Enzymatic methylation of arsenic species and other new approaches to arsenic toxicity

Annual Review of Pharmacology and Toxicology

Volumn 37, Issue , 1997, Pages 397-419

  Aposhian, H Vasken ^a  

^a University of Arizona   (United States)

Author keywords

arsenic biotransformation; biomethylation; evolution; methyltransferases

Indexed keywords

ARSENIC DERIVATIVE; ARSENIC TRIOXIDE; CACODYLIC ACID; METHANEARSONIC ACID; METHYLTRANSFERASE;

ANIMAL EXPERIMENT; BIOTRANSFORMATION; HUMAN; METHYLATION; NONHUMAN; PRIORITY JOURNAL; RABBIT; REVIEW; RHESUS MONKEY; SPECIES DIFFERENCE;

ANIMALIA; MACACA MULATTA; ORYCTOLAGUS CUNICULUS; PAN TROGLODYTES;

EID: 0008517022     PISSN: 00664251     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.pharmtox.37.1.397     Document Type: Review

References (76)

1. Sancha AM, Vega F, Venturino H, Fuentes S, Salazar AM, et al. 1992. The arsenic health problem in northern Chile: evaluation and control. A case study preliminary report. In Proc. Int. Semin. Arsenic in the Environment and Its Incidence on Health, pp. 187-202. Santiago, Chile: Universidad de Chile
2. Cebrian ME, Albores A, Aguilar M, Blakely E. 1983. Chronic arsenic poisoning in the north of Mexico. Hum. Toxicol. 2:121-33
3. Chen CJ, Chuang YC, Lin TM, Wu HY. 1985. Malignant neoplasms among residents of a Blackfoot disease-endemic area in Taiwan: high-arsenic artesian well water and cancers. Cancer Res. 45:5895-99
4. Mazumder DNG, Chakraborty AK, Ghose A, Gupta JD, Chakraborty DP, et al. 1988. Chronic arsenic toxicity from drinking water in rural West Bengal. Bull. World Health Org. 66:499-506
5. Bencko V, Symon K. 1977. Health aspects of burning coal with a high arsenic content. I. Arsenic in hair, urine and blood in children residing in a polluted area. Environ. Res. 13:328-85
6. Bates MN, Smith AH, Hopenhayn-Rich C. 1992. Arsenic ingestion and internal cancers: a review. Am. J. Epidemiol. 135:462-76
7. de Wolff FA, Edelbroek PM. 1994. Neurotoxicity of arsenic and its compounds. Handbook Clin. Neurol. 20(64):283-91
8. Joliffe DM. 1993. A history of the use of arsenicals in man. J. R. Soc. Med. 86:287-89
9. Stöhrer G. 1991. Arsenic: opportunity for risk assessment. Arch. Toxicol. 65:525-31
10. Cullen WR, McBride BC, Reglinski J. 1984. The reaction of methylarsenicals with thiols: some biological implications. J. Inorg. Biochem. 21:179-94
11. Cullen WR, Reimer KJ. 1989. Arsenic speciation in the environment. Chem. Rev. 89:713-64
12. 74As) arsenite in mice and rabbits. Chem.-Biol. Interact. 50:49-57
13. Buchet JP, Lauwerys R. 1985. Study of inorganic arsenic methylation by rat liver in vitro: relevance for the interpretation of observations in man. Arch. Toxicol. 57:125-29
14. Buchet JP, Lauwerys R. 1988. Role of thiols in the in vitro methylation of inorganic arsenic by rat liver cytosol. Biochem. Pharmacol. 37:3149-53
15. Styblo M, Yamauchi H, Thomas DJ. 1995. Comparative in vitro methylation of trivalent and pentavalent arsenicals. Toxicol. Appl. Pharmacol. 135:172-78
16. Styblo M, Delnomdedieu M, Thomas DJ. 1996. Mono- and dimethylation of arsenic in rat liver cytosol in vitro. Chem.-Biol. Interact. 99:147-64
17. National Research Council. 1977. Medical and Biologic Effects of Environmental Pollutants, Arsenic. Washington, DC: Natl. Acad. Sci.
18. 74As-arsenite. Arch. Toxicol. 51:65-77
19. Vahter M, Marafante E. 1988. In vivo methylation and detoxication of arsenic. In The Biological Alkylation of Heavy Elements, Special Publication, ed. PJ Craig, F Glocking, 66:105-19. London: R. Soc. Chem.
20. Slilaty SN, Aposhian HV. 1983. Gene transfer by polyoma-like particles assembled in a cell-free system. Science 220:725-27
21. Geubel AP, Mairlot MC, Buchet JP, Dive C, Lauwerys R. 1988. Abnormal methylation capacity in human liver cirrhosis. Int. J. Clin. Pharmacol. Res. 8:117-22
22. Zakharyan RA, Wu Y, Bogdan GM, Aposhian HV. 1995. Enzymatic methylation of arsenic compounds. I. Assay, partial purification, and properties of arsenite methyltransferase and monomethylarsonic acid methyltransferase of rabbit liver. Chem. Res. Toxicol. 8:1029-38
23. Zakharyan RA, Wildfang E, Aposhian HV. 1996. Enzymatic methylation of arsenic compounds. III. The marmoset and tamarin, but not the rhesus, monkey are deficient in methyltransferases that methylate inorganic arsenic. Toxicol. Appl. Pharmacol. 140:77-84
24. Borchardt RT. 1981. Catechol O-methyltransferase. Methods Enzymol. 77:267-72
25. Aposhian HV, Zakharyan RA, Wu Y, Healy S, Aposhian MM. 1997. Enzymatic methylation of arsenic compounds. II. An overview. In Arsenic Exposure and Human Health, Vol. 2, ed. C Abernethy, R Calderon, W Chappell. London: Chapman & Hall. In press
26. Styblo M, Delnomdedieu M, Thomas DJ. 1995. Biological mechanisms and toxicological consequences of methylation of arsenic. In Toxicology of Metals: Biochemical Aspects, ed. RA Goyer, MG Cherian, pp. 407-33. Berlin: Springer Verlag
27. Healy SM, Zakharyan RA, Aposhian HV. 1996. Enzymatic methylation of arsenic compounds. IV. In vitro and in vivo deficiency of the methylation of arsenite and monomethylarsonic acid in the guinea pig. Mutat. Res. In press
28. Deleted in proof
29. Zimmerman AE, Moule ML, Yip CC. 1974. Guinea pig insulin. II. Biological activity. J. Biol. Chem. 249:4026-29
30. Smith LF. 1966. Species variation in the amino acid sequence of insulin. Am. J. Med. 40:662-66
31. Sato P, Udenfriend S. 1978. Scurvy-prone animals, including man, monkey and guinea pig, do not express the gene for gulonolactone oxidase. Arch. Biochem. Biophys. 187:158-62
32. Clementi A. 1922. Dsamidation enzymatique de l'asparagine. Arch. Interact. Physiol. 19:369-98
33. Yamanaka K, Hasegawa A, Sawamura R, Okada S. 1989. Dimethylated arsenics induce DNA strand breaks in lung via the production of active oxygen in mice. Biochem. Biophys. Res. Commun. 165:43-50
34. Yamanaka K, Hoshino M, Okamoto M, Sawamura R, Hasegawa A, Okada S. 1990. Induction of DNA damage by dimethylarsine, a metabolite of inorganic arsenics, is for the major part likely due to its peroxyl radical. Biochem. Biophys. Res. Commun. 168:58-64
35. Vahter M, Concha G, Nermell B, Nilsson R, Duluot F, Natarajan A. 1995. A unique metabolism of inorganic arsenic in native Andean women. Eur. J. Pharmacol. 293:455-62
36. Vahter M, Couch R, Nermell B, Nilsson R. 1995. Lack of methylation of inorganic arsenic in the chimpanzee. Toxicol. Appl. Pharmacol. 133:262-68
37. Fairlamb AH, Cerami A. 1985. Identification of a novel, thiol containing cofactor essential for glutathione reductase enzyme activity in trypanomatids. Mol. Biochem. Parasitol. 14:187-98
38. Fairlamb AH, Henderson GB, Cerami A. 1989. Trypanothione is the primary target for arsenical drugs against African trypanosomes. Proc. Natl. Acad. Sci. USA 86:2607-11
39. Deleted in proof
40. Aposhian HV. 1983. DMSA and DMPS-water soluble antidotes for heavy metal poisoning. Annu. Rev. Pharmacol. Toxicol. 23:193-215
41. Gonzalez-Ramirez D, Maiorino RM, Zuniga-Charles M, Xu Z, Hurlbut KM, et al. 1995. Sodium 2,3-dimercaptopropane-1-sulfonate challenge test for mercury in humans. II. Urinary mercury, porphyrins and neurobehavioral changes of dental workers in Monterrey, Mexico. J. Pharmacol. Exp. Ther. 272:264-74
42. Maiorino RM, Gonzalez-Ramirez D, Zuniga-Charles M, Xu Z, Hurlbut KM, et al. 1996. Sodium 2,3-dimercaptopropane-1-sulfonate challenge test for mercury in humans. III. Urinary mercury after exposure to mercurous chloride. J. Pharmacol. Exp. Ther. 277:938-44
43. Aposhian HV, Bruce DC, Alter W, Dart RC, Hurlbut KM, Aposhian MM. 1992. Urinary mercury after administration of 2,3-dimercaptopropane-1-sulfonic acid: correlation with dental amalgam score. FASEB J. 6:2472-76
44. Kemper FH, Jekat FW, Bertram HP, Eckard R. 1990. New chelating agents. In Basic Science in Toxicology, Proc. 5th Int. Congr. Toxicology, England 1989, ed. GN Volans, J Sims, FM Sullivan, P Turner, pp. 523-46. London: Taylor & Francis
45. Lorscheider FL, Vimy MJ, Summers AO. 1995. Mercury exposure from "silver" tooth fillings: emerging evidence questions a traditional dental paradigm. FASEB J. 9:504-8
46. Domingo JL, Bosque MA, Llobet JM, Corbella J. 1992. Amelioration by BAL (2,3-dimercapto-1-propanol) and DMPS (sodium 2,3-dimercapto-1-propanesulfonic acid) of arsenite developmental toxicity in mice. Ecotoxicol. Environ. Safety 23:274-81
47. Domingo JL. 1995. Prevention by chelating agents of metal-induced developmental toxicity. Reproduce Toxicol. 9:105-13
48. Moore DF, O'Callaghan CA, Berlyne G, Ogg CS, Alban Davies H, et al. 1994. Acute arsenic poisoning: absence of polyneuropathy after treatment with 2,3-dimercaptopropanesulphonate (DMPS). J. Neurol. Neurosurg. Psych. 57:1133-35
49. Klimecki WT, Carter DE. 1995. Arsine toxicity: chemical implications and mechanistic implications. J. Toxicol. Environ. Health 46:399-409
50. Hatlelid KM, Brailsford C, Carter DE. 1995. An in vitro model for arsine toxicity using isolated red blood cells. Fund. Appl. Toxicol. 25:302-6
51. Hatlelid KM, Brailsford C, Carter DE. 1996. Reactions of arsine with hemoglobin. J. Toxicol. Environ. Health 47:145-57
52. Winski SL, Carter DE. 1995. Interactions of rat red blood cell sulfhydryls with arsenate and arsenite. J. Toxicol. Environ. Health 46:379-97
53. Blair PC, Thompson MB, Bechtold M, Wilson RE, Moorman MP, Fowler BA. 1990. Evidence for oxidative damage to red blood cells in mice induced by arsine gas. Toxicology 63:25-34
54. Hatlelid KM, Carter DE. 1996. Reactive oxygen species do not cause arsine-induced hemoglobin damage. J. Toxicol. Environ. Health. In press
55. Roscoe HE. 1862. On the alleged practice of arsenic-eating in Styria. Mem. Lit. Philos. Soc. Manchester, London, Ser. 3 1:208-21
56. Maclagen RC. 1864. On the arsenic-eaters of Styria. Edinburgh Med. J. 10:200-7
57. Maclagen RC. 1875. Arsenic-eaters of Styria. Edinburgh Med. J. 21:526-28
58. Bednarczyk LR, Matusiak W. 1982. Case report: an arsenic murder. J. Anal. Toxicol. 6:260-61
59. Chatterjee A, Das D, Mandal BK, Chowdhury TR, Samanta G, Chakraborty D. 1995. Arsenic in ground water in six districts of West Bengal, India: the biggest arsenic calamity in the world. Part I. Arsenic species in drinking water and urine of the affected people. Analyst 120:643-50
60. Tseng WP. 1977. Effects and dose-response relationships of skin cancer and Blackfoot disease with arsenic. Environ. Health Persp. 19:109-19
61. Guo HR, Lu FJ. 1994. Re: Arsenic ingestion and internal cancers: a review. Am. J. Epidemiol. 139:1233-34
62. Chen SL, Yeh SJ, Yang MH, Lin TH. 1995. Trace element concentration and arsenic speciation in the well water of a Taiwan area with endemic Blackfoot disease. Biol. Trace Elem. Res. 48:263-74
63. Uthus EO. 1992. Evidence for arsenic essentiality. Environ. Geochem. Health 14:55-58
64. Brouwer OF, Onkenhout W, Edelbroek PM, de Kom JFM, de Wolff FA, Peters ACB. 1992. Increased neurotoxicity of arsenic in methylenetetrahydrofolate reductase deficiency. Clin. Neurol. Neurosurg. 94:307-10
65. Vahter M. 1994. Species differences in the metabolism of arsenic compounds. Appl. Organometal. Chem. 8:175-82
66. Vahter M, Marafante E. 1985. Reduction and binding of arsenate in marmoset monkeys. Arch. Toxicol. 57:119-24
67. Bogdan GM, Sampayo-Reyes A, Aposhian HV. 1994. Arsenic binding proteins of mammalian systems. I. Isolation of three arsenite-binding proteins of rabbit liver. Toxicology 93:175-93
68. Centeno JA, Feliu LA, Polanco A, Hernandez SP. 1995. Interaction of arsenic species with sulfhydryl-containing biological molecules: a Raman spectroscopy study. Prep. Am. Chem. Soc. (Div. Environ. Chem.) 35:121-24
69. Naredi P, Heath DD, Enns RE, Howell SB. 1995. Cross-resistance between cis-platin, antimony potassium tartrate and arsenite in human tumor cells. J. Clin. Invest. 95:1193-98
70. Wang Z, Rossman TG. 1993. Stable and inducible arsenite resistance in Chinese hamster cells. Toxicol. Appl. Pharmacol. 118:80-86
71. Wang Z, Dey S, Rosen BP, Rossman TG. 1996. Efflux-mediated resistance to arsenicals in arsenic-resistant and -hypersensitive Chinese hamster cells. Toxicol. Appl. Pharmacol. 137:112-19
72. Silver S, Nucifora G, Chu L, Misra TK. 1989. Bacterial resistance ATPases: primary pumps for exporting toxic cations and anions. Trends Biochem. Sci. 14:76-80
73. Tisa LS, Rosen BP. 1990. Molecular characterization of an anion pump. J. Biol. Chem. 265:190-94
74. Ostrosky-Wegman P, Gonsebatt ME, Montero R, Vega L, Barba H, et al. 1991. Lymphocyte proliferation kinetics and genotoxic findings in a pilot study on individuals chronically exposed to arsenic in Mexico. Mutat. Res. 250:477-82
75. Garcia-Vargas GG, Del Razo LM, Cebrian ME, Albores A, Ostrosky-Wegman P, et al. 1994. Altered urinary porphyrin excretion in a human population chronically exposed to arsenic in Mexico. Human Exp. Toxicol. 13:839-47
76. Nriagu JO. 1996. A history of global metal pollution. Science 272:223-24