Reaction mechanism underlying the in vitro transformation of thioarsenicals

Toxicology and Applied Pharmacology

Volumn 231, Issue 3, 2008, Pages 328-335

  Naranmandura, Hua ^a   Suzuki, Noriyuki ^a   Suzuki, Kazuo T ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Arsenic; Dimethyldithioarsinic acid; Dimethylmonothioarsinic acid; Hemoglobin; Sulfide; Thioarsenical

Indexed keywords

ARSENIC; CACODYLIC ACID; DIMETHYLARSINOUS ACID; DIMETHYLDITHIOARSINIC ACID; DIMETHYLMONOTHIOARSINIC ACID S 34; HEMOGLOBIN; ORGANOARSENIC DERIVATIVE; RADIOISOTOPE; SODIUM DISULFIDE; SULFIDE; SULFUR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; ERYTHROCYTE; HEMOLYSATE; HYDROLYSIS; IN VITRO STUDY; MALE; NONHUMAN; RAT; REACTION ANALYSIS; REDUCTION;

ANIMALS; ARSENICALS; BIOTRANSFORMATION; ERYTHROCYTES; MALE; RATS; RATS, SPRAGUE-DAWLEY; SULFHYDRYL COMPOUNDS;

MAMMALIA; RATTUS;

EID: 50849088646     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2008.05.005     Document Type: Article

References (38)

1. Adair B.M., Moore T., Conklin S.D., Creed J.T., Wolf D.C., and Thomas D.J. Tissue distribution and urinary excretion of dimethylated arsenic and its metabolites in dimethylarsinic acid- or arsenate-treated rats. Toxicol. Appl. Pharmacol. 222 (2007) 235-242
2. Aposhian H.V., Gurzau E.S., Le X.C., Gurzau A., Healy S.M., Lu X., Ma M., Yip L., Zakharyan R.A., Maiorino R.M., Dart R.C., Tircus M.G., Gonzalez-Ramirez D., Morgan D.L., Avram D., and Aposhian M.M. Occurrence of monomethylarsonous acid in urine of humans exposed to inorganic arsenic. Chem. Res. Toxicol. 13 (2000) 693-697
3. Bates M.N., Smith A.H., and Hopenhayn-Rich C. Arsenic ingestion and internal cancers: a review. Am. J. Epidemiol. 135 (1992) 462-476
4. Cohen S.M., Ohnishi T., Arnold L.L., and Le X.C. Arsenic-induced bladder cancer in an animal model. Toxicol. Appl. Pharmacol. 222 (2007) 258-263
5. Dopp E., Hartmann L.M., Florea A.M., Von Recklinghausen U., Pieper R., Shokouhi B., Rettenmeier A.W., Hirner A.V., and Obe G. Uptake of inorganic and organic derivatives of arsenic associated with induced cytotoxic and genotoxic effects in Chinese hamster ovary (CHO) cells. Toxicol. Appl. Pharmacol. 201 (2004) 156-165
6. Gregus Z., Gyurasics A., and Csanaky I. Biliary and urinary excretion of inorganic arsenic: Monomethylarsonous acid as a major biliary metabolite in rats. Toxicol. Sci. 56 (2000) 18-25
7. Hansen H.R., Raab A., Jaspars M., Milne B.F., and Feldmann J. Sulfur-containing arsenical mistaken for dimethylarsinous acid [DMA(III)] and identified as a natural metabolite in urine: major implications for studies on arsenic metabolism and toxicity. Chem. Res. Toxicol. 17 (2004) 1086-1091
8. Hirano S., Cui X., Li S., Kanno S., Kobayashi Y., Hayakawa T., and Shraim A. Difference in uptake and toxicity of trivalent and pentavalent inorganic arsenic in rat heart microvessel endothelial cells. Arch. Toxicol. 77 (2003) 305-312
9. Kala S.V., Neely M.W., Kala G., Prater C.I., Atwood D.W., Rice J.S., and Lieberman M.W. The MRP2/cMOAT transporter and arsenic-glutathione complex formation are required for biliary excretion of arsenic. J. Biol. Chem. 275 (2000) 33404-33408
10. Kitchin K.T., and Ahmad S. Oxidative stress as a possible mode of action for arsenic carcinogenesis. Toxicol. Lett. 137 (2003) 3-13
11. Kligerman A.D. Methylated trivalent arsenic species are genotoxic. Chem. Res. Toxicol. 14 (2001) 355-361
12. III) for two years. Toxicol. Appl. Pharmacol. 224 (2007) 89-97
13. Lu M., Wang H., Li X.F., Arnold L.L., Cohen S.M., and Le X.C. Binding of dimethylarsinous acid to cys-13alpha of rat hemoglobin is responsible for the retention of arsenic in rat blood. Chem. Res. Toxicol. 20 (2007) 27-37
14. Mandal B.K., Ogra Y., and Suzuki K.T. Identification of dimethylarsinous and monomethylarsonous acids in human urine of the arsenic affected areas in West Bengal, India. Chem. Res. Toxicol. 14 (2001) 371-378
15. Mass M.J., Tennant A., Roop B.C., Cullen W.R., Styblo M., Thomas D.J., and Kligerman A.D. Methylated trivalent arsenic species are genotoxic. Chem. Res. Toxicol. 14 (2001) 355-361
16. Naranmandura H., and Suzuki K.T. Formation of dimethylthioarsenicals in red blood cells. Toxicol. Appl. Pharmacol. 227 (2008) 390-399
17. Naranmandura H., Suzuki N., and Suzuki K.T. Trivalent arsenicals are bound to proteins during reductive methylation. Chem. Res. Toxicol. 19 (2006) 1010-1018
18. Naranmandura H., Ibata K., and Suzuki K.T. Toxicity of dimethylmonothioarsinic acid toward human epidermoid carcinoma A431. Chem. Res. Toxicol. 20 (2007) 1120-1125
19. Naranmandura H., Suzuki N., Iwata K., Hirano S., and Suzuki K.T. Arsenic metabolism and thioarsenicals in hamsters and rats. Chem. Res. Toxicol. 20 (2007) 616-624
20. NRC (National Research Council). Arsenic in the Drinking Water (1999), National Academy Press, Washington, DC
21. NRC (National Research Council). Arsenic in the Drinking Water 2001 Update. National Academy Press (2001) Washington, DC
22. Ochi T., Kita K., Suzuki T., Rumpler A., Goessler W., and Francesconi K.A. Cytotoxic, genotoxic and cell-cycle disruptive effects of thio-dimethylarsinate in cultured human cells and the role of glutathione. Toxicol. Appl. Pharmacol. 228 (2008) 59-67
23. Ogra Y., Kitaguchi T., Suzuki N., and Suzuki K.T. In vitro translation with [(34)S]-labeled methionine, selenomethionine, and telluromethionine. Anal. Bioanal. Chem. 390 (2008) 45-51
24. Raab A., Wright S.H., Jaspars M., Meharg A.A., and Feldmann J. Pentavalent arsenic can bind to biomolecules. Angew. Chem. Int. Ed. Engl. 46 (2007) 2594-2597
25. Raml R., Rumpler A., Goessler W., Vahter M., Li L., Ochi T., and Francesconi K.A. Thio-dimethylarsinate is a common metabolite in urine samples from arsenic-exposed women in Bangladesh. Toxicol. Appl. Pharmacol. 222 (2007) 374-380
26. Sakurai T., Qu W., Sakurai M.H., and Waalkes M.P. A major human arsenic metabolite, dimethylarsinic acid, requires reduced glutathione to induce apoptosis. Chem. Res. Toxicol. 15 (2002) 629-637
27. Shiobara Y., Ogra Y., and Suzuki K.T. Animal species difference in the uptake of dimethylarsinous acid (DMA(III)) by red blood cells. Chem. Res. Toxicol. 14 (2001) 1446-1452
28. Styblo M., Del Razo L.M., Vega L., Germolec D.R., LeCluyse E.L., Hamilton G.A., Reed W., Wang C., Cullen W.R., and Thomas D.J. Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells. Arch. Toxicol. 74 (2000) 289-299
29. Suzuki K.T., Tomita T., Ogra Y., and Ohmichi M. Glutathione-conjugated arsenics in the potential hepato-enteric circulation in rats. Chem. Res. Toxicol. 14 (2001) 1604-1611
30. Suzuki K.T., Katagiri A., Sakuma Y., Ogra Y., and Ohmichi M. Distributions and chemical forms of arsenic after intravenous administration of dimethylarsinic and monomethylarsonic acids to rats. Toxicol. Appl. Pharmacol. 19 (2004) 336-344
31. Suzuki K.T., Mandal B.K., Katagiri A., Sakuma Y., Kawakami A., Ogra Y., Yamaguchi K., Sei Y., Yamanaka K., Anzai M., Ohmichi H., Takayama H., and Aimi N. Dimethylthioarsenicals as arsenic metabolites and their chemical preparation. Chem. Res. Toxicol. 17 (2004) 914-921
32. Suzuki K.T., Iwata K., Naranmandura H., and Suzuki N. Metabolic differences between two dimethylthioarsenicals in rats. Toxicol. Appl. Pharmacol. 218 (2007) 166-173
33. Suzuki N., Naranmandura H., Hirano S., and Suzuki K.T. Theoretical calculations and reaction analysis on the interaction of pentavalent thioarsenicals with biorelevant thiol compounds. Chem. Res. Toxicol. 21 (2008) 550-553
34. van Gemert M., and Eldan M. Chronic carcinogenecity assessment of cacodylic acid. 3rd International Conference on Arsenic Exposure and Health Effects, San Diego, CA (1998)
35. Waalkes M.P., Ward J.M., Liu J., and Diwan B.A. Transplacental carcinogenicity of inorganic arsenic in the drinking water: induction of hepatic, ovarian, pulmonary, and adrenal tumors in mice. Toxicol. Appl. Pharmacol. 186 (2003) 7-17
36. Wei M., Arnold L., Cano M., and Cohen S.M. Effects of co-administration of antioxidants and arsenicals on the rat urinary bladder epithelium. Toxicol. Sci. 83 (2005) 237-245
37. Yamanaka K., and Okada S. Induction of lung-specific DNA damage by metabolically methylated arsenics via the production of free radicals. Environ. Health Perspect. 102 Suppl. 3 (1994) 37-40
38. Yoshida K., Kuroda K., Zhou X., Inoue Y., Date Y., Wanibuchi H., Fukushima S., and Endo G. Urinary sulfur-containing metabolite produced by intestinal bacteria following oral administration of dimethylarsinic acid to rats. Chem. Res. Toxicol. 16 (2003) 1124-1129