CYP2E1-dependent bioactivation of 1,1-dichloroethylene in murine lung: Formation of reactive intermediates and glutathione conjugates

Toxicology and Applied Pharmacology

Volumn 139, Issue 1, 1996, Pages 42-48

  Dowsley, Tylor F ^a   Ulreich, Judith B ^b   Bolton, Judy L ^c   Park, Sang S ^d   Forkert, Poh Gek ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 ISOENZYME; VINYLIDENE CHLORIDE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; FEMALE; METABOLIC ACTIVATION; MICROSOME; MOUSE; NONHUMAN; XENOBIOTIC METABOLISM;

ANIMALIA; MURINAE;

EID: 0030200743     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1996.0141     Document Type: Article

References (31)

1. Andersen, M. E., Thomas, O. E., Gargas, M. L., Jones, R. A., and Jenkins, L. J., Jr. (1980). The significance of multiple detoxification pathways for reactive metabolites in the toxicity of 1,1-dichloroethylene. Toxicol. Appl. Pharmacol. 52, 422-432.
2. Coleman, W. E., Lingg, R. D., Melton, R. G., and Kopfler, F. C. (1976). The occurrence of volatile organics in five drinking water supplies using gas chromatography/mass spectrophotometry. In Identification and Analysis of Organic Pollutants in Water (L. H. Keith, Ed.), pp. 305-327. Ann Arbor Science Publishers, Ann Arbor, MI.
3. Costa, A. K., and Ivanetich, K. M. (1984). Chlorinated ethylenes: Their metabolism and effect on DNA repair in hepatocytes. Carcinogenesis 5, 1629-1636.
4. Dowsley, T. F., Forkert, P. G., Benesch, L. A., and Bolton, J. L. (1995). Reaction of glutathione with the electrophilic metabolites of 1,1-dichloroethylene. Chem.-Biol. Interact. 95, 227-244.
5. Forkert, P. G., Hofley, M., and Racz, W. J. (1987). Metabolic activation of 1,1-dichloroethylene by mouse lung and liver microsomes. Can. J. Physiol. Pharmacol. 65, 1496-1499.
6. Forkert, P. G., Massey, T. E., Jones, A. B., Park, S. S., Gelboin, H. V., and Anderson, L. M. (1991). Distribution of cytochrome CYP2E1 in murine liver after ethanol and acetone administration. Carcinogenesis 12, 2259-2268.
7. Forkert, P. G., and Moussa, M. (1991). 1,1-Dichloroethylene elicits dose-dependent alterations in covalent binding and glutathione in murine liver. Drug Metab. Dispos. 19, 580-586.
8. Forkert, P. G., and Moussa, M. (1993). Temporal effects of 1,1-dichloroethylene on nonprotein sulfhydryl content in murine lung and liver. Drug Metab. Dispos. 21, 770-776.
9. Forkert, P. G., and Reynolds, E. S. (1982). 1,1-Dichloroethylene-induced pulmonary injury. Exp. Lung Res. 3, 57-68.
10. Forkert, P. G., Stringer, V., and Troughton, K. M. (1986). Pulmonary toxicity of 1,1-dichloroethylene: Correlation of early changes with covalent binding. Can. J. Physiol. Pharmacol. 64, 112-121.
11. Guengerich, F. P., Kim, D. H., and Iwasaki, M. (1991). Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4, 168-179.
12. Jaeger, R. J., Connolly, R. B., and Murphy, S. D. (1973). Diurnal variation of hepatic glutathione concentration and its correlation with 1,1-dichloroethylene inhalation toxicity in rats. Res. Commun. Chem. Pathol. Pharmacol. 6, 465-471.
13. Jaeger, R. J., Connolly, R. B., and Murphy, S. D. (1974). Effect of 18-hour fast and glutathione depletion on 1,1-dichloroethylene-induced hepatotoxicity and lethality in rats. Exp. Mol. Pathol. 20, 187-198.
14. Johansson, I., Ekström, G., Scholte, B., Puzycki, D., Jörnvall, H., and Ingelman-Sundberg, M. (1988). Ethanol-, fasting- and acetone-inducible cytochromes P-450 in rat liver: Regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies. Biochemistry 27, 1925-1934.
15. Jones, B. K., and Hathway, D. E. (1978). The biological fate of vinylidene chloride in rats. Chem.-Biol. Interact. 20, 27-41.
16. Kainz, A., Cross, H., Freeman, S., Gescher, A., and Chipman, J. K. (1993). Effects of 1,1-dichloroethene and of some of its metabolites on the functional viability of mouse hepatocytes. Fundam. Appl. Toxicol. 21, 140-148.
17. Ko, I. Y., Park, S. S., Song, B. J., Patten, C., Tan, Y., Hah, Y. C., Yang, C. S., and Gelboin, H. V. (1987). Monoclonal antibodies to ethanol-induced rat liver cytochrome P-450 that metabolizes aniline and nitrosamines. Cancer Res. 47, 3101-3109.
18. Krijgsheld, K. R., Lowe, M. C., Mimnaugh, E. G., Trush, M. A., Ginsburg, E., and Gram, T. E. (1983). Lung-selective impairment of cytochrome P450-dependent monoxygenases and cellular injury by 1,1-dichlorethylene in mice. Biochem. Biophys. Res. Commun. 110, 675-681.
19. Lee, R. P., and Forkert, P. G. (1994). In vitro biotransformation of 1,1-dichloroethylene by hepatic cytochrome P450 2E1 in mice. J. Pharmacol. Exp. Ther. 270, 371-376.
20. Lee, R. P., and Forkert, P. G. (1995). Pulmonary CYP2E1 bioactivates 1,1-dichloroethylene in male and female mice. J. Pharmacol. Exp. Ther. 273, 561-567.
21. Liebler, D. C., and Guengerich, F. P. (1983). Olefin oxidation by cytochrome P-450: Evidence for group migration in catalytic intermediates formed with vinylidene chloride and trans-1-phenyl-1-butene. Biochemistry 22, 5482-5489.
22. Liebler, D. C., Latwesen, D. G., and Reeder, T. C. (1988). S-(2-Chloroacetyl)glutathione, a reactive glutathione thiol ester and putative metabolite of 1,1-dichloroethylene. Biochemistry 27, 3652-3657.
23. Liebler, D. C., Meredith, M. J., and Guengerich, F. P. (1985). Formation of glutathione conjugates by reactive metabolites of vinylidene chloride in microsomes and isolated hepatocytes. Cancer Res. 45, 186-193.
24. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951). Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
25. Matsubara, T., Prough, R. A., Burk, M. D., and Estabrook, R. W. (1974). The preparation of microsomal fractions of rodent respiratory tract and their characterization. Cancer Res. 34, 2196-2203.
26. McKenna, M. J., Zempel, J. A., Madrid, E. O., Braun, W. H., and Gehring, P. J. (1978). Metabolism and pharmacokinetic profile of vinylidene chloride in rats following oral administration. Toxicol. Appl. Pharmacol. 45, 821-835.
27. Moussa, M., and Forkert, P. G. (1992). 1,1-Dichloroethylene-induced alterations in glutathione and covalent binding in murine lung: Morphological, histochemical and biochemical studies. J. Pathol. 166, 199-207.
28. Mraz, J., Hyland, R., Jheeta, P., Gescher, A., Threadgill, M. D., and Thummel, K. (1993). Investigation of the mechanistic basis of N,N-dimethylformamide toxicity. Metabolism of N,N-dimethylformamide and its deuterated isotopomers by cytochrome P-450 2E1. Chem. Res. Toxicol. 6, 197-207.
29. 14C] 1,1 -dichloroethylene by mouse liver, kidney and lung. Biochem. Pharmacol. 35, 2789-2795.
30. Smith-Gill, S. J., Wilson, A. C., Potter, M., Prager, E. M., Feldmann, R. J., and Mainhart, C. R. (1982). Mapping the antigenic isotope for a monoclonal antibody against lysozyme. J. Immunol. 128, 314-322.
31. Thomas, P. E., Bandiera, S., Maines, S. L., Ryan, D. E., and Levin, W. (1987). Regulation of cytochrome P-450j, a high affinity N-nitrosodimethylamine demethylase, in rat hepatic microsomes. Biochemistry 26, 2280-2289.