Species and tissue differences in the toxicity of 3-butene-1,2-diol in male Sprague-Dawley rats and B6C3F1 mice

Toxicological Sciences

Volumn 80, Issue 1, 2004, Pages 3-13

  Sprague, Christopher L ^a   Phillips, Lynette A ^b   Young, Karen M ^b   Elfarra, Adnan A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

1 3 butadiene; 3 butene 1,2 diol; Glutathione depletion; Hepatotoxicity; Hypoglycemia; Rat sensitive

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 3 BUTENE 1,2 DIOL; GLUTATHIONE; GLUTATHIONE DISULFIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; HISTOPATHOLOGY; HYPOGLYCEMIA; LIVER DYSFUNCTION; LIVER INJURY; LIVER TOXICITY; MALE; MOUSE; MOUSE STRAIN; NONHUMAN; PLASMA HALF LIFE; RAT; RAT STRAIN; SPECIES DIFFERENCE; TISSUE LEVEL; TOXICITY TESTING;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENVIRONMENTAL POLLUTANTS; GLUTATHIONE; GLYCOLS; HALF-LIFE; HEPATITIS, TOXIC; LIVER; MALE; MICE; RATS; RATS, SPRAGUE-DAWLEY; SPECIES SPECIFICITY; TISSUE DISTRIBUTION;

EID: 3042842515     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1093/toxsci/kfh156     Document Type: Article

References (34)

1. Atzori, L., Dore, M., and Congiu, L. (1989). Aspects of allyl alcohol toxicity. Drug Metab. Drug Inter. 7, 295-319.
2. Bechtold, W. E., Strunk, M. R., Chang, I. Y., Ward, J. B., and Henderson, R. F. (1994). Species differences in urinary butadiene metabolites: Comparisons of metabolite ratios between mice, rats, and humans. Toxicol. Appl. Pharmacol. 127, 44-49.
3. Brass, E. P., Fennessey, P. V., and Miller, L. V. (1986). Inhibition of oxidative metabolism by propionic acid and its removal by carnitine in isolated rat hepatocytes. Biochem. J. 236, 131-136.
4. Chung, F.-L., Tanka, T., and Hecht, S. S. (1986). Induction of liver tumors in F344 rats by crotonaldehyde. Cancer Res. 46, 1285-1289.
5. Csanady, G. A., Guengerich, F. P., and Bond, J. A. (1992). Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats, and mice. Carcinogenesis 13, 1143-1153.
6. Duescher, R. J., and Elfarra, A. A. (1994). Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: Evidence for major roles by cytochrome P450-2A6 and -2E1. Arch. Biochem. Biophys. 311, 339-342.
7. Eigenberg, D. A., Carter, D. E., Schram, K. H., and Sipes, I. G. (1986). Examination of the differential hepatotoxicity of diallyl phthalate in rats and mice. Toxicol. App. Pharmacol. 86, 12-21.
8. Ferrali, M., Ciccoli, L., Signorini, C., and Comporti, M. (1990). Iron release and erythrocyte damage in allyl alcohol intoxication in mice. Biochem. Pharmacol. 40, 1485-1490.
9. Fontaine, F. R., Dunlop, R. A., Petersen, D. R., and Burcham, P. C. (2002). Oxidative bioactivation of crotyl alcohol to the toxic endogenous aldehyde crotonaldehyde: Association of protein carbonylation with toxicity in mouse hepatocytes. Chem. Res. Toxicol. 15, 1051-1058.
10. Gatley, S.J., and Sherratt, H. S. (1977). The synthesis of hippurate from benzoate and glycine by rat liver mitochondria. Biochem. J. 166, 39-47.
11. Gebhardt, R. (1992). Metabolic zonation of the liver: Regulation and implications for liver function. Pharmacol. Ther. 53, 275-354.
12. Griffith, O. W. (1980). Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine. Anal. Biochem. 106, 207-212.
13. Gunnarsdottir, D., Rucki, M., and Elfarra, A. A. (2002). Novel glutathione-dependent thiopurine prodrugs: Evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice. J. Pharmacol. Exp. Ther. 301, 77-86.
14. Jaeschke, H., Kleinwaechter, C., and Wendel, A. (1987). The role of acrolein in allyl alcohol-induced lipid peroxidation and liver cell damage in mice. Biochem. Pharmacol. 36, 51-51.
15. Kemper, R. A., and Elfarra, A. A. (1996). Oxidation of 3-butene-1,2-diol by alcohol dehydrogenase. Chem. Res. Toxicol. 9, 1127-1134.
16. Kemper, R. A., Elfarra, A. A., and Myers, S. R. (1998). Metabolism of 3-butene-1,2-diol in B6C3F1 mice: Evidence for involvement of alcohol dehydrogenase and cytochrome P450. Drug Metab. Dispos. 26, 914-920.
17. Krause, R. J., Kemper, R. A., and Elfarra, A. A. (2001). Hydroxymethylvinyl ketone: A reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes. Chem. Res. Toxicol. 14, 1590-1595.
18. Krause, R. J., Sharer, J. E., and Elfarra, A. A. (1997). Epoxide hydrolase-dependent metabolism of butadiene monoxide to 3-butene-1,2-diol in mouse, rat, and human liver. Drug Metab. Dispos. 25, 1013-1015.
19. Landrigan, P. J. (1993). Critical assessment of epidemiological studies on the carcinogenicity of 1,3-butadiene and styrene. IARC Scientific Publications 127, 375-388.
20. Melnick, R. L., Huff, J. E., Roycroft, J. H., Chou, B. J., and Miller, R. A. (1990). Inhalation toxicology and carcinogenicity of 1,3-butadiene in B6C3F1 mice following 65 weeks of exposure. Environ. Health Perspect. 86, 27-36.
21. 13C]butadiene. Chem. Res. Toxicol. 9, 764-773.
22. Occupational Safety and Health Administration (OSHA), Department of Labor (1996). Occupational exposure to 1,3-butadiene: Final rule. Federal Register 61, 56746-56856.
23. Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987). Inhalation toxicity studies with 1,3-butadiene: III. Two-year toxicity/carcinogenicity study in rats. Am. Indust. Hyg. Assoc. J. 48, 407-413.
24. 2-Propanodeoxyguanosine adducts of the 1,3-butadiene metabolite, hydroxymethylvinyl ketone. Chem. Res. Toxicol. 16, 1448-1454.
25. Reid, W. D. (1972). Mechanism of allyl alcohol-induced hepatic necrosis. Experientia 28, 1058-1061.
26. 14C-1,3-butadiene in rats and mice: Relevance to cancer susceptibility. Toxicol. Sci. 49, 186-201.
27. Santos-Burgoa, C., Matanoski, G. M., Zeger, S., and Schwartz, L. (1992). Lymphohematopoietic cancer in styrene-butadiene polymerization workers. Am. J. Epidemiol. 136, 843-854.
28. Seymour, M. A., Millburn, P., and Tait, G. H. (1987). Species variations in the hepatic and renal conjugation of benzoic acid with glycine or glucuronic acid. Biochem. Soc. Trans. 15, 451-452.
29. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1992). Species and tissue differences in the microsomal oxidation of 1,3-butadiene and the glutathione conjugation of butadiene monoxide in mice and rats: Possible role in 1,3-butadiene-induced toxicity. Drug Metab. Dispos. 20, 658-664.
30. Sherratt, H. S. A. (1985). Acyl-CoA esters of xenobiotic carboxylic acids as biochemically active intermediates. Biochem. Soc. Trans. 13, 856-858.
31. Sprague, C. L., and Elfarra, A. A. (2003). Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. Drug Metab. Dispos. 31, 986-992.
32. Tietze, F. (1969). Enzymatic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Anal. Biochem. 27, 505-522.
33. U.S. Environmental Protection Agency (EPA) (2002). Health assessment of 1,3-butadiene. Office of Research and Development, National Center for Environmental Assessment, Washington, DC, Section 6.
34. Wild, A. C., and Mulcahy, R. T. (1999). Pyrrolidine dithiocarbamate upregulates the expression of the genes encoding the catalytic and regulatory subunits of γ-glutamylcysteine synthetase and increases intracellular glutathione levels. Biochem. J. 338, 659-665.