Biotransformation of organophosphorus compounds

Toxicology - Tập 166 Số 3 - Trang 139-160 - 2001
Milan Jokanović1
1Department of Toxicology, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000, Belgrade, Yugoslavia.

Tóm tắt

Từ khóa


Tài liệu tham khảo

Abbott, 1995, Serum paraoxonase activity, concentration, and phenotype distribution in Diabetes Mellitus and its relationship to serum lipids and lipoproteins, Aterioscl. Thromb. Vasc. Biol., 15, 1812, 10.1161/01.ATV.15.11.1812

Aldridge, 1953, Serum esterases. I. Two types of esterases (A and B) hydrolysing p-nitrophenyl acetate, propionate, butyrate and a method for their determination, Biochem. J., 53, 110, 10.1042/bj0530110

Anders, 1988, Biosynthesis and biotransformation of glutathione S-conjugates to toxic metabolites, CRC Crit. Rev. Toxicol., 18, 311, 10.3109/10408448809037470

Ashani, 1991, Prophylaxis against organophosphate poisoning by an enzyme hydrolysing organophosphorus compounds in mice, Life Sci., 49, 367, 10.1016/0024-3205(91)90444-G

Augustinsson, 1958, Electrophoretic separation and classification of blood plasma esterases, Nature, 131, 1786, 10.1038/1811786a0

Aviram, 1998, Paraoxonase inhibits high-density lipoprotein oxidation and preserves its function, J. Clin. Invest., 101, 1581, 10.1172/JCI1649

Barril, 1999, Peripheral nerve soluble esterases are spontaneously reactivated after inhibition by paraoxon: implications for a new definition of neuropathy target esterase, Chem. Biol. Interact., 119–120, 541, 10.1016/S0009-2797(99)00068-X

Benning, 1994, Three-dimensional structure of phosphotriesterase: an enzyme capable of detoxifying organophosphate nerve agents, Biochemistry, 33, 15001, 10.1021/bi00254a008

Blatter, 1993, Identification of a distinct human high-density lipoprotein subspecies defined by a lipoprotein assocoated protein, K-45. Identity of K-45 with paraoxonase, Eur. J. Biochem., 211, 871, 10.1111/j.1432-1033.1993.tb17620.x

Bošković, 1979, The influence of 2-(o-cresyl)-4H-1:3:2-benzodioxaphosphorin-2-oxide (CBDP) on organophosphate poisoning and its therapy, Arch. Toxicol., 42, 207, 10.1007/BF00353713

Bošković, 1984, Effects of sarin, soman and tabun on plasma and brain aliesterase activity in the rat, 365

Brealey, 1980, A-esterase activity in relation to the differential toxicity of pirimiphos-methyl to birds and mammals, Pestic. Sci., 11, 546, 10.1002/ps.2780110512

Butler, 1993, Inhibition and inactivation of constitutive cytochromes P450 in rat liver by parathion, Mol. Pharmacol., 43, 902

Butler, 1997, Biotransformation of parathion in human liver: Participation of CYP3A4 and its inactivation during microsomal parathion oxidation, J. Pharmacol. Exp. Ther., 280, 966

Cashman, 1995, Structural and catalytic properties of the mammalian flavin-containing monooxygenase, Chem. Res. Toxicol., 8, 165, 10.1021/tx00044a001

Cashman, 1996, Pharmacokinetics and molecular detoxication, Environ. Health Perspect., 104, 23, 10.1289/ehp.96104s123

Chambers, 1992, The role of target site activation of phosphorothionates in acute toxicity, 229

Clement, 1982, Plasma aliesterase – A possible depot for soman (pinacolylmethyl-phosphonofluoridate) in the mouse, Biochem. Pharmacol., 31, 4085, 10.1016/0006-2952(82)90663-3

Clement, 1984, Role of aliesterase in organophosphate poisoning, Fundam. Appl. Toxicol., 4, S96, 10.1016/0272-0590(84)90141-6

Costa, 1983, Unidirectional cross-tolerance between the carbamate insecticide propoxyr and the organophosphate disulfoton in mice, Fundam. Appl. Toxicol., 3, 483, 10.1016/S0272-0590(83)80024-4

Costa, 1984, Interaction bewteen acetaminophen and organophosphates in mice, Res. Commun. Chem. Pathol. Pharmacol., 44, 389

Costa, 1990, Serum paraoxonase and its influence on paraoxon and chlorpyriphos-oxon toxicity in rats, Toxicol. Appl. Pharmacol., 103, 66, 10.1016/0041-008X(90)90263-T

Dauterman, 1971, Biological and nonbiological modification of organophosphorus compounds, Bull. WHO, 44, 133

Davies, 1975, Human pesticide poisonings by a fat-soluble organophosphate insecticide, Arch. Environ. Health, 30, 608, 10.1080/00039896.1975.10666790

De Jong, 1984, Formation of soman (1,2,2-trimethylpropyl methylphosphonofluoridate) via fluoride-induced reactivation of soman-inhibited aliesterase in rat plasma, Biochem. Pharmacol., 33, 663, 10.1016/0006-2952(84)90323-X

De Matteis, 1974, Covalent binding of sulphur to microsomes and loss of cytochrome P450 during oxidative desulfuration of several chemicals, Molec. Pharmacol., 10, 849

Di Ilio, 1995, Binding of pesticides to alpha, mu and pi class glutathione transferase, Toxicol. Lett., 76, 173, 10.1016/0378-4274(94)03210-X

Dinsdale, 2001, Cell-specific loss of cytochrome P450 2B1 in rat lung following treatment with pneumotoxic and non-pneumotoxic trialkylphosphoro-thioates, Biochem. Pharmacol., 61, 493, 10.1016/S0006-2952(00)00572-4

Dorough, 1983, Toxicological significance of pesticide conjugates, J. Toxicol. Clin. Toxicol., 19, 637, 10.3109/15563658208990396

Ecobichon, 1977, Acute fenitrothion poisoning, Can. Med. Assoc. J., 116, 377

Eto, 1962, Hydroxylation of cyclization reactions involved in the metabolism of tri-o-cresyl phosphate, Biochem. Pharmacol., 11, 337, 10.1016/0006-2952(62)90056-4

Eto, 1974

Fonnum, 1981, Factors modifying the toxicity of organophosphorus compounds including soman and sarin, Fundam. Appl. Toxicol., 1, 143, 10.1016/S0272-0590(81)80050-4

Frawley, 1957, Marked potentiation of mammalian toxicity from simultaneous administration of two anticholinesterase compounds, J. Pharmacol. Exp. Ther., 121, 96

Fukami, 1966, Nature of a soluble glutathione-dependent enzyme system active in cleavage of methyl parathion to desmethyl parathion, J. Econ. Entomol., 59, 1338, 10.1093/jee/59.6.1338

Fukuto, 1969, Metabolism of insecticides in plants and animals, Ann. NY Acad. Sci., 160, 97, 10.1111/j.1749-6632.1969.tb15830.x

Fukuto, 1990, Mechanism of action of organophosphorus and carbamate in-secticides, Environ. Health Perspect., 87, 245, 10.1289/ehp.9087245

Furlong, 2000, The PON1 gene and detoxication, Neurotoxicology, 21, 581

Gallo, 1991, Organic phosphorus pesticides, 2, 917

Geldmacher von Mallincrodt, 1988, The human serum paraoxonase – polymorphism and specificity, Toxicol. Environ. Chem., 18, 79, 10.1080/02772248809357310

Goeptar, 1995, Oxygen and xenobiotic reductase activities of cytochrome P450, CRC Crit. Rev. Toxicol., 25, 25, 10.3109/10408449509089886

Guengerich, 1984, Chemical mechanisms of catalysis by cytochromes P-450: A unified view, Acc. Chem. Res., 17, 9, 10.1021/ar00097a002

Guengerich, 1985, Enzymatic activation of chemicals to toxic metabolites, CRC Crit. Rev. Toxicol., 14, 259, 10.3109/10408448509037460

Gupta, 1985, Mechanisms involved in the development of tolerance of DFP toxicity, Fundam. Appl. Toxicol., 5, S17, 10.1016/0272-0590(85)90111-3

Halpert, 1980, Inactivation of purified rat liver cytochrome P-450 during metabolism of parathion (diethyl-p-nitrophenyl phosphoro-thionate), J. Biol. Chem., 255, 1080, 10.1016/S0021-9258(19)86145-8

Hodgson, 1991, Metabolism, 1, 107

Hosokawa, 1995, Clonning and analysis of cDNA encoding novel carboxylesterase isoenzymes from mammals and humans, Internatl. Toxicologist, 7, 24-PF-7

International Union of Biochemistry, 1992. Enzyme Nomenclature, Recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology on the Nomenclature and Classification of Enzymes. San Diego: Academic Press.

Johnson, 1982, The target for initiation of delayed neurotoxicity by organo-phosphorus esters: biochemical studies and toxicological applications, Rev. Biochem. Toxicol., 4, 141

Jokanović, 1989, Role of carboxylesterase in soman, sarin and tabun poisoning in rats, Pharmacol. Toxicol., 65, 181, 10.1111/j.1600-0773.1989.tb01152.x

Jokanović, 1990, Liver esterases and soman toxicity in the rat following partial hepatectomy, Biochem. Pharmacol., 39, 797, 10.1016/0006-2952(90)90162-E

Jokanović, 1996, Interaction of organophosphorus compounds with carboxylesterases in the rat, Arch. Toxicol., 70, 444, 10.1007/s002040050297

Junge, 1975, The carboxylesterases/amidases of mammalian liver and their possible significance, CRC Crit. Rev. Toxicol., 3, 371, 10.3109/10408447509079864

Kadar, 1985, Distribution of 3H-soman in mice, Arch. Toxicol., 58, 45, 10.1007/BF00292616

Kamataki, 1976, Studies of the metabolism of parathion with an apparently homogenous preparation of rabbit liver microsomal cytochrome P450, Drug Metab. Dispos., 4, 180

Kulkarni, 1980, Metabolism of insecticides by mixed function oxidase systems, Pharmacol. Ther., 8, 379, 10.1016/0163-7258(80)90054-6

La Du, 1993, Studies on human serum paraoxonase/arylesterase, Chem.–Biol. Interact., 87, 25, 10.1016/0009-2797(93)90022-Q

Lauwerys, 1969, Interaction between paraoxon and tri-o-tolyl phosphate in rats, Toxicol. Appl. Pharmacol., 14, 348, 10.1016/0041-008X(69)90116-1

Levi, 1988, Stereospecificity in the oxidation of phorate and phorate sulfoxide by purified FAD-containing monooxygenase and cytochrome P-450 isozymes, Xenobiotica, 18, 29, 10.3109/00498258809055134

Levi, 1992, Metabolism of organophosphorus compounds by the flavin-containing monooxygenase, 141

Li, 1993, Serum paraoxonase status: a major factor in determining resistance to organophosphates, J. Toxicol. Environ. Health, 40, 337, 10.1080/15287399309531798

Li, 1995, Paraoxonase protects against chlorpyrifos toxicity in mice, Toxicol. Lett., 76, 219, 10.1016/0378-4274(95)80006-Y

Lucier, 1970, Nature of oxydative metabolites of dimethoate formed in rats, liver microsomes and bean plants, J. Agric. Food Chem., 18, 698, 10.1021/jf60170a034

Mackness, 1989, A-esterases: enzymes looking for a role?, Biochem. Pharmacol., 38, 385, 10.1016/0006-2952(89)90376-6

Mackness, 1993, Is paraoxonase related to atherosclerosis, Chem.–Biol. Interact., 87, 161, 10.1016/0009-2797(93)90038-Z

Main, 1956, The role of A-esterase in the acute toxicity of paraoxon, TEPP and parathion, Canad. J. Biochem. Physiol., 34, 197, 10.1139/o56-023

Mannervik, 1992, Nomenclature for human glutathione transferases, Biochem. J., 282, 305, 10.1042/bj2820305

Maxwell, D.M. (1989). Nerve agent specificity of scavenger protection by carboxylesterase. Proceedings of the Third International Symposium on Protection Against Chemical Warfare Agents, Umeå, Sweden, 175–182.

Maxwell, 1992, The specificity of carboxylesterase protection against the toxicity of organophosphorus compounds, Toxicol. Appl. Pharmacol., 114, 306, 10.1016/0041-008X(92)90082-4

Motoyama, 1980, Glutathione S-transferases: their role in the metabolism of organophosphorus insecticides, Rev. Biochem. Toxicol., 2, 49

Murphy, 1959, Potentiation of toxicity of malathion by triorthotolyl phosphate, Proc. Soc. Exp. Biol. Med., 100, 382, 10.3181/00379727-100-24668

Nakatsugawa, 1992, Hepatic disposition of organophosphorus insecticides: a synthesis of in vitro, in situ and in vivo data, 201

Nebert, 1994, Cytochrome P450: Evolution and functional diversity, Prog. Liver Dis., 12, 63

Nelson, 1996, P450 superfamily: update on new sequences, gene mapping, accession numbers, and nomenclature, Pharmacogenetics, 6, 1, 10.1097/00008571-199602000-00002

Omiecinski, 1999, Concise review of the cytochrome P450s and their roles in toxicology, Toxicol. Sci., 48, 151, 10.1093/toxsci/48.2.151

Parkinson, 1996, Biotransformation of xenobiotics, 113

Reed, 1990, Glutathione: toxicological implications, Annu. Rev. Pharmacol. Toxicol., 30, 603, 10.1146/annurev.pa.30.040190.003131

Reiner, 1979, Regeneration of cholinesterase activities in humans and rats after inhibition by O,O-dimethyl-2,2-dichlorvinyl phosphate, Toxicol. Appl. Pharmacol., 49, 451, 10.1016/0041-008X(79)90445-9

Salonen, 1999, Polymorphism in high density lipoprotein paraoxonase gene and risk of acute myocardial infarction in men: prospective nested case-control study, Brit. Med. J., 319, 487, 10.1136/bmj.319.7208.487

Satoh, 1998, The mammalian carboxylesterases: from molecules to functions, Annu. Rev. Pharmacol. Toxicol., 38, 257, 10.1146/annurev.pharmtox.38.1.257

Sultatos, 1982, Factors involved in the differential acute toxicities of the insecticides chlorpyrifos and methyl chlorpyrifos in mice, Toxicol. Appl. Pharmacol., 65, 144, 10.1016/0041-008X(82)90372-6

Sultatos, 1992, Role of glutathione in the mammalian detoxication of organophosphorus insecticides, 155

Sultatos, 1995, Mammalian toxicology of organophosphorus pesticides, J. Toxicol. Environ. Health, 43, 271, 10.1080/15287399409531921

Tuovinen, 1994, Phosphotriesterase – a promising candidate for use in detoxication of organophosphates, Fundam. Appl. Toxicol., 23, 578, 10.1006/faat.1994.1143

Van Dongen, 1986, Further evidence for the effect of pinacolyl dimethylphosphinate on soman storage in muscle tissue, Eur. J. Pharmacol., 127, 135, 10.1016/0014-2999(86)90215-3

Van Helden, 1983, Evidence for an intramuscular depot of the cholinesterase inhibitor soman in the rat, Eur. J. Pharmacol., 89, 271, 10.1016/0014-2999(83)90504-6

Vilanova, 1999, The role of phosphotriesterases in the detoxication of organophosphorus compounds, Crit. Rev. Toxicol., 29, 21, 10.1080/10408449991349177

Vitarius, 1995, The role of calcium in hydrolysis of the organophosphate paraoxon by human serum A-esterase, Life Sci., 56, 125, 10.1016/0024-3205(94)00422-O

Walker, 1987, ‘A’ esterases and their role in regulating the toxicity of organophosphates, Arch. Toxicol., 60, 30, 10.1007/BF00296942

Walker, 1993, The classification of esterases which hydrolyse organophosphates: Recent developments, Chem.–Biol. Interact., 87, 17, 10.1016/0009-2797(93)90021-P

WHO, 1986. Organophosphorus insecticides: a general introduction. Environmental Health Criteria 63, Geneva.

Ziegler, 1988, Flavin-containing monooxygenases: catalytic mechanism and substrate specificities, Drug Metab. Rev., 19, 1, 10.3109/03602538809049617