Formation of mono- and bis-Michael adducts by the reaction of nucleophilic amino acids with hydroxymethylvinyl ketone, a reactive metabolite of 1,3-butadiene

Chemical Research in Toxicology

Volumn 22, Issue 5, 2009, Pages 918-925

  Barshteyn, Nella ^a   Elfarra, Adnan A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ACETYLCYSTEINE; AMINO ACID; HYDROXYMETHYLVINYL KETONE; KETONE DERIVATIVE; N ACETYLLYSINE; NUCLEOPHILE; UNCLASSIFIED DRUG; VALINAMIDE;

ARTICLE; CONTROLLED STUDY; HETERONUCLEAR SINGLE QUANTUM COHERENCE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINO ACIDS; BUTADIENES; BUTANONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LYSINE;

EID: 67449083759     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900006b     Document Type: Article

References (29)

1. Hesterberg, T. W., Lapin, C. A., and Bunn, W. B. (2008) A comparison of emissions from vehicles fueled with diesel or compressed natural gas. Environ. Sci. Technol. 42, 6437-6445.
2. Adam, T., Mitschke, S., Streibel, T., Baker, R. R., and Zimmermann, R. (2006) Quantitative puff-by-puff resolved characterization of selected toxic compounds in cigarette mainstream smoke. Chem. Res. Toxicol. 19, 511-520.
3. National Toxicology Program (NTP) (2005) Report on Carcinogens, 11th ed., U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, Research Triangle Park, NC.
4. Grosse, Y., Baan, R., Straif, K., Secretan, B., El Ghissassi, F., Bouvard, V., Altieri, A., and Cogliano, V. (2007) Carcinogenicity of 1,3-butadiene, ethylene oxide, vinyl chloride, vinyl fluoride, and vinyl bromide. Lancet Oncol. 8, 679-680.
5. 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.
6. 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/ carcinogenity study in rats. Am. Ind. Hyg. Assoc. J. 48, 407-413.
7. Graff, J. J., Sathiakumar, N., Macaluso, M., Maldonado, G., Matthews, R., and Delzell, E. (2005) Chemical exposures in the synthetic rubber industry and lymphohematopoietic cancer mortality. J. Occup. Environ. Med. 47, 916-932.
8. Ward, E. M., Fajen, J. M., Ruder, A. M., Rinsky, R. A., Halperin, W. E., and Fessler-Flesch, C. A. (1995) Mortality study of workers in 1,3-butadiene production units identified from a chemical workers cohort. Environ. Health Perspect. 103, 598-603.
9. Duescher, R. J., and Elfarra, A. A. (1994) Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: Evidence for major roles by P450 2A6 and 2E1. Arch. Biochem. Biophys. 311, 342-349.
10. Duescher, R. J., and Elfarra, A. A. (1992) 1,3-Butadiene oxidation of human myeloperoxidase: Role of chloride ion in catalysis of divergent pathways. J. Biol. Chem. 267, 19859-19865.
11. 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.
12. 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.
13. 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.
14. Kemper, R. A., and Elfarra, A. A. (1996) Oxidation of 3-butene-1,2-diol by alcohol dehydrogenase. Chem. Res. Toxicol. 96, 1127-1134.
15. 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.
16. 14C]- butadiene. Chem.-Biol. Interact. 147, 213-232.
17. Sprague, C. L., and Elfarra, A. A. (2004) Mercapturic acid urinary metabolites of 3-butene-1,2-diol as in vivo evidence for the formation of hydroxymethylvinyl ketone in mice and rats. Chem. Res. Toxicol. 17, 819-826.
18. Barshteyn, N., Krause, R. J., and Elfarra, A. A. (2007) Mass spectral analyses of hemoglobin adducts formed after in vitro exposure of erythrocytes to hydroxymethylvinyl ketone. Chem.-Biol. Interact. 166, 176-181.
19. Swaminathan, S., and Narayanan, K. V. (1971) The Rupe and Meyer-Schuster rearrangements. Chem. Rev. 71, 429-438.
20. Barshteyn, N., and Elfarra, A. A. (2007) Formation of N-acetyl-Lcysteine monoadducts and a diadduct by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with N-acetyl-L- cysteine at physiological conditions: Chemical mechanisms and toxicological implications. Chem. Res. Toxicol. 20, 1563-1569.
21. Doorn, J. A., and Petersen, D. R. (2003) Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal. Chem.-Biol. Interact. 143-144, 93-100.
22. Uchida, K., Kanematsu, M., Morimitsu, Y., Osawa, T., Noguchi, N., and Niki, E. (1998) Acrolein is a product of lipid peroxidation reaction. Formation of free acrolein and its conjugate with lysine residues in oxidized low-density lipoproteins. J. Biol. Chem. 273, 16058-16066.
23. Smithgall, T. E., Harvey, R. G., and Penning, T. M. (1988) Spectroscopic Identification of ortho-quionones as products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. J. Biol. Chem. 263, 1814-1820.
24. Giles, N. M., Watts, A. B., Giles, G. I., Fry, F. H., Littlechild, J. A., and Jacob, C. (2003) Metal and redox modulation of cysteine protein function. Chem. Biol. 10, 677-693.
25. Dairou, J., Atmane, N., Rodrigues-Lima, F., and Dupret, J. (2004) Peroxynitrite irreversibly inactivates the human xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1) in human breast cancer cells. A cellular and mechanistic study. J. Biol. Chem. 279, 7708-7714.
26. Szweda, L. I., Uchida, K., Tsai, L., and Stadtman, E. R. (1993) Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. J. Biol. Chem. 268, 3342-3347.
27. Furuhata, A., Nakamura, M., Osawa, T., and Uchida, K. (2002) Thiolation of protein-bound carcinogenic aldehyde. An electrophilic acrolein-lysine adduct that covalently binds to thiols. J. Biol. Chem. 277, 27919-27926.
28. Shamoto-Nagai, M., Maruyama, W., Hashizume, Y., Yoshida, M., Osawa, T., Riederer, P., and Naoi, M. (2007) In parkinsonian substantia nigra, alpha-synuclein is modified by acrolein, a lipid-peroxidation product, and accumulates in the dopamine neurons with inhibition of proteasome activity. J. Neural Transm. 114, 1559-1567.
29. Swenberg, J. A., Christova-Gueorguieva, N. I., Upton, P. B., Ranasinghe, A., Scheller, N., Wu, K., Yen, T., and Hayes, R. (2000) 1,3-Butadiene: cancer, mutations, and adducts. Part V: Hemoglobin adducts as biomarkers of 1,3-butadiene exposure and metabolism. Res. Rep. Health Eff. Inst. 92, 191-210.