Characterization of amino acid and glutathione adducts of cis-2-butene- 1,4-dial, a reactive metabolite of furan

Chemical Research in Toxicology

Volumn 10, Issue 8, 1997, Pages 866-874

  Chen, Ling Jen ^a,b   Hecht, Stephen S ^a,c   Peterson, Lisa A ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^c UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTENE 1,4 DIAL; AMINO ACID; CARCINOGEN; FURAN DERIVATIVE; GLUTATHIONE; INDUSTRIAL CHEMICAL; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTICLE; CHEMICAL CARCINOGENESIS; DNA REPAIR; LIVER CANCER; LIVER CARCINOGENESIS; LIVER MICROSOME METABOLISM; MALE; NONHUMAN; OCCUPATIONAL EXPOSURE; RAT; TOXICOKINETICS;

ALDEHYDES; AMINO ACIDS; ANIMALS; FURANS; GLUTATHIONE; MALE; MICROSOMES, LIVER; RATS; RATS, INBRED F344;

ANIMALIA;

EID: 0030753035     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9700174     Document Type: Article

References (25)

1. Maga, J. (1979) Furans in foods. Crit. Rev. Food Sci. Nutr. 11, 355-366.
2. Wilson, D. M., Goldsworthy, T. L., Popp, J. A., and Butterworth, B. E. (1992) Evaluation of genotoxicity, pathological lesions, and cell proliferation in livers of rats and mice treated with furan. Environ. Mol. Mutagen. 19, 209-222.
3. 1 mice, NTP Technical Report No. 402, U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC.
4. 14C]furan in the male F344 rat. J. Toxicol. Environ. Health 34, 245-257.
5. Mortelmans, K., Haworth, S., Lawlor, T., Speck, W., Tainer, B., and Zeiger, E. (1986) Salmonella mutagenicity tests. II. Results from the testing of 270 chemicals. Environ. Mutagen. 7 (Suppl.), 1-119.
6. Parmar, D., and Burka, L. T. (1993) Studies on the interaction of furan with hepatic cytochrome P-450. J. Biochem. Toxicol. 8, 1-9.
7. Carfagna, M. A., Held, S. D., and Kedderis, G. L. (1993) Furan-induced cytolethality in isolated rat hepatocytes: Correspondence with in vivo dosimetry. Toxicol. Appl. Pharmacol. 123, 265-273.
8. Kedderis, G. L., Carfagna, M. A., Held, S. D., Batra, R., Murphy, J. E., and Gargas, M. L. (1993) Kinetic analysis of furan biotransformation by F-344 rats in vivo and in vitro. Toxicol. Appl. Pharmacol. 123, 274-282.
9. Chen, L. J., Hecht, S. S., and Peterson, L. A. (1995) Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan. Chem. Res. Toxicol. 8, 903-906.
10. Ravindranath, V., Burka, L. T., and Boyd, M. R. (1984) Reactive metabolites from the bioactivation of toxic methylfurans. Science 224, 884-886.
11. Ravindranath, V., and Boyd, M. R. (1985) Metabolic activation of 2-methylfuran by rat microsomal systems. Toxicol. Appl. Pharmacol. 78, 370-376.
12. Zhang, K. E., Naue, J. A., Arison, B., and Vyas, K. P. (1996) Microsomal metabolism of the 5-lipoxygenase inhibitor L-739,010: Evidence for furan bioactivation. Chem. Res. Toxicol. 9, 547-554.
13. Guengerich, F. P. (1982) Microsomal enzymes involved in toxicology-Analysis and separation. In Principles and Methods of Toxicology (Hayes, A. W., Ed.) pp 609-634, Raven Press, New York.
14. Baker, J. T., and Sifniades, S. (1979) Synthesis and properties of pyrrolin-2-ones. J. Org. Chem. 44, 2798-2800.
15. 13C spectra of some 2-substituted furans, thiophenes, selenophenes and tellurophenes. Acta Chem. Scand. B28, 175-184.
16. Alvarez-Coque, M. C. G., Hernandez, M. J. M., Camañas, R. M. V., and Fernàndez, C. M. (1989) Formation and instability of o-phthalaldehyde derivatives of amino acids. Anal. Biochem. 178, 1-7.
17. Gronowitz, S., and Kada, R. (1984) Sulfur derivatives of 1-methylpyrrole. J. Heterocycl. Chem. 21, 1041-1043.
18. Zhu, M., Spink, D. C., Yan, B., Bank, S., and DeCaprio, A. P. (1995) Inhibition of 2,5-hexanedione-induced protein cross-linking by biological thiols: chemical mechanisms and toxicological implications. Chem. Res. Toxicol. 8, 764-771.
19. Koga, N., Inskeep, P. B., Harris, T. M., and Guengerich, F. P. (1986) S-[2-(N7-Guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane. Biochemistry 25, 2192-2198.
20. Ribó, J. M., and Vallés, A. (1987) Tautomerism of 2-hydroxypyrrole and some related derivatives studied by MINDO/3 and MNDO methods. J. Chem. Res. (S), 284-285.
21. Simons, S. S., Jr., and Johnson, D. F. (1978) Reaction of o-phthalaldehyde and thiols with primary amines: formation of 1-alkyl(and aryl)thio-2-alkylisoindoles. J. Org. Chem. 43, 2886-2891.
22. Fiorenza, M., Reginato, G., Ricci, A., and Taddei, M. (1984) Regioselective functionalization of heterocyclic rings: synthesis and reactions of 1-methyl-2-(trimethylsiloxy)pyrrole and 2-(trimethylsiloxy)thiophene. J. Org. Chem. 49, 551-553.
23. DeCaprio, A., and O'Neill, E. A. (1985) Alterations in rat axonal cytoskeletal proteins induced by in vitro and in vivo 2,5-hexanedione exposure. Toxicol. Appl. Pharmacol. 78, 235-247.
24. Graham, D. G., Anthony, D. C., Boekelheide, K., Maschmann, N. A., Richards, R. G., Wolfram, J. W., and Shaw, B. R. (1982) Studies of the molecular pathogenesis of hexane neuropathy. II. Evidence that pyrrole derivatization of lysyl residues leads to protein crosslinking. Toxicol. Appl. Pharmacol. 64, 415-422.
25. Fukui, H., Shimokawa, S., Sohma, J., Owadare, T., and Esumi, N. (1971) Analysis of the NMR spectrum of 3-methyl-pyrrole. J. Mol. Spectrom. 39, 521-524.