QSAR for Acetylcholinesterase Inhibition and Toxicity of Two Classes of Phosphoramidothioates

References

• Voss , G. , Neumann , R. and Kobel , W. 1995 . “ Economy-society-environment: How fit are organophosphorus insecticides? ” . In Progress and Prospects of Organophosphorus Agrochemicals , Edited by: Eto , M. and Casida , J. E. 31 – 41 . Fukuoka, , Japan : Kyushu University Press .
   Google Scholar
• Quistad , G. B. , Fukuto , T. R. and Metcalf , R. L. 1970 . Insecticidal, anticholinesterase and hydrolytic properties of phosphoramidothiolates . J. Agr. Food Chem. , 18 : 189 – 194 .
   PubMed Web of Science ®Google Scholar
• Crisp , C. E. and Look , M. 1982 . Effect of esterification and side-chain alkylation on alteration of translocation characteristics of methamidophos . Xenobiotica , 12 : 469 – 479 .
   PubMed Web of Science ®Google Scholar
• Robinson , C. P. and Beiergrohslein , D. 1980 . Cholinesterase inhibition by methamidophos and its subsequent reactivation . Pest. Biochem. Phys. , 13 : 267 – 273 .
   Google Scholar
• Ware , G. W. 1989 . The Pesticide Book. , Third edition 340 Fresno, California : Thomson publications .
   Google Scholar
• Khasawinah , A. M. A. , March , R. B. and Fukuto , T. R. 1978 . Insecticidal properties, antiesterase activities, and metabolism of methamidophos . Pestic. Biochem. Physiol. , 9 : 211 – 221 .
   Google Scholar
• Eto , M. , Okabe , S. , Ozoe , Y. and Maekawa , K. 1977 . Oxidative activation of O,S-dimethyl phosphoramidothiolate . Pestic. Biochem. Physiol. , 7 : 367 – 377 .
   Web of Science ®Google Scholar
• Bull , D. L. 1979 . Fate and efficacy of acephate after application to plants and insects . J. Agric. Food Chem. , 27 : 268 – 272 .
   Web of Science ®Google Scholar
• Kao , T. S. and Fukuto , T. R. 1977 . Metabolism of O,S-dimethyl-, propionyl- and hexanoyl phosphoramidothioate in the housefly and white mouse . Pestic. Biochem. Physiol. , 7 : 83 – 95 .
   Web of Science ®Google Scholar
• Suksayretrup , P. and Plapp , F. W. Jr. 1977 . Mechanisms by which methamidophos and acephate circumvent resistance to organophosphate insecticide in the housefly . J. Agric. Food Chem. , 25 : 481 – 485 .
   PubMed Web of Science ®Google Scholar
• Magee , P. S. 1982 . “ Structure-activity relationships in phosphoramidates ” . In Insecticide Mode of Action , Edited by: Coats , J. R. 101 – 161 . Academic Press, Inc. .
   Google Scholar
• Hussain , M. A. 1987 . Anticholinesterase properties of methamidophos and acephate in insects and mammals . Bull. Environ. Contam. Toxicol. , 38 : 131 – 138 .
   PubMedGoogle Scholar
• Behera , B. C. and Bhunya , S. P. 1989 . Studies on the genotoxicity of asataf (acephate), an organophosphate insecticide, in a mammalian in vivo system . Mut. Res. , 223 : 287 – 293 .
   PubMedGoogle Scholar
• Singh , A. K. 1984 . Improved analysis of acephate and methamidophos in biological samples by selective ion monitoring gas-chromatography-mass spectrometry . J. Chromatogr. , 301 : 465 – 469 .
   PubMedGoogle Scholar
• Mahajna , M. , Quistad , G. B. and Casida , J. E. 1997 . Acephate insecticide toxicity: Safety conferred by inhibition of the bioactivating carboxyamidase by the metabolite methamidophos . Chem. Res. Toxicol. , 10 : 64 – 69 .
   PubMed Web of Science ®Google Scholar
• Singh , A. K. 1986 . Kinetic analysis of acetylcholinesterase inhibition by combination of acephate and methamidophos . Toxicology , 42 : 143 – 156 .
   PubMedGoogle Scholar
• Singh , A. K. 1990 . Molecular properties and inhibition kinetics of acetylcholinesterase from rat brain and cockroach ganglion . Toxicol. Ind. Health , 6 : 551 – 570 .
   PubMedGoogle Scholar
• Magee , P. S. 1974 . Structure and bioactivity of orthene insecticide analogs . Residue Rev. , 53 : 3 – 18 .
   Google Scholar
• Mekenyan , O. , Karabunarliev , S. and Bonchev , D. 1990 . The microcomputer OASIS system for predicting the biological activity of chemical compounds . Comput. Chem. , 14 : 193 – 200 .
   Google Scholar
• Mekenyan , O. , Karabunarliev , S. and Bonchev , D. 1990 . The OASIS concept for predicting the biological activity of chemical compounds . J. Math. Chem. , 4 : 207 – 215 .
   Web of Science ®Google Scholar
• Mekenyan , O. , Karabunarliev , S. , Ivanov , J. and Dimitrov , D. 1994 . A new development of the OASIS computer system for modeling molecular properties . Computers Chem. , 18 : 173 – 187 .
   Google Scholar
• Stewart , J. J. P. 1985 . MOPAC6. , USA : Frank J. Seiler laboratory, US Air Force Acad., Fort Collins, CO .
   Google Scholar
• Hansch , C. and Leo , A. 1979 . “ Substituent Constants for Correlation Analysis in Chemistry and Biology ” . 339 New York : Wiley and Sons .
   Google Scholar
• Viswanadhan , V. N. , Ghose , A. K. , Revankar , G. R. and Robins , R. K. 1989 . Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics . J. Chem. Inf. Comput. Sci. , 29 : 163 – 172 .
   Google Scholar
• Barton , A. 1983 . “ Handbook of Solubility Parameters and Other Cohesion Parameters ” . 594 Boca Raton : CRC press .
   Google Scholar
• Mekenyan , O. G. , Ivanov , J. M. , Veith , G. D. and Bradbury , S. P. 1994 . Dynamic QSAR: A new search for active conformations and significant stereoelectronic indices . Quant. Struct.-Act. Relat. , 13 : 302 – 307 .
   Google Scholar
• Johnson , H. , Kenley , R. A. , Rynard , C. and Golub , M. A. 1985 . QSAR for cholinesterase inhibition by organophosphorus esters and CNDO/2 calculations for organophosphorus ester hydrolysis . Quant. Struct.-Act. Relat. , 4 : 172 – 180 .
   Web of Science ®Google Scholar
• Sussman , J. L. , Harel , M. , Frolow , F. , Oefner , C. , Goldman , A. , Toker , L. and Silman , I. 1991 . Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein . Science , 253 : 872 – 879 .
   PubMed Web of Science ®Google Scholar
• Taylor , P. and Radic , Z. 1994 . The cholinesterases: From genes to proteins . Annu. Rev. Pharmacol. Toxicol. , 34 : 281 – 320 .
   PubMed Web of Science ®Google Scholar
• Taylor , P. , Radic , Z. , Hosea , N. , Camp , S. , Marchot , P. and Berman , H. 1995 . Structural bases for the specificity of cholinesterase catalysis and inhibition . Toxicol. Letters , 82/83 : 453 – 458 .
   Google Scholar
• Fournier , D. , Karch , F. , Bride , J.-M. , Hall , L. , Berge , J.-B. and Spierer , P. 1989 . Drosophila melanogaster acetylcholinesterase gene. Structure, evolution and mutations . J. Mol. Biol. , 210 : 15 – 22 .
   PubMedGoogle Scholar
• Mutero , A. and Fournier , D. 1992 . Post-translational modifications of Drosophila acetylcholinesterase . J. Biol. Chem. , 267 : 1695 – 1700 .
   PubMed Web of Science ®Google Scholar
• Hall , L. and Spierer , P. 1986 . The Ace locus of Drosophila melanogaster: Structural gene for acetylcholinesterase with an unusual 5' leader . EMBO J. , 5 : 2949 – 2954 .
   PubMed Web of Science ®Google Scholar
• Fournier , D. , Bride , J.-M. , Karch , F. and Berge , J.-B. 1988 . Acetylcholinesterase from Drosophila melanogaster. Identification of two subunits encoded by the same gene . FEBS Lett. , 238 : 333 – 337 .
   PubMedGoogle Scholar
• Singh , A. K. , White , T. , Spassova , D. and Jiang , Y. 1998 . Physicochemical, molecular-orbital and electronic properties of acephate and methamidophos . Comp. Biochem. Physiol. , 119C ( 1 ) : 107 – 117 .
   Google Scholar