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Volumn 321, Issue 3, 2007, Pages 1095-1101

S-(1,2,2-trichlorovinyl)-L-cysteine sulfoxide, a reactive metabolite of S-(1,2,2-trichlorovinyl)-L-cysteine formed in rat liver and kidney microsomes, is a potent nephrotoxicant

Author keywords

[No Author keywords available]

Indexed keywords

(1,2,2 TRICHLOROVINYL)CYSTEINE; (1,2,2 TRICHLOROVINYL)CYSTEINE SULFOXIDE; 1 BENZYLIMIDAZOLE; CATALASE; DEFEROXAMINE; POTASSIUM CYANIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE DISMUTASE; TETRACHLOROETHYLENE; THIAMAZOLE; TOXIC SUBSTANCE; UNCLASSIFIED DRUG;

EID: 34248576155     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.107.120444     Document Type: Article
Times cited : (24)

References (37)
  • 1
    • 0036360511 scopus 로고    scopus 로고
    • The effects of methidathion on lipid peroxidation and some liver enzymes: Role of vitamins E and C
    • Altuntas I, Delibas N, Demirci M, Kilinc I, and Tamer N (2002) The effects of methidathion on lipid peroxidation and some liver enzymes: role of vitamins E and C. Arch Toxicol 76:470-473.
    • (2002) Arch Toxicol , vol.76 , pp. 470-473
    • Altuntas, I.1    Delibas, N.2    Demirci, M.3    Kilinc, I.4    Tamer, N.5
  • 2
    • 0027960682 scopus 로고
    • Ras proto-oncogene activation in dichloroacetic acid-, trichloroethylene- and tetrachloroethylene-induced liver tumors in B6C3F1 mice
    • Anna CH, Maronpot RR, Pereira MA, Foley JF, Markley DE, and Anderson MW (1994) Ras proto-oncogene activation in dichloroacetic acid-, trichloroethylene- and tetrachloroethylene-induced liver tumors in B6C3F1 mice. Carcinogenesis 15:2255-2261.
    • (1994) Carcinogenesis , vol.15 , pp. 2255-2261
    • Anna, C.H.1    Maronpot, R.R.2    Pereira, M.A.3    Foley, J.F.4    Markley, D.E.5    Anderson, M.W.6
  • 3
    • 0029075402 scopus 로고
    • Cancer incidence among Finnish workers exposed to halogenated hydrocarbons
    • Antilla A, Pukkala E, Sallmen M, Hernberg S, and Hemminki K (1995) Cancer incidence among Finnish workers exposed to halogenated hydrocarbons. J Occup Med 37:797-806.
    • (1995) J Occup Med , vol.37 , pp. 797-806
    • Antilla, A.1    Pukkala, E.2    Sallmen, M.3    Hernberg, S.4    Hemminki, K.5
  • 4
    • 0030045843 scopus 로고    scopus 로고
    • N-Acteyl-S-(1,2, 2-trichlorovinyl)-L-cysteine and 2,2,2-trichloroethanol. Two novel metabolites of tetrachloroethene in humans after occupational exposure
    • Birner G, Rutkowska A, and Dekant W (1996) N-Acteyl-S-(1,2, 2-trichlorovinyl)-L-cysteine and 2,2,2-trichloroethanol. Two novel metabolites of tetrachloroethene in humans after occupational exposure. Drug Metab Dispos 24:41-48.
    • (1996) Drug Metab Dispos , vol.24 , pp. 41-48
    • Birner, G.1    Rutkowska, A.2    Dekant, W.3
  • 5
    • 0022724047 scopus 로고
    • Identification of S-1,2,2-trichlorovinyl-N-acetylcysteine as a urinary metabolite of tetrachloroethylene: Bioactivation through glutathione conjugation as a possible explanation of its nephrocarcinogenicity
    • Dekant W, Metzler M, and Henschler D (1986) Identification of S-1,2,2-trichlorovinyl-N-acetylcysteine as a urinary metabolite of tetrachloroethylene: bioactivation through glutathione conjugation as a possible explanation of its nephrocarcinogenicity. J Biochem Toxicol 1:57-72.
    • (1986) J Biochem Toxicol , vol.1 , pp. 57-72
    • Dekant, W.1    Metzler, M.2    Henschler, D.3
  • 6
    • 0023937244 scopus 로고
    • Thioacylating intermediates as metabolites of S-(1,2-dichlorovinyl)- L-cysteine and S-(1,2,2-trichlorovinyl)-L-cysteine formed by cysteine conjugate β-lyase
    • Dekant W, Berthold K, Vamvakas S, Henschler D, and Anders MW (1988) Thioacylating intermediates as metabolites of S-(1,2-dichlorovinyl)- L-cysteine and S-(1,2,2-trichlorovinyl)-L-cysteine formed by cysteine conjugate β-lyase. Chem Res Toxicol 1:175-178.
    • (1988) Chem Res Toxicol , vol.1 , pp. 175-178
    • Dekant, W.1    Berthold, K.2    Vamvakas, S.3    Henschler, D.4    Anders, M.W.5
  • 7
    • 0023500127 scopus 로고
    • Bioactivation of tetrachloroethylene: Role of glutathione S-transferase- catalyzed conjugation versus cytochrome P-450-dependent phospholipid alkylation
    • Dekant W, Martens G, Vamvakas S, Metzler M, and Henschler D (1987) Bioactivation of tetrachloroethylene: role of glutathione S-transferase- catalyzed conjugation versus cytochrome P-450-dependent phospholipid alkylation. Drug Metab Dispos 15:702-709.
    • (1987) Drug Metab Dispos , vol.15 , pp. 702-709
    • Dekant, W.1    Martens, G.2    Vamvakas, S.3    Metzler, M.4    Henschler, D.5
  • 8
    • 0028245447 scopus 로고
    • Flavin-containing monooxygenase (FMO)-dependent metabolism of methionine and evidence for FMO3 being the major FMO involved in methionine sulfoxidation in rabbit liver and kidney microsomes
    • Duescher RJ, Lawton MP, Philpot RM, and Elfarra AA (1994) Flavin-containing monooxygenase (FMO)-dependent metabolism of methionine and evidence for FMO3 being the major FMO involved in methionine sulfoxidation in rabbit liver and kidney microsomes. J Biol Chem 269:17525-17530.
    • (1994) J Biol Chem , vol.269 , pp. 17525-17530
    • Duescher, R.J.1    Lawton, M.P.2    Philpot, R.M.3    Elfarra, A.A.4
  • 9
    • 0021741999 scopus 로고
    • Mortality among laundry and dry cleaning workers in Oklahoma
    • Duh RW and Asal NR (1984) Mortality among laundry and dry cleaning workers in Oklahoma. Am J Public Health 74:1278-1280.
    • (1984) Am J Public Health , vol.74 , pp. 1278-1280
    • Duh, R.W.1    Asal, N.R.2
  • 10
    • 0012194987 scopus 로고    scopus 로고
    • Halogenated hydrocarbons
    • Goldstein RS ed Elsevier Science, New York
    • Elfarra AA (1997) Halogenated hydrocarbons, in Comprehensive Toxicology (Goldstein RS ed) vol. 7, pp 601-616, Elsevier Science, New York.
    • (1997) Comprehensive Toxicology , vol.7 , pp. 601-616
    • Elfarra, A.A.1
  • 13
    • 0025210067 scopus 로고
    • Perchloroethylene-induced rat kidney tumors: An investigation of the mechanisms involved and their relevance to humans
    • Green T, Odum J, Nash JA, and Foster JR (1990) Perchloroethylene-induced rat kidney tumors: an investigation of the mechanisms involved and their relevance to humans. Toxicol Appl Pharmacol 103:77-89.
    • (1990) Toxicol Appl Pharmacol , vol.103 , pp. 77-89
    • Green, T.1    Odum, J.2    Nash, J.A.3    Foster, J.R.4
  • 14
    • 0029429522 scopus 로고
    • Dry cleaning, some chlorinated solvents and other industrial chemicals
    • International Agency for Research on Cancer , International Agency for Research on Cancer, Lyon, France
    • International Agency for Research on Cancer (1995) Dry cleaning, some chlorinated solvents and other industrial chemicals, in IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, vol. 63, pp 159-221, International Agency for Research on Cancer, Lyon, France.
    • (1995) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans , vol.63 , pp. 159-221
  • 15
    • 0019513335 scopus 로고
    • Female laundry and dry cleaning workers in Wisconsin: Mortality analysis
    • Katz RM and Jowett D (1981) Female laundry and dry cleaning workers in Wisconsin: mortality analysis. Am J Public Health 71:305-307.
    • (1981) Am J Public Health , vol.71 , pp. 305-307
    • Katz, R.M.1    Jowett, D.2
  • 16
    • 0036786389 scopus 로고    scopus 로고
    • Sulfoxides as urinary metabolites of S-allyl-L-cysteine in rats: Evidence for the involvement of flavin-containing monooxygenases
    • Krause RJ, Glocke SC, and Elfarra AA (2002) Sulfoxides as urinary metabolites of S-allyl-L-cysteine in rats: evidence for the involvement of flavin-containing monooxygenases. Drug Metab Dispos 30:1137-1142.
    • (2002) Drug Metab Dispos , vol.30 , pp. 1137-1142
    • Krause, R.J.1    Glocke, S.C.2    Elfarra, A.A.3
  • 17
    • 0037214432 scopus 로고    scopus 로고
    • Human kidney flavin-containing monooxygenases (FMOs) and their potential roles in cysteine S-conjugate metabolism and nephrotoxicity
    • Krause RJ, Lash LH, and Elfarra AA (2003) Human kidney flavin-containing monooxygenases (FMOs) and their potential roles in cysteine S-conjugate metabolism and nephrotoxicity. J Pharmacol Exp Ther 304:185-191.
    • (2003) J Pharmacol Exp Ther , vol.304 , pp. 185-191
    • Krause, R.J.1    Lash, L.H.2    Elfarra, A.A.3
  • 18
    • 0025228615 scopus 로고
    • Purification and characterization of human kidney cystolic cysteine conjugate β-lyase activity
    • Lash LH, Nelson RM, Van Dyke RA, and Anders MW (1990) Purification and characterization of human kidney cystolic cysteine conjugate β-lyase activity. Drug Metab Dispos 18:50-54.
    • (1990) Drug Metab Dispos , vol.18 , pp. 50-54
    • Lash, L.H.1    Nelson, R.M.2    Van Dyke, R.A.3    Anders, M.W.4
  • 19
    • 0028268997 scopus 로고
    • Roles of cysteine conjugate β-lyase and S-oxidase in nephrotoxicity: Studies with S-(1,2-dichlorovinyl)-L-cysteine and S-(1,2-dichlorovinyl)-L-cysteine sulfoxide
    • Lash LH, Sausen PJ, Duescher RJ, Cooley AJ, and Elfarra AA (1994) Roles of cysteine conjugate β-lyase and S-oxidase in nephrotoxicity: studies with S-(1,2-dichlorovinyl)-L-cysteine and S-(1,2-dichlorovinyl)-L-cysteine sulfoxide. J Pharmacol Exp Ther 269:374-383.
    • (1994) J Pharmacol Exp Ther , vol.269 , pp. 374-383
    • Lash, L.H.1    Sausen, P.J.2    Duescher, R.J.3    Cooley, A.J.4    Elfarra, A.A.5
  • 20
    • 0035018536 scopus 로고    scopus 로고
    • Hepatic and renal toxicities associated with perchloroethylene
    • Lash LH and Parker JC (2001) Hepatic and renal toxicities associated with perchloroethylene. Pharmacol Rev 53:177-208.
    • (2001) Pharmacol Rev , vol.53 , pp. 177-208
    • Lash, L.H.1    Parker, J.C.2
  • 21
    • 0031808523 scopus 로고    scopus 로고
    • Glutathione conjugation of perchloroethylene in rats and mice in vitro: Sex-, species-, and tissue-dependent differences
    • Lash LH, Qian W, Putt DA, Desai K, Elfarra AA, Sicuri AR, and Parker JC (1998) Glutathione conjugation of perchloroethylene in rats and mice in vitro: sex-, species-, and tissue-dependent differences. Toxicol Appl Pharmacol 150:49-57.
    • (1998) Toxicol Appl Pharmacol , vol.150 , pp. 49-57
    • Lash, L.H.1    Qian, W.2    Putt, D.A.3    Desai, K.4    Elfarra, A.A.5    Sicuri, A.R.6    Parker, J.C.7
  • 22
    • 0037087716 scopus 로고    scopus 로고
    • Renal toxicity of perchloroethylene and S-(1,2,2-trichlorovinyl) glutathione in rats and mice: Sex- and species-dependent differences
    • Lash LH, Qian W, Putt DA, Hueni SE, Elfarra AA, Sicuri AR, and Parker JC (2002) Renal toxicity of perchloroethylene and S-(1,2,2-trichlorovinyl) glutathione in rats and mice: sex- and species-dependent differences. Toxicol Appl Pharmacol 179:163-171.
    • (2002) Toxicol Appl Pharmacol , vol.179 , pp. 163-171
    • Lash, L.H.1    Qian, W.2    Putt, D.A.3    Hueni, S.E.4    Elfarra, A.A.5    Sicuri, A.R.6    Parker, J.C.7
  • 23
    • 0038137502 scopus 로고    scopus 로고
    • Roles of necrosis, apoptosis, and mitochondrial dysfunction in S-(1,2- dichlorovinyl)-L-cysteine sulfoxide-induced cytotoxicity in primary cultures of human renal proximal tubular cells
    • Lash LH, Putt DA, Hunei SE, Krause RJ, and Elfarra AA (2003) Roles of necrosis, apoptosis, and mitochondrial dysfunction in S-(1,2- dichlorovinyl)-L-cysteine sulfoxide-induced cytotoxicity in primary cultures of human renal proximal tubular cells. J Pharmacol Exp Ther 305:1163-1172.
    • (2003) J Pharmacol Exp Ther , vol.305 , pp. 1163-1172
    • Lash, L.H.1    Putt, D.A.2    Hunei, S.E.3    Krause, R.J.4    Elfarra, A.A.5
  • 26
    • 34248535231 scopus 로고
    • Toxicology and carcinogenesis studies of tetrachloroethylene (perchloroethylene) (CAS no. 127-18-4) in F344/N rats and B6C3F1 mice (inhalation studies)
    • National Toxicology Program , 86-2567. National Toxicology Program, National Institutes of Health, Bethesda, MD
    • National Toxicology Program (1986) Toxicology and carcinogenesis studies of tetrachloroethylene (perchloroethylene) (CAS no. 127-18-4) in F344/N rats and B6C3F1 mice (inhalation studies). Department of Health and Human Services-National Institutes of Health Report 86-2567. National Toxicology Program, National Institutes of Health, Bethesda, MD.
    • (1986) Department of Health and Human Services-National Institutes of Health Report
  • 27
    • 0344327101 scopus 로고    scopus 로고
    • Dose-dependent protein adduct formation in kidney, liver, and blood of rats and in human blood after perchloroethene inhalation
    • Pähler A, Parker J, and Dekant W (1999) Dose-dependent protein adduct formation in kidney, liver, and blood of rats and in human blood after perchloroethene inhalation. Toxicol Sci 48:5-13.
    • (1999) Toxicol Sci , vol.48 , pp. 5-13
    • Pähler, A.1    Parker, J.2    Dekant, W.3
  • 28
    • 0032969264 scopus 로고    scopus 로고
    • Species and sex differences in expression of flavin-containing monooxygenase form 3 in liver and kidney microsomes
    • Ripp SL, Itagaki K, Philpot RM, and Elfarra AA (1999) Species and sex differences in expression of flavin-containing monooxygenase form 3 in liver and kidney microsomes. Drug Metab Dispos 27:46-52.
    • (1999) Drug Metab Dispos , vol.27 , pp. 46-52
    • Ripp, S.L.1    Itagaki, K.2    Philpot, R.M.3    Elfarra, A.A.4
  • 29
    • 0030893969 scopus 로고    scopus 로고
    • Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin containing monooxygenases: Studies with S-(1,2 dichlorovinyl)-L-cysteine, S-(1,2,2 trichlorovinyl)-L-cysteine, S-allyl-L-cysteine and S-benzyl-L-cysteine
    • Ripp SL, Overby LH, Philpot RM, and Elfarra AA (1997) Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin containing monooxygenases: studies with S-(1,2 dichlorovinyl)-L-cysteine, S-(1,2,2 trichlorovinyl)-L-cysteine, S-allyl-L-cysteine and S-benzyl-L-cysteine. Mol Pharmacol 51:507-515.
    • (1997) Mol Pharmacol , vol.51 , pp. 507-515
    • Ripp, S.L.1    Overby, L.H.2    Philpot, R.M.3    Elfarra, A.A.4
  • 30
    • 0025262447 scopus 로고
    • Cysteine conjugate S-oxidase
    • Sausen PJ and Elfarra AA (1990) Cysteine conjugate S-oxidase. J Biol Chem 265:6139-6145.
    • (1990) J Biol Chem , vol.265 , pp. 6139-6145
    • Sausen, P.J.1    Elfarra, A.A.2
  • 31
    • 0025824680 scopus 로고
    • Reactivity of cysteine S-conjugate sulfoxides: Formation of S-[1-chloro-2-(S-glutathionyl)vinyl]- L-cysteine sulfoxide by reaction of S-(1,2-dichlorovinyl)- L-cysteine sulfoxide with glutathione
    • Sausen PJ and Elfarra AA (1991) Reactivity of cysteine S-conjugate sulfoxides: formation of S-[1-chloro-2-(S-glutathionyl)vinyl]- L-cysteine sulfoxide by reaction of S-(1,2-dichlorovinyl)- L-cysteine sulfoxide with glutathione. Chem Res Toxicol 4:655-660.
    • (1991) Chem Res Toxicol , vol.4 , pp. 655-660
    • Sausen, P.J.1    Elfarra, A.A.2
  • 32
    • 0016236020 scopus 로고
    • Biochemical and immunological studies on isolated brush border membranes of human kidney cortex and their membrane surface proteins
    • Scherberich JE, Falkenberg FW, Mondorf AW, Müller H, and Pfleiderer G (1974) Biochemical and immunological studies on isolated brush border membranes of human kidney cortex and their membrane surface proteins. Clin Chim Acta 55:179-197.
    • (1974) Clin Chim Acta , vol.55 , pp. 179-197
    • Scherberich, J.E.1    Falkenberg, F.W.2    Mondorf, A.W.3    Müller, H.4    Pfleiderer, G.5
  • 33
    • 0024625073 scopus 로고
    • Mutagenicity of tetrachloroethene in the Ames test: Metabolic activation by conjugation with glutathione
    • Vamvakas S, Herkenhoff M, Dekant W, and Henschler D (1989a) Mutagenicity of tetrachloroethene in the Ames test: metabolic activation by conjugation with glutathione. J Biochem Toxicol 4:21-27.
    • (1989) J Biochem Toxicol , vol.4 , pp. 21-27
    • Vamvakas, S.1    Herkenhoff, M.2    Dekant, W.3    Henschler, D.4
  • 34
    • 0024470691 scopus 로고
    • Cytotoxicity of cysteine S-conjugates: Structure-activity relationships
    • Vamvakas S, Kochling A, Berthold K, and Dekant W (1989b) Cytotoxicity of cysteine S-conjugates: structure-activity relationships. Chem Biol Interact 71:79-90.
    • (1989) Chem Biol Interact , vol.71 , pp. 79-90
    • Vamvakas, S.1    Kochling, A.2    Berthold, K.3    Dekant, W.4
  • 35
    • 0032925383 scopus 로고    scopus 로고
    • Occupational exposure to tetrachloroethene and its effects on the kidneys
    • Verplanke AJW, Leumens MHL, and Herber RFM (1999) Occupational exposure to tetrachloroethene and its effects on the kidneys. J Occup Environ Med 41:11-16.
    • (1999) J Occup Environ Med , vol.41 , pp. 11-16
    • Verplanke, A.J.W.1    Leumens, M.H.L.2    Herber, R.F.M.3
  • 36
    • 0032210675 scopus 로고    scopus 로고
    • Biotransformation of perchloroethene: Dose-dependent excretion of trichloroacetic acid, dichloroacetic acid, and N-acetyl-S- (trichlorovinyl)-L-cysteine in rats and humans after inhalation
    • Völkel W, Friedewald M, Lederer E, Pähler A, Parker J, and Dekant W (1998) Biotransformation of perchloroethene: dose-dependent excretion of trichloroacetic acid, dichloroacetic acid, and N-acetyl-S- (trichlorovinyl)-L-cysteine in rats and humans after inhalation. Toxicol Appl Pharmacol 153:20-27.
    • (1998) Toxicol Appl Pharmacol , vol.153 , pp. 20-27
    • Völkel, W.1    Friedewald, M.2    Lederer, E.3    Pähler, A.4    Parker, J.5    Dekant, W.6
  • 37
    • 0030071456 scopus 로고    scopus 로고
    • Sulfoxidation of mercapturic acids derived from tri- and tetrachloroethene by cytochromes P450 3A: A bioactivation reaction in addition to deacetylation and cysteine conjugate β-lyase mediated cleavage
    • Werner M, Birner G, and Dekant W (1996) Sulfoxidation of mercapturic acids derived from tri- and tetrachloroethene by cytochromes P450 3A: a bioactivation reaction in addition to deacetylation and cysteine conjugate β-lyase mediated cleavage. Chem Res Toxicol 9:41-49.
    • (1996) Chem Res Toxicol , vol.9 , pp. 41-49
    • Werner, M.1    Birner, G.2    Dekant, W.3


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