Synthesis and Characterization of N-Acetyl-L-cysteine S-Conjugates of Butadiene Monoxide and Their Detection and Quantitation in Urine of Rats and Mice Given Butadiene Monoxide

Chemical Research in Toxicology

Volumn 8, Issue 1, 1995, Pages 68-76

  Elfarra, Adnan A ^a   Sharer, Jane E ^a   Duescher, Renee J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ACETYLCYSTEINE DERIVATIVE; DRUG METABOLITE;

ANIMAL EXPERIMENT; ARTICLE; CARCINOGENICITY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; MOUSE; MUTAGENICITY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SYNTHESIS; URINARY EXCRETION; URINE;

ACETYLCYSTEINE; ANIMAL; CARCINOGENS; EPOXY COMPOUNDS; MALE; MICE; MUTAGENS; RATS; RATS, SPRAGUE-DAWLEY; SUPPORT, U.S. GOV'T, P.H.S.;

ANIMALIA;

EID: 0028794711     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00043a009     Document Type: Article

References (27)

1. NIOSH (1989) National Occupational Exposure Survey, National Institute for Occupational Safety and Health, Cincinnati, OH.
2. Fajen, J. M., Roberts, D. R., Ungers, L. J., and Krishnan, E. R. (1990) Occupational exposure of workers to 1,3-butadiene. Environ. Health Perspect. 86, 11–18.
3. Miller, L. M. (1978) Investigation of selected potential environmental contaminants: butadiene and its oligomers. In EPA-560/2-78-008, U.S. Environmental Protection Agency, Washington, DC.
4. Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987) Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/carcinogenicity study in rats. Am. Ind. Hyg. Assoc. J. 48, 407–413.
5. 1 mice at low exposure concentrations. Cancer Res. 50, 6592–6599.
6. International Agency for Research on Cancer (1987) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Suppl. 7, World Health Organization, Lyon.
7. Matanoski, G. M., Santos-Burgoa, C., and Schwartz, L. (1990) Mortality of a cohort of workers in the styrene-butadiene polymer manufacturing industry (1943–1982). Environ. Health Perspect. 86, 107–117.
8. Deuscher, R. J., and Elfarra, A. A. (1994) Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation. Evidence for major roles by cytochromes P450 2A6 and 2E1. Arch. Biochem. Biophys. 311, 342–439.
9. Elfarra, A. A., Duescher, R. J., and Pasch, C. M. (1991) Mechanisms of 1,3-butadiene oxidations to butadiene monoxide and crotonaldehyde by mouse liver microsomes and chloroperoxidase. Arch. Biochem. Biophys. 286, 244–251.
10. Duescher, R. J., and Elfarra, A. A. (1992) 1,3-Butadiene oxidation by human myeloperoxidase: role of chloride ion in catalysis of divergent pathways. J. Biol. Chem. 267, 19859–19865.
11. Bolt, H. M., Schmiedel, G., Filser, J., Rolzhauser, H., Lieser, K., Wistuba, D., and Schurig, V. (1983) Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats. J. Cancer Res. Clin. Oncol. 106, 112–116.
12. Schurig, V., and Wistuba, D. (1984) Asymmetric microsomal epoxidation of simple prochiral olefins. Angew. Chem., Int. Ed. Engl. 23, 796–797.
13. de Meester, C., Poncelet, F., Roberfroid, M., and Mercier, M. (1978) Mutagenicity of butadiene and butadiene monoxide. Biochem. Biophys. Res. Commun. 80, 298–305.
14. Sharief, Y., Brown, A. M., Backer, L. C., Campbell, J. A., Westbrook-Collins, B., Stead, A. G., and Allen, J. W. (1986) Sister chromatid exchange and chromosome aberration analyses in mice after in vivo exposure to acrylonitrile, styrene, or butadiene monoxide. Environ. Mutagen. 8, 439–448.
15. Van Duuren, B. L., Nelson, N., Orris, L., Palmes, E. D., and Schmitt, F. L. (1963) Carcinogenicity of epoxides, lactones, and peroxy compounds. J. Natl. Cancer Inst. 31, 41–55.
16. 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.
17. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1991) Formation, stability, and rearrangements of the glutathione conjugates of butadiene monoxide: evidence for the formation of stable sulfurane intermediates. Chem. Res. Toxicol. 4, 430–436.
18. Sharer, J. E., and Elfarra, A. A. (1992) S-(2-Hydroxy-3-buten-1-yl)glutathione and S-(1-hydroxy-3-buten-2-yl)glutathione are in vivo metabolites of butadiene monoxide: detection and quantitation in bile. Chem. Res. Toxicol. 5, 787–790.
19. Osterman-Golkar, S., Kautiainen, A., Bergmark, E., Hakansson, K., and Maki Paakkanen, J. (1991) Hemoglobin adducts and urinary mercapturic acids in rats as biological indicators of butadiene exposure. Chem.-Biol. Interact. 80, 291–302.
20. Slatter, J. G., Rashed, M. S., Pearson, P. G., Han, D., and Baillie, T. A. (1991) Biotransformation of methyl isocyanate in the rat. Evidence for glutathione conjugation as a major pathway of metabolism and implications for isocyanate-mediated toxicities. Chem. Res. Toxicol. 4, 157–161.
21. Sabourin, P. J., Burka, L. T., Bechtold, W. E., Dahl, A. R., Hoover, M. E., Chang, I. Y., and Henderson, R. F. (1992) Species differences in urinary butadiene metabolites; identification of 1,2-dihydroxy-4-(N-acetylcysteinyl)butane, a novel metabolite of butadiene. Carcinogenesis 13, 1633–1638.
22. van Weilie, R. T. H., van Dijck, R. G. J. M., and Vermeulen, N. P. E. (1992) Mercapturic acids, protein adducts, and DNA adducts as biomarkers of electrophilic chemicals. CRC Crit. Rev. Toxicol. 22, 271–306.
23. Onkenhout, W., Van Bergen, E. J. C., Van der wart, J. H. F., Vos, G. P., Buijs, W., and Vermeulen, N. P. E. (1986) Identification and quantitative determination of four different mercapturic acids formed from 1,3-dibromopropane and its 1,1,3,3-tetradeutero analogue by the rat. Xenobiotica 16, 21–33.
24. Zoetemelk, C. E. M., van Hove, W., van der Laan, W. L. J., van Meeteren-Walchli, B., van der Gen, A., and Breimer, D. D. (1987) Glutathione conjugation of 1,2-dibromo-1-phenylethane in rats in vivo. Drug Metab. Dispos. 15, 418–425.
25. Kreiling, R., Laib, R. J., Filser, J. G., and Bolt, H. M. (1987) Inhalation pharmacokinetics of 1,2-epoxybutene-3 reveal species differences between rats and mice sensitive to butadiene-induced carcinogenesis. Arch. Toxicol. 61, 7–11.
26. Bond, J. A., Dahl, A. R., Henderson, R. F., Dutcher, J. S., Mauderly, J. L., and Birnbaum, L. S. (1986) Species differences in the disposition of inhaled butadiene. Tox. Appl. Pharmacol. 84, 617–627.
27. 14C]1,3-butadiene. Toxicol. Lett. 30, 131–136.