Methylated Organic Metabolites of Arsenic and their Cardiovascular Toxicities |
Bae, Ok-Nam
(College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University)
Lim, Kyung-Min (College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University) Noh, Ji-Yoon (College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University) Kim, Keun-Young (College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University) Lim, Eun-Kyung (College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University) Chung, Jin-Ho (College of Pharmacy, Institute of Pharmaceutical Sciences, Seoul National University) |
1 | Abernathy, C.O., Thomas, D.J. and Calderon, R.L. (2003). Health effects and risk assessment of arsenic. J. Nutr., 133, 1536S-1538S |
2 | Aposhian, H.V., Zheng, B., Aposhian, M.M., Le, X.C., Cebrian, M.E., Cullen, W., Zakharyan, R.A., Ma, M., Dart, R.C., Cheng, Z., Andrewes, P., Yip, L., O'Malley, G.F., Maiorino, R.M., Van Voorhies, W., Healy, S.M. and Titcomb, A. (2000b). DMPS-arsenic challenge test. II. Modulation of arsenic species, including monomethylarsonous acid (MMA(III)), excreted in human urine. Toxicol. Appl. Pharmacol., 165, 74-83 DOI ScienceOn |
3 | Buchet, J.P., Pauwels, J. and Lauwerys, R. (1994). Assessment of exposure to inorganic arsenic following ingestion of marine organisms by volunteers. Environ. Res., 66, 44-51 DOI ScienceOn |
4 | Edmonds, J.S., Shibata, Y., Francesconi, K.A., Rippingale, R.J. and Moritaet, M. (1997). Arsenic transformations in short marine food chains studied by HPLC-ICP MS. Appl. Organomet. Chem., 11, 281-287 DOI ScienceOn |
5 | Eguchi, N., Kuroda, K. and Endo, G. (1997). Metabolites of arsenic induced tetraploids and mitotic arrest in cultured cells. Arch. Environ. Contam. Toxicol., 32, 141-145 DOI |
6 | Gregus, Z. and Nemeti, B. (2002). Purine nucleoside phosphorylase as a cytosolic arsenate reductase. Toxicol. Sci., 70, 13-19 DOI ScienceOn |
7 | Hopenhayn-Rich, C., Biggs, M.L., Fuchs, A., Bergoglio, R., Tello, E.E., Nicolli, H. and Smith, A.H. (1996). Bladder cancer mortality associated with arsenic in drinking water in Argentina. Epidemiology, 7, 117-124 DOI |
8 | Kligerman, A.D., Doerr, C.L., Tennant, A.H., Harrington-Brock, K., Allen, J.W., Winkfield, E., Poorman-Allen, P., Kundu, B., Funasaka, K., Roop, B.C., Mass, M.J. and DeMarini, D.M. (2003). Methylated trivalent arsenicals as candidate ultimate genotoxic forms of arsenic: induction of chromosomal mutations but not gene mutations. Environ. Mol. Mutagen., 42, 192-205 DOI ScienceOn |
9 | Kruger, K., Repges, H., Hippler, J., Hartmann, L.M., Hirner, A.V., Straub, H., Binding, N. and Musshoff, U. (2007). Effects of dimethylarsinic and dimethylarsinous acid on evoked synaptic potentials in hippocampal slices of young and adult rats. Toxicol. Appl. Pharmacol., 225, 40-46 DOI ScienceOn |
10 | Le, X.C., Ma, M., Cullen, W.R., Aposhian, H.V., Lu, X. and Zheng, B. (2000b). Determination of monomethylarsonous acid, a key arsenic methylation intermediate, in human urine. Environ. Health Perspect, 108, 1015-1018 DOI |
11 | Lewis, D.R., Southwick, J.W., Ouellet-Hellstrom, R., Rench, J. and Calderon, R.L. (1999). Drinking water arsenic in Utah: A cohort mortality study. Environ. Health Perspect, 107, 359-365 DOI |
12 | Li, B., Sun, Y., Sun, X., Wang, Y., Li, X., Kumagai, Y. and Sun, G. (2007). Monomethylarsonous acid induced cytotoxicity and endothelial nitric oxide synthase phosphorylation in endothelial cells. Bull. Environ. Contam. Toxicol., 78, 455-458 DOI |
13 | Mead, M.N. (2005). Arsenic: in search of an antidote to a global poison. Environ. Health Perspect, 113, A378-386 DOI ScienceOn |
14 | Simeonova, P.P., Hulderman, T., Harki, D. and Luster, M.I. (2003). Arsenic exposure accelerates atherogenesis in apolipoprotein E(-/-) mice. Environ. Health Perspect., 111, 1744-1748 DOI |
15 | Valenzuela, O.L., Borja-Aburto, V.H., Garcia-Vargas, G.G., Cruz-Gonzalez, M.B., Garcia-Montalvo, E.A., Calderon- Aranda, E.S. and Del Razo, L.M. (2005). Urinary trivalent methylated arsenic species in a population chronically exposed to inorganic arsenic. Environ. Health Perspect., 113, 250-254 DOI ScienceOn |
16 | Simeonova, P.P. and Luster, M.I. (2004). Arsenic and atherosclerosis. Toxicol. Appl. Pharmacol., 198, 444-449 DOI ScienceOn |
17 | Styblo, M., Drobna, Z., Jaspers, I., Lin, S. and Thomas, D.J. (2002). The role of biomethylation in toxicity and carcinogenicity of arsenic: a research update. Environ. Health Perspect., 110 Suppl 5, 767-771 DOI |
18 | Suzuki, K.T., Tomita, T., Ogra, Y. and Ohmichi, M. (2001). Glutathione-conjugated arsenics in the potential hepato enteric circulation in rats. Chem. Res. Toxicol., 14, 1604-1611 DOI ScienceOn |
19 | Xia, Y. and Liu, J. (2004). An overview on chronic arsenism via drinking water in PR China. Toxicology, 198, 25-29 DOI ScienceOn |
20 | Yu, H.S., Lee, C.H. and Chen, G.S. (2002). Peripheral vascular diseases resulting from chronic arsenical poisoning. J. Dermatol., 29, 123-130 DOI |
21 | Hasegawa, H., Sohrin, Y., Matsui, M., Hojo, M. and Kawashima, M. (1994). Speciation of arsenic in natural waters by solvent extraction and hydride generation atomic absorption spectrometry. Anal. Chem., 66, 3247-3252 DOI ScienceOn |
22 | Lee, M.Y., Lee, Y.H., Lim, K.M., Chung, S.M., Bae, O.N., Kim, H., Lee, C.R., Park, J.D. and Chung, J.H. (2005). Inorganic arsenite potentiates vasoconstriction through calcium sensitization in vascular smooth muscle. Environ. Health Perspect., 113, 1330-1335 DOI ScienceOn |
23 | Petrick, J.S., Jagadish, B., Mash, E.A. and Aposhian, H.V. (2001). Monomethylarsonous acid (MMA(III)) and arsenite: LD(50) in hamsters and in vitro inhibition of pyruvate dehydrogenase. Chem. Res. Toxicol., 14, 651-656 DOI ScienceOn |
24 | Vahter, M. (2002). Mechanisms of arsenic biotransformation. Toxicology, 181-182, 211-217 DOI ScienceOn |
25 | Caceres, D.D., Pino, P., Montesinos, N., Atalah, E., Amigo, H. and Loomis, D. (2005). Exposure to inorganic arsenic in drinking water and total urinary arsenic concentration in a Chilean population. Environ. Res., 98, 151-159 DOI ScienceOn |
26 | Hughes, M.F., Devesa, V., Adair, B.M., Conklin, S.D., Creed, J.T., Styblo, M., Kenyon, E.M. and Thomas, D.J. (2008). Tissue dosimetry, metabolism and excretion of pentavalent and trivalent dimethylated arsenic in mice after oral administration. Toxicol. Appl. Pharmacol., 227, 26-35 DOI ScienceOn |
27 | Soucy, N.V., Klei, L.R., Mayka, D.D. and Barchowsky, A. (2004). Signaling pathways for arsenic-stimulated vascular endothelial growth factor-a expression in primary vascular smooth muscle cells. Chem. Res. Toxicol., 17, 555-563 DOI ScienceOn |
28 | Bunderson, M., Brooks, D.M., Walker, D.L., Rosenfeld, M.E., Coffin, J.D. and Beall, H.D. (2004). Arsenic exposure exacerbates atherosclerotic plaque formation and increases nitrotyrosine and leukotriene biosynthesis. Toxicol. Appl. Pharmacol., 201, 32-39 DOI ScienceOn |
29 | Gebel, T.W. (1999). Arsenic and drinking water contamination. Science, 283, 1458-1459 |
30 | Chouchane, S. and Snow, E.T. (2001). In vitro effect of arsenical compounds on glutathione-related enzymes. Chem. Res. Toxicol., 14, 517-522 DOI ScienceOn |
31 | Olguin, A., Jauge, P., Cebrian, M. and Albores, A. (1983). Arsenic levels in blood, urine, hair and nails from a chronically exposed human population. Proc. West Pharmacol. Soc., 26, 175-177 |
32 | Radabaugh, T.R. and Aposhian, H.V. (2000). Enzymatic reduction of arsenic compounds in mammalian systems: reduction of arsenate to arsenite by human liver arsenate reductase. Chem. Res. Toxicol., 13, 26-30 DOI ScienceOn |
33 | Wildfang, E., Radabaugh, T.R. and Aposhian, H.V. (2001). Enzymatic methylation of arsenic compounds. IX. Liver arsenite methyltransferase and arsenate reductase activities in primates. Toxicology, 168, 213-221 DOI ScienceOn |
34 | Bhattacharyya, R., Chatterjee, D., Nath, B., Jana, J., Jacks, G. and Vahter, M. (2003). High arsenic groundwater: mobilization, metabolism and mitigation--an overview in the Bengal Delta Plain. Mol. Cell. Biochem., 253, 347-355 DOI ScienceOn |
35 | Hirano, S., Kobayashi, Y., Cui, X., Kanno, S., Hayakawa, T. and Shraim, A. (2004). The accumulation and toxicity of methylated arsenicals in endothelial cells: important roles of thiol compounds. Toxicol. Appl. Pharmacol., 198, 458-467 DOI ScienceOn |
36 | Yoshida, T., Yamauchi, H. and Fan Sun, G. (2004). Chronic health effects in people exposed to arsenic via the drinking water: dose-response relationships in review. Toxicol. Appl. Pharmacol., 198, 243-252 DOI ScienceOn |
37 | Lee, M.Y., Bae, O.N., Chung, S.M., Kang, K.T., Lee, J.Y. and Chung, J.H. (2002). Enhancement of platelet aggregation and thrombus formation by arsenic in drinking water: a contributing factor to cardiovascular disease. Toxicol. Appl. Pharmacol., 179, 83-88 DOI ScienceOn |
38 | Pi, J., Kumagai, Y., Sun, G., Yamauchi, H., Yoshida, T., Iso, H., Endo, A., Yu, L., Yuki, K., Miyauchi, T. and Shimojo, N. (2000). Decreased serum concentrations of nitric oxide metabolites among Chinese in an endemic area of chronic arsenic poisoning in inner Mongolia. Free Radic. Biol. Med., 28, 1137-1142 DOI ScienceOn |
39 | Sampayo-Reyes, A., Zakharyan, R.A., Healy, S.M. and Aposhian, H.V. (2000). Monomethylarsonic acid reductase and monomethylarsonous acid in hamster tissue. Chem. Res. Toxicol., 13, 1181-1186 DOI ScienceOn |
40 | Aposhian, H.V. (1997). Enzymatic methylation of arsenic species and other new approaches to arsenic toxicity. Annu. Rev. Pharmacol. Toxicol., 37, 397-419 DOI ScienceOn |
41 | 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 DOI ScienceOn |
42 | Smedley P.L. and Kinniburgh D.G. (2002). A review of the source, behaviour and distribution of arsenic in natural waters. Appl. Geochem., 17, 517-568 DOI ScienceOn |
43 | Berg, M., Tran, H.C., Nguyen, T.C., Pham, H.V., Schertenleib, R. and Giger, W. (2001). Arsenic contamination of groundwater and drinking water in Vietnam: a human health threat. Environ. Sci. Technol., 35, 2621-2626 DOI ScienceOn |
44 | Tsou, T.C., Tsai, F.Y., Wu, M.C. and Chang, L.W. (2003). The protective role of NF-kappaB and AP-1 in arsenite-induced apoptosis in aortic endothelial cells. Toxicol. Appl. Pharmacol., 191, 177-187 DOI ScienceOn |
45 | Concha, G., Vogler, G., Lezcano, D., Nermell, B. and Vahter, M. (1998). Exposure to inorganic arsenic metabolites during early human development. Toxicol. Sci., 44, 185-190 DOI |
46 | Del Razo, L.M., Styblo, M., Cullen, W.R. and Thomas, D.J. (2001). Determination of trivalent methylated arsenicals in biological matrices. Toxicol. Appl. Pharmacol., 174, 282-293 DOI ScienceOn |
47 | Kumagai, Y. and Pi, J. (2004). Molecular basis for arsenicinduced alteration in nitric oxide production and oxidative stress: implication of endothelial dysfunction. Toxicol. Appl. Pharmacol., 198, 450-457 DOI ScienceOn |
48 | Aposhian, H.V., Zakharyan, R.A., Avram, M.D., Sampayo- Reyes, A. and Wollenberg, M.L. (2004). A review of the enzymology of arsenic metabolism and a new potential role of hydrogen peroxide in the detoxication of the trivalent arsenic species. Toxicol. Appl. Pharmacol., 198, 327-335 DOI ScienceOn |
49 | Lee, T.C., Tanaka, N., Lamb, P.W., Gilmer, T.M. and Barrett, J.C. (1988). Induction of gene amplification by arsenic. Science, 241, 79-81 DOI |
50 | Mandal, B.K., Ogra, Y., Anzai, K. and Suzuki, K.T. (2004). Speciation of arsenic in biological samples. Toxicol. Appl. Pharmacol., 198, 307-318 DOI ScienceOn |
51 | Tseng, C.H., Chong, C.K., Tseng, C.P., Hsueh, Y.M., Chiou, H.Y., Tseng, C.C. and Chen, C.J. (2003). Long-term arsenic exposure and ischemic heart disease in arseniasis- hyperendemic villages in Taiwan. Toxicol. Lett., 137, 15-21 DOI ScienceOn |
52 | Zakharyan, R.A. and Aposhian, H.V. (1999). Arsenite methylation by methylvitamin B12 and glutathione does not require an enzyme. Toxicol. Appl. Pharmacol., 154, 287-291 DOI ScienceOn |
53 | Oremland, R.S. and Stolz, J.F. (2003). The ecology of arsenic. Science, 300, 939-944 DOI ScienceOn |
54 | Petrick, J.S., Ayala-Fierro, F., Cullen, W.R., Carter, D.E. and Aposhian, H.V. (2000). Monomethylarsonous acid (MMA(III)) is more toxic than arsenite in Chang human hepatocytes. Toxicol. Appl. Pharmacol., 163, 203-207 DOI ScienceOn |
55 | Buchet, J.P., Lauwerys, R. and Roels, H. (1981). Comparison of the urinary excretion of arsenic metabolites after a single oral dose of sodium arsenite, monomethylarsonate, or dimethylarsinate in man. Int. Arch. Occup. Environ. Health, 48, 71-79 DOI |
56 | Jan, K.Y., Wang, T.C., Ramanathan, B. and Gurr, J.R. (2006). Dithiol compounds at low concentrations increase arsenite toxicity. Toxicol. Sci., 90, 432-439 DOI |
57 | Nemeti, B. and Gregus, Z. (2002). Mitochondria work as reactors in reducing arsenate to arsenite. Toxicol. Appl. Pharmacol., 182, 208-218 DOI ScienceOn |
58 | Shiobara, Y., Ogra, Y. and Suzuki, K.T. (2001). Animal species difference in the uptake of dimethylarsinous acid (DMA(III)) by red blood cells. Chem. Res. Toxicol., 14, 1446-1452 DOI ScienceOn |
59 | Le, X.C., Lu, X., Ma, M., Cullen, W.R., Aposhian, H.V. and Zheng, B. (2000a). Speciation of key arsenic metabolic intermediates in human urine. Anal. Chem., 72, 5172-5177 DOI ScienceOn |
60 |
Bae, O.N., Lim, E.K., Lim, K.M., Noh, J.Y., Chung, S.M., Lee, M.Y., Yun, Y.P., Kwon, S.C., Lee, J.H., Nah, S.Y., and Chung, J.H. (2008). Vascular smooth muscle dysfunction induced by monomethylarsonous acid ( |
61 | 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 DOI ScienceOn |
62 | Vahter, M. and Marafante, E. (1983). Intracellular interaction and metabolic fate of arsenite and arsenate in mice and rabbits. Chem. Biol. Interact., 47, 29-44 DOI ScienceOn |
63 | Bae, O.N., Lim, K.M., Noh, J.Y., Chung, S.M., Kim, H., Lee, C.R., Park, J.D. and Chung, J.H. (2007). Arsenite-enhanced procoagulant activity through phosphatidylserine exposure in platelets. Chem. Res. Toxicol., 20, 1760-1768 DOI ScienceOn |
64 | Liu, Z., Shen, J., Carbrey, J.M., Mukhopadhyay, R., Agre, P. and Rosen, B.P. (2002). Arsenite transport by mammalian aquaglyceroporins AQP7 and AQP9. Proc. Natl. Acad. Sci. USA, 99, 6053-6058 |
65 | Hayakawa, T., Kobayashi, X., 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 DOI |
66 | Lin, S., Del Razo, L.M., Styblo, M., Wang, C., Cullen, W.R. and Thomas, D.J. (2001). Arsenicals inhibit thioredoxin reductase in cultured rat hepatocytes. Chem. Res. Toxicol., 14, 305-311 DOI ScienceOn |
67 | 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 DOI ScienceOn |
68 | Hirano, S., Cui, X., Li, S., Kanno, S., Kobayashi, Y., Hayakawa, T. and Shraim, A. (2003). Difference in uptake and toxicity of trivalent and pentavalent inorganic arsenic in rat heart microvessel endothelial cells. Arch. Toxicol., 77, 305-312 DOI |
69 | Nesnow, S., Roop, B.C., Lambert, G., Kadiiska, M., Mason, R.P., Cullen, W.R. and Mass, M.J. (2002). DNA damage induced by methylated trivalent arsenicals is mediated by reactive oxygen species. Chem. Res. Toxicol., 15, 1627-1634 DOI ScienceOn |
70 | Sakurai, T., Qu, W., Sakurai, M.H. and Waalkes, M.P. (2002). A major human arsenic metabolite, dimethylarsinic acid, requires reduced glutathione to induce apoptosis. Chem. Res. Toxicol., 15, 629-637 DOI ScienceOn |
71 | Lamm, S.H., Engel, A., Kruse, M.B., Feinleib, M., Byrd, D.M., Lai, S. and Wilson, R. (2004). Arsenic in drinking water and bladder cancer mortality in the United States: an analysis based on 133 U.S. counties and 30 years of observation. J. Occup. Environ. Med., 46, 298-306 DOI ScienceOn |
72 | Lee, M.Y., Jung, B.I., Chung, S.M., Bae, O.N., Lee, J.Y., Park, J.D., Yang, J.S., Lee, H. and Chung, J.H. (2003). Arsenic-induced dysfunction in relaxation of blood vessels. Environ. Health Perspect., 111, 513-517 |
73 | 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. (2000). Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells. Arch. Toxicol., 74, 289-299 DOI |
74 | Heydorn, K. (1970). Environmental variation of arsenic levels in human blood determines by neutron activation analysis. Clin. Chim. Acta, 28, 349-357 DOI ScienceOn |
75 | Kwok, R.K., Mendola, P., Liu, Z.Y., Savitz, D.A., Heiss, G., Ling, H.L., Xia, Y., Lobdell, D., Zeng, D., Thorp, J.M. Jr., Creason, J.P. and Mumford, J.L. (2007). Drinking water arsenic exposure and blood pressure in healthy women of reproductive age in Inner Mongolia, China. Toxicol. Appl. Pharmacol., 222, 337-343 DOI ScienceOn |
76 | 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. (2000a). Occurrence of monomethylarsonous acid in urine of humans exposed to inorganic arsenic. Chem. Res. Toxicol., 13, 693-697 DOI ScienceOn |
77 | Bates, M.N., Smith, A.H. and Hopenhayn-Rich, C. (1992). Arsenic ingestion and internal cancers: a review. Am. J. Epidemiol., 135, 462-476 DOI |
78 | Cebrian, M.E., Albores, A., Aguilar, M. and Blakely, E. (1983). Chronic arsenic poisoning in the north of Mexico. Hum. Toxicol., 2, 121-133 DOI |
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