasonography, infusion tomography of the gall-bladder and sup(99m)Tc-diethyl acetanilide iminodiacetic acid (DIDA) hepatobiliary scanning were compared in a prospective investigation of 45 consecutive patients in whom acute cholecystitis was suspected clinically. The definitive diagosis of acute cholecystitis was established or excluded at operation in 35 patients, by oral cholecystography in five and by intravenous cholangiography in five. The predictive values of positive and negative results of investigation were 100% and 83%. respectively, with ultrasonography and 98% and 88%, respectively, in hepatobiliary scanning. The corresponding values for infusion tomography were 87% and 33%, respectively. It is concluded from these results that ultrasonography and sup(99m)Tc-DIDA hepatobiliary scanning are capable of establishing the diagnosis rapidly and with certainty in cases of suspected acute cholecystitis. A preliminary account of the results of routine employment of sup(99m)Tc-DIDA hepatobiliary scanning in 29 consecutive patients revealed no erroneous diagnoses. In the majority of patients with acute cholecystitis, operation proved possible within 48 hours of admission.

  14. Polymer matrices obtained by ionizing radiation for using in controlled drug delivery systems

    Two kinds of controlled drug delivery system were obtained by gamma radiation induced polymerization. One of the system was obtained from an acrylic derivative of acetaminophen (40-hydroxyacetanilide), by copolymerization of 4-(acryloyloxy) acetanilide and N,N-dimethylacrylamide (DMAA) in dimethylformamide solution with 0,16 kGy/h dose rate and 54 Gy dose. The values of reactivity rate, r-DMAA = 0,31 ± 0,02 e rAOA -0,07 ± 0,12, were determined by Fineman-Ross method. The acetaminophen hydrolysis was carried out in alkaline and enzymatic (trypsin) media. Another kind of drug delivery system studied was solvent controlled type, being the drug immobilized in the hydrogel,. The hydrogels prepared by radiation polymerization of acryloyl-L-propine methylester (A-Pro-OMe) with 10 Gy dose, showed thermosensible property, swelling or shrinking in water with decreased or increased temperatures. The hydrogels were obtained with different crosslink density, trimethylolpropane trimethacrylate, and the monomers N, N-dimethyl acrylamide (DMAA) and 2-cyanoethyl acrylate to study the influence of the composition in the drug delivery rate. It was verified that the porous size besides being a characteristic of the matrix composition, it was also temperature dependent (thermosensible). The analgesic drug acetaminophen was immobilized by entrapment and by physical adsorption into the hydrogels matrices for 'in vitro' study. The insulin was immobilized by adsorption for 'in vivo' study. (author)

  15. Motor activity of the gallbladder and gastrointestinal tract as determinants of enterohepatic circulation. A scintigraphic and manometric study

    The aims of the study were to describe the dynamics of the enterohepatic circulation in relation to gallbladder and gastrointestinal motility in the interdigestive as well as the postprandial period. Furthermore, to investigate the level of circulating cholecystokinin, secretin, pancreatic polypeptide, motilin and bile acids in relation to gallbladder motility and MMC during the interdigestive period. All investigations were carried out on healthy male volunteers aged 18-40 years. The most suitable method for studying various characteristics of the enterohepatic circulation, and especially gallbladder motility in humans, is scintigraphy. It is non-invasive, and allows a continuing dynamic investigation of the partitioning of the radioactive marker between the various compartment. Two entirely different pharmacological substances may be use. HIDA (diethyl-acetanilide-iminodiacetic acid) which is semisynthetic and closely related to lidocaine forms a chelate with 99mTc for intravenous administration only. The transport of 99mTc-HIDA across the hepatocyte is a carrier-mediated organic anion pathway, similar to the hepatic handling of bilirubin. Homocholic-acid-taurine (HCAT) is a synthetic bile acid analogue, corresponding to the naturally occurring bile acid cholic acid-taurine. It is marked with 75Se and is available for peroral use only. The 75SeHCAT is adsorbed in the same manner as the naturally occurring conjugated trihydroxy bile acids, involving specific carrier systems for absorption and secretion, i.e. with a high first pass extraction and a secretory rate proportional to the blood concentration. (EG) 24 refs

  16. Monitoring impact of mefenacet treatment on soil microbial communities by PCR-DGGE fingerprinting and conventional testing procedures

    2006-01-01

    The effect of acetanilide herbicide mefenacet on soil microbial communities was studied using paddy soil samples with different short-term treatments. The culturable bacteria (plate counts), dehydrogenase activity and changes in community structure(denaturing gradient gel electrophoresis (DGGE) analysis) were used for biological community assessments. Mefenacet was a significant stimulus to cultural aerobic bacteria and dehydrogenase activity while Sphingobacterium multivorum Y1, a bacterium efficiently degrading the mefenacet, only induced the increasing colony-forming unit (CFU) of bacteria but little effect on dehydrogenase activity during the whole experiment. The degree of similarity between the 16S rDNA profiles of the communities was quantified by numerically analyzing the DGGE band patterns. Similarity dendrograms showed that the microbial community structures of the mefenacet-treated and non-treated soils were not significantly different. But supplement ofS. multivorum Y1 could increase the diversity of the microbial community in the mefenacet-polluted paddy soil. This work is a new attempt to apply the S. multivorum Y1for remediation of the mefenacet-polluted environments.

  17. Polymer matrices obtained by ionizing radiation for using in controlled drug delivery systems; Matrizes polimericas obtidas mediante radiacao ionizante para sua utilizacao como sistemas de liberacao controlada de farmacos

    Martellini, Flavia

    1998-07-01

    Two kinds of controlled drug delivery system were obtained by gamma radiation induced polymerization. One of the system was obtained from an acrylic derivative of acetaminophen (40-hydroxyacetanilide), by copolymerization of 4-(acryloyloxy) acetanilide and N,N-dimethylacrylamide (DMAA) in dimethylformamide solution with 0,16 kGy/h dose rate and 54 Gy dose. The values of reactivity rate, r-D{sub MAA} = 0,31 {+-} 0,02 e r{sub AOA} -0,07 {+-} 0,12, were determined by Fineman-Ross method. The acetaminophen hydrolysis was carried out in alkaline and enzymatic (trypsin) media. Another kind of drug delivery system studied was solvent controlled type, being the drug immobilized in the hydrogel,. The hydrogels prepared by radiation polymerization of acryloyl-L-propine methylester (A-Pro-OMe) with 10 Gy dose, showed thermosensible property, swelling or shrinking in water with decreased or increased temperatures. The hydrogels were obtained with different crosslink density, trimethylolpropane trimethacrylate, and the monomers N, N-dimethyl acrylamide (DMAA) and 2-cyanoethyl acrylate to study the influence of the composition in the drug delivery rate. It was verified that the porous size besides being a characteristic of the matrix composition, it was also temperature dependent (thermosensible). The analgesic drug acetaminophen was immobilized by entrapment and by physical adsorption into the hydrogels matrices for 'in vitro' study. The insulin was immobilized by adsorption for 'in vivo' study. (author)

  18. Conformers and non-covalent interactions studied by laser spectroscopies and ab initio calculations

    Ullrich, S

    2001-01-01

    The model peptides, formanilide and acetanilide, and their weakly bound complexes were studied in the gas-phase using resonance enhanced multi-photon ionisation (REMPI) and zero electron kinetic energy (ZEKE) photoelectron spectroscopy. Both, cis- and trans-isomers of formanilide, were observed under molecular beam conditions. Trans-formanilide displayed predominantly in-plane vibrational excitation indicative of a planar geometry with modest geometry changes upon excitation and ionisation. In cis-formanilide the side-chain is twisted compared to the phenyl plane in the S sub 0 state, but planar in the S sub 1 and D sub 0 states, revealed in characteristic side-chain torsional and out-of-plane bending excitations. Additionally, the ZEKE spectra provide evidence that excess cationic charge is delocalised from the aromatic ring to the side chain. The work on trans-formanilide was extended to its van der Waals complex with Argon with the purpose of investigating the torsional potential of the side-chain and prob...

  19. Studies on maize inbred lines susceptibility to herbicides

    Stefanović Lidija

    2010-01-01

    Full Text Available This paper presents the analysis of results obtained during long- term studies on the response of maize inbred lines to herbicides. Under the agroecological conditions of Zemun Polje the response (reaction of maize inbred lines to herbicides of different classes was investigated. Biological tests were performed and some agronomic, morphological, physiological and biochemical parameters were determined when the response of maize inbred lines to herbicides was estimated. The use of active ingredients of herbicides from triazine, acetanilide, thiocarbamate to new chemical groups (sulfonylurea etc., have been resulted in changes in weed suppression and susceptibility of inbred lines. Obtained results show that effects of herbicides on susceptible maize genotypes can be different: they can slowdown the growth and development and affect the plant height; they can also affect the stages of the tassel and ear development and at the end they can reduced grain yield of the tested inbreds. Numerous studies confirmed the existence of differences in susceptibility level of maize genotypes in relation to herbicides. According to gained results the recommendations for growers are made on the possibility of the application of new herbicides in the hybrid seed production.

  20. Effect of systemic herbicides on N2-fixing and phosphate solubilizing microorganisms in relation to availability of nitrogen and phosphorus in paddy soils of West Bengal.

    Das, Amal Chandra; Debnath, Anjan

    2006-11-01

    A field experiment has been conducted with four systemic herbicides viz., butachlor [N-(butoxymethyl)-2-chloro-2',6'-diethyl-acetanilide], fluchloralin [N-(2-chloroethyl)-(2,6-dinitro-N-propyl-4-trifluoromethyl) aniline], oxadiazon [5-terbutyl-3-(2,4-dichloro-5-isopro poxyphenyl)-1,3,4-oxadiazol-2-one] and oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenyl)-4-(trifluoromethyl) benzene] at their recommended field rates (2.0, 1.5, 0.4 and 0.12kga.i.ha(-1), respectively) to investigate their effects on growth and activities of aerobic non-symbiotic N(2)-fixing bacteria and phosphate solubilizing microorganisms in relation to availability of nitrogen and phosphorus in the rhizosphere soils as well as yield of the rice crop (Oryza sativa L cv. IR-36). Application of herbicides, in general, highly stimulated the population and activities of the target microorganisms, which resulted in a greater amount of atmospheric nitrogen fixation and phosphate solubilization in the rhizosphere soils of the test crop. The greater microbial activities subsequently augmented the mineralization and availability of nitrogen and phosphorus in the soil solution, which in turn increased the yield of the crop. Among the herbicides, oxyfluorfen was most stimulative followed by fluchloralin and oxadiazon in augmenting the microbial activities in soil. Butachlor also accentuated the mineralization and availability of nitrogen due to higher incitement of non-symbiotic N(2)-fixing bacteria in paddy soil. The grain and straw yields of the crop were also significantly increased due to the application of oxyfluorfen (20.2% and 21%) followed by fluchloralin (13.1% and 15.4%) and butachlor (9.1% and 10.2%), respectively. PMID:16630642

  1. Decadal-scale changes of pesticides in ground water of the United States, 1993-2003

    Bexfield, L.M.

    2008-01-01

    Pesticide data for ground water sampled across the United States between 1993-1995 and 2001-2003 by the U.S. Geological Survey National Water-Quality Assessment Program were evaluated for trends in detection frequency and concentration. The data analysis evaluated samples collected from a total of 362 wells located in 12 local well networks characterizing shallow ground water in agricultural areas and six local well networks characterizing the drinking water resource in areas of variable land use. Each well network was sampled once during 1993-1995 and once during 2001-2003. The networks provide an overview of conditions across a wide range of hydrogeologic settings and in major agricultural areas that vary in dominant crop type and pesticide use. Of about 80 pesticide compounds analyzed, only six compounds were detected in ground water from at least 10 wells during both sampling events. These compounds were the triazine herbicides atrazine, simazine, and prometon; the acetanilide herbicide metolachlor; the urea herbicide tebuthiuron; and an atrazine degradate, deethylatrazine (DEA). Observed concentrations of these compounds generally were <0.12 ??g L-1. At individual wells, changes in concentrations typically were <0.02 ??g L-1. Data analysis incorporated adjustments for changes in laboratory recovery as assessed through laboratory spikes. In wells yielding detectable concentrations of atrazine, DEA, and prometon, concentrations were significantly lower (?? = 0.1) in 2001-2003 than in 1993-1995, whereas detection frequency of these compounds did not change significantly. Trends in atrazine concentrations at shallow wells in agricultural areas were found to be consistent overall with recent atrazine use data. Copyright ?? 2008 by the American Society of Agronomy, Crop Science Society of America, and Soil Science Society of America. All rights reserved.

  2. TRPV1 in brain is involved in acetaminophen-induced antinociception.

    Christophe Mallet

    Full Text Available BACKGROUND: Acetaminophen, the major active metabolite of acetanilide in man, has become one of the most popular over-the-counter analgesic and antipyretic agents, consumed by millions of people daily. However, its mechanism of action is still a matter of debate. We have previously shown that acetaminophen is further metabolized to N-(4-hydroxyphenyl-5Z,8Z,11Z,14Z -eicosatetraenamide (AM404 by fatty acid amide hydrolase (FAAH in the rat and mouse brain and that this metabolite is a potent activator of transient receptor potential vanilloid 1 (TRPV(1 in vitro. Pharmacological activation of TRPV(1 in the midbrain periaqueductal gray elicits antinociception in rats. It is therefore possible that activation of TRPV(1 in the brain contributes to the analgesic effect of acetaminophen. METHODOLOGY/PRINCIPAL FINDINGS: Here we show that the antinociceptive effect of acetaminophen at an oral dose lacking hypolocomotor activity is absent in FAAH and TRPV(1 knockout mice in the formalin, tail immersion and von Frey tests. This dose of acetaminophen did not affect the global brain contents of prostaglandin E(2 (PGE(2 and endocannabinoids. Intracerebroventricular injection of AM404 produced a TRPV(1-mediated antinociceptive effect in the mouse formalin test. Pharmacological inhibition of TRPV(1 in the brain by intracerebroventricular capsazepine injection abolished the antinociceptive effect of oral acetaminophen in the same test. CONCLUSIONS: This study shows that TRPV(1 in brain is involved in the antinociceptive action of acetaminophen and provides a strategy for developing central nervous system active oral analgesics based on the coexpression of FAAH and TRPV(1 in the brain.

  3. Enantioselective Degradation and Chiral Stability of Metalaxyl-M in Tomato Fruits.

    Jing, Xu; Yao, Guojun; Wang, Peng; Liu, Donghui; Qi, Yanli; Zhou, Zhiqiang

    2016-05-01

    Metalaxyl is an important chiral acetanilide fungicide, and the activity almost entirely originates from the R-enantiomer. Racemic metalaxyl has been gradually replaced by the enantiopure R-enantiomer (metalaxyl-M). In this study a chiral residue analysis method for metalaxyl and the metabolite metalaxyl acid was set up based on high-performance liquid chromatography tandem mass spectroscopy (HPLC-MS/MS). The enantioselective degradation and chiral stability of metalaxyl-M in tomato fruits in two geographically distinct regions of China (Heilongjiang and Hunan Province) were evaluated and the enantioselectivity of metalaxyl acid was also investigated. Tomato plants grew under field conditions with a one-time spray application of metalaxyl-M wettable powder. It was found that R-metalaxyl was not chirally stable and the inactive S-metalaxyl was detected in tomato fruits. At day 40, S-metalaxyl derived from R-metalaxyl accounted for 32% and 26% of the total amount of metalaxyl, respectively. The metabolites R-metalaxyl acid and S-metalaxyl acid were both observed in tomato, and the ratio of S-metalaxyl acid to the sum of S- and R-metalaxyl acid was 36% and 28% at day 40, respectively. For both metalaxyl and metalaxyl acid, the half-life of the S-enantiomer was longer than the R-enantiomer. The results indicated that the enantiomeric conversion should be considered in the bioactivity evaluation and environmental pollution assessment. Chirality 28:382-386, 2016. © 2016 Wiley Periodicals, Inc. PMID:27008381

  4. Motor activity of the gallbladder and gastrointestinal tract as determinants of enterohepatic circulation. A scintigraphic and manometric study

    Qvist, N. [Odense University Hospital, Dept. of Surgical Gastroenterology and Clinical Physiology, Div. of Nuclear Medicine, Odense (Denmark)

    1995-12-31

    The aims of the study were to describe the dynamics of the enterohepatic circulation in relation to gallbladder and gastrointestinal motility in the interdigestive as well as the postprandial period. Furthermore, to investigate the level of circulating cholecystokinin, secretin, pancreatic polypeptide, motilin and bile acids in relation to gallbladder motility and MMC during the interdigestive period. All investigations were carried out on healthy male volunteers aged 18-40 years. The most suitable method for studying various characteristics of the enterohepatic circulation, and especially gallbladder motility in humans, is scintigraphy. It is non-invasive, and allows a continuing dynamic investigation of the partitioning of the radioactive marker between the various compartment. Two entirely different pharmacological substances may be use. HIDA (diethyl-acetanilide-iminodiacetic acid) which is semisynthetic and closely related to lidocaine forms a chelate with {sup 99m}Tc for intravenous administration only. The transport of {sup 99m}Tc-HIDA across the hepatocyte is a carrier-mediated organic anion pathway, similar to the hepatic handling of bilirubin. Homocholic-acid-taurine (HCAT) is a synthetic bile acid analogue, corresponding to the naturally occurring bile acid cholic acid-taurine. It is marked with {sup 75}Se and is available for peroral use only. The {sup 75}SeHCAT is adsorbed in the same manner as the naturally occurring conjugated trihydroxy bile acids, involving specific carrier systems for absorption and secretion, i.e. with a high first pass extraction and a secretory rate proportional to the blood concentration. (EG) 24 refs.

  5. Complex monitoring system for analytical detection and biological evaluation of soil micropollutants for a sustainable environment

    Complete text of publication follows. In the development of a complex soil contamination monitoring system including the detection of agriculture-related micropollutants, heavy metal contamination and ecotoxicity, a survey has been carried out in Bekes county (Hungary) using different techniques for the characterisation of soil and surface water status. Besides the representativity-optimisation of the sampling technique, in situ sensoric methods, instrumental analysis, biological tests (soil biology, ecotoxicity and mutagenicity) were also applied, and results obtained were presented in a spatial informatics system. The target group, indicators and methodology is in compliance with recommendations of the EEA monitoring working group. Contamination in arable lands and industrial areas has been investigated in 13 plots with 5 replications. Sampling has been carried out by using drilling machine and contaminant concentrations of soil profiles have been characterised down to ground water table. Pesticide residues were monitored by using GC-MS. Target analytes included triazine, phenoxyacetic acid, acetanilide and dinitroaniline herbicides, chlorinated hydrocarbon (CHC), organophosphate and carbamate insecticides, an insect hormonal agonist and a triazole fungicide. Besides banned persistent CHC insecticides (DDT, HCH, etc.), atrazine and acetochlor herbicides are common contaminants in Hungary, reaching 200 ng/g and 300 ng/ml concentration in the soil and surface water samples studied, and trifluralin and metolachlor were also detected in some cases. Heavy metal contamination was detected by ICP AES, and within-plot heterogeneities were studied throughout soil profiles. Nickel has been fund as a relatively common contaminant in arable lands in the area; however relation to fertilisers could not be confirmed. Even in small spatial scale (50x50 meters) a very high variability has been demonstrated in half of the experimental plots. The effects of pesticide residues in

  6. Liquid Chromatogram and Mass-spectrography for Rapid Determination of Illegally Added Amidopyrine in Pediatric Qingjie Particles%液相色谱-质谱法快速测定小儿清解颗粒中非法添加的氨基比林

    隋译

    2016-01-01

    OBJECTIVE:To establish a rapid accurate identification method of illegally added amidopyrine in pediatric Qingjie particles .METHODS:Illegally added acetanilide detumescence chemical drug amidopyrine from four different companies were screened by liquid chromatogram ( LC ) and mass-spectrography ( MS ) , and reference substance of secondary mass spectra were compared .RESULTS: In the sample mass spectrum , there were three samples were not consistent with the reference substance of primary and secondary mass spectrum peak , and a manufacturer of sample pattern was consistent with the reference substance of primary and secondary mass spectrum peak.CONCLUSIONS: Application of LC and MS method can accurately identify whether Chinese medicine preparations contains illegal added amidopyrine , and the content of aminopyrine can be calculated accurately .%目的:建立快速准确鉴定小儿清解颗粒中非法添加氨基比林的方法。方法:用液相色谱质谱联用技术对4种不同厂家小儿清解颗粒中非法添加消肿止痛类化学药品氨基比林进行筛查,与氨基比林对照品的一、二级质谱图进行比较。结果:在样品质谱图中有3家样品的图谱与对照品有不一致的一级质谱峰与二级质谱峰,1个厂家的样品图谱有与对照品有一致的一级质谱峰与二级质谱峰。结论:应用液相色谱-质谱法可快速准确鉴定出中药制剂中是否含有非法添加的氨基比林,并可以准确计算添加氨基比林的含量。

  7. CYP1A1 and CYP1A2 expression: Comparing 'humanized' mouse lines and wild-type mice; comparing human and mouse hepatoma-derived cell lines

    Human and rodent cytochrome P450 (CYP) enzymes sometimes exhibit striking species-specific differences in substrate preference and rate of metabolism. Human risk assessment of CYP substrates might therefore best be evaluated in the intact mouse by replacing mouse Cyp genes with human CYP orthologs; however, how 'human-like' can human gene expression be expected in mouse tissues? Previously a bacterial-artificial-chromosome-transgenic mouse, carrying the human CYP1A1CYP1A2 locus and lacking the mouse Cyp1a1 and Cyp1a2 orthologs, was shown to express robustly human dioxin-inducible CYP1A1 and basal versus inducible CYP1A2 (mRNAs, proteins, enzyme activities) in each of nine mouse tissues examined. Chimeric mice carrying humanized liver have also been generated, by transplanting human hepatocytes into a urokinase-type plasminogen activator(+/+)severe-combined-immunodeficiency (uPA/SCID) line with most of its mouse hepatocytes ablated. Herein we compare basal and dioxin-induced CYP1A mRNA copy numbers, protein levels, and four enzymes (benzo[a]pyrene hydroxylase, ethoxyresorufin O-deethylase, acetanilide 4-hydroxylase, methoxyresorufin O-demethylase) in liver of these two humanized mouse lines versus wild-type mice; we also compare these same parameters in mouse Hepa-1c1c7 and human HepG2 hepatoma-derived established cell lines. Most strikingly, mouse liver CYP1A1-specific enzyme activities are between 38- and 170-fold higher than human CYP1A1-specific enzyme activities (per unit of mRNA), whereas mouse versus human CYP1A2 enzyme activities (per unit of mRNA) are within 2.5-fold of one another. Moreover, both the mouse and human hepatoma cell lines exhibit striking differences in CYP1A mRNA levels and enzyme activities. These findings are relevant to risk assessment involving human CYP1A1 and CYP1A2 substrates, when administered to mice as environmental toxicants or drugs.

  8. Evaluating the combined effects of pretilachlor and UV-B on two Azolla species.

    Prasad, Sheo Mohan; Kumar, Sushil; Parihar, Parul; Singh, Anita; Singh, Rachana

    2016-03-01

    The present study assessed the comparative responses of two agronomic species of Azolla (A.microphylla and A. pinnata) exposed to man-made and natural stressors by evaluating biomass accumulation, pigments (chlorophyll a and b and carotenoid contents), photosynthetic activity and nitrogen metabolism. The study was carried out in field where two species of Azolla were cultured and treated with various concentrations (5, 10 and 20 μg ml(-1)) of herbicide; pretilachlor [2-chloro-2,6-diethyl-N-(2-propoxyethyl) acetanilide] and enhanced levels (UV-B1: ambient +2.2 kJ m(-2) day(-1) and UV-B2: ambient +4.4 kJ m(-2) day(-1)) of UV-B, alone as well as in combination. Biomass accumulation, photosynthetic pigments; chlorophyll a, b and carotenoids, photosynthetic oxygen yield and photosynthetic electron transport activities i.e. photosystem II (PS II) and photosystem I (PS I) in both the species declined with the increasing doses of pretilachlor and UV-B radiation, which further declined when applied in combination. The lower doses (5 and 10 μg ml(-1)) of pretilachlor and UV-B (UV-B1 and UV-B2) alone, damaged mainly the oxidation side of PS II, whereas higher dose (20 μg ml(-1)) of pretilachlor alone and in combination with UV-B1 and UV-B2 caused damage to PS II reaction centre and beyond this towards the reduction side. A significant enhancement in respiration was also noticed in fronds of both the Azolla species following pretilachlor and UV-B treatment, hence indicating strong damaging effect. The nitrate assimilating enzymes - nitrate reductase and nitrite reductase and ammonium assimilating enzymes - glutamine synthetase and glutamate synthase were also severely affected when treated either with pretilachlor and/or UV-B while glutamate dehydrogenase exhibited a stimulatory response. The study suggests that both the species of Azolla showed considerable damage under pretilachlor and UV-B treatments alone, however, in combination the effect was more intense. Further, in

  9. 双氯芬酸栓加黄体酮在肾绞痛中的临床应用%Clinical Analysis of Diclofenac Suppository Combined with Progesterone in the Treatment of Renal Colic

    张汝; 杨于钢

    2015-01-01

    Objective To study diclofenac suppository plus progestin in clinical application of renal colic. Methods Our hospital since November 2001 to November 2011 application of diclofenac suppository plus progestin treatment of 210 cases of renal colic, renal colic onset rectal drug diclofenac suppository 50 mg and 40 mg muscle injection of progesterone, on pain relief and functional every 6~12 h can repeat use drug 1 times, a total of 3~4 d. Results 210 cases, 150 cases had marked ef ect, al eviate the 45 cases, 15 cases, 30 cases of recur ence, the recur ence rate of 14.28%, every 6 ~ 12 h repeat use drug 1 times. Conclusion Diclofenac suppository is a new kind of potent anti-inflammatory analgesic, by inhibiting the ef ect of prostaglandin synthetase, reduce the synthesis and release of prostaglandins in the body, thus the pain eased, the role of 2 times more than indomethacin, progesterone is a kind of progesterone, a major role in beta receptors, make the ureteral smooth muscle relaxation, thereby spasmolysis acetanilide, and diuresis and solute.%目的探讨双氯芬酸栓加黄体酮在肾绞痛中的临床应用。方法我院自2001年11月~2011年11月应用双氯芬酸栓加黄体酮治疗肾绞痛210例,肾绞痛发作时直肠给药双氯芬酸栓50 mg和肌注黄体酮40 mg,对疼痛缓解欠佳者,每隔6~12 h可重复用药1次,共3~4 d。结果210例中,显效150例,缓解45例,无效15例,复发30例,复发率14.28%,每隔6~12 h重复用药1次均得到缓解。结论双氯芬酸栓是一种新型强效消炎镇痛药,通过抑制前列腺素合成酶的作用,减少体内前列腺素的合成与释放,从而疼痛得以缓解,其作用较消炎痛强2倍,黄体酮为一种孕激素,主要作用于β受体,使输尿管平滑肌松弛,从而起到解痉止痛,且还有溶质性利尿。

  10. Biotransformation of pesticides in saturated-zone materials

    Hoyle, Blythe L.; Arthur, Ellen L.

    Many studies have been conducted to evaluate pesticide contamination of groundwater in the United States, but investigations of pesticide biotransformation in saturated zones are much less numerous than in surface soils. Because results of studies using soils are not directly applicable to the subsurface, the purpose of this paper is to illustrate examples of pesticide biotransformation in saturated-zone materials. Although it must be considered with caution, the US Environmental Protection Agency's (EPA) "Pesticides in Ground Water Database" was used to focus the discussion on the biotransformation potential of dibromoethane (EDB), atrazine, acetanilide herbicides, and aldicarb, all of which have been detected in groundwater in the United States. Results of more than two dozen studies indicate that a biotransformation potential for these pesticides exists in saturated-zone materials, although for any given pesticide substantial differences in biotransformation occurred. These variations were due both to differences in experimental methods and to heterogeneities in the subsurface materials under investigation. However, because biotransformation mechanisms were not well investigated, it is generally not possible to extrapolate predictions of biotransformation potential beyond the specific sites investigated. These results highlight the need to better understand microbial genetic regulation of biotransformation processes so that genetic information may be effectively incorporated into future investigations of biotransformation potential in the subsurface. Résumé De nombreuses études ont été réalisées pour évaluer le degré de pollution des aquifères par les pesticides aux États-Unis, mais les recherches concernant la biotransformation des pesticides dans les eaux souterraines sont beaucoup moins nombreuses que dans les sols. Du fait que les résultats des études concernant les sols ne sont pas directement applicables au milieu souterrain, le propos de cet

  11. Biotransformation of pesticides in saturated-zone materials

    Hoyle, Blythe L.; Arthur, Ellen L.

    Many studies have been conducted to evaluate pesticide contamination of groundwater in the United States, but investigations of pesticide biotransformation in saturated zones are much less numerous than in surface soils. Because results of studies using soils are not directly applicable to the subsurface, the purpose of this paper is to illustrate examples of pesticide biotransformation in saturated-zone materials. Although it must be considered with caution, the US Environmental Protection Agency's (EPA) "Pesticides in Ground Water Database" was used to focus the discussion on the biotransformation potential of dibromoethane (EDB), atrazine, acetanilide herbicides, and aldicarb, all of which have been detected in groundwater in the United States. Results of more than two dozen studies indicate that a biotransformation potential for these pesticides exists in saturated-zone materials, although for any given pesticide substantial differences in biotransformation occurred. These variations were due both to differences in experimental methods and to heterogeneities in the subsurface materials under investigation. However, because biotransformation mechanisms were not well investigated, it is generally not possible to extrapolate predictions of biotransformation potential beyond the specific sites investigated. These results highlight the need to better understand microbial genetic regulation of biotransformation processes so that genetic information may be effectively incorporated into future investigations of biotransformation potential in the subsurface. Résumé De nombreuses études ont été réalisées pour évaluer le degré de pollution des aquifères par les pesticides aux États-Unis, mais les recherches concernant la biotransformation des pesticides dans les eaux souterraines sont beaucoup moins nombreuses que dans les sols. Du fait que les résultats des études concernant les sols ne sont pas directement applicables au milieu souterrain, le propos de cet

  12. Calixarene receptors in the selective separation of alachlor. Characterization of the separated complexes; Receptores calixarenicos en la separacion selectiva de alaclor. Caracterizacion de los complejos separados

    Garcia G, M.C

    2004-07-01

    while 165 h were necessary with H{sub n}bL{sup n} in dilute as concentrate solutions, solvents as chloroform and acetonitrile did not interfere in the formation of the species. At the same time and based on the structure of the reactants and information from the scientific literature related to this particular topic, using the M M3, CONFLEX and MOPAC/PM5/COSMO procedures, we calculated the optimized geometry which rendered the most stable molecular structures of reactants and products, this means those with the lowest minimum energies, the lowest energies of the most stable conformers and the heat of formation of the most stable conformational structures of the calixarene-substrate species. The latter were those formed by hydrogen bonding and {pi}-{pi} interactions. Species formed with H{sub n}bL{sup n} stabilized by hydrogen bonding through CH{sub 2}-Cl interaction of alachlor with OH groups of the calixarenes. Concerning the phosphinoylated calixarenes, the P=O groups immobilize the alachlor by hydrogen bonding with the benzyl of the acetanilide. However, the species formed with alachlor and parents or functionalized calixarenes demanded a second interaction between calixarene phenyl-{pi}-{pi}-benzyl-alachlor to be stabilised. Heat of formation of reactants and products allowed to calculate the heat o reaction associated to the formation of the hosts...guest species, these results were surprising in line with the experimental results. Based on the solution and computational results we synthesized and isolated the calixarene---alachlor complexes in sizeable amounts. The latter were characterized by spectroscopic techniques like IR, UV-Vis, luminescence and elemental analysis. The results from the solution and solid studies of the reagents and products as molar absorption coefficients, the features of the luminescence and IR spectra, luminescence lifetimes and minimum formulae of the isolated complexes are in good agreement with the parameters and tendencies of the

  13. Calixarene receptors in the selective separation of alachlor. Characterization of the separated complexes

    concentrate solutions, solvents as chloroform and acetonitrile did not interfere in the formation of the species. At the same time and based on the structure of the reactants and information from the scientific literature related to this particular topic, using the M M3, CONFLEX and MOPAC/PM5/COSMO procedures, we calculated the optimized geometry which rendered the most stable molecular structures of reactants and products, this means those with the lowest minimum energies, the lowest energies of the most stable conformers and the heat of formation of the most stable conformational structures of the calixarene-substrate species. The latter were those formed by hydrogen bonding and π-π interactions. Species formed with HnbLn stabilized by hydrogen bonding through CH2-Cl interaction of alachlor with OH groups of the calixarenes. Concerning the phosphinoylated calixarenes, the P=O groups immobilize the alachlor by hydrogen bonding with the benzyl of the acetanilide. However, the species formed with alachlor and parents or functionalized calixarenes demanded a second interaction between calixarene phenyl-π-π-benzyl-alachlor to be stabilised. Heat of formation of reactants and products allowed to calculate the heat o reaction associated to the formation of the hosts...guest species, these results were surprising in line with the experimental results. Based on the solution and computational results we synthesized and isolated the calixarene---alachlor complexes in sizeable amounts. The latter were characterized by spectroscopic techniques like IR, UV-Vis, luminescence and elemental analysis. The results from the solution and solid studies of the reagents and products as molar absorption coefficients, the features of the luminescence and IR spectra, luminescence lifetimes and minimum formulae of the isolated complexes are in good agreement with the parameters and tendencies of the minimum energies of the geometrical and conformational structures found. With respect to the

  14. Toxicology and carcinogenesis studies of a binary mixture of 3,3',4,4',5-pentachlorobiphenyl (PCB 126) (Cas No. 57465-28-8) and 2,3',4,4',5-pentachlorobiphenyl (PCB 118) (Cas No. 31508-00-6) in female Harlan Sprague-Dawley rats (gavage studies).

    2006-11-01

    TEQ/kg at 53 weeks. Cytochrome P450 Enzyme Activities: CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) and CYP1A2-associated acetanilide-4-hydroxylase (A4H) activities were evaluated at the 14-, 31-, and 53-week interim evaluations to evaluate the expression of known dioxin-responsive genes. In addition, CYP2B-associated pentoxyresorufin-O-deethylase (PROD) activity was also analyzed. Hepatic and pulmonary EROD (CYP1A1) activity, hepatic A4H (CYP1A2) activity, and hepatic PROD (CYP2B1) activity were significantly greater in all dosed groups compared to the vehicle controls at weeks 14, 31, and 53. Determinations of PCB 126 and PCB 118 Concentrations in Tissues: The tissue disposition of PCB 126 and PCB 118 was analyzed in the liver, lung, fat, and blood of up to 10 rats in each group at the 14-, 31-, and 53-week interim evaluations, except for the 360 ng TEQ/kg group at 53 weeks. The tissue disposition of PCB 126 and PCB 118 was also analyzed in 10 rats per group at the end of the 2-year study in the vehicle control, 7, 22, and 72 ng TEQ/kg core study groups and the 360 ng TEQ/kg stop-exposure group. Detectable concentrations of PCB 126 and PCB 118 were observed in the liver, fat, lung, and blood. The highest levels of PCB 126 were seen in the liver whereas the highest levels of PCB 118 were seen in the fat. In general, tissue concentrations increased with increasing doses of the mixture and increasing duration of exposure. Hepatic levels of PCB 126 and PCB 118 in the 72 ng TEQ/kg group at the end of the 2-year study were 284 ng/g and 3,769 ng/g, respectively. On a TCDD equivalents basis this corresponds to 28 ng TEQ/g and 0.4 ng TEQ/g for PCB 126 and PCB 118, respectively. Cessation of administration of the mixture in the stop-exposure group led to declines in the tissue concentrations of both PCB 126 and PCB 118 to levels comparable to those observed in the 7 ng TEQ/kg group at the end of the 2-year study. Pathology and Statistical Analyses: At 14, 31, and

  15. Toxicology and carcinogenesis studies of a mixture of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (Cas No. 1746-01-6), 2,3,4,7,8-pentachlorodibenzofuran (PeCDF) (Cas No. 57117-31-4), and 3,3',4,4',5-pentachlorobiphenyl (PCB 126) (Cas No. 57465-28-8) in female Harlan Sprague-Dawley rats (gavage studies).

    2006-09-01

    CDF, and 333 ng/kg PCB 126. Up to 10 rats per group were evaluated at 14, 31, or 53 weeks. Survival of all dosed groups of rats was similar to that of the vehicle control group. Mean body weights of the 22 and 46 ng TEQ/kg groups were less than those of the vehicle control groups after week 69 of the study. Mean body weights of the 100 ng TEQ/kg group were less than those of the vehicle control group after week 37 of the study. Thyroid Hormone Concentrations: Alterations in serum thyroid hormone concentrations were evaluated at the 14-, 31-, and 53-week interim evaluations. At 14, 31, and 53 weeks, there were dose-dependent reductions in total serum and free thyroxine concentrations. There were dose-dependent increases in serum triiodothyronine concentrations at 14 and 31 weeks. No changes in serum thyroid stimulating hormone concentrations were observed at any time point. Hepatic Cell Proliferation Data: To evaluate hepatocyte replication, analysis of labeling of replicating hepatocytes with 5-bromo-2'-deoxyuridine was conducted at the interim evaluations. At 14 weeks, no effects on the hepatocellular labeling index were observed in the dosed groups compared to the vehicle controls. At 31 and 53 weeks, the hepatocellular labeling index was significantly higher in the 46 and 100 ng TEQ/kg groups compared to the vehicle controls. Cytochrome P450 Enzyme Activities: To evaluate the expression of known dioxin-responsive genes, CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) activity and CYP1A2-associated acetanilide-4-hydroxylase (A4H) activity were evaluated at the interim time points. Liver and lung EROD (CYP1A1) activities and hepatic A4H (CYP1A2) activities were significantly greater in all dosed groups than in the vehicle controls at all interim evaluations (14, 31, and 53 weeks). Determinations of TCDD, PeCDF, and PCB 126 Concentrations in Tissues: Tissue concentrations of TCDD, PeCDF, and PCB 126 were analyzed in the fat, liver, lung, and blood at each interim

  16. Toxicology and carcinogenesis studies of 2,3,4,7,8-pentachlorodibenzofuran (PeCDF) (Cas No. 57117-31-4) in female Harlan Sprague-Dawley rats (gavage studies).

    2006-09-01

    free and total T(4) concentrations and increases in serum T(3) levels. Serum TSH levels in dosed groups at 31 and 53 weeks were not significantly different than in the vehicle controls. Hepatic Cell Proliferation Data: To evaluate hepatocyte replication, analysis of labeling of replicating hepatocytes with 5-bromo-2'-deoxyuridine (BrdU) was conducted at the 14-, 31-, and 53-week interim evaluations. At 14 and 53 weeks, hepatocyte BrdU-labeling indices were significantly higher in the 200 ng/kg groups compared to time-matched vehicle controls. No significant differences were observed between the dosed groups and vehicle controls at 31 weeks. Cytochrome P450 Enzyme Activities: To evaluate the expression of known dioxin-responsive genes, CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) activity and CYP1A2-associated acetanilide-4-hydroxylase (A4H) activity were evaluated at the 14-, 31-, and 53-week interim evaluations. Hepatic EROD and A4H activities were significantly higher in all groups administered PeCDF relative to the vehicle controls at all three interim evaluations. Pulmonary EROD was also significantly higher in all dosed groups compared to vehicle controls at 14, 31, and 53 weeks. Determinations of PeCDF Concentrations in Tissues: The tissue disposition of PeCDF was analyzed in the liver, lung, fat, and blood of all animals at the 14-, 31-, and 53-week interim evaluations, and in 10 animals per group at the end of the 2-year study (105 weeks). In the liver of vehicle controls, PeCDF concentrations were detectable at 105 weeks. Measurable concentrations of PeCDF were not detected in fat or lung from vehicle control rats at any of the interim evaluations or at 105 weeks. Hepatic and fat concentrations were higher in groups with increasing doses of PeCDF, demonstrating a dose-related increase in tissue burden of PeCDF at each time point. No measurable concentrations of PeCDF were detected in the lungs of vehicle controls or any of the dosed groups at 14

  17. NTP technical report on the toxicology and carcinogenesis studies of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (CAS No. 1746-01-6) in female Harlan Sprague-Dawley rats (Gavage Studies).

    2006-04-01

    year 2 of the study, and those of 22 ng/kg rats were less than those of the vehicle controls the last 10 weeks of the study. THYROID HORMONE CONCENTRATIONS: Alterations in serum thyroid hormone levels were evaluated at the 14-, 31- and 53-week interim evaluations. At 14 weeks, there were significant decreases in serum total and free thyroxine (T4) levels and increases in serum total triiodothyronine (T3) and thyroid stimulating hormone (TSH). At 31 weeks, there were significant decreases in serum total and free T4 levels and increases in serum total T3 but no significant effect on TSH. At 53 weeks, there were significant decreases in serum total T4 levels and increases in serum total T3. There were no significant effects on total T4 or TSH levels. HEPATIC CELL PROLIFERATION DATA: To evaluate hepatocyte replication, analysis of labeling of replicating hepatocytes with 5-bromo-2'-deoxyuridine was conducted at the 14-, 31-, and 53-week interim evaluations. The hepatocellular labeling index was significantly higher in the 22 ng/kg group compared to vehicle controls at 14 weeks. At the 31-week interim evaluation, the labeling indices in hepatocytes were significantly higher in all dosed groups than in the vehicle controls. At 53 weeks, labeling indices were significantly higher in the 46 and 100 ng/kg groups than in the vehicle controls. CYTOCHROME P450 ENZYME ACTIVITIES: To evaluate the expression of known dioxin-responsive genes, CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) activity and CYP1A2-associated acetanilide-4-hydroxylase (A4H) activity were evaluated at 14, 31, and 53 weeks. In addition, pentoxyresorufin-O-deethylase (PROD) activity was analyzed. Hepatic EROD, PROD, and A4H activities were significantly higher in all dosed groups relative to vehicle controls at the 14-, 31-, and 53-week interim evaluations. Pulmonary EROD was also significantly higher in all dosed groups compared to vehicle controls at 14, 31, and 53 weeks. DETERMINATIONS OF TCDD

  18. NTP toxicology and carcinogenesis studies of 3,3',4,4',5-pentachlorobiphenyl (PCB 126) (CAS No. 57465-28-8) in female Harlan Sprague-Dawley rats (Gavage Studies).

    2006-01-01

    ENZYME ACTIVITIES: To evaluate the expression of known dioxin-responsive genes, CYP1A1 associated 7-ethoxyresorufin-O-deethylase (EROD) activity and CYP1A2-associated acetanilide 4-hydroxylase (A-4-H) activity were evaluated at the 14-, 31-, and 53-week interim evaluations. In addition, CYP2B associated pentoxyresorufin-O-deethylase (PROD) activity was also analysed. Hepatic PROD (CYP2B1) and hepatic and pulmonary EROD (CYP1A1) activity were significantly greater in all dosed groups than in vehicle controls at weeks 14, 31, and 53. Hepatic A-4-H (CYP1A2) activity was significantly greater in the 30, 100, 175, 300, 550, and 1,000 ng/kg groups compared to vehicle controls at weeks 14, 31, and 53. DETERMINATIONS of PCB 126 CONCENTRATIONS IN TISSUES: The tissue disposition of PCB 126 was analyzed in the liver, lung, fat, and blood of all rats in vehicle controls and all dosed groups at the 14-, 31-, and 53-week interim evaluations and in 10 rats per group including vehicle controls at the end of the 2-year study (104 weeks). Detectable concentrations of PCB 126 were observed in the liver, fat, lung, and blood. Measurable concentrations of PCB 126 were present in the liver and fat at weeks 31, 53, and 104. Hepatic and fat concentrations increased with increasing doses of PCB 126. Measurable concentrations of PCB 126 were present in vehicle control lung tissue at 53 and 104 weeks. No PCB 126 was observed in the blood from the vehicle control rats. Lung and blood concentrations tended to increase with increasing doses of PCB 126, with a few exceptions. In the stop-exposure group, PCB 126 concentrations in liver and fat were lower than the levels observed in the 30 ng/kg group. In the stop-exposure group, lung tissue PCB 126 concentrations were equivalent to the levels observed in the 30 ng/kg group. In blood from the stop-exposure group, PCB 126 concentrations were equivalent to the levels observed in the 100 ng/kg group. PATHOLOGY AND STATISTICAL ANALYSES: Absolute and

  19. Toxicology and carcinogenesis studies of a binary mixture of 3,3',4,4',5-pentachlorobiphenyl (PCB 126) (Cas No. 57465-28-8) and 2,2',4,4',5,5'-hexachlorobiphenyl (PCB 153) (CAS No. 35065-27-1) in female Harlan Sprague-Dawley rats (gavage studies).

    2006-08-01

    Group 6, which had the highest proportion of PCB 153 compared to the other varying ratio groups. Cytochrome P450 Enzyme Activities: To evaluate the expression of known PCB 126-responsive genes, CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) and CYP1A2-associated acetanilide-4-hydroxylase (A4H) activities were evaluated at the 14-, 31-, and 53-week interim evaluations. In addition, PCB 153-inducible CYP2B-associated 7-pent-oxyresorufin-O-dealkylase (PROD) activity was analyzed. In the constant ratio Groups 2, 3, 5, and 7, hepatic and pulmonary EROD (CYP1A1) activities, hepatic A4H (CYP1A2) activities, and hepatic PROD (CYP2B) activities were significantly greater in all dosed groups compared to the vehicle controls at weeks 14, 31, and 53. In the varying ratio groups, hepatic EROD, A4H, and PROD activities at 14 weeks were higher in groups receiving a greater proportion of PCB 153 in the PCB mixture. At 31 and 53 weeks, hepatic CYP1A1 and CYP1A2 enzyme activities in Group 6 were generally lower than in Groups 4 and 5. Determinations of PCB 126 and PCB 153 Concentrations in Tissues: Concentrations of PCB 126 and PCB 153 were determined in fat, liver, lung, and blood at the 14-, 31-, and 53-week interim evaluations and at the end of the 2-year study (105 weeks). PCB 126 was not detectable in vehicle control animals, but increased with increasing dose of PCB 126 and duration of exposure; the highest concentrations were found in liver and fat, and lower levels were seen in lung and blood. Increasing the proportion of PCB 153 in the mixture relative to PCB 126 led to a general decrease in the amount of PCB 126 in liver and lung at the later time points, whereas in fat and blood, there was generally either no effect of PCB 153 on the disposition of PCB 126, or there was an increase in the amount of PCB 126 in the tissue. In vehicle control animals, PCB 153 was detectable in the fat at all time points, in the lung at all time points except 53 weeks, and in the liver