메뉴 건너뛰기




Volumn 9, Issue 7, 1996, Pages 1202-1206

S-methylation of O,O-dialkyl phosphorodithioic acids: O,O,S-trimethyl phosphorodithioate and phosphorothiolate as metabolites of dimethoate in mice

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHOATE; PHOSPHORODITHIOIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID O,O,S TRIMETHYL ESTER;

EID: 0029860118     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9600715     Document Type: Article
Times cited : (13)

References (30)
  • 1
    • 0015395702 scopus 로고
    • Potentiation of toxicity of organophosphorus compounds containing carboxylic ester functions toward warm-blooded animals by some organophosphorus impurities
    • Pellegrini, G., and Santi, R. (1972) Potentiation of toxicity of organophosphorus compounds containing carboxylic ester functions toward warm-blooded animals by some organophosphorus impurities. J. Agric. Food Chem. 20, 944-950.
    • (1972) J. Agric. Food Chem. , vol.20 , pp. 944-950
    • Pellegrini, G.1    Santi, R.2
  • 2
    • 0017687590 scopus 로고
    • Effect of impurities on the mammalian toxicity of technical malathion and acephate
    • Umetsu, N., Grose, F. H., Allahyari, R., Abu-El-Haj, S., and Fukuto, T. R. (1977) Effect of impurities on the mammalian toxicity of technical malathion and acephate. J. Agric. Food Chem. 25, 946-953.
    • (1977) J. Agric. Food Chem. , vol.25 , pp. 946-953
    • Umetsu, N.1    Grose, F.H.2    Allahyari, R.3    Abu-El-Haj, S.4    Fukuto, T.R.5
  • 3
    • 0018839759 scopus 로고
    • Identification and toxicological evaluation of impurities in technical malathion and fenthion
    • Toia, R. F., March, R. B., Umetsu, N., Mallipudi, N. M., Allahyari, R., and Fukuto, T. R. (1980) Identification and toxicological evaluation of impurities in technical malathion and fenthion. J. Agric. Food Chem. 28, 599-604.
    • (1980) J. Agric. Food Chem. , vol.28 , pp. 599-604
    • Toia, R.F.1    March, R.B.2    Umetsu, N.3    Mallipudi, N.M.4    Allahyari, R.5    Fukuto, T.R.6
  • 4
    • 0020047155 scopus 로고
    • Toxicity of O,O,S-trialkyl phosphorothioates to the rat
    • Ali, F. A. F., and Fukuto, T. R. (1982) Toxicity of O,O,S-trialkyl phosphorothioates to the rat. J. Agric. Food Chem, 30, 126-130.
    • (1982) J. Agric. Food Chem , vol.30 , pp. 126-130
    • Ali, F.A.F.1    Fukuto, T.R.2
  • 5
    • 0020642098 scopus 로고
    • Toxicological properties of trialkyl phosphorothioate and dialkyl alkyl- And arylphosphonothioate esters
    • Fukuto, T. R. (1983) Toxicological properties of trialkyl phosphorothioate and dialkyl alkyl- and arylphosphonothioate esters. J. Environ. Sci. Health B18, 89-117.
    • (1983) J. Environ. Sci. Health , vol.B18 , pp. 89-117
    • Fukuto, T.R.1
  • 6
    • 0021673553 scopus 로고
    • Metabolism of O,O,S-trimethyl phosphorothioate in rats after oral administration of a toxic dose, and the effect of coadministration of its antagonistic thionate isomer
    • Gray, A. J., and Fukuto, T. R. (1984) Metabolism of O,O,S-trimethyl phosphorothioate in rats after oral administration of a toxic dose, and the effect of coadministration of its antagonistic thionate isomer. Pestic. Biochem. Physiol. 22, 295-311.
    • (1984) Pestic. Biochem. Physiol. , vol.22 , pp. 295-311
    • Gray, A.J.1    Fukuto, T.R.2
  • 8
    • 0025105825 scopus 로고
    • Protection against chemical-induced lung injury by inhibition of pulmonary cytochrome P-450
    • Verschoyle, R. D., and Dinsdale, D. (1990) Protection against chemical-induced lung injury by inhibition of pulmonary cytochrome P-450. Environ. Health Perspect. 85, 95-100.
    • (1990) Environ. Health Perspect. , vol.85 , pp. 95-100
    • Verschoyle, R.D.1    Dinsdale, D.2
  • 9
    • 0027962414 scopus 로고
    • Aldehyde dehydrogenase of mice inhibited by thiocarbamate herbicides
    • Quistad, G. B., Sparks, S. E., and Casida, J. E. (1994) Aldehyde dehydrogenase of mice inhibited by thiocarbamate herbicides. Life Sci. 55, 1537-1544.
    • (1994) Life Sci. , vol.55 , pp. 1537-1544
    • Quistad, G.B.1    Sparks, S.E.2    Casida, J.E.3
  • 10
    • 0028865343 scopus 로고
    • S-Methylation as a bioactivation mechanism for mono- And dithiocarbamate pesticides as aldèhyde dehydrogenase inhibitors
    • Staub, R. E., Sparks, S. E., Quistad, G. B., and Casida, J. E. (1995) S-Methylation as a bioactivation mechanism for mono- and dithiocarbamate pesticides as aldèhyde dehydrogenase inhibitors. Chem. Res. Toxicol. 8, 1063-1069.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 1063-1069
    • Staub, R.E.1    Sparks, S.E.2    Quistad, G.B.3    Casida, J.E.4
  • 11
    • 0028594076 scopus 로고
    • Biological monitoring of exposure to organophosphorus insecticides by assay of urinary alkylphosphates: Influence of protective measures during manual operations with treated plants
    • Aprea, C., Sciarra, G., Sartorelli, P., Desideri, E., Amati, R., and Sartorelli, E. (1994) Biological monitoring of exposure to organophosphorus insecticides by assay of urinary alkylphosphates: influence of protective measures during manual operations with treated plants. Int. Arch. Occup. Environ. Health 66, 333-338.
    • (1994) Int. Arch. Occup. Environ. Health , vol.66 , pp. 333-338
    • Aprea, C.1    Sciarra, G.2    Sartorelli, P.3    Desideri, E.4    Amati, R.5    Sartorelli, E.6
  • 12
    • 0028024434 scopus 로고
    • Organophosphorus compounds
    • Jeyaratnam, J., and Maroni, M. (1994) Organophosphorus compounds. Toxicology 91, 15-27.
    • (1994) Toxicology , vol.91 , pp. 15-27
    • Jeyaratnam, J.1    Maroni, M.2
  • 13
    • 0004058001 scopus 로고
    • British Crop Protection Council, Farnham, Surrey, U.K.
    • Tomlin, C., Ed. (1994) The Pesticide Manual, 10th ed., British Crop Protection Council, Farnham, Surrey, U.K.
    • (1994) The Pesticide Manual, 10th Ed.
    • Tomlin, C.1
  • 14
    • 0021275703 scopus 로고
    • Studies on Organophosphorus impurities in technical malathion: Inhibition of carboxylesterases and the stability of isomalathion
    • Lin, P. T., Main, A. R., Tucker, W. P., Motoyama, N., and Dauterman, W. C (1984) Studies on Organophosphorus impurities in technical malathion: inhibition of carboxylesterases and the stability of isomalathion. Pestic. Biochem. Physiol. 21, 223-231.
    • (1984) Pestic. Biochem. Physiol. , vol.21 , pp. 223-231
    • Lin, P.T.1    Main, A.R.2    Tucker, W.P.3    Motoyama, N.4    Dauterman, W.C.5
  • 15
    • 0005958358 scopus 로고
    • Chemistry of the aliphatic esters of thiophosphoric acids. II. O,O,S-Trialkyl thionophosphates by the addition of O,O-dialkyl thiolthionophosphoric acids to olefins
    • Norman, G. R., LeSuer, W. M., and Mastin, T. W. (1952) Chemistry of the aliphatic esters of thiophosphoric acids. II. O,O,S-Trialkyl thionophosphates by the addition of O,O-dialkyl thiolthionophosphoric acids to olefins. J. Am. Chem. Soc. 74, 161-163.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 161-163
    • Norman, G.R.1    LeSuer, W.M.2    Mastin, T.W.3
  • 16
    • 0040261233 scopus 로고
    • Bovine metabolism of Organophosphorus insecticides. Metabolism and residues associated with oral administration of dimethoate to rats and three lactating cows
    • Dauterman, W. C., Casida, J. E., Knaak, J. B., and Kowalczyk, T. (1959) Bovine metabolism of Organophosphorus insecticides. Metabolism and residues associated with oral administration of dimethoate to rats and three lactating cows. J. Agric. Food Chem. 7, 188-193.
    • (1959) J. Agric. Food Chem. , vol.7 , pp. 188-193
    • Dauterman, W.C.1    Casida, J.E.2    Knaak, J.B.3    Kowalczyk, T.4
  • 17
    • 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
  • 18
    • 0003428490 scopus 로고
    • Bureau of Sport Fisheries and Wildlife, Special Scientific Report-Wildlife No. 127, Washington, DC
    • Menzie, C. M. (1969) Metabolism of Pesticides, Bureau of Sport Fisheries and Wildlife, Special Scientific Report-Wildlife No. 127, 487 pp, Washington, DC.
    • (1969) Metabolism of Pesticides
    • Menzie, C.M.1
  • 20
    • 10244232541 scopus 로고
    • Metabolism and transport related mechanisms in organ-directed toxicity
    • Rags- dale, N. N., Kearney, P. C., and Plimmer, J. R., Eds. American Chemical Society, Washington, DC
    • Mücke, W., and Thanei, P. (1995) Metabolism and transport related mechanisms in organ-directed toxicity. In Eighth International Congress of Pesticide Chemistry-Options 2000 (Rags- dale, N. N., Kearney, P. C., and Plimmer, J. R., Eds.) pp 244-256, American Chemical Society, Washington, DC.
    • (1995) Eighth International Congress of Pesticide Chemistry-Options 2000 , pp. 244-256
    • Mücke, W.1    Thanei, P.2
  • 21
    • 0012719350 scopus 로고
    • Oxidative conversion of phosphorothiolates to phosphinyloxysulfonates probably via phosphorothiolate S-oxides
    • Segall, Y., and Casida, J. E. (1982) Oxidative conversion of phosphorothiolates to phosphinyloxysulfonates probably via phosphorothiolate S-oxides. Tetrahedron Lett. 23, 139-142.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 139-142
    • Segall, Y.1    Casida, J.E.2
  • 22
    • 0021367532 scopus 로고
    • Role of metabolic activation, covalent binding, and glutathione depletion in pulmonary toxicity produced by an impurity of malathion
    • Imamura, T., and Hasegawa, L. (1984) Role of metabolic activation, covalent binding, and glutathione depletion in pulmonary toxicity produced by an impurity of malathion. Toxicol. Appl. Pharmacol. 72, 476-483.
    • (1984) Toxicol. Appl. Pharmacol. , vol.72 , pp. 476-483
    • Imamura, T.1    Hasegawa, L.2
  • 23
    • 0022005652 scopus 로고
    • Mutagenic and alkylating activities of organophosphate impurities of commercial malathion
    • Imamura, T., and Talcott, R. E. (1985) Mutagenic and alkylating activities of organophosphate impurities of commercial malathion. Mutat. Res. 155, 1-6.
    • (1985) Mutat. Res. , vol.155 , pp. 1-6
    • Imamura, T.1    Talcott, R.E.2
  • 24
    • 0021264461 scopus 로고
    • O,S,S-Trimethyl phosphorodithioate and O,O,S-triethyl phosphorothioate: Pharmacokinetics in rats and effect of pretreatment with compounds affecting the drug processing systems
    • Aldridge, W. N., Verschoyle, R. D., and Peal, J. A. (1984) O,S,S-Trimethyl phosphorodithioate and O,O,S-triethyl phosphorothioate: pharmacokinetics in rats and effect of pretreatment with compounds affecting the drug processing systems. Pestic. Biochem. Physiol. 21, 265-274.
    • (1984) Pestic. Biochem. Physiol. , vol.21 , pp. 265-274
    • Aldridge, W.N.1    Verschoyle, R.D.2    Peal, J.A.3
  • 25
    • 0028092850 scopus 로고
    • Enhanced levels of lipid peroxidation and xanthine oxidase activity in the lung of male Sprague-Dawley rats following treatment with O,O,S-trimethyl phosphorothioate
    • Ohtaka, K., and Koizumi, A. (1994) Enhanced levels of lipid peroxidation and xanthine oxidase activity in the lung of male Sprague-Dawley rats following treatment with O,O,S-trimethyl phosphorothioate. Pharmacol. Toxicol. 75, 206-211.
    • (1994) Pharmacol. Toxicol. , vol.75 , pp. 206-211
    • Ohtaka, K.1    Koizumi, A.2
  • 27
    • 0024212462 scopus 로고
    • Morphogenesis of O,O,S-trimethyl phosphorothioate-induced pulmonary injury in mice
    • Durham, S. K., and Imamura, T. (1988) Morphogenesis of O,O,S-trimethyl phosphorothioate-induced pulmonary injury in mice. Toxicol. Appl. Pharmacol. 96, 417-428.
    • (1988) Toxicol. Appl. Pharmacol. , vol.96 , pp. 417-428
    • Durham, S.K.1    Imamura, T.2
  • 28
    • 0023229967 scopus 로고
    • The interaction between phosphorothionate insecticides, pneumotoxic trialkyl phosphorothiolates and effects on lung 7-ethoxycoumarin O-deethylase activity
    • Verschoyle, R. D., and Aldridge, W. N. (1987) The interaction between phosphorothionate insecticides, pneumotoxic trialkyl phosphorothiolates and effects on lung 7-ethoxycoumarin O-deethylase activity. Arch. Toxicol. 60, 311-318.
    • (1987) Arch. Toxicol. , vol.60 , pp. 311-318
    • Verschoyle, R.D.1    Aldridge, W.N.2
  • 29
    • 0027382051 scopus 로고
    • Inhibition and induction of cytochrome P450 isoenzymes in rat lung
    • Verschoyle, R. D., Dinsdale, D., and Wolf, C. R. (1993) Inhibition and induction of cytochrome P450 isoenzymes in rat lung. J. Pharmacol. Exp. Ther. 265, 386-391.
    • (1993) J. Pharmacol. Exp. Ther. , vol.265 , pp. 386-391
    • Verschoyle, R.D.1    Dinsdale, D.2    Wolf, C.R.3
  • 30
    • 0023123105 scopus 로고
    • Neurotoxic effects of organophosphorus insecticides: An intermediate syndrome
    • Senanayake, N., and Karalliedde, L. (1987) Neurotoxic effects of organophosphorus insecticides: an intermediate syndrome. N. Engl J. Med. 316, 761-763.
    • (1987) N. Engl J. Med. , vol.316 , pp. 761-763
    • Senanayake, N.1    Karalliedde, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.