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Volumn 19, Issue 2, 2006, Pages 209-216

Mechanistic insight into acetylcholinesterase inhibition and acute toxicity of organophosphorus compounds: A molecular modeling study

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; LIGAND; ORGANOPHOSPHORUS COMPOUND;

EID: 33644510766     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050090r     Document Type: Article
Times cited : (45)

References (53)
  • 1
    • 0004039659 scopus 로고    scopus 로고
    • Taylor and Francis, London and New York
    • Flanagan, J., and Jones, A. L. (2001) Antidotes, pp 87-114, Taylor and Francis, London and New York.
    • (2001) Antidotes , pp. 87-114
    • Flanagan, J.1    Jones, A.L.2
  • 2
    • 0002783901 scopus 로고    scopus 로고
    • Organophosphates
    • (Wexler, P., Ed.), Academic Press, San Diego, CA
    • Enrich, M. (1998) Organophosphates. In Encyclopedia of Toxicology (Wexler, P., Ed.) pp 467-471, Academic Press, San Diego, CA.
    • (1998) Encyclopedia of Toxicology , pp. 467-471
    • Enrich, M.1
  • 3
    • 0026751004 scopus 로고
    • Chemical warfare agents: II. Nerve agents
    • Sidell, F. R., and Borak, J. (1992) Chemical warfare agents: II. Nerve agents. Ann. Emerg. Med. 21, 865-871.
    • (1992) Ann. Emerg. Med. , vol.21 , pp. 865-871
    • Sidell, F.R.1    Borak, J.2
  • 4
    • 0027281533 scopus 로고
    • Organophosphate poisoning
    • Marrs, T. C. (1993) Organophosphate poisoning. Pharmacol. Ther. 58, 51-66.
    • (1993) Pharmacol. Ther. , vol.58 , pp. 51-66
    • Marrs, T.C.1
  • 5
    • 0025778840 scopus 로고
    • Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein
    • 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.
    • (1991) Science , vol.253 , pp. 872-879
    • Sussman, J.L.1    Harel, M.2    Frolow, F.3    Oefner, C.4    Goldman, A.5    Toker, L.6    Silman, I.7
  • 6
    • 0038682446 scopus 로고    scopus 로고
    • Acetylcholinesterase active centre and gorge conformations analysed by combinatorial mutations and enantiomeric phosphonates
    • Kovarik, Z., Radic, Z., Berman, H. A., Simeon-Rudolf, V., Reiner, E., and Taylor, P. (2003) Acetylcholinesterase active centre and gorge conformations analysed by combinatorial mutations and enantiomeric phosphonates. Biochem. J. 373, 33-40.
    • (2003) Biochem. J. , vol.373 , pp. 33-40
    • Kovarik, Z.1    Radic, Z.2    Berman, H.A.3    Simeon-Rudolf, V.4    Reiner, E.5    Taylor, P.6
  • 8
    • 0033369584 scopus 로고    scopus 로고
    • Organophosphorus pesticides: Do they all have the same mechanism of toxicity?
    • Pope, C. N. (1999) Organophosphorus pesticides: do they all have the same mechanism of toxicity? J. Toxicol. Environ. Health. Part B 2, 161-181.
    • (1999) J. Toxicol. Environ. Health. Part B , vol.2 , pp. 161-181
    • Pope, C.N.1
  • 9
    • 1842425982 scopus 로고    scopus 로고
    • Physicochemical and biological data for the development of predictive organophosphorus pesticide QSARs and PBPK/PD models for human risk assessment
    • Knaak, J. B., Dary, C. C., Power, F., Thompson, C. B., and Blancato, J. N. (2004) Physicochemical and biological data for the development of predictive organophosphorus pesticide QSARs and PBPK/PD models for human risk assessment. Crit. Rev. Toxicol. 34, 143-207.
    • (2004) Crit. Rev. Toxicol. , vol.34 , pp. 143-207
    • Knaak, J.B.1    Dary, C.C.2    Power, F.3    Thompson, C.B.4    Blancato, J.N.5
  • 10
    • 0035468084 scopus 로고    scopus 로고
    • Towards improved acetylcholinesterase inhibitors: A structural and computational approach
    • Barril, X., Orozco, M., and Luque, F. J. (2001) Towards improved acetylcholinesterase inhibitors: a structural and computational approach. Mini Rev. Med. Chem. 1, 255-266.
    • (2001) Mini Rev. Med. Chem. , vol.1 , pp. 255-266
    • Barril, X.1    Orozco, M.2    Luque, F.J.3
  • 11
    • 0037125501 scopus 로고    scopus 로고
    • Studying enzyme binding specificity in acetylcholinesterase using a combined molecular dynamics and multiple docking approach
    • Kua, J., Zhang, Y., and McCammon, J. A. (2002) Studying enzyme binding specificity in acetylcholinesterase using a combined molecular dynamics and multiple docking approach. J. Am. Chem. Soc. 124, 8260-8267.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8260-8267
    • Kua, J.1    Zhang, Y.2    McCammon, J.A.3
  • 12
    • 6044238257 scopus 로고    scopus 로고
    • A docking score function for estimating ligand-protein interactions: Application to acetylcholinesterase inhibition
    • Guo, J.-X., Hurley, M. M., Wright, J. B., and Lushington, G. H. (2004) A docking score function for estimating ligand-protein interactions: application to acetylcholinesterase inhibition. J. Med. Chem. 47, 5492-5500.
    • (2004) J. Med. Chem. , vol.47 , pp. 5492-5500
    • Guo, J.-X.1    Hurley, M.M.2    Wright, J.B.3    Lushington, G.H.4
  • 14
    • 0033610449 scopus 로고    scopus 로고
    • Reaction products of acetylcholinesterase and VX reveal a mobile histidine in the catalytic triad
    • Millard, C. B., Koellner, G., Ordentlich, A., Shafferman, A., Silman, I., and Sussman, J. L. (1999) Reaction products of acetylcholinesterase and VX reveal a mobile histidine in the catalytic triad. J. Am. Chem. Soc. 121, 9883-9884.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9883-9884
    • Millard, C.B.1    Koellner, G.2    Ordentlich, A.3    Shafferman, A.4    Silman, I.5    Sussman, J.L.6
  • 15
    • 0037413712 scopus 로고    scopus 로고
    • Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site
    • Bourne, Y., Taylor, P., Radic, Z., and Marchot, P. (2003) Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site. EMBO J. 22, 1-12.
    • (2003) EMBO J. , vol.22 , pp. 1-12
    • Bourne, Y.1    Taylor, P.2    Radic, Z.3    Marchot, P.4
  • 16
    • 0027470996 scopus 로고
    • Cloning and expression of a rat acetylcholinesterase subunit: Generation of multiple molecular forms and complementarity with a Torpedo collagenic subunit
    • Legay, C., Bon, S., Vernier, P., Coussen, F., and Massoulie, J. (1993) Cloning and expression of a rat acetylcholinesterase subunit: generation of multiple molecular forms and complementarity with a Torpedo collagenic subunit. J. Neurochem. 60, 337-346.
    • (1993) J. Neurochem. , vol.60 , pp. 337-346
    • Legay, C.1    Bon, S.2    Vernier, P.3    Coussen, F.4    Massoulie, J.5
  • 17
    • 84988053694 scopus 로고
    • An all atom force field for simulations of proteins and nucleic acids
    • Weiner, S. J., Kollman, P. A., Nguyen, D. T., and Case, D. A. (1986) An all atom force field for simulations of proteins and nucleic acids. J. Comput. Chem. 7, 230-252.
    • (1986) J. Comput. Chem. , vol.7 , pp. 230-252
    • Weiner, S.J.1    Kollman, P.A.2    Nguyen, D.T.3    Case, D.A.4
  • 18
    • 5544242529 scopus 로고    scopus 로고
    • MMFF VI. MMFF94s option for energy minimization studies
    • Halgren, T. A. (1999) MMFF VI. MMFF94s option for energy minimization studies. J. Comput. Chem. 20, 720-729.
    • (1999) J. Comput. Chem. , vol.20 , pp. 720-729
    • Halgren, T.A.1
  • 21
    • 33644544479 scopus 로고
    • Stewart Computational Chemistry, Colorado Springs, CO.
    • Stewart, J. J. P. (1993) MOPAC7, version 7, Stewart Computational Chemistry, Colorado Springs, CO.
    • (1993) MOPAC7, Version 7
    • Stewart, J.J.P.1
  • 22
    • 0000782536 scopus 로고
    • A new approach to probing conformational space with molecular mechanics: Random incremental pulase search
    • Ferguson, D. M., and Raber, D. J. (1989) A new approach to probing conformational space with molecular mechanics: random incremental pulase search. J. Am. Chem. Soc. 111, 4371-4378.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4371-4378
    • Ferguson, D.M.1    Raber, D.J.2
  • 23
    • 33644516381 scopus 로고    scopus 로고
    • Umereics AB, Umea, Sweden, July
    • SIMCA-P, Umereics AB, Umea, Sweden, July, 2001.
    • (2001) SIMCA-P
  • 24
    • 21144467893 scopus 로고
    • Hydrogen-bonding capacity and brain pentration
    • Van der Waterbeemed, H., and Kansy, M. (1992) Hydrogen-bonding capacity and brain pentration. Chimia 46, 299-303.
    • (1992) Chimia , vol.46 , pp. 299-303
    • Van Der Waterbeemed, H.1    Kansy, M.2
  • 25
    • 5444258177 scopus 로고    scopus 로고
    • ADME evaluation in drug discovery. 5. Correlation of Caco-2 permeation with simple molecular properties
    • Hou, T. J., Zhang, W., Xia, K., Qiao, X. B., and Xu, X. J. (2004) ADME evaluation in drug discovery. 5. Correlation of Caco-2 permeation with simple molecular properties. J. Chem. Inf. Comput. Sci. 44, 1585-1600.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1585-1600
    • Hou, T.J.1    Zhang, W.2    Xia, K.3    Qiao, X.B.4    Xu, X.J.5
  • 26
    • 0035498339 scopus 로고    scopus 로고
    • Development of quantitative structure-property relationship models for early ADME evaluation in drug discovery. 2. Blood-brain barrier penetration
    • Liu, R., Sun, H., and So, S.-S. (2001) Development of quantitative structure-property relationship models for early ADME evaluation in drug discovery. 2. Blood-brain barrier penetration. J. Chem. Inf. Comput. Sci. 41, 1623-1632.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 1623-1632
    • Liu, R.1    Sun, H.2    So, S.-S.3
  • 29
    • 0001751073 scopus 로고
    • Structure-activity relationship of the organophosphorus anticholinesterase agents
    • Holmstedt, B. (1963) Structure-activity relationship of the organophosphorus anticholinesterase agents. Handb. Exp. Toxicol. 15, 428-485.
    • (1963) Handb. Exp. Toxicol. , vol.15 , pp. 428-485
    • Holmstedt, B.1
  • 31
    • 0142205282 scopus 로고    scopus 로고
    • Effects on acute organophosphorus poisoning in rats in aging and solubility of organophosphates
    • Yamanaka, S., Ohta, K., Tamita, Y., Takayanagi, A., Nomura, T., and Takaesu, Y. (1996) Effects on acute organophosphorus poisoning in rats in aging and solubility of organophosphates. Environ. Health Prev. Med. 1, 119-127.
    • (1996) Environ. Health Prev. Med. , vol.1 , pp. 119-127
    • Yamanaka, S.1    Ohta, K.2    Tamita, Y.3    Takayanagi, A.4    Nomura, T.5    Takaesu, Y.6
  • 32
    • 0018853395 scopus 로고
    • Quantitative high-performance liquid chromatography and mass spectrometry for the analysis of the in vitro metabolism of the insecticide azinphos-methyl (guthion) by rat liver homogenates
    • Lin, S. N., Chen, C. Y., Murphy, S. D., and Caprioli, R. M. (1980) Quantitative high-performance liquid chromatography and mass spectrometry for the analysis of the in vitro metabolism of the insecticide azinphos-methyl (guthion) by rat liver homogenates. J. Agric. Food Chem. 28, 85-88.
    • (1980) J. Agric. Food Chem. , vol.28 , pp. 85-88
    • Lin, S.N.1    Chen, C.Y.2    Murphy, S.D.3    Caprioli, R.M.4
  • 33
    • 0014822491 scopus 로고
    • Nature of oxidative metabolites of dimethoate formed in rats, liver microsomes, and bean plants
    • Lucier, G. W., and Menzer, R. E. (1970) Nature of oxidative metabolites of dimethoate formed in rats, liver microsomes, and bean plants. J. Agric. Food Chem. 18, 698-704.
    • (1970) J. Agric. Food Chem. , vol.18 , pp. 698-704
    • Lucier, G.W.1    Menzer, R.E.2
  • 34
    • 0016606195 scopus 로고
    • Gas-liquid chromatographic determination of ethion, ethion monooxon, and ethion dioxon in tissues of turkeys and cattle
    • Ivey, M. C., and Mann, H. D. (1975) Gas-liquid chromatographic determination of ethion, ethion monooxon, and ethion dioxon in tissues of turkeys and cattle. J. Agric. Food Chem. 23, 319-321.
    • (1975) J. Agric. Food Chem. , vol.23 , pp. 319-321
    • Ivey, M.C.1    Mann, H.D.2
  • 35
    • 0347226280 scopus 로고
    • Relation between metabolism and differential toxicity of malathion in insects and mice
    • Krueger, H. R., and O'Brien, R. D. (1959) Relation between metabolism and differential toxicity of malathion in insects and mice. J. Econ. Entomol. 52, 1063-1067.
    • (1959) J. Econ. Entomol. , vol.52 , pp. 1063-1067
    • Krueger, H.R.1    O'Brien, R.D.2
  • 36
    • 0019829316 scopus 로고
    • Studies on the in vitro metabolism of methidathion by rat and mouse liver
    • Chopade, H. M., and Dauterman, W. C. (1981) Studies on the in vitro metabolism of methidathion by rat and mouse liver. Pestic. Biochem. Physiol. 15, 105-119.
    • (1981) Pestic. Biochem. Physiol. , vol.15 , pp. 105-119
    • Chopade, H.M.1    Dauterman, W.C.2
  • 37
    • 0001234664 scopus 로고
    • Enzymic and immunohistochemical studies on the role of cytochrome p450 and the flavin-containing monooxygenase of mouse skin in the metabolism of pesticides and other xenobiotics
    • Venkatesh, K., Levi, P. E., Inman, A. O., Monteiro-Riveiere, N. A., Misra, R., and Hodgson, E. (1992) Enzymic and immunohistochemical studies on the role of cytochrome p450 and the flavin-containing monooxygenase of mouse skin in the metabolism of pesticides and other xenobiotics. Pestic. Biochem. Physiol. 43, 53-66.
    • (1992) Pestic. Biochem. Physiol. , vol.43 , pp. 53-66
    • Venkatesh, K.1    Levi, P.E.2    Inman, A.O.3    Monteiro-Riveiere, N.A.4    Misra, R.5    Hodgson, E.6
  • 39
    • 0018346376 scopus 로고
    • Effects of sulprofos and its sulfoxide and sulfone metabolites on laying hens fed the compounds in the diet
    • Clark, D. E., Ivie, G. W., Crookshank, H. R., and Devaney, J. A. (1979) Effects of sulprofos and its sulfoxide and sulfone metabolites on laying hens fed the compounds in the diet. J. Agric. Food Chem. 27, 103-107.
    • (1979) J. Agric. Food Chem. , vol.27 , pp. 103-107
    • Clark, D.E.1    Ivie, G.W.2    Crookshank, H.R.3    Devaney, J.A.4
  • 40
    • 0032970576 scopus 로고    scopus 로고
    • Metabolism of terbufos in rat liver
    • Li, J.-T., Sheng, S.-J., and Du, X.-L. (1999) Metabolism of terbufos in rat liver. J. Occup. Health 41, 62-68.
    • (1999) J. Occup. Health , vol.41 , pp. 62-68
    • Li, J.-T.1    Sheng, S.-J.2    Du, X.-L.3
  • 41
    • 69749113251 scopus 로고
    • Insecticide metabolism and mode of action
    • Fukuto, T. R. (1978) Insecticide metabolism and mode of action. Pure Appl. Chem. 50, 9-10.
    • (1978) Pure Appl. Chem. , vol.50 , pp. 9-10
    • Fukuto, T.R.1
  • 42
    • 0035990650 scopus 로고    scopus 로고
    • LC_MS determination of oxydemeton-methyl and its main metabolite demeton-s-methylsulfon in biological sepcimens-applicatin to a forensic case
    • Beike, J., Ortmann, C., Meiners, T., Brinkmann, B., and Kohler, H. (2002) LC_MS determination of oxydemeton-methyl and its main metabolite demeton-s-methylsulfon in biological sepcimens-applicatin to a forensic case. J. Anal. Toxicol. 25, 308-312.
    • (2002) J. Anal. Toxicol. , vol.25 , pp. 308-312
    • Beike, J.1    Ortmann, C.2    Meiners, T.3    Brinkmann, B.4    Kohler, H.5
  • 44
    • 0035877333 scopus 로고    scopus 로고
    • Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography
    • Abu-Qare, A. W., and Abou-Donia, M. B. (2001) Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography. J. Chromatogr., B: Biomed. Sci. Appl. 757, 295-300.
    • (2001) J. Chromatogr., B: Biomed. Sci. Appl. , vol.757 , pp. 295-300
    • Abu-Qare, A.W.1    Abou-Donia, M.B.2
  • 45
    • 0022904839 scopus 로고
    • Fate and metabolism of the radiolabeled insecticide coumaphos in egyptian lactating goats
    • Osman, A. Z., Zayed, S. M. A. F. D., and Hazzaa, N. I. (1986) Fate and metabolism of the radiolabeled insecticide coumaphos in egyptian lactating goats. Isot. Radiat. Res. 18, 139-146.
    • (1986) Isot. Radiat. Res. , vol.18 , pp. 139-146
    • Osman, A.Z.1    Zayed, S.M.A.F.D.2    Hazzaa, N.I.3
  • 47
    • 0025856512 scopus 로고
    • Metabolic activation of the organophosphorus insecticides chlorpyrifos and fenitrothion by perfused rat liver
    • Sultatos, L. G. (1991) Metabolic activation of the organophosphorus insecticides chlorpyrifos and fenitrothion by perfused rat liver. Toxicology 68, 1-9.
    • (1991) Toxicology , vol.68 , pp. 1-9
    • Sultatos, L.G.1
  • 48
    • 0026027741 scopus 로고
    • High-performance liquid chromatographic separation of fenthion and its metabolites
    • Cabras, P., Plumitallo, A., and Spanedda, L. (1991) High-performance liquid chromatographic separation of fenthion and its metabolites. J. Chromatogr. 540, 406-410.
    • (1991) J. Chromatogr. , vol.540 , pp. 406-410
    • Cabras, P.1    Plumitallo, A.2    Spanedda, L.3
  • 49
    • 0017111026 scopus 로고
    • Metabolism of O, O-dimethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate in sheep and rats and of 3,5,6-trichloro-2-pyridinol in sheep
    • Bakke, J. E., and Price, C. E. (1976) Metabolism of O, O-dimethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate in sheep and rats and of 3,5,6-trichloro-2-pyridinol in sheep. J. Environ. Sci. Health, Part B 11, 9-22.
    • (1976) J. Environ. Sci. Health, Part B , vol.11 , pp. 9-22
    • Bakke, J.E.1    Price, C.E.2
  • 50
    • 0034618576 scopus 로고    scopus 로고
    • Urinary excretion of metabolites following a single dermal dose of [14C]methyl parathion in pregnant rats
    • Abu-Qare, A. W., and Abou-Donia, M. B. (2000) Urinary excretion of metabolites following a single dermal dose of [14C]methyl parathion in pregnant rats. Toxicology 150, 119-127.
    • (2000) Toxicology , vol.150 , pp. 119-127
    • Abu-Qare, A.W.1    Abou-Donia, M.B.2
  • 51
    • 0026542178 scopus 로고
    • Biotransformation of the insecticide parathion by mouse brain
    • Soranno, T. M., and Sultatos, L. G. (1992) Biotransformation of the insecticide parathion by mouse brain. Toxicol. Lett. 60, 27-37.
    • (1992) Toxicol. Lett. , vol.60 , pp. 27-37
    • Soranno, T.M.1    Sultatos, L.G.2
  • 52
    • 0018797587 scopus 로고
    • High-performance liquid chromatography of pirimiphos methyl and five metabolites
    • Berealey, C. J., and Lawrence, D. K. (1979) High-performance liquid chromatography of pirimiphos methyl and five metabolites. J. Chromatogr. 168, 461-469.
    • (1979) J. Chromatogr. , vol.168 , pp. 461-469
    • Berealey, C.J.1    Lawrence, D.K.2
  • 53
    • 0000233678 scopus 로고
    • Bioactivation of isofenphos and analogs by oxidative N-dealkylation and desulfuration
    • Gorder, G. W., Kirino, O., Hirashima, A., and Casida, J. E. (1986) Bioactivation of isofenphos and analogs by oxidative N-dealkylation and desulfuration. J. Agric. Food Chem. 34, 941-947.
    • (1986) J. Agric. Food Chem. , vol.34 , pp. 941-947
    • Gorder, G.W.1    Kirino, O.2    Hirashima, A.3    Casida, J.E.4


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