Dimethylarsinothioyl glutathione as a metabolite in human multiple myeloma cell lines upon exposure to Darinaparsin

Chemical Research in Toxicology

Volumn 27, Issue 5, 2014, Pages 754-764

  Yehiayan, Lucy ^a   Stice, Szabina ^a   Liu, Guangliang ^a   Matulis, Shannon ^b   Boise, Lawrence H ^b   Cai, Yong ^a  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC; CELL EXTRACT; CYSTEINE; DARINAPARSIN; DIMETHYLARSINOTHIOYL GLUTATHIONE; DRUG METABOLITE; GLUTAMIC ACID; GLUTATHIONE DERIVATIVE; GLYCINE; SULFUR; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; GLUTATHIONE; ORGANOARSENIC DERIVATIVE;

APOPTOSIS; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; MULTIPLE MYELOMA; MULTIPLE MYELOMA CELL LINE; TANDEM MASS SPECTROMETRY; ANALOGS AND DERIVATIVES; DRUG EFFECTS; METABOLISM; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; ARSENICALS; CELL LINE, TUMOR; GLUTATHIONE; HUMANS; MULTIPLE MYELOMA;

EID: 84901044477     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400386c     Document Type: Article

References (35)

1. Abernathy, C. and Morgan, A. (2001) Chapter 3: Exposure and Health Effects, United Nations Synthesis Report on Arsenic in Drinking Water, World Health Organization, Geneva, Switzerland.
2. Mandal, B. (2002) Arsenic round the world: a review Talanta 58, 201-235 (Pubitemid 34857394)
3. Waxman, S. and Anderson, K. C. (2001) History of the development of arsenic derivatives in cancer therapy Oncologist 6, 3-10 (Pubitemid 32405843)
4. Campas, C. and Castaner, R. (2009) Darinaparsin. Organic arsenical, apoptosis inducer, oncolytic Drug Future 34, 97-100
5. Wu, J., Henderson, C., Feun, L., Van Veldhuizen, P., Gold, P., Zheng, H., Ryan, T., Blaszkowsky, L. S., Chen, H., Costa, M., Rosenzweig, B., Nierodzik, M., Hochster, H., Muggia, F., Abbadessa, G., Lewis, J., and Zhu, A. X. (2010) Phase II study of darinaparsin in patients with advanced hepatocellular carcinoma Invest. New Drugs 28, 670-676
6. Mason, T. A., Kolobova, E., Liu, J., Roland, J. T., Chiang, C., and Goldenring, J. R. (2011) Darinaparsin is a multivalent chemotherapeutic which induces incomplete stress response with disruption of microtubules and Shh signaling PLoS One 6, e27699
7. 3-resistant and MRP1/ABCC1- overexpressing cell lines Leukemia 22, 1853-1863
8. Matulis, S. M., Morales, A. A., Yehiayan, L., Croutch, C., Gutman, D., Cai, Y., Lee, K. P., and Boise, L. H. (2009) Darinaparsin induces a unique cellular response and is active in an arsenic trioxide-resistant myeloma cell line Mol. Cancer Ther. 8, 1197-1206
9. Mann, K. K., Wallner, B., Lossos, I. S., and Miller, W. H., Jr. (2009) Darinaparsin: a novel organic arsenical with promising anticancer activity Expert Opin. Invest. Drugs 18, 1727-1734
10. Petrick, J. S., Jagadish, B., Mash, E. A., and Aposhian, H. V. (2000) Monomethylarsonous acid (MMAIII) is more toxic than arsenite in chang human hepatocytes Toxicol. Appl. Pharmacol. 163, 203-207 (Pubitemid 30152096)
11. 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 (Pubitemid 32367468)
12. Hayakawa, T., Kobayashi, Y., Cui, X., and Hirano, S. (2005) A new metabolic pathway of arsenite: arsenic-glutathione complexes are substrates for human arsenic methyltransferase Cyt19 Arch. Toxicol. 79, 183-191 (Pubitemid 40603183)
13. Kojima, C., Sakurai, T., Waalkes, M. P., and Himeno, S. (2005) Cytolethality of glutathione conjugates with monomethylarsenic or dimethylarsenic compounds Biol. Pharm. Bull. 28, 1827-1832 (Pubitemid 41437065)
14. Hirano, S. and Kobayashi, Y. (2006) Cytotoxic effects of S-(dimethylarsino)-glutathione: A putative intermediate metabolite of inorganic arsenicals Toxicology 227, 45-52 (Pubitemid 44402848)
15. Sakurai, T., Kojima, C., Kobayashi, Y., Hirano, S., Sakurai, M. H., Waalkes, M. P., and Himeno, S. (2006) Toxicity of a trivalent organic arsenic compound, dimethylarsinous glutathione in a rat liver cell line (TRL 1215) Br. J. Pharmacol. 149, 888-897 (Pubitemid 44851713)
16. Marapakala, K., Qin, J., and Rosen, B. P. (2012) Identification of catalytic residues in the As (III) S-adenosylmethionine methyltransferase Biochemistry 51, 944-951
17. Cui, X., Kobayashi, Y., Hayakawa, T., and Hirano, S. (2004) Arsenic speciation in bile and urine following oral and intravenous exposure to inorganic and organic arsenics in rats Toxicol. Sci. 82, 478-487 (Pubitemid 39600075)
18. Kala, S. V., Kala, G., Prater, C. I., Sartorelli, A. C., and Lieberman, M. W. (2004) Formation and urinary excretion of arsenic triglutathione and methylarsenic diglutathione Chem. Res. Toxicol. 17, 243-249 (Pubitemid 38252504)
19. Leslie, E. M. (2012) Arsenic-glutathione conjugate transport by the human multidrug resistance proteins (MRPs/ABCCs) J. Inorg. Biochem. 108, 141-149
20. Kala, S. V., Neely, M. W., Kala, G., Prater, C. I., Atwood, D. W., Rice, J. S., and Lieberman, M. W. (2000) The MRP2/cMOAT transporter and arsenic-glutathione complex formation are required for biliary excretion of arsenic J. Biol. Chem. 275, 33404-33408
21. Naranmandura, H., Ibata, K., and Suzuki, K. T. (2007) Toxicity of dimethylmonothioarsinic acid toward human epidermoid carcinoma A431 cells Chem. Res. Toxicol. 20, 1120-1125 (Pubitemid 47372990)
22. Naranmandura, H., Ogra, Y., Iwata, K., Lee, J., Suzuki, K. T., Weinfeld, M., and Le, X. C. (2009) Evidence for toxicity differences between inorganic arsenite and thioarsenicals in human bladder cancer cells Toxicol. Appl. Pharmacol. 238, 133-140
23. Suzuki, K. T., Mandal, B. K., Katagiri, A., Sakuma, Y., Kawakami, A., Ogra, Y., Yamaguchi, 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 (Pubitemid 38955350)
24. Naranmandura, H., Suzuki, N., Iwata, K., Hirano, S., and Suzuki, K. T. (2007) Arsenic metabolism and thioarsenicals in hamsters and rats Chem. Res. Toxicol. 20, 616-624 (Pubitemid 46762096)
25. Raml, R., Rumpler, A., Goessler, W., Vahter, M., Li, L., Ochi, T., and Francesconi, K. A. (2007) Thio-dimethylarsinate is a common metabolite in urine samples from arsenic-exposed women in Bangladesh Toxicol. Appl. Pharmacol. 222, 374-380 (Pubitemid 47198276)
26. Naranmandura, H. and Suzuki, K. T. (2008) Formation of dimethylthioarsenicals in red blood cells Toxicol. Appl. Pharmacol. 227, 390-399
27. Naranmandura, H., Suzuki, N., and Suzuki, K. T. (2008) Reaction mechanism underlying the in vitro transformation of thioarsenicals Toxicol. Appl. Pharmacol. 231, 328-335
28. Raab, A., Wright, S. H., Jaspars, M., Meharg, A. A., and Feldmann, J. (2007) Pentavalent arsenic can bind to biomolecules Angew. Chem., Int. Ed. 46, 2594-2597 (Pubitemid 46973540)
29. Yehiayan, L., Membreno, N., Matulis, S., Boise, L. H., and Cai, Y. (2011) Extraction tool and matrix effects on arsenic speciation analysis in cell lines Anal. Chim. Acta 699, 187-192
30. Yehiayan, L., Pattabiraman, M., Kavallieratos, K., Wang, X., Boise, L. H., and Cai, Y. (2009) Speciation, formation, stability and analytical challenges of human arsenic metabolites J. Anal. At. Spectrom. 24, 1397-1405
31. Yehiayan, L. (2010) Interactions of Different Arsenic Species with Thols: Chemical and Biological Implications, Ph.D. Dissertation, Florida International University, Miami, FL.
32. Lu, M., Wang, H., Li, X. F., Lu, X., Cullen, W. R., Arnold, L. L., Cohen, S. M., and Le, X. C. (2004) Evidence of hemoglobin binding to arsenic as a basis for the accumulation of arsenic in rat blood Chem. Res. Toxicol. 17, 1733-1742 (Pubitemid 39665567)
33. Ngu, T. T. and Stillman, M. J. (2006) Arsenic Binding to Human Metallothionein J. Am. Chem. Soc. 128, 12473-12483 (Pubitemid 44476638)
34. Suzuki, N., Naranmandura, H., Hirano, S., and Suzuki, K. T. (2008) Theoretical calculations and reaction analysis on the interaction of pentavalent thioarsenicals with biorelevant thiol compounds Chem. Res. Toxicol. 21, 550-553
35. Garnier, N., Redstone, G., Dahabieh, M. S., Nichol, J. N., Del Rincon, S. V., Gu, Y., Bohle, D. S., Sun, Y., Conklin, D. S., and Mann, K. K. (2014) The novel arsenical darinaparsin is transported by cystine importing systems Mol. Pharmacol. 85, 576-585