Metabolism, Toxicity, and Carcinogenicity of Trichloroethylene

References

• International Agency for Research on Cancer. Trichloroethylene, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. LyonFrance 1979; 20: 545
   Google Scholar
• National Institute for Occupational Safety and Health. Special Occupational Hazard Review of Trichloroethylene. Washington, DC 1978, DHEW Publ. No. 78–130
   Google Scholar
• Conglio W. A., Miller K., Mackeever D. The Occurrence of Volatile Organics in Drinking Water, Criteria and Standards Division. Science and Technology Branch. Environmental Protection Agency, Washington, DC 1980
   Google Scholar
• Westrick J. J., Mello J. W., Thomas R. F. The groundwater supply survey. J. Am. Water Works Assoc. 1984; 76: 52
   Web of Science ®Google Scholar
• Josephson J. Implementing superfund. Environ. Sci. Technol. 1986; 20: 23
   PubMedGoogle Scholar
• National Cancer Institute. Carcinogenesis Bioassay of Trichloroethylene. NCI-CG-TR-2., Washington, DC 1976, CAS NO. 79–01–6
   Google Scholar
• National Toxicology Program. Carcinogenesis Bioassay of Trichloroethylene (Without Epichlorohydrin) in F344/N rats and B6C3F1/N mice (Gavage Studies). U.S. Department of Health and Human Services, Washington, DC 1983, Tech. Rep. 243, NIH Publ. No. 83–1799
   Google Scholar
• Fukuda K., Takemoto K., Tsuruta H. Inhalation carcinogenicity of trichloroethylene in mice and rats. Ind. Health 1983; 21: 243
   PubMedGoogle Scholar
• Maltoni C., Lefemine G., Cotti G., Perino G. Long-term carcinogenicity bioassays on trichloroethylene administered by inhalation to Sprague-Dawley rats and Swiss and B6C3FI mice. Ann. N.Y. Acad. Sci. 1988; 534: 316
   PubMed Web of Science ®Google Scholar
• National Toxicology Program. Toxicology and Carcinogenesis Studies of Trichloroethylene in Four Strains of Rats (ACI. August, Marshall, Osborne-Mendel). NTP TR 273. NIH Publ. No. 88–2529. U.S. Department of Health and Human Services, Bethesda, MD 1987
   Google Scholar
• Environmental Protection Agency. Health Assessment Document for Trichloroethylene. Research Triangle Park, NC 1985, EPA/600/8–82/006F. Final Report
   Google Scholar
• Angelo M. J., Pritchard A. B. Simulations of methylene chloride pharmacokinetics using a physiologically based model. Reg. Toxicol. Pharmacol. 1984; 4: 329
   PubMedGoogle Scholar
• Andersen M. W., Clewell H. J., III, Gargas M. L., Smith F. A., Reitz R. H. Physiologically based pharmacokinetics and the risk assessment process for methylene chloride. Toxicol. Appl. Pharmacol. 1987; 87: 185
   PubMed Web of Science ®Google Scholar
• Reitz R. H., Nolan R. J., Schumann A. M. Development of multispecies, multiroute pharmacokinetic models for methylene chloride and 1,1,1-trichloroethane (methyl chloroform). Pharmacokinetics in Risk Assessment – Drinking Water and Health. National Academy Press, Washington, DC 1987; Vol. 8: 391
   Google Scholar
• Andersen M. W., Hoel D. G., Kaplan N. L. A general scheme for the incorporation of pharmacokinetics in low-dose estimation for chemical carcinogens: example – vinyl chloride. Toxicol. Appl. Pharmacol. 1980; 55: 154
   PubMedGoogle Scholar
• Chen C. W., Blancato J. N. Incorporation of biological mechanisms in cancer risk assessment: example – vinyl chloride. Presented to the Society of Toxicology, Washington, DC 1987, in preparation
   Google Scholar
• D'Souza R. W., Andersen M. W. Physiologically based pharmacokinetic model for vinylidene chloride. Toxicol. Appl. Pharmacol. 1988; 95: 230
   PubMed Web of Science ®Google Scholar
• Chen C. W., Blancato J. N. Role of pharmacokinetic modeling in risk assessment: perchloroethylene as an example. Pharmacokinetics in Risk Assessment – Drinking Water and Health. National Academy Press, Washington, DC 1987; Vol. 8: 369
   Google Scholar
• Paustenbach D. J., Clewell H. J., III, Gargas M. L., Andersen M. E. Development of a physiologically based pharmacokinetic model for multiday inhalation of carbon tetrachloride. Pharmacokinetics in Risk Assessment – Drinking Water and Health. National Academy Press, Washington, DC 1987; Vol. 8: 312
   Google Scholar
• Ikeda M., Ohtsuji H., Imamura T., Komoike Y. Urinary excretion of total trichloro-compounds, trichloroethanol, and trichloroacetic acid as a measure of exposure to trichloroethylene and tetrachloroethylene. Br. J. Ind. Med. 1972; 29: 328
   PubMedGoogle Scholar
• Bonse G., Henschler D. Chemical reactivity, biotransformation and toxicity of polychlorinated aliphatic compounds. CRC Crit. Rev. Toxicol. 1976; 10: 395
   Google Scholar
• Bolt H. M., Laib R. J., Filser J. G. Reactive metabolites and carcinogenicity of halogenated ethylenes. Biochem. Pharmacol. 1982; 31: 1
   PubMed Web of Science ®Google Scholar
• Henschler D., Hoos W. R., Fetz H., Dallmier E., Metzler M. Reactions of trichloroethylene epoxide in aqueous systems. Biochem. Pharmacol. 1979; 29: 543
   Google Scholar
• Miller R. E., Guengerich F. P. Oxidation of trichloroethylene by liver microsomal cytochrome P-450: evidence for chlorine migration in a transition state not involving trichloroethylene oxide. Biochemistry 1982; 21: 1090
   PubMed Web of Science ®Google Scholar
• Miller R. E., Guengerich F. P. Metabolism of trichloroethylene in isolated hepatocytes, microsomes and reconstituted systems containing cytochrome P-450. Cancer Res. 1983; 43: 1145
   PubMed Web of Science ®Google Scholar
• Buben J. A., O'Flaherty E. J. Delineation of the role of metabolism in the hepatotoxicity of trichloroethylene and perchloroethylene: a dose-effect study. Toxicol. Appl. Pharmacol. 1985; 78: 105
   PubMed Web of Science ®Google Scholar
• Rouisse L., Chakrabarti S. K. Dose-dependent metabolism of trichloroethylene and its relevance to hepatotoxicity in rats. Environ. Res. 1986; 40: 450
   PubMedGoogle Scholar
• Chakrabarti S. K., Tuchweber B. Studies of acute nephrotoxic potential of trichloroethylene in Fischer-344 rats. J. Toxicol. Environ. Health 1988; 23: 147
   PubMed Web of Science ®Google Scholar
• Dekant W., Schulz A., Metzler M., Henschler D. Absorption, elimination and metabolism of trichloroethylene: a quantitative comparison between rats and mice. Xenobiotica 1986; 16: 143
   PubMed Web of Science ®Google Scholar
• Stott W. T., Quast J. F., Watanabe P. G. The pharmacokinetics and macromolecular interactions of trichloroethylene in mice and rats. Toxicol. Appl. Pharmacol. 1982; 62: 137
   PubMed Web of Science ®Google Scholar
• Dekant W., Metzler M., Henschler D. Novel metabolites of trichloroethylene through dechlorination reactions in rats, mice and humans. Biochem. Pharmacol. 1984; 33: 2021
   PubMed Web of Science ®Google Scholar
• Prout M. S., Provan W. M., Green T. Species differences in response to trichloroethylene. I. Pharmacokinetics in rats and mice. Toxicol. Appl. Pharmacol. 1985; 79: 389
   PubMed Web of Science ®Google Scholar
• Hathway D. E. Consideration of the evidence for mechanisms of 1,1,2-trichloroethylene metabolism, including new identification of its dichloroacetic acid and trichloroacetic acid metabolites in mice. Cancer Lett. 1980; 8: 263
   PubMed Web of Science ®Google Scholar
• Nelson M. A., Bull R. J. Induction of strand breaks in DNA by trichloroethylene and metabolites in rat and mouse liver in vivo. Toxicol. Appl. Pharmacol. 1988; 94: 45
   PubMed Web of Science ®Google Scholar
• Herren-Freund S. L., Pereira M. A., Khoury M. D., Olson G. The carcinogenicity of trichloroethylene and its metabolites, trichloroacetic acid and dichloroacetic acid, in mouse liver. Toxicol. Appl. Pharmacol. 1987; 90: 183
   PubMed Web of Science ®Google Scholar
• Henschler D. Metabolism and mutagenicity of halogenated olefins – a comparison of structure and activity. Environ. Health Perspect. 1977; 21: 61
   PubMed Web of Science ®Google Scholar
• Van Duuren B. L., Kline S. A., Melchionne S., Seidman I. Chemical structure and carcinogenicity relationships of some chloroalkene oxides and their parent olefins. Cancer Res. 1983; 43: 159
   PubMed Web of Science ®Google Scholar
• Walles S. A. S. Induction of single-strand breaks in DNA of mice by trichloroethylene and tetrachloroethylene. Toxicol. Lett. 1986; 31: 31
   PubMedGoogle Scholar
• Elcombe C. R. Species differences in carcinogenicity and peroxisome proliferation due to trichloroethylene: a biochemical human hazard assessment. Arch. Toxicol. 1985; 8: 6
   Google Scholar
• Goldsworthy T. L., Popp J. A. Chlorinated hydrocarbon-induced peroxisomal enzyme activity in relation to species and organ carcinogenicity. Toxicol. Appl. Pharmacol. 1987; 88: 225
   PubMed Web of Science ®Google Scholar
• Nelson M. A., Bull R. J. Dichloroacetate (DCA) induced DNA strand breaks appear before peroxisome proliferation. Toxicologist 1988; 8: 665
   Google Scholar
• Green T., Prout M. S. Species differences in response to trichloroethylene. II. Biotransformation in rats and mice. Toxicol. Appl. Pharmacol. 1985; 79: 401
   PubMed Web of Science ®Google Scholar
• Elcombe C. R., Rose M. S., Pratt I. S. Biochemical, histological, and ultrastructural changes in rat and mouse liver following the administration of trichloroethylene: possible relevance to species differences in hepatocarcinogenicity. Toxicol. Appl. Pharmacol. 1985; 79: 365
   PubMed Web of Science ®Google Scholar
• DeAngelo A. B., Herren-Freund S., Pereira M. A., Schults N. E., Klaunig J. E. Species sensitivity to the induction of peroxisome proliferation by trichloroethylene and its metabolites. Toxicologist 1986; 6: 113
   Google Scholar
• Reddy J. K., Lalwani N. D. Carcinogenesis by hepatic peroxisome proliferators: evaluation of the risk of hypolipidemic drugs and industrial plasticizers to humans. CRC Crit. Rev. Toxicol. 1983; 12: 1
   Web of Science ®Google Scholar
• Uehleke H., Poplawski-Tabarelli S. Irreversible binding of14C-labelled trichloroethylene to mice liver constituentsin vivo in vitro. Arch. Toxicol. 1977; 37: 289
   PubMed Web of Science ®Google Scholar
• VanDuuren B. L., Benerjee S. Covalent interaction of metabolites of the carcinogen trichloroethylene in rat hepatic microsomes. Cancer Res. 1976; 36: 2419
   PubMedGoogle Scholar
• Laib R. J., Stockle G., Bolt H. M., Kunz W. Vinyl chloride and trichloroethylene: comparison of alkylating effects of metabolites and induction of preneoplastic enzyme deficiencies in rat liver. J. Cancer Res. Clin. Oncol. 1979; 94: 139
   PubMed Web of Science ®Google Scholar
• Banerjee S., Van Duuren B. L. Covalent binding of the carcinogen trichloroethylene to hepatic microsomal proteins and exogenous DNA in vitro. J. Cancer Res. 1978; 38: 776
   Google Scholar
• DiRenzo A. B., Gandolfi A. J., Sipes I. G. Microsomal bioactivation and covalent binding of aliphatic halides to DNA. Toxicol. Lett. 1982; 11: 243
   PubMed Web of Science ®Google Scholar
• Bergman K. Interactions of trichloroethylene with DNAin vitro and with DNA and RNA in various mouse tissues in vivo. Arch. Toxicol. 1983; 54: 181
   PubMed Web of Science ®Google Scholar
• Parchman L. G., Magee P. N. Metabolism of (14C)trichloroethylene to1 4CO2 and interaction of a metabolite with liver DNA in rats and mice. J. Toxicol. Environ. Health 1982; 9: 797
   PubMed Web of Science ®Google Scholar
• Litterst C. L., Mimnaugh E. G., Reagan R. L., Grain T. E. Comparison ofin vitro drug metabolism by lung, liver, and kidney of several common laboratory species. Drug Metab. Dispos. 1975; 3: 259
   PubMed Web of Science ®Google Scholar
• Hook G. E. R., Bend J. R. Pulmonary metabolism of xenobiotics. Life Sci. 1976; 18: 279
   PubMed Web of Science ®Google Scholar
• Baron J., Kawabata T. T., Redick J. A., Knapp S. A., Wick D. G., Wallace R. B., Jakoby W. B., Guengerich F. P. Localization of carcinogen metabolizing enzymes in human and animal tissue. Extrahepatic Drug Metabolism and Chemical Carcinogenesis. Elsevier, New York 1983
   Google Scholar
• Rush G. F., Smith J. H., Newton J. F., Hook J. B. Chemically induced nephrotoxicity: role of metabolic activation. CRC Crit. Rev. Toxicol. 1984; 13: 99
   Web of Science ®Google Scholar
• Bergman K. Application and results of whole-body autoradiography in distribution studies of organic solvents. CRC Crit. Rev. Toxicol. 1983; 12: 59
   Web of Science ®Google Scholar
• Bolt H. M., Filser J. G. Irreversible binding of chlorinated ethylenes to macromolecules. Environ. Health Perspect. 1977; 21: 107
   PubMed Web of Science ®Google Scholar
• Hobara T., Kobayashi H., Kawamoto T., Iwamoto S., Hirota S., Shimazu W., Sakal T. Extrahepatic organs metabolism of inhaled trichloroethylene. Toxicology 1986; 41: 289
   PubMedGoogle Scholar
• Hobara T., Kobayashi H., Higashihara E., Kawamoto T., Sakai T. Experimental studies of trichloroethylene toxicity. II. Changes in trichloroethylene metabolites in blood serum and in urine during and after exposure to trichloroethylene. Jpn. J. Hyg. 1983; 38: 772
   PubMedGoogle Scholar
• Hobara T., Kobayashi H., Kawamoto T., Iwamoto S., Sekai T. Extrahepatic metabolism of chloral hydrate, trichloroethanol and trichloroacetic acid in dogs. Pharmacol. Toxicol. 1987; 61: 58
   PubMedGoogle Scholar
• Dalbey W., Bingham E. Metabolism of trichloroethylene by the isolated perfused lung. Toxicol. Appl. Pharmacol. 1978; 43: 267
   PubMed Web of Science ®Google Scholar
• Kawamoto T. Metabolism of trichloroethylene in the isolated perfused rat liver. Yamaguchi Igaku 1984; 33: 527
   Google Scholar
• Forkert P. G., Sylvestre P. L., Poland J. S. Lung injury induced by trichloroethylene. Toxicology 1985; 35: 143
   PubMed Web of Science ®Google Scholar
• Devereux T., Smith B., Bend J., Fouts J. Xenobiotic metabolism in Clara and alveolar type II cells isolated from rabbit lung. Pharmacologist 1981; 23: 172
   Google Scholar
• Serabjit-Singh C. J., Wolf C. R., Philpot R. M., Plopper C. G. CytochromeP-450: localization in rabbit lung. Science 1980; 207: 1469
   PubMed Web of Science ®Google Scholar
• Boyd M. R., Stratham C. N., Longo N. S. The pulmonary Clara cell as a target for toxic chemicals requiring metabolic activation; studies with carbon tetrachloride. J. Pharmacol. Exp. Ther. 1980; 212: 109
   PubMed Web of Science ®Google Scholar
• Boyd M. R. Biochemical mechanisms in chemical-induced lung injury: roles of metabolic activation. CRC Crit. Rev. Toxicol. 1980; 7: 103
   Web of Science ®Google Scholar
• Tong S. S., Hirokata Y., Trush M. A., Mimnaugh E. G., Ginsburg E., Lowe M. C., Gram T. E. Clara cell damage and inhibition of pulmonary mixed-function oxidase activity by naphthalene. Biochem. Biophys. Res. Commun. 1981; 100: 944
   PubMed Web of Science ®Google Scholar
• Lewis G. D., Reynolds R. C., Johnson A. R. Some effects of trichloroethylene on mouse lungs and livers. Gen. Pharmacol. 1984; 15: 139
   PubMedGoogle Scholar
• Boyd M. R., Stratham C. N. The effect of hepatic metabolism on the production and toxicity of reactive metabolites in extrahepatic organs. Drug Metab. Rev. 1983; 14: 35
   PubMed Web of Science ®Google Scholar
• Guengerich F. P., Liebler D. C. Enzymatic activation of chemicals to toxic metabolites. CRC Crit. Rev. Toxicol. 1985; 14: 259
   Web of Science ®Google Scholar
• Guengerich F. P., Mason P. S., Stott W. T., Fox T. R., Watanabe P. G. Roles of 2-haloethylene oxides and 2-haloacetalde-hydes derived from vinyl bromide and vinyl chloride in irreversible binding to protein and DNA. Cancer Res. 1981; 41: 4391
   PubMed Web of Science ®Google Scholar
• Shen A. L., Fahl W. E., Jefcoate C. R. Metabolism of benzo(a)pyrene by isolated hepatocytes and factors affecting covalent binding of benzo(a)pyrene metabolites to DNA in hepatocyte and microsomal systems. Arch. Biochem. Biophys. 1980; 204: 511
   PubMed Web of Science ®Google Scholar
• Umbenhauer D. R., Pegg A. E. Alkylation of intracellular and extracellular DNA by dimethylnitrosamine following activation by isolated rat hepatocytes. Cancer Res. 1981; 41: 3471
   PubMed Web of Science ®Google Scholar
• Elfarra A. A., Anders M. W. Renal processing of glutathione conjugates. Role in nephrotoxicity. Biochem. Pharmacol. 1984; 33: 3729
   PubMed Web of Science ®Google Scholar
• Elfarra A. A., Jakobson I., Anders M. W. Mechanism ofS-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. Biochem. Pharmacol. 1986; 35: 283
   PubMed Web of Science ®Google Scholar
• Hughey R. P., Rankin B. B., Elce J. S., Curthoys N. P. Specificity of a particulate rat renal peptidase and its localization along with other enzymes of mercapturic acid synthesis. Arch. Biochem. Biophys. 1978; 186: 211
   PubMed Web of Science ®Google Scholar
• Dekant W., Metzler M., Henschler D. Identification ofS-1,2-dichlorovinyl-N-acetyl-cysteine as a urinary metabolite of trichloroeth-ylene: a possible explanation for its nephrocarcinogenicity in male rats. Biochem. Pharmacol. 1986; 35: 2455
   PubMed Web of Science ®Google Scholar
• Green T., Odum J. Structure/activity studies on the nephrotoxic and mutagenic action of cysteine conjugates of chloro- and fluoroalkenes. Chem.- Biol. Interactions 1985; 54: 15
   PubMed Web of Science ®Google Scholar
• Bonhaus D. W., Gandolfi A. J. Conjugation and bioactivation of chlorotrifluoroethylene. Life Sci. 1981; 29: 2399
   PubMed Web of Science ®Google Scholar
• Bhattacharya R. K., Schultze M. O. Properties of DNA treated withS-(1–2-dichlorovinyl)-L-cysteine and a lyase. Arch. Biochem. Biophys. 1972; 153: 105
   PubMed Web of Science ®Google Scholar
• Jaffe D. R., Gandolfi A. J., Nagle R. B. Chronic toxicity ofS-(trans-1,2-dichlorovinyl)-L-cysteine in mice. J. Appl. Toxicol. 1984; 4: 315
   PubMed Web of Science ®Google Scholar
• Meadows S. D., Gandolfi A. J., Nagle R. B., Shivley J. W. Enhancement of DMN-induced kidney tumors by 1,2-dichlorovinylcysteine in Swiss-Webster mice. Drug Chem. Toxicol. 1988; 11: 307
   PubMed Web of Science ®Google Scholar
• Terracini B., Parker V. H. A pathological study on the toxicity ofS-dichlorovinyl-L-cysteine. Food Cosmet. Toxicol. 1965; 3: 67
   PubMedGoogle Scholar
• National Research Council. Dose-route extrapolations: using inhalation toxicity data to set drinking water limits. Drinking Water and Health. National Academy Press, Washington, DC 1986; Vol. 6, chap. 6
   Google Scholar
• Dass P. D., Misra R. P., Welbourne T. C. Renal γ-glutamyltranspeptidase:in situ antiluminal localization. J. Histochem. Cytochem. 1982; 30: 148
   PubMedGoogle Scholar