Covalent binding and inhibition of cytochrome P4502E1 by trichloroethylene

References

• ALLEMAND, H., PESSAYRE, D., DESCATOIRE, V., DEGOTT, C., FELDMANN, G. and BENHAMOU, J. P., 1978, Metabolic activation of trichloroethylene into a chemically reactive metabolite toxic to the liver. Journal of Pharmacology and Experimental Therapeutics, 204,714–723.
   PubMed Web of Science ®Google Scholar
• BOURDI, M., CHEN, W., PETER, R. M., MARTIN, J. L., BUTERS, J. T. M., NELSON, S. D. and PoHL, L. R., 1996, Human P4502E1 is a major autoantigen associated with halothane hepatitis. Chemical Research in Toxicology, 9, 1159–1166.
   Google Scholar
• BRUCKNER, J. V., DAVIS, B. D. and BLANCATO, J. N., 1989, Metabolism, toxicity, and carcinogenicity of trichloroethylene. Critical Reviews in Toxicology, 20, 31–50.
   PubMed Web of Science ®Google Scholar
• BUBEN, J. A. and O'FLAHERTY, E. J., 1985, Delineation of the role of metabolism in the hepatotoxicity of trichloroethylene and perchloroethylene: a dose-effect study. Toxicology and Applied Phar-macology, 78, 105–122.
   Google Scholar
• DAVIDSON, L W. and BELILES, R. P., 1991, Consideration of the target organ toxicity of trichloroethylene in terms of metabolite toxicity and pharmacokinetics. Drug Metabolism Reviews, 23,493–599.
   PubMed Web of Science ®Google Scholar
• ELIASSON, E. and KENNA, J. G., 1996, Cytochrome P450 2E1 is a cell surface autoantigen in halothane hepatitis. Molecular Pharmacology, 50, 573–582.
   PubMed Web of Science ®Google Scholar
• GOEPTAR, A. R., COMMANDEUR, J. N. M., VAN OMMEN, B., VAN BLADEREN, P. J. and VERMEULEN N. P. E., 1995, Metabolism and kinetics of trichloroethylene in relation to toxicity and carcinogenicity. Relevance of the mercapturic acid pathway. Chemical Research in Toxicology, 8, 3–21.
   Google Scholar
• GREEN, T., 1990, Chloroethylenes : a mechanistic approach to human risk evaluation. Annual Reviews in Pharmacology, 30, 73–89.
   Google Scholar
• HALMES, N. C., MCMILLAN, D. C., OATTS, J. J. E. and PUMFORD, N. R., 1996a, Immunochemical detection of protein adducts in mice treated with trichloroethylene. Chemical Research in Toxicology, 9,451–456.
   Google Scholar
• HALMES, N. C., HINSON, J. A., MARTIN, B. A. and PUMFORD, N. R., 1996b, Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen. Chemical Research in Toxicology, 9, 541–546.
   PubMed Web of Science ®Google Scholar
• HENSCHLER, D., VAMVAKAS, S., LAMMERT, M., DEKANT W., KRAUS, B., THOMAS, B. and ULm, K., 1995, Increased incidence of renal cell tumors in a cohort of cardboard workers exposed to trichloroethylene. Archives of Toxicology, 69,291–299.
   Google Scholar
• IARC, 1995, Dry cleaning, some chlorinated solvents and other industrial chemicals. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans (Lyon: World Health Organization, International Agency for Research on Cancer), pp. 75–158.
   Google Scholar
• KHAN, M. F., KAPHALIA, B. S., PRABHAKAR, B. S., KANZ, M. F. and ANSARI, G. A., 1995, Trichloroethane -induced autoimmune response in female MRL +/+ mice. Toxicology and Applied Pharmacology, 134, 155–160.
   PubMed Web of Science ®Google Scholar
• KILBURN, K. H. and WARSHAW, R. H., 1992, Prevalence of symptoms of systemic lupus erythematosus (SLE) and of fluorescent antinuclear antibodies associated with chronic exposure to trichloro-ethylene and other chemicals in well water. Environmental Research, 57, 1–9.
   PubMed Web of Science ®Google Scholar
• KOOP, D. R., 1986, Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a. Molecular Pharmacology, 29,399–404.
   PubMed Web of Science ®Google Scholar
• LECOEUR, S., BONTERBALE, E., CHALLINE, D., GAUTIER, J. C., VALADON, P., DANSETIE, P. M., CATINOT R., BALLET, F., MANSUY, D. and BEAUNE, P. H., 1994, Specificity of in vitro covalent binding of tienilic acid metabolites to human liver microsomes in relationship to the type of hepatotoxicity: comparison with two directly hepatotoxic drugs. Chemical Research in Toxicology, 7, 43/1 /142.
   Google Scholar
• LOCKEY, J. E., KELLY, C. R., CANNON, G. W., COLBY, T. V., ALDRICH, V. and LIVINGSTON, G. K., 1987, Progressive systemic sclerosis associated with exposure to trichloroethylene. Journal of Oc-cupational Medicine, 29,493–496.
   PubMed Web of Science ®Google Scholar
• LOWRY, O. H., ROSEBROUGH, N. J., FAR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193,265–275.
   PubMed Web of Science ®Google Scholar
• MILLER, R. E. and GUENGEIUCH, F. P., 1983, Metabolism of trichloroethylene in isolated hepatocytes, microsomes, and reconstituted enzyme systems containing cytochrome P-450. Cancer Research, 43, 1145–1152.
   PubMed Web of Science ®Google Scholar
• ORTIZ DE MONTELLANO, P. R., 1995, Oxygen activation and reactivity. In CytochrorneP450 : Structure, Mechanism, and Biochemistry, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 245–303.
   Google Scholar
• ORTIZ DE MONTELLANO, P. R. and CORREIA, M. A., 1983, Suicidal destruction of cytochrome P-450 during oxidative drug metabolism. Annual Review of Phannacology and Toxicology, 23,481–503.
   PubMed Web of Science ®Google Scholar
• ORTIZ DE MONTELIANO, P. R. and CORREIA, M. A., 1995, Inhibition of cytochrome P450 enzymes. In Cytochrorne P450 : Structure, Mechanism, and Biochemistry, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 305–364.
   Google Scholar
• OSAWA, Y. and Poim, L. R., 1989, Covalent binding of the prosthetic heme to protein: a potential mechanism for the suicide inactivation or activation of hemoproteins. Chemical Research in Toxicology, 2, 131–141.
   PubMed Web of Science ®Google Scholar
• PHOON, W. H., CHAN, M. O., RAJAN, V. S., TAN, K. J., THIRUMOORTHY, T. and Gm, C. L., 1984, Stevens- Johnson syndrome associated with occupational exposure to trichloroethylene. Contact Dennatitis, 10, 270–276.
   PubMed Web of Science ®Google Scholar
• POULOS, T. L., 1986, The crystal structure of cytochrome P450m, . In Cytochrorne P450: Structure, Mechanism, and Biochemistry, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 505–523.
   Google Scholar
• TIERNEY, D. J., HAAS, A. L. and KOOP, D. R., 1992, Degradation of cytochrome P450 2E1: selective loss after labilization of the enzyme. Archives of Biochemistry and Biophysics, 293, 9–16.
   PubMed Web of Science ®Google Scholar
• WALLER, P. A., CLAUW, D., CUPPS, T., METCALF, J. S., SILVER, R. M. and LERov, E. C., 1994, Fasciitis (not scleroderma) following prolonged exposure to an organic solvent (trichloroethylene). Journal of Rheurnatology, 21, 1567–1570.
   PubMed Web of Science ®Google Scholar
• WEISS, N. S., 1996, Cancer in relation to occupational exposure to trichloroethylene. Occupational and Environmental Medicine, 53, 1–5.
   PubMed Web of Science ®Google Scholar
• YANEZ DIAZ, S., MORAN, M., UNAMUNO, P. and ARMIJO, M., 1992, Silica and trichloroethylene-induced progressive systemic sclerosis. Dermatology, 184, 98–102.
   PubMed Web of Science ®Google Scholar