Glutathione transferase theta 1-1-dependent metabolism of the water disinfection byproduct bromodichloromethane

Chemical Research in Toxicology

Volumn 16, Issue 2, 2003, Pages 216-226

  Ross, Matthew K ^a   Pegram, Rex A ^b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 (4' NITROXYPHENOL)PROPANE; BROMODICHLOROMETHANE; BUTANE; DEOXYGUANOSINE; DRINKING WATER; FORMALDEHYDE DEHYDROGENASE; GLUTATHIONE TRANSFERASE; GLUTATHIONE TRANSFERASE THETA 1 1; NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CONJUGATION; DISINFECTION; DNA ADDUCT; ENVIRONMENTAL TEMPERATURE; ENZYME ACTIVITY; ENZYME SPECIFICITY; FEMALE; GENOTOXICITY; HALF LIFE TIME; HUMAN; LIVER CYTOSOL; MALE; MOUSE; MUTAGENICITY; NONHUMAN; PROTEIN EXPRESSION; RAT; WATER TREATMENT;

ALDEHYDE OXIDOREDUCTASES; ANIMALS; CYTOSOL; DISINFECTANTS; FEMALE; GLUTATHIONE TRANSFERASE; HUMANS; KINETICS; LIVER; MALE; MICE; MICE, INBRED STRAINS; RATS; RATS, INBRED F344; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY; TRIHALOMETHANES; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

ANIMALIA; SALMONELLA;

EID: 0037325160     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0200820     Document Type: Article

References (59)

1. IARC (1991) Bromodichloromethane. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans: Chlorinated Drinking-Water; Chlorination Byproducts; Some Other Halogenated Compounds; Cobalt and Cobalt Compounds. 52, pp 179-212, IARC, Lyon.
2. Nieuwenhuijsen, M. J., Toledano, M. B., Eaton, N. E., Fawell, J., and Elliot, P. (2000) Chlorination disinfection byproducts in water and their association with adverse reproductive outcomes: A review. Occup. Environ. Med. 57, 73-85.
3. King, W. D., and Marrett, L. D. (1996) Case-control study of bladder cancer and chlorination byproducts in treated water (Ontario, Canada). Cancer Causes Control 7, 596-604.
4. Koivusalo, M., Pukkla, E., Vartianen, T., Jaakkola, J. J. K., Hakulinen, T. (1997) Drinking water chlorination and cancer: A historical cohort study in Finland. Cancer Causes Control 8, 192-200.
5. Morris, R. D. (1995) Drinking water and cancer. Environ. Health Perspect. 103, 225-231.
6. Waller, K., Swan, S. H., DeLorenze, G., and Hopkins, B. (1998) Trihalomethanes in drinking water and spontaneous abortion. Epidemiology 9, 134-140.
7. Bove, F., Shim, Y., and Zeitz, P. (2002) Drinking water contaminants and adverse pregnancy outcomes: A review. Environ. Health Perspect. 110 (Suppl. 1), 61-74.
8. Krasner, S. W., McGuire, M. J., Jacangelo, J. G., Patania, N. L., Reagan, K. M., and Aieta E. M. (1989) The occurrence of disinfection byproducts in USA drinking water. J. Am. Water Works Assoc. 81, 41-53.
9. U.S. EPA (1994) Disinfectants and disinfection byproducts: proposed rule. Fed. Regist. 59, 38668-38829.
10. Boorman, G. A., Dellarco, V., Dunnick, J. K., Chapin, R. E., Hunter, S., Hauchman, F., Gardner, H., Cox, M., and Sills, R. C. (1999) Drinking Water Disinfection Products: Review and Approach to Toxicity Evaluation. Environ. Health Perspect. 107 (Suppl. 1), 207-217.
11. U.S. EPA (1998) National Drinking Water Regulations: Disinfectants and disinfection byproducts notice of data availability; proposed rule. Fed. Regist. 63, 15674-15692.
12. National Toxicology Program (1987) Toxicology and Carciongenesis Studies of Bromodichloromethane in F344/N Rats and B6C3F1 Mice (Gavage Studies), Technical Report Series No. 321, U. S. Department of Health and Human Services, Research Triangle Park, NC.
13. Dunnick, J. K., Eustis, S. L., and Lilja, H. S. (1987) Bromodichloromethane, a trihalomethane that produces neoplasms in rodents. Cancer Res. 47, 5189-5193.
14. Lilly, P. D., Ross, T. M., and Pegram, R. A. (1997) Trihalomethane comparative toxicity: acute renal and hepatic toxicity of chloroform and bromodichloromethane following aqueous gavage. Fundam. Appl. Toxicol. 40, 101-110.
15. Keegan, T. E., Simmons, J. E., and Pegram, R. A. (1998) NOAEL and LOAEL determinations of acute hepatotoxicity for chloroform and bromodichloromethane delivered in an aqueous vehicle to F344 rats. J. Toxicol. Environ. Health A 55, 65-75.
16. Kroll, R. B., Robinson, G. D., and Chung, J. H. (1994) Characterization of trihalomethane (THM)-induced renal dysfunction in the rat: 2. Relative potency of Trihalomethanes in promoting renal dysfunction. Arch. Environ. Contam. Toxicol. 27, 5-7.
17. Pegram, R. A., Andersen, M. E., Warren, S. H., Ross, T. M., and Claxton, L. D. (1997) Glutathione transferase-mediated mutagenicity of trihalomethanes in Salmonella typhimurium: contrasting results with bromodichloromethane and chloroform. Toxicol. Appl. Pharmacol. 144, 183-188.
18. Landi, S. (2000) Mammalian class theta GST and differential susceptibility to carcinogens: A review. Mutat. Res. 463, 247-283.
19. m for glutathione in glutathione transferases of the alpha, mu and pi classes. Xenobiotica 23, 823-834.
20. Pemble, S., Schroeder, K. R., Spencer, S. R., Meyer, D. J., Hallier, E., Bolt, H. M., Ketterer, B., and Taylor, J. B. (1994) Human glutathione transferase theta (GSTT1): cDNA cloning and the characterization of a genetic polymorphism. Biochem. J. 300, 271-276.
21. DeMarini, D. M., Shelton, M. L., Warren, S. H., Ross, T. M., Shim, J.-Y., Richard, A. M., and Pegram, R. A. (1997) Glutathione transferase-mediated induction of GC→AT transitions by halomethanes in Salmonella. Environ. Mol. Mutagen. 30, 440-447.
22. Thornton-Manning, J. R., Seely, J. C., and Pegram, R. A. (1994) Toxicity of bromodichloromethane in female rats and mice after repeated oral dosing. Toxicology 94, 3-18.
23. Lilly, P. D., Andersen, M. E., Ross, T. M., and Pegram, R. A. (1997) Physiologically based estimation of in vivo rates of bromodichloromethane metabolism. Toxicology 124, 141-152.
24. Uotila, L. (1981) Thioesters of glutathione. Methods Enzymol. 77, 424-430.
25. Uotila, L. (1973) Preparation and assay of glutathione thiol esters. Survey of human liver glutathione thiol esterases. Biochemistry 12, 3938-3943.
26. Guengerich, F. P. (2001) in Principles and Methods of Toxicology (Hayes, A. W., Ed.) 4th ed., pp 1632-1633, Taylor and Francis, Philadelphia, PA.
27. Thier, R., Taylor, J. B., Pemble, S. E., Humphreys, W. G., Persmark, M., Ketterer, B., and Guengerich, F. P. (1993) Expression of mammalian glutathione transferase 1-1 in Salmonella typhimurium leads to base-pair mutations upon exposure to dihalomethanes. Proc. Natl. Acad. Sci. U.S.A. 90, 8576-8580.
28. Habig, W. H., and Jakoby, W. B. (1981) Assays for differentiation of glutathione transferases. Methods Enzymol. 77, 398-405.
29. Sherratt, P. J., Manson, M. M., Thomson, A. M., Hissink, E. A. M., Neal, G. E., van Bladeren, P. J., Green, T., and Hayes, J. D. (1998) Increased bioactivation of dihaloalkanes in rat liver due to induction of class theta glutathione transferase T1-1. Biochem. J. 335, 619-630.
30. Reitz, R. H., Mendrala, A. L., and Guengerich, F. P. (1989) In vitro metabolism of methylene chloride in human and animal tissues: Use in physiologically based pharmacokinetic models. Toxicol. Appl. Pharmacol. 97, 230-246.
31. Johnson, M. K. (1966) Metabolism of iodomethane in the rat. Biochem J. 98, 38-43.
32. Hollingworth, R. M. (1969) Dealkylation of organophosphorus esters by mouse liver enzymes in vitro and in vivo. J. Agric. Food Chem. 17, 987-996.
33. Sanghani, P. C., Stone, C. L., Ray, B. D., Pindel, E. V., Hurley, T. D., and Bosron, W. F. (2000) Kinetic mechanism of human glutathione-dependent formaldehyde dehydrogenase. Biochemistry 39, 10720-10729.
34. Allis, J. W., and Zhao, G. (2002) Quantitative evaluation of bromodichloromethane metabolism by recombinant rat and human cytochrome P450s. Chem.-Biol. Interact. 140, 137-153.
35. Uotila, L., and Koivusalo, M. (1974) Formaldehyde dehydrogenase from human liver: Purification, properties, and evidence for the formation of glutathione thiol esters by this enzyme. J. Biol. Chem. 249, 7653-7663.
36. Ahmed, A. E., and Anders, M. W. (1978) Metabolism of dihalomethanes to formaldehyde and inorganic halide-II: Studies on the mechanism of the reaction. Biochem. Pharmacol. 27, 2021-2025.
37. van Bladeren, P. J. (2000) Glutathione conjugation as a bioactivation reaction. Chem.-Biol. Interact. 129, 61-76.
38. 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.
39. Cmarik, J. L., Inskeep, P. B., Meredith, M. J., Meyer, D. J., Ketterer, B., and Guengerich, F. P. (1990) Selectivity of rat and human glutathione transferases in activation of ethylene dibromide by glutathione conjugation and DNA binding and induction of unscheduled DNA synthesis in human hepatocytes. Cancer Res. 50, 2747-2752.
40. Lash, L. H., Qian, W., Putt, D. A., Jacobs, K., Elfarra, A. A., Krause, R. J., and Parker, J. C. (1998) Glutathione conjugation of trichloroethylene in rats and mice: sex-, species-, and tissue-dependent differences. Drug Metab. Dispos. 26, 12-19.
41. Lash, L. H., Lipscomb, J. C., Putt, D. A., and Parker, J. C. (1999) Glutathione conjugation of trichloroethylene in human liver and kidney: kinetics and individual variation. Drug Metab. Dispos. 27, 351-359.
42. Green, T. (1997) Methylene chloride induced mouse liver and lung tumours: an overview of the role of mechanistic studies in human safety assessment. Hum. Exp. Toxicol. 16, 3-13.
43. Wheeler, J. B., Stourman, N. V., Thier, R., Dommermuth, A., Vuilleumier, S., Rose, J. A., Armstrong, R. N., and Guengerich, F. P. (2001) Conjugation of haloalkanes by bacterial and mammalian glutathione transferases: mono- and dihalomethanes. Chem. Res. Toxicol. 14, 1118-1127.
44. Gisi, D., Leisinger, T., and Vuilleumier, S. (1999) Enzymemediated dichloromethane toxicity and mutagenicity of bacterial and mammalian dichloromethane-active glutathione transferases. Arch. Toxicol. 73, 71-79.
45. Lilly, P. D., Andersen, M. E., Ross, T. M., and Pegram, R. A. (1998) A physiologically based pharmacokinetic description of the oral uptake, tissue dosimetry, and rates of metabolism of bromodichloromethane in the male rat. Toxicol. Appl. Pharmacol. 150, 205-217.
46. Mainwaring, G. W., Williams, S. M., Foster, J. R., Tugwood, J., and Green, T. (1996) The distribution of theta-class glutathione transferases in the liver and lung of mouse, rat and human. Biochem. J. 318, 297-303.
47. Meyer, D. J., Coles, B., Pemble, S. E., Gilmore, K. S., Fraser, G. M., and Ketterer, B. (1991) Theta, a new class of glutathione transferases purified from rat and man. Biochem. J. 271, 409-414.
48. Livesey, J. C., Anders, M. W., Langvardt, P. W., Putzig, C. L., and Reitz, R. H. (1982) Stereochemistry of the glutathionedependent biotransformation of vicinal-dihaloalkanes to alkenes. Drug Metab. Dispos. 10, 201-204.
49. Brundin, A., Ratnayake, J. H., Sunram, J. M., and Anders, M. W. (1982) Glutathione-dependent reductive dehalogenation of 2,2′,4′-trichloroacetophenone to 2′,4′-dichloroacetophenone. Biochem. Pharmacol. 31, 3885-3890.
50. Sparks, S. E., Quistad, G. B., and Casida, J. E. (1997) Chloropicrin: reactions with biological thiols and metabolism in mice. Chem. Res. Toxicol. 10, 1001-1007.
51. 13C]dichloromethane in mouse, rat, and human liver cytosol: 13C nuclear magnetic resonance spectroscopic studies. Chem. Res. Toxicol. 7, 291-296.
52. Nash, T. (1953) The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 55, 416-421.
53. 13C NMR spectroscopy of S-(hydroxymethyl)glutathione as a transient intracellular intermediate. Biochemistry 25, 4504-4507.
54. Naylor, S., Mason, R. P., Sanders, J. K., Williams, D. H., and Moneti, G. (1988) Formaldehyde adducts of glutathione. Structure elucidation by two-dimensional NMR spectroscopy and fast-atombombardment tandem mass spectrometry. Biochem J. 249, 573-579.
55. Uotila, L., and Koivusalo, M. (1974) Purification and properties of S-formylglutathione hydrolase from human liver. J. Biol. Chem. 249, 7664-7672.
56. Harms, N., Ras, J., Reijnders, W. N., van Spanning, R. J., and Stouthamer, A. H. (1996) S-formylglutathione hydrolase of Paracoccus denitrificans is homologous to human esterase D: A universal pathway for formaldehyde detoxification? J. Bacteriol. 178, 6296-6299.
57. Allis, J. W., Anderson, B. P., Zhao, G., Ross, T. M., and Pegram, R. A. (2002) Evidence for the involvement of CYP1A2 in the metabolism ofbromodichloromethane in rat liver. Toxicology 176, 25-37.
58. Hissink, A. M., Wormhoudt, L. W., Sherratt, P. J., Hayes, J. D., Commandeur, J. N., Vermeulen, N. P., and van Bladeren, P. J. (2000) A physiologically based pharmacokinetic (PB-PK) model for ethylene dibromide: relevance of extrahepatic metabolism. Food Chem. Toxicol. 38, 707-716.
59. Meyer, D. J., and Ketterer, B. (1995) Purification of soluble human glutathione transferases. Methods Enzymol. 252, 53-65.