Selective inhibition of cytochrome P450 2E1 in vivo and in vitro with trans-1,2-dichloroethylene

Chemical Research in Toxicology

Volumn 11, Issue 7, 1998, Pages 778-785

  Mathews, James M ^a   Etheridge, Amy S ^b   Raymer, James H ^b   Black, Sherry R ^b   Pulliam Jr , Donald W ^b   Bucher, John R ^b  

^a RTI INTERNATIONAL   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHYLENE; CYTOCHROME P450;

ANIMAL TISSUE; ARTICLE; DRUG OXIDATION; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME INHIBITION; IMMUNOBLOTTING; LIVER MICROSOME; NONHUMAN; RAT;

ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE; ANIMALS; BLOTTING, WESTERN; CYTOCHROME P-450 CYP2E1; CYTOSOL; DICHLOROETHYLENES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME INHIBITORS; MALE; MITOCHONDRIA, LIVER; RATS; RATS, INBRED F344;

EID: 0031873912     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970227g     Document Type: Article

References (55)

1. 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.
2. Gonzalez, F. J., and Gelboin, H. V. (1994) Roles of cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metab. Rev. 26, 165-184.
3. Kim, R. B., and O'Shea, D. (1995) Interindividual variability of chlorzoxazone 6-hydroxylation in men and women and its relationship to P450 2E1 genetic polymorphisms. Clin. Pharmacol. Ther. 57, 645-655.
4. Kim, R. B., Yamazaki, H., Chiba, K., O'Shea, D., Mimura, M., Guengerich, F. P., Ishizaki, T., Shimada, T., and Wilkinson, G. R. (1996) In vivo and in vitro characterization of P450 2E1 activity in Japanese and Caucasians. J. Pharmacol. Exp. Ther. 279, 4-11.
5. Stephens, E. A., Taylor, J. A., Kaplan, N., Yang, C.-H., Hsieh, L. L., Lucier, G. W., and Bell, D. A. (1994) Ethnic variation in the P450 2E1 gene: polymorphism analysis of 695 African-Americans, European-Americans and Taiwanese. Pharmacogenetics 4, 185-192.
6. Kato, S., Shields, P. G., Caporaso, N. E., Sugimura, H., Trivers, G. E., Tucker, M. A., Trump, B. F., Weston, A., and Harris, C. C. (1994) Analysis of cytochrome P450 2E1 genetic polymorphisms in relation to human lung cancer. Cancer Epidemiol. Biomarkers Prev. 3, 515-518.
7. Freundt, K. J., Liebaldt, G. P., and Lieberwirth, E. (1977) Toxicity studies on trans-1,2-dichloroethylene. Toxicology 7, 141-153.
8. ATSDR. (1990) Toxicological profile for 1,2-dichloroethenes Agency for Toxic Substances and Disease Registry, U.S. Public Health Service.
9. Andersen, M. E., Gargas, M. L., and Clewell, H. J., III. (1986) Suicide inactivation of microsomal oxidation by cis- and transdichloroethylene in male Fischer rats in vivo. Toxicologist 6, 12.
10. Thornton-Manning, J. R., Lilly, P. D., and Andersen, M. E. (1994) Inhibition of P450 2E1 in rat liver microsomes by dichloroethylene isomers. Toxicologist 14, 54.
11. Gargas, M. L., Clewell, H. J., III, and Andersen, M. E. (1990) Gas uptake inhalation techniques and the rates of metabolism of chloromethanes, chloroethanes, and chloroethylenes in the rat Inhal. Toxicol. 2, 295-319.
12. Andersen, M. E., Clewell, H. J., III, Mahle, D. A., and Gearhart, J. M. (1994) Gas uptake studies of deuterium isotope effects or dichloromethane metabolism in female B6C3F1 mice in vivo Toxicol. Appl. Pharmacol. 128, 158-165.
13. Mathews, J. M., Raymer, J. H., Velez, G. R., Garner, C. E., and Bucher, J. R. (1996) The influence of cytochrome P450 enzyme activity on the composition and quantity of volatile organics expired in breath. Biomarkers 1, 196-201.
14. Nash, T. (1953) The colorimetric estimation of formaldehyde by means of the Hanstzsch reaction. Biochem. J. 55, 416-421.
15. Miners, J. O., Smith, K. J., Robson, R. A., McManus, M. E., Veronese, M. E., and Birkett, D. J. (1988) Tolbutamide hydroxylation by human liver microsomes: Kinetic characterization and relationship to other cytochrome P450 dependent xenobiotic oxidations. Biochem. Pharmacol. 37, 1137-1144.
16. Zysset, T., Zeugin, T., and Kupfer, A. (1988) In vivo and in vitro dextromethorphan metabolism in SD and DA rat. Biochem. Pharmacol. 37, 3155-3160.
17. Laurenzana, E. M., Sorrels, S. L., and Owens, S. M. (1995) Antipeptide antibodies targeted against specific regions of rat P450 2D1 and human P450 2D6. Drug Metab. Dispos. 23, 271-278.
18. Wood, A. W., Ryan, D. E., Thomas, P. E., and Levin, W. (1983) Regio- and stereoselective metabolism of two C19 steroids by five highly purified and reconstituted rat hepatic cytochrome P-450 isozymes. J. Biol. Chem. 258, 8839-8847.
19. Brabec, M. J., Gray, R. H., and Bernstein, I. A. (1974) Restoration of hepatic mitochondria during recovery from carbon tetrachloride intoxication. Biochem. Pharmacol. 23, 3227-3238.
20. Tottmar, S. O. C., Pettersson, H., and Kiessling, K.-H. (1973) The subcellular distribution and properties of aldehyde dehydrogenases in rat liver. Biochem. J. 135, 577-586.
21. Horecker, B. L., and Kornberg, A. (1948) The extinction coefficients of the reduced band of pyridine nucleotides. J. Biol. Chem. 175, 385-390
22. Crow, K. E., Cornell, N. W., and Veech, R. L. (1977) The rate of ethanol metabolism in isolated rat hepatocytes Alcohol: Clin. Exp. Res. 1, 43-47.
23. Schenkman, J. B., Thummel, K. E., and Favreau, L. V. (1989) Physiological and pathophysiological alterations in rat hepatic cytochrome P-450. Drug Metab. Rev. 20, 557-584.
24. Costa, A. K., and Ivanetich, K. M. (1982). The 1,2-dichloroethylenes: their metabolism by hepatic cytochrome P-450 in vitro. Biochem. Pharmacol. 31, 2093-2102.
25. Hu, Y., Mishin, V., Johansson, I., von Bahr, C., Cross, A., Ronis, M. J. J., Badger, T. M., and Ingelman-Sundberg, M. (1994) Chlormethiazole as an efficient inhibitior of cytochrome P450 2E1 expression in rat liver. J. Pharmacol. Exp. Ther. 269, 1286-1291.
26. Mathews, J. M., Raymer, J. H., Etheridge, A. S., Velez, G. R., and Bucher, J. R. (1997) Do endogenous volatile organic chemicals measured in breath reflect and maintain P450 2E1 levels in vivo? Toxicol. Appl. Pharmacol. 146, 255-260.
27. Brady, J. F., Xiao, F., Wang, M. H., Li, Y., Ning, S. M., Gapac, J. M., and Yang, C. S. (1991) Effects of disulfiram on hepatic P450 2E1, other microsomal enzymes, and hepatotoxicity in rats. Toxicol. Appl. Pharmacol. 108, 366-373.
28. Brady, J. F., Li, D., Ishizaki, H., and Yang, C. S. (1988) Effect of diallylsulfide on rat liver microsomal nitrosamine metabolism and other monooxygenase activities. Cancer Res. 48, 5937-5940.
29. Zhukov, A., Werlinder, V., and Ingelman-Sundberg, M. (1993) Purification and characterization of two membrane bound serine proteinases from rat liver microsomes active in degradation of cytochrome P450. Biochem. Biophys. Res. Commun. 197, 221-228.
30. Song, B.-J., Veech, R. L., Park, S. S., Gelboin, H. V., and Gonzalez, K. J. (1989) Induction of rat hepatic N-nitrosodimethylamine demethylase by acetone is due to protein stabilization J. Biol. Chem. 264, 3568-3572.
31. Staub, R. E., Sparks, S. E., Quistad, G. B., and Casida, J. E. (1995) S-Methylation as a bioactivitation mechanism for mono- and dithiocarbamate pesticides as aldehyde dehydrogenase inhibitors. Chem. Res. Toxicol. 8, 1063-1069.
32. Fiala, E. S., Bobotas, G., Kulkas, C., Wattenberg, L. W., and Weisburger, J. H. (1977) The effects of disulfiram and related compounds on the metabolism in vivo of the colon carcinogen, 1,2-dimethylhydrazine. Biochem. Pharmacol. 26, 1763-1768.
33. Deitrich, R. A., and Erwin, V. G. (1971) Mechanism of the inhibition of aldehyde dehydrogenase in vivo by disulfiram and diethyldithiocarbamate. Mol. Pharmacol. 7, 301-307.
34. Eneanya, D. I., Bianchine, J. R., Duran, D. O., and Andresen, B. D. (1981) The actions and metabolic fate of disulfiram. Annu. Rev. Pharmacol. Toxicol. 21, 575-596.
35. Valentine, W. M., Amarnath, V., Amarnath, K., Rimmele, F., and Graham, D. G. (1995) Carbon disulfide mediated protein crosslinking by N,N-diethyldithiocarbamate. Chem. Res. Toxicol. 8, 96-102.
36. Vaccari, A., Saba, P. L., Ruiu, S., Collu, M., and Devoto, P. (1996) Disulfiram and diethyldithiocarbamate intoxication affects the storage and release of striatal dopamine. Toxicol. Appl. Pharmacol. 139, 102-108.
37. Kedderis, G. L., Batra, R., and Koop, D. R. (1993) Epoxidation of acrylonitrile by rat and human cytochromes P450. Chem. Res. Toxicol. 6, 866-871.
38. Valentine, W. M., Amarnath, V., Amarnath, K., and Graham, D. G. (1995) Characterization of protein adducts produced by N-methyldithiocarbamate and N-methyldithiocarbamate esters. Chem. Res. Toxicol. 8, 254-261.
39. Brady, J. F., Wang, M.-H., Hong, J.-Y., Xiao, F., Li, Y., Yoo, J.-S. H., Ning, S. M., Lee, M.-J., Fukuto, J. M., Gapac, J. M., and Yang, C. S. (1991) Modulation of rat hepatic microsomal monooxygenase enzymes and toxicity by diallyl sulfide. Toxicol. Appl. Pharmacol. 108, 342-354.
40. Lindros, K. O., Badger, T., Ronis, M., Ingelman-Sundberg, M., and Koivusalo, M. (1995) Phenethyl isothiocyanate, a new dietary liver aldehyde dehydrogenase inhibitor. J. Pharmacol. Exp. Ther. 275, 79-83.
41. Ishizaki, H., Brady, J. F., Ning, S. M., and Yang, C. S. (1990) Effect of phenethyl isothiocyanate on microsomal N-nitrosodim-ethylamine (NDMA) metabolism and other monooxygenase activities. Xenobiotica 20, 255-264.
42. Guo, Z., Smith, T. J., Wang, E., Sadrieh, N., Ma, Q., Thomas, P. E., and Yang, C. S. (1992) Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 13, 2205-2210.
43. Thomsen, M. S., Loft, S., Roberts, D. W., and Poulsen, H. E. (1995) Cytochrome P450 2E1 inhibition by propylene glycol prevents acetaminophen (paracetamol) hepatotoxicity in mice without cytochrome P450 1A2 inhibition. Pharmacol. Toxicol. 76, 395-399.
44. Komura, S. (1974) Effects of ethylene glycol dinitrate and related compounds on ethanol preference and ethanol metabolism. Acta Pharmacol. Toxicol. 35, 145-154.
45. Koop, D. R. (1990) Inhibition of ethanol-inducible cytochrome P450IIE1 by 3-amino-1,2,4-triazole. Chem. Res. Toxicol. 3, 377-383.
46. Baron, J., and Tephly, T. R. (1968) Effect of 3-amino-1,2,4-triazole on the stimulation of hepatic microsomal heme synthesis and induction of hepatic microsomal oxidases produced by phenobarbital. Mol. Pharmacol. 5, 10-20.
47. Steinhoff, D., Weber, H., Mohr, U., and Boehme, K. (1983) Evaluation of amitrole (aminotriazole) for potential carcinogenicity in orally dosed rats, mice, and golden hamsters. Toxicol. Appl. Pharmacol. 69, 161-169.
48. Feierman, D. E., and Cederbaum, A. I. (1987) Increased sensitivity of the microsomal oxidation of ethanol to inhibition by pyrazole and 4-methylpyrazole after chronic ethanol treatment. Biochem. Pharmacol. 36, 3277-3283.
49. Winters, D. K., and Cederbaum, A. I. (1992) Time course characterization of the induction of cytochrome P-450 2E1 by pyrazole and 4-methylpyrazole. Biochim. Biophys. Acta 1117, 15-24
50. Lieber, G. S., Rubin, E., DeCarli, L. M., Misra, P., and Gang, H. (1970) Effects of pyrazole on hepatic function and structure. Lab. Invest. 22, 615-621.
51. Magnusson, G., Nyberg, J. A., Bodin, N. O., and Hansson, E. (1972) Toxicity of pyrazole and 4-methylpyrazole in mice and rats Experientia 28, 1198-1200.
52. Heinemann, F., and Assion, H. J. (1996) Hepatotoxic side-effect of clomethiazole. Pharmacopsychiatry 29, 196-197.
53. Lee, I. J., Jeong, K. S., Roberts, B. J., Kallarakal, A. T., Fernandez-Salguero, P., Gonzalez, F. J., and Song, B. J. (1996) Transcriptional induction of the cytochrome P4501A1 gene by a thiazolium compound, YH439. Mol. Pharmacol. 49, 980-988.
54. Choi, E. Y., Kim, S. G., Lee, J. W., Yoo, J. K., Shin, J. K., and Kim, N. D. (1996) Suppression of rat hepatic cytochrome P450 2E1 expression by isopropyl 2-(1,3-dithioetane-2-ylidene)-2-[N-(4-methyl-thiazol-2-yl)carbamoyl]acetate (YH439), an experimental hepatoprotectant: protective role against hepatic injury. Biochem. Pharmacol. 52, 1219-1225.
55. Jeong, K.-S., Lee, I. J., Roberts, B. J., Soh, Y., Yoo, J. K., Lee, J. W., and Song, B. J. (1996) Transcriptional inhibition of cytochrome P4502E1 by a synthetic compound, YH439. Arch. Biochem. Biophys. 326, 137-144.