Chlorothioketene, the ultimate reactive intermediate formed by cysteine,conjugate β-lyase-mediated cleavage of the trichloroethene metabolite S-(1,2-dichlorovinyl)-L-cysteine, forms cytosine adducts in organic solvents, but not in aqueous solution

Chemical Research in Toxicology

Volumn 11, Issue 9, 1998, Pages 1082-1088

  Völkel, Wolfgang ^a   Dekant, Wolfgang ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

TRICHLOROETHYLENE;

ARTICLE; DNA ADDUCT; DRUG DNA INTERACTION; ENVIRONMENTAL TEMPERATURE; MOLECULAR STABILITY; TOXICITY TESTING;

ACETATES; ANIMALS; CARBON-SULFUR LYASES; CATTLE; CYSTEINE; CYTOSINE; DNA; DNA ADDUCTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KETONES; SENSITIVITY AND SPECIFICITY; SOLUTIONS; SOLVENTS; WATER;

EID: 0031670446     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980084d     Document Type: Article

References (26)

1. Dekant, W., Vamvakas, S., Berthold, K., Schmidt, S., Wild, D., and Henschler, D. (1986) Bacterial β-lyase mediated cleavage and mutagenicity of cysteine conjugates derived from the nephrocarcinogenic alkenes trichloroethylene, tetrachloroethylene and hexachlorobutadiene. Chem.-Biol. Interact. 60, 31-45.
2. Schaumann, E. (1988) The chemistry of thioketenes: Tetrahedron Report No. 231. Tetrahedron 44, 1827-1871.
3. Birner, G., Richling, C., Henschler, D., Anders, M. W., and Dekant, W. (1994) Metabolism of tetrachloroethene in rats: identification of Nε-dichloroacetyl)-L-lysine and Nε-(trichloroacetyl)-L-lysine as protein adducts. Chem. Res. Toxicol. 7, 724-732.
4. Dekant, W., Urban, G., Görsman, C., and Anders, M. W. (1991) Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S-conjugates. J. Am. Chem. Soc. 113, 5120-5122.
5. Vamvakas, S., Dekant, W., and Henschler, D. (1989) Genotoxicity of haloalkene and haloalkane glutathione S-conjugates in porcine kidney cells. Toxicol in Vitro 3, 151-156.
6. Vamvakas, S., Dekant, W., and Henschler, D. (1989) Assessment of unscheduled DNA synthesis in a cultured line of renal epithelial cells exposed to cysteine S-conjugates of haloalkenes and haloalkanes. Mutat. Res. 222, 329-335.
7. National Toxicology Program, National Cancer Institute (1977) Bioassay of tetrachloroethylene for possible carcinogenicity. Technical Report No. 13, U.S. Department of Health and Human Services, Washington, DC.
8. National Toxicology Program, National Cancer Institute (1986) Carcinogenesis bioassay of tetrachloroethylene. Technical Report No. 232, U.S. Department of Health and Human Services, Washington, DC.
9. National Toxicology Program, National Cancer Institute (1986) Carcinogenesis bioassay of trichloroethylene. Technical Report No. 311, U.S. Department of Health and Human Services, Washington, DC.
10. National Toxicology Program, National Cancer Institute (1988) Toxicology and Carcinogenesis studies of trichloroethylene in four strains of rats (ACI, August, Marshall, Osborne-Mendel) (gavage studies). Technical Report No. 273, U.S. Department of Health and Human Services, Washington, DC.
11. Kanhai, W., Dekant, W., and Henschler, D. (1989) Metabolism of the nephrotoxin dichloroacetylene by glutathione conjugation. Chem. Res. Toxicol 2, 51-56.
12. Pedersen, B. S., and Lawesson, S.-O. (1979) Studies on Organophosphorus Compounds-XXVIII. Tetrahedron 35, 2433-2437.
13. 6 acylated cytosines. Tetrahedron Lett., 289-291.
14. 2,3-ethenoguanine based on electrophore labeling. Carcinogenesis 11, 1279-1285.
15. Müller, M., Birner, G., and Dekant, W. (1998) Reactivity of haloketenes and halothioketenes with nucleobases: chemical characterization of reaction products. Chem. Res. Toxicol 11, 454-463.
16. Müller, M., Birner, G., Sander, M., and Dekant, W. (1998) Reactivity of haloketenes and halothioketenes with nucleobases; reactions in vitro with DNA. Chem. Res. Toxicol 11, 464-470.
17. Raasch, M. S. (1970) Bis(trifluoromethyl)thioketene. I. Synthesis and cycloaddition reactions. J. Org. Chem. 35, 3470-3483.
18. Seybold, G., and Heibl, C. (1975) Blitzhermolyse von 1,2,3-Thiadiazolen: ein einfacher Weg zu Thioketenen (Flash thermolysis of 1,2,3-thiadiazoles. Simple route to thioketenes). Angew. Chem. 87, 171-172.
19. Elam, E. U., Rash, F. H., Dougherty, J. T., Goodlett, V. W., and Brannock, K. C. (1968) Di-tert-butylthioketene. J. Org. Chem. 33, 2738-2741.
20. Dekant, W., Berthold, K., Vamvakas, S., Henschler, D., and Anders, M. W. (1988) Thioacylating intermediates as metabolites of S-(l,2-dichlorovinyl)-L-cysteine and S-(l,2,2-trichlorovinyl)-Lcysteine formed by cysteine conjugate β-lyase. Chem. Res. Toxicol 1, 175-178.
21. Goody, R. S., and Walker, R. T. (1971) The preparation and properties of some cytosine derivatives. J. Org. Chem. 36, 727-730.
22. Anders, M. W. (1988) Bioactivation mechanisms and hepatocellular damage. In The Liver: Biology and Pathology (Arias, I. M., Jakoby, W. B., Popper, H., Schachter, D., and Shafritz, D. A., Eds.) 2nd ed., pp 389-400, Raven Press, Ltd., New York.
23. Nelson, S. D., and Pearson, P. G. (1990) Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals. Annu. Rev. Pharmacol. Toxicol. 30, 169-195.
24. Hinson, J. A., and Roberts, D. W. (1992) Role of covalent and noncovalent interactions in cell toxicity: effects on proteins. Annu. Rev. Pharmacol. Toxicol 32, 471-510.
25. Dekant, W., Metzler, M., and Henschler, D. (1986) Identification of S-l,2-dichlorovinyl-N-acetylcysteine as a urinary metabolite of trichloroethylene: A possible explanation for its nephrocarcinogenicity in male rats. Biochem. Pharmacol. 35, 2455-2458.
26. Dekant, W., Metzler, M., and Henschler, D. (1986) Identification of S-l,2,2-trichlorovinyl-N-acetylcysteine as a urinary metabolite of tetrachloroethylene: bioactivation through glutathione conjugation as a possible explanation of its nephrocarcinogenicity. J. Biochem. Toxicol. 1, 57-72.