Inactivation of glutathione transferase zeta by dichloroacetic acid and other fluorine-lacking α-haloalkanoic acids

Chemical Research in Toxicology

Volumn 12, Issue 12, 1999, Pages 1144-1149

  Anderson, Wayne B ^a   Board, Philip G ^b   Gargano, Bryan ^a   Anders, M W ^a  

^a UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

^b Biology and Environment   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOIC ACID; DICHLOROACETIC ACID; DRINKING WATER; FLUORINE; GLUTATHIONE TRANSFERASE; GLUTATHIONE TRANSFERASE ZETA; GLYOXYLIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CARCINOGENICITY; CHLORINATION; CONTROLLED STUDY; LACTIC ACIDOSIS; LIVER CARCINOGENESIS; LIVER CYTOSOL; MALE; NONHUMAN; RAT; WATER CONTAMINATION; WATER SUPPLY;

ANIMALS; BIOTRANSFORMATION; CYTOSOL; DICHLOROACETATE; ENZYME INHIBITORS; GLUTATHIONE TRANSFERASE; HALF-LIFE; HYDROCARBONS, HALOGENATED; LIVER; MALE; RATS; RATS, INBRED F344;

ANIMALIA;

EID: 0033391126     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990085l     Document Type: Article

References (40)

1. Krasner, S. W., McGuire, M. J., Jacangelo, J. G., Patania, N. L., Reagan, K. M., and Aieta, E. M. (1989) The occurrence of disinfection by-products in US drinking water. J. Am. Water Works Assoc. 81, 41-53.
2. Weisel, C. P., Kim, H., Haltmeier, P., and Klotz, J. B. (1998) Exposure estimates to disinfection by-products of chlorinated drinking water. Environ. Health Perspect. 107, 103-110.
3. Dekant, W., Metzler, M., and Henschler, D. (1984) Novel metabolites of trichloroethylene through dechlorination reactions in rats, mice and humans. Biochem. Pharmacol. 33, 2021-2027.
4. Larson, J. L., and Bull, R. J. (1992) Species differences in the metabolism of trichloroethylene to the carcinogenic metabolites trichloroacetate and dichloroacetate. Toxicol. Appl. Pharmacol. 115, 278-285.
5. Henderson, G. N., Yan, Z., James, M. O., Davydova, N., and Stacpoole, P. W. (1997) Kinetics and metabolism of chloral hydrate in children: identification of dichloroacetate as a metabolite. Biochem. Biophys. Res. Commun. 235, 695-698.
6. Völkel, W., Friedewald, M., Lederer, E., Pähler, A., Parker, J., and Dekant, W. (1998) Biotransformation of perchloroethene: dose-dependent excretion of trichloroacetic acid, dichloroacetic acid, and N-acetyl-S-(trichlorovinyl)-L-cysteine in rats and humans after inhalation. Toxicol. Appl. Pharmacol. 153, 20-27.
7. DeAngelo, A. B., Daniel, F. B., Stober, J. A., and Olson, G. R. (1991) The carcinogenicity of dichloroacetic acid in the male B6C3F1 mouse. Fundam. Appl. Toxicol. 16, 337-347.
8. DeAngelo, A. B., Daniel, F. B., Most, B. M., and Olson, G. R. (1996) The carcinogenicity of dichloroacetic acid in the male Fischer 344 rat. Toxicology 114, 207-221.
9. Stacpoole, P. W. (1989) The pharmacology of dichloroacetate. Metabolism 38, 1124-1144.
10. Peeling, J., Sutherland, G., Brown, R. A., and Curry, S. (1996) Protective effect of dichloroacetate in a rat model of forebrain ischemia. Neurosci. Lett. 208, 21-24.
11. Larson, J. L., and Bull, R. J. (1992) Metabolism and lipoperoxidative activity of trichloroacetate and dichloroacetate in rats and mice. Toxicol. Appl. Pharmacol. 115, 268-277.
12. Lin, E. L. C., Mattox, J. K., and Daniel, F. B. (1993) Tissue distribution, excretion, and urinary metabolites of dichloroacetic acid in the male Fischer 344 rat. J. Toxicol. Environ. Health 38, 19-32.
13. 14C]-dichloroacetate in male Sprague-Dawley rats. Identification of glycine conjugates, including hippurate, as urinary metabolites of dichloroacetate. Drug Metab. Dispos. 26, 1134-1143.
14. Lipscomb, J. C., Mahle, D. A., Brashear, W. T., and Barton, H. A. (1995) Dichloroacetic acid: metabolism in cytosol. Drug Metab. Dispos. 23, 1202-1205.
15. James, M. O., Cornett, R., Yan, Z., Henderson, G. N., and Stacpoole, P. W. (1997) Glutathione-dependent conversion to glyoxylate, a major metabolite of dichloroacetate biotransformation in hepatic cytosol from humans and rats, is reduced in dichloroacetate-treated rats. Drug Metab. Dispos. 25, 1223-1227.
16. Tong, Z., Board, P. G., and Anders, M. W. (1998) Glutathione transferase Zeta catalyzes the oxygenation of the carcinogen dichloroacetic acid to glyoxylic acid. Biochem. J. 331, 371-374.
17. Tong, Z., Board, P. G., and Anders, M. W. (1998) Glutathione transferase Zeta-catalyzed biotransformation of dichloroacetic acid and other α-haloacids. Chem. Res. Toxicol. 11, 1332-1338.
18. Fernández-Cañón, J. M., and Peñalva, M. A. (1998) Characterization of a fungal maleylacetoacetate isomerase gene and identification of its human homologue. J. Biol. Chem. 273, 329-337.
19. Curry, S. H., Chu, P.-I., Baumgartner, T. G., and Stackpoole, P. W. (1985) Plasma concentrations and metabolic effects of intravenous sodium dichloroacetate. Clin. Pharmacol. Ther. 37, 89-93.
20. Curry, S. H., Lorenz, A., Chu, P.-I., Limacher, M., and Stacpoole, P. W. (1991) Disposition and pharmacodynamics of dichloroacetate (DCA) and oxalate following oral DCA doses. Biopharm. Drug Dispos. 12, 375-390.
21. Henderson, G. N., Curry, S. H., Derendorf, H., Wright, E. C., and Stacpoole, P. W. (1997) Pharmacokinetics of dichloroacetate in adult patients with lactic acidosis. J. Clin. Pharmacol. 37, 416-425.
22. Gonzalez-Leon, A., Schultz, I. R., Xu, G., and Bull, R. J. (1997) Pharmacokinetics and metabolism of dichloroacetate in the F344 rat after prior administration in drinking water. Toxicol. Appl. Pharmacol. 146, 189-195.
23. Board, P. G., Baker, R. T., Chelvanayagam, G., and Jermiin, L. S. (1997) Zeta, a novel class of glutathione transferases in a range of species from plants to humans. Biochem. J. 328, 929-935.
24. Williamson, K. L. (1987) Microscale Organic Experiments, D. C. Heath, Lexington, MA.
25. Dohn, D. R., and Anders, M. W. (1982) Assay of cysteine conjugate β-lyase activity with S-(2-benzothiazolyl)cysteine as the substrate. Anal. Biochem. 120, 379-386.
26. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
27. Vogels, G. D., and Van Der Drift, C. (1970) Differential analyses of glyoxylate derivatives. Anal. Biochem. 33, 143-157.
28. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
29. Price, V. E., Sterling, W. R., Tarantola, V. A., Hartley, R. W., Jr., and Rechcigl, M., Jr. (1962) The kinetics of catalase synthesis and destruction in vivo. J. Biol. Chem. 237, 3468-3475.
30. Goldberg, A. L., and Dice, J. F. (1974) Intracellular protein degradation in mammalian and bacterial cells. Annu. Rev. Biochem. 43, 835-869.
31. Smith, K., and Rennie, M. J. (1996) The measurement of tissue protein turnover. Baillieres Clin. Endocrinol. Metab. 10, 469-495.
32. Gonzalez-Leon, A., Merdink, J. L., Bull, R. J., and Schultz, I. R. (1999) Inhibition of metabolism by chlorinated and brominated di-haloacetates and differential recovery in B6C3F1 mice and F344 rats. Toxicol. Sci. 48 (1-S), 206.
33. Stacpoole, P. W., Henderson, G. N., Yan, Y., Cornett, R., and James, M. O. (1998) Pharmacokinetics, metabolism, and toxicology of dichloroacetate. Drug Metab. Rev. 30, 499-539.
34. Wempe, M. F., Anderson, W. B., Tzeng, H.-F., Board, P. G., and Anders, M. W. (1999) Glutathione transferase zeta-catalyzed biotransformation of deuterated dihaloacetic acids. Biochem. Biophys. Res. Commun. 261, 779-783.
35. Mulder, G. J., and Ouwerkerk-Mahadevan, S. (1997) Modulation of glutathione conjugation in vivo: how to decrease glutathione conjugation in vivo or in intact cellular systems in vitro. Chem. Biol. Interact. 105, 17-34.
36. Zheng, J., Mitchell, A. E., Jones, A. D., and Hammock, B. D. (1996) Haloenol lactone is a new isozyme-selective and active site-directed inactivator of glutathione S-transferase. J. Biol. Chem. 271, 20421-20425.
37. Tamai, K., Satoh, K., Tsuchida, S., Hatayama, I., Maki, T., and Sato, K. (1990) Specific inactivation of glutathione S-transferases in class pi by SH-modifiers. Biochem. Biophys. Res. Commun. 167, 331-338.
38. Ploemen, J. H. T. M., Bogaards, J. J. P., Veldink, G. A., van Ommen, B., Jansen, D. H. M., and van Bladeren, P. J. (1993) Isoenzyme selective irreversible inhibition of rat and human glutathione S-transferases by ethacrynic acid and two brominated derivatives. Biochem. Pharmacol. 45, 633-639.
39. Aragno, M., Tamagno, E., Danni, O., Chiarpotto, E., Biasi, F., Scavazza, A., Albano, E., Poli, G., and Dianzani, M. U. (1996) In vivo potentiation of 1,2-dibromoethane hepatotoxicity by ethanol through inactivation of glutathione S-transferase. Chem.-Biol. Interact. 99, 277-288.
40. Ouwerkerk-Mahadevan, S., van Boom, J. H., and Mulder, G. J. (1996) Isoenzyme-selective inhibition of glutathione conjugation in vivo: selective inhibition of the conjugation of S-2-bromoisovalerylurea in the rat. J. Pharmacol. Exp. Ther. 276, 923-928.