Chromatographic separation and identification of products from the reaction of dimethylarsinic acid with hydrogen sulfide

Chemical Research in Toxicology

Volumn 18, Issue 12, 2005, Pages 1821-1829

  Fricke, Michael W ^a   Zeller, Matthias ^b   Sun, Hongsui ^c   Lai, Vivian W M ^c   Cullen, William R ^c   Shoemaker, Jody A ^a   Witkowski, Mark R ^d   Creed, John T ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b YOUNGSTOWN STATE UNIVERSITY   (United States)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^d CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC; ARSINIC ACID DERIVATIVE; CACODYLIC ACID; CHEMICAL COMPOUND; DEUTERIUM OXIDE; DIMETHYLARSINODIMETHYLDITHIOARSINIC ACID; DIMETHYLDITHIOARSINIC ACID; DIMETHYLTHIOARSINIC ACID; HYDROGEN SULFIDE; REACTION PRODUCT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARCINOGENICITY; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; ELUTION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MEAN RESIDENCE TIME; PROCESS MONITORING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION MONITORING; RETENTION TIME; SOLUBILIZATION; SOLVATION;

CACODYLIC ACID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN SULFIDE; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 29644445242     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050227d     Document Type: Article

References (44)

1. Bunsen, R. (1843) Untersuchungen über die Kakodylreihe. Justus Liebigs Ann. Chem. 46, 1-18.
2. Zingaro, R. A., Irgolic, K. J., O'Brien, D. H., and Edmonson, L. J. (1971) A rearrangement of tetramethyldiarsine disulfide. J. Am. Chem. Soc. 93, 5677-5681.
3. Camerman, N., and Trotter, J. (1964) Stereochemistry of arsenic. Part XI. "Cacodyl disulphide," dimethylarsino dimethyldithioarsinate. J. Chem. Soc., 219-227.
4. Cullen, W. R. (1963) Perfluoroalkyl arsenicals Part VIII. Reaction of arsenic sulphides with perfluoroalkyl iodides. Can. J. Chem. 41, 2424-2428.
5. Silaghi-Dumitrescu, L., Silaghi-Dumitrescu, I., and Haiduc, I. (1989) The sulfotropic rearrangement of tetraorganoarsine disulfides. Rev. Roum. Chim. 34, 305-315.
6. Cullen, W. R., and Reimer, K. J. (1989) Arsenic speciation in the environment. Chem. Rev. 89, 713-764.
7. Aposhian, H. V. (1997) Enzymatic methylation of arsenic species and other new approaches to arsenic toxicity. Annu. Rev. Pharmacol. Toxicol. 37, 397-419.
8. Aposhian, H. V., Zakharyan, R. A., Avram, M. D., Kopplin, M. J., and Wolenberg, M. L. (2003) Oxidation and detoxification of trivalent arsenic species. Toxicol. Appl. Phamacol. 193, 1-8.
9. Francesconi, K. A., Tanggaard, R., McKenzie, C. J., and Goessler, W. (2002) Arsenic metabolites in human urine after ingestion of an arsenosugar. Clin. Chem. 48, 92-101.
10. Kaise, T., Yamauchi, H., Horiguchi, Y., Tani, T., Watanbe, S., Hirayama, T., and Fukui, S. (1989) A comparative study on acute toxicity of methyl arsonic acid, dimethylarsinic acid and trimethylarsine oxide in mice. Appl. Organomet. Chem. 3, 273-277.
11. Kenyon, E. M., and Hughes, M. F. (2001) A concise review of the toxicity and carcinogenicity of dimethylarsinic acid. Toxicology 160, 227-236.
12. Mass, M. J., Tennant, A., Roop, B. C., Cullen, W. R., Styblo, M., Thomas, D. J., and Kligerman, A. D. (2001) Methylated trivalent arsenic species are genotoxic. Chem. Res. Toxicol. 14, 355-361.
13. Quinn, J. P., and McMullan, G. (1995) Carbon-arsenic bond cleavage by a newly isolated Gram-negative bacterium, strain ASV2. Microbiology 141, 721-727.
14. Yoshida, K., Chen, H., Inoue, Y., Wanibuchi, H., Fukushima, S., Kurada, K., and Endo, G. (1997) The urinary excretion of arsenic metabolites after a single oral administration of dimethylarsinic acid to rats. Arch. Environ. Contam. Toxicol. 32, 416-421.
15. Cullen, W. R., McBride, B. C., Manji, H., Pickett, A. W., and Reglinski, J. (1989) The metabolism of methylarsine oxide and sulfide. Appl. Organomet. Chem. 3, 71-78.
16. Lu, X., Arnold, L. L., Cohen, S. M., Cullen, W. R., and Le, X. C. (2003) Speciation of dimethylarsinous acid and trimethylarsine oxide in urine from rats fed with dimethylarsinic acid and dimercaptopropane sulfonate. Anal. Chem. 75, 6463-6468.
17. Cullen, W. R., McBride, B. C., and Reglinski, J. (1984) The reaction of methylarsenicals with thiols: some biological implications. J. Inorg. Biochem. 21, 179-194.
18. Styblo, M., Serves, S. V., Cullen, W. R., and Thomas, D. J. (1997) Comparative inhibition of yeast glutathione reductase by arsenicals and arsenothiols. Chem. Res. Toxicol. 10, 27-33.
19. Waters, S. B., Devesa, V., Fricke, M. W., Creed, J. T., Stýblo, M., and Thomas, D. J. (2004) Glutathione modulates recombinant rat arsenic (+3 oxidation state) methyltransferase-catalyzed formation of trimethylarsine oxide and trimethylarsine. Chem. Res. Toxicol. 17, 1621-1629.
20. Sakurai, T., Qu, W., Sakurai, M. H., and Waalkes, M. P. (2002) A major arsenic metabolite, dimethylarsinic acid, requires reduced glutathione to induce apoptosis. Chem. Res. Toxicol. 15, 629-637.
21. Ochi, T., Kaise, T., and Oya-Ohta, Y. (1994) Glutathione plays different roles in the induction of the cytotoxic effects of inorganic and organic arsenic compounds in cultured BALB/c 3T3 cells. Experientia 50, 115-120.
22. Marafante, E., Vahter, M., Norin, H., Envall, J., Sandström, M., Christakopoulos, A., and Ryhage, R. (1987) Biotransformation of dimethylarsinic acid in mouse, hamster and man. J. Appl. Toxicol. 7, 111-117.
23. Tsao, D. H. H., and Maki, A. H. (1991) Optically detected magnetic resonance study of an arsenic(III) derivative of cacodylic acid with EcoRi methyl transferase. Biochem. 30, 4565-4572.
24. Yoshida, K., Kuroda, K., Zhou, X., Inoue, Y., Date, Y., Wanibuchi, H., Fukushima, S., and Endo, G. (2003) Urinary sulfur-containing metabolite produced by intestinal bacteria following oral administration of dimethylarsinic acid to rats. Chem. Res. Toxicol. 16, 1124-1129.
25. Kuroda, K., Yoshida, K., Yoshimura, M., Endo, Y., Wanibuchi, H., Fukushima, S., and Endo, G. (2004) Microbial metabolite of dimethylarsinic acid is highly toxic and genotoxic. Toxicol. Appl. Phamacol. 198, 345-353.
26. Hansen, H. R., Pickford, R., Thomas-Oates, J., and Feldmann, J. (2004) 2-Dimethylarsinothioyl acetic acid identified in a biological sample: the first occurrence of a mammalian arsinothioyl metabolite. Angew. Chem., Int. Ed. 43, 337-340.
27. Hansen, H. R., Jaspars, M., and Feldmann, J. (2004) Arsinothioylsugars produced by in vitro incubation of seaweed extract with liver cytosol analysed by HPLC coupled simultaneously to ES-MS and ICP-MS. Analyst 129, 1058-1064.
28. Suzuki, K. T., Mandal, B. K., Katagiri, A., Sakuma, Y., Kawakami, A., Orga, Y., Tamaguchi, K., Sei, Y., Yamanaka, K., Anzai, K., Ohmichi, M., Takayama, H., and Aimi, N. (2004) Dimethylthioarsenicals as arsenic metabolites and their chemical preparations. Chem Res. Toxicol. 17, 914-921.
29. Hansen, H. R., Raab, A., Jaspars, M., Milne, B. F., and Feldmann, J. (2004) 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, 1086-1091.
30. Ackerman, A. H., Creed, P. A., Parks, A. N., Fricke, M. W., Schwegel, C. A., and Creed, J. T. (2005) Comparison of a chemical and enzymatic extraction of arsenic from rice and an assessment of the arsenic absorption from contaminated water by cooked rice. Environ. Sci. Technol. 39, 5241-5246.
31. Fricke, M. W., Zeller, M., Cullen, W. R., Witkowski, M. R., and Creed, J. T. (2005) Unpublished results.
32. 2. J. Organomet. Chem. 549, 187-192.
33. Burrows, G. J., and Turner, E. E. (1920) A new type of compound containing arsenic. J. Chem. Soc., Trans., 1373-1380.
34. Fricke, M. W., Creed, P. A., Parks, A. N., Shoemaker, J. A., Schwegel, C. A., and Creed, J. T. (2004) Extraction and detection of a new arsine sulfide containing arsenosugar in molluscs by IC-ICP-MS and IC-ESI-MS/MS. J. Anal. At. Spectrom. 19, 1-8.
35. Creed, J. T., and Brockhoff, C. A. (1999) Isotope dilution analysis of bromate in drinking water matrixes by ion chromatography with inductively coupled plasma mass spectrometric detection. Anal. Chem. 71, 722-726.
36. Lai, V. W.-M., Cullen, W. R., Harrington, C. F., and Reimer, K. J. (1997) The characterization of arsenosugars in commercially available algal products including a Nostoc species of terrestrial origin. Appl. Organomet. Chem. 11, 797-803.
37. Shibata, Y., and Morita, M. (1992) Characterization of organic arsenic compounds in bivalves. Appl. Organomet. Chem. 6, 343-349.
38. Bruker (1997) SAINT (version 6.02), SMART for WNT/2000 (version 5.625), and SHELXTL. Bruker AXS, Inc., Madison, WI.
39. Gottlieb, H. E., Kotlyar, V., and Nudelman, A. (1997) NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 62, 7512-7515.
40. Förster, M., Hertel, H., and Kuchen, W. (1970) Sodium dimethyldithioarsinate, a new complexing agent. Angew. Chem., Int. Ed. Engl. 9, 811.
41. Casey, A. T., Ham, N. S., Mackey, D. J., and Martin, R. L. (1970) Synthesis and infrared spectra of some dithiocacodylate complexes. Aust. J. Chem. 23, 1117-1123.
42. -. Rev. Roum. Chim. 27, 911-916.
43. Cullen, W. R., McBride, B. C., and Reglinski, J. (1984) The reduction of trimethylarsine oxide to trimethylarsine by thiols: a mechanistic model for the biological reduction of arsenicals. J. Inorg. Biochem. 21, 45-60.
44. 2O. Polyhedron 17, 4115-4119.