Metabolism of hexachloro-1,3-butadiene in mice: in vivo and in vitro evidence for activation by glutathione conjugation

References

• Dekant W., Vamvakas S., Berthold K., Schmidt S., Wild D., Henschler D. Bacterial β-lyase mediated cleavage and mutagenicity of cysteine conjugates derived from the nephocarcinogenic alkenes trichloroethylene, tetrachloroethylene and hexachlorobutadiene. Chemico-Biological Interactions 1986a; 60: 31–45
   PubMed Web of Science ®Google Scholar
• Dekant W., Metzler M., Henschler D. 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. Journal of Biochemical Toxicology 1986b; 1: 57–72
   PubMedGoogle Scholar
• Dekant W., Schulz A., Metzler M., Henschler D. Absorption, elimination and metabolism of trichloroethylene: a quantitative comparison between rats and mice. Xenobtotica 1986c; 16: 143–152
   PubMed Web of Science ®Google Scholar
• Dekant W., Martens M., Vamvakas S., Metzler M., Henschler D. Bioactivation of tetrachloroethylene: Role of glutathione S-transferases catalyzed conjugation versus cytochrome P-450 dependent phospholipid alkylation. Drug Metabolism and Disposition 1987; 15: 702–709
   PubMed Web of Science ®Google Scholar
• Dohn D. R., Anders M. W. Assay of cysteine conjugate β-lyase activity with S-(2-benzothiazolyl)cysteine as the substrate. Analytical Biochemistry 1982; 120: 379–386
   PubMed Web of Science ®Google Scholar
• Dohn D. R., Quebbemann A. J., Borch R. F., Anders M. W. Enzymatic reaction of chlorotrifluoroethene with glutathione: 19F-NMR evidence for stereochemical control of the reaction. Biochemistry 1985; 24: 5137–5143
   PubMed Web of Science ®Google Scholar
• Duffel M. W., Jakoby W. B. Cysteine S-conjugate N-acetyltransferase from rat kidney microsomes. Molecular Pharmacology 1982; 21: 444–448
   PubMed Web of Science ®Google Scholar
• Elfarra A. A., Anders M. W. Renal processing of glutathione conjugates: role in nephrotoxicity. Biochemical Pharmacology 1984; 33: 3729–3732
   PubMed Web of Science ®Google Scholar
• Elfarra A. A., Jakobson I., Anders M. W. Mechanism of S-(1,2-dichloro-vinyl)glutathione-induced nephrotoxicity. Biochemical Pharmacology 1986; 35: 283–288
   PubMed Web of Science ®Google Scholar
• Green T., Odum J. Structure/activity studies of the nephrotoxic and mutagenic action of cysteine conjugates of chloro- and fluoroalkenes. Chemico-Biological Interactions 1985; 54: 15–31
   PubMed Web of Science ®Google Scholar
• Henschler D. Halogenated alkenes and alkynes. Bioactivation of Foreign Compounds, M. W. Anders. Academic Press, New York 1985; 317–347
   Google Scholar
• Inoue M., Kinne R., Tran T., Biempica L., Arias I. M. Rat liver canalicular membrane vesicles. The Journal of Biological Chemistry 1983; 258: 5183–5188
   PubMed Web of Science ®Google Scholar
• Jones T. W., Gerdes R. G., Ormstad K., Orrenius S. The formation of both a mono- and a bis-substituted glutathione conjugate of hexachlorobutadiene by isolated hepatocytes and following in vivo administration to the rat. Chemico-Biological Interactions 1985; 56: 251–267
   PubMed Web of Science ®Google Scholar
• Kociba R. J., Keyes D. G., Jersey G. C., Ballard J. J., Dittenber D. A., Quast J. F., Wade C. E., Humiston C. G., Schwetz B. A. Results of a two year chronic toxicity study with hexachlorobutadiene in rats. American Industrial Hygiene Association Journal 1977; 38: 589–602
   PubMedGoogle Scholar
• Larsen G. L., Stevens J. L. Cysteine Conjugate β-lyase in the gastrointestinal bacterium Eubacterium limosum. Molecular Pharmacology 1985; 29: 97–103
   Web of Science ®Google Scholar
• Lash L. H., Jones D. P. Renal glutathione transport. The Journal of Biological Chemistry 1984; 259: 14508–14514
   PubMed Web of Science ®Google Scholar
• Lash L. H., Jones D. P. Uptake of the glutathione conjugate S-(1,2-dichlorovinyl)glutathione by renal basallateral membrane vesicles and isolated kidney cells. Molecular Pharmacology 1985; 28: 278–282
   PubMed Web of Science ®Google Scholar
• Lock E. A., Ishmael J. The acute toxic effects of hexachlorobutadiene on the rat kidney. Archives of Toxicology 1979; 43: 47–57
   PubMed Web of Science ®Google Scholar
• Lock E. A., Ishmael J. Hepatic and renal non-protein sulfhydryl concentration following toxic doses of hexachloro-1,3-butadiene in the rat: The effect of Arochlor 1254, phenobarbitone, or SKF 525A treatment. Toxicology and Applied Pharmacology 1981; 57: 79–87
   PubMed Web of Science ®Google Scholar
• Lock E. A., Ishmael J., Hook J. B. Nephrotoxicity of Hexachloro-1,3-butadiene in the mouse: The effect of age, sex, strain, monooxygenase modifiers, and the role of glutathione. Toxicology and Applied Pharmacology 1984; 72: 484–494
   PubMed Web of Science ®Google Scholar
• Nash J. A., King L. J., Lock E. A., Green T. The metabolism and disposition of hexachloro-1:3-butadiene in the rat and its relevance to nephrotoxicity. Toxicology and Applied Pharmacology 1984; 73: 124–137
   PubMed Web of Science ®Google Scholar
• Newton J. F., Hoefle D., Gemborys M. W., Mudge G. H., Hook J. B. Metabolism and excretion of a glutathione conjugate of acetaminophen in the isolated perfused rat kidney. The Journal of Pharmacology and Experimental Therapeutics 1986; 237: 519–524
   PubMed Web of Science ®Google Scholar
• Prout M. S., Proven W. M., Green T. Species differences in response to trichloroethylene. Toxicology and Applied Pharmacology 1985; 79: 389–400
   PubMed Web of Science ®Google Scholar
• Reichert D., Neudecker T., Schutz S. Mutagenicity of hexachlorobutadiene, perchlorobutenoic acid and perchlorobutenoic acid chloride. Mutation Research 1984; 137: 89–93
   PubMed Web of Science ®Google Scholar
• Reichert D., Schutz S., Metzler M. Excretion pattern and metabolism of hexachlorobutadiene in rats. Biochemical Pharmacology 1985; 34: 499–505
   PubMed Web of Science ®Google Scholar
• Reichert D., Schutz S. Mercapturic acid formation is an activation and intermediary step in the metabolism of hexachlorobutadiene. Biochemical Pharmacology 1986; 35: 1271–1275
   PubMed Web of Science ®Google Scholar
• Rush G. F., Smith J. H., Newton J. F., Hook J. B. Chemically induced nephrotoxicity: role of metabolic activation. CRC Critical Reviews in Toxicology 1984; 13: 99–160
   Web of Science ®Google Scholar
• Schumann A. M., Quast J. F., Watanabe P. G. The pharmacokinetics and macromolecular interactions of perchloroethylene in mice and rats as related to oncogenicity. Toxicology and Applied Pharmacology 1980; 55: 207–219
   PubMed Web of Science ®Google Scholar
• Smith A. G., Francis J. E. Evidence for the active renal secretion of S-pentachlorophenyl-N-acetyl-L-cysteine by female rats. Biochemical Pharmacology 1983; 32: 3797–3801
   PubMed Web of Science ®Google Scholar
• Stott W. T., Quast J. F., Watanabe. The pharmacokinetics and macromolecular interactions of trichloroethylene in mice and rats. Toxicology and Applied Pharmacology 1982; 62: 137–151
   PubMed Web of Science ®Google Scholar
• Tate S. Enzymes of mercapturic acid formation, In: ed. Enzymatic Basic of Detoxication, W. B. Jacoby. Academic Press, New York 1980; 95–121
   Google Scholar
• Vamvakas S., Dekant W., Berthold K., Schmidt S., Wild D., Henschler D. Enzymatic transformation of mercapturic acids derived from halogenated alkenes to reactive and mutagenic intermediates. Biochemical Pharmacology 1987; 36: 2741–2748
   PubMed Web of Science ®Google Scholar
• Wolf R. C., Berry P. N., Nash J. A., Green T., Lock E. A. Role of microsomal and cytosolic glutathione S-transferases in the conjugation of hexachloro-1:3-butadiene and its possible relevance to toxicity. Journal of Pharmacology and Experimental Therapeutics 1984; 228: 202–208
   PubMed Web of Science ®Google Scholar