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Chemical Compound Review

ARSENOBETAINE     2-trimethylarsoniumylethanoate

Synonyms: CCRIS 5277, AG-G-41842, BCR626_FLUKA, AC1L2HXX, LS-21924, ...
This record was replaced with 47365.
 
 
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Disease relevance of carboxymethyl-trimethyl-arsanium

  • Cellular retention, toxicity and carcinogenic potential of seafood arsenic. I. Lack of cytotoxicity and transforming activity of arsenobetaine in the BALB/3T3 cell line [1].
  • When tested in the Ames' Salmonella typhimurium system for chemical mutagens, both in the presence and absence of liver microsomal oxidase fraction, arsenobetaine gave consistently negative results [2].
 

High impact information on carboxymethyl-trimethyl-arsanium

  • Thus, the low retention efficiency of arsenobetaine, its inability to interact with intracellular components and the absence of biotransformation in the cell could explain the lack of cytotoxicity and transforming potential observed in the BALB/3T3 cells [1].
  • Combined arsenobetaine and arsenocholine (so-called fish arsenic), extracted from a certified control material of dogfish muscle (DORM-1), were completely recovered with Pd-S2O8 matrix modification, but not with nickel [3].
  • Cytotoxicity, morphological neoplastic transformation, intracellular retention and metabolic behaviour have been investigated in BALB/3T3 Cl A 31-1-1 cells for arsenobetaine, the main form of arsenic in certain seafoods, in comparison to inorganic sodium arsenite [1].
  • About 95% of the intracellular arsenobetaine was present in the cytosol fraction and the attempt to detect any intracellular degradation of the organoarsenic compound failed [1].
  • Modulation of cell adhesion and viability of cultured murine bone marrow cells by arsenobetaine, a major organic arsenic compound in marine animals [4].
 

Biological context of carboxymethyl-trimethyl-arsanium

  • The clearance of arsenobetaine from plasma and most tissues was fast (somewhat faster in mice than in rabbits) and seemed to follow first-order kinetics [5].
  • As arsenic body burden increased, the percentage of arsenobetaine present decreased in a dose dependent manner, although its absolute concentration rose with increasing arsenic burden [6].
  • However, seawater adaptation had no effect on the levels of accumulated arsenobetaine in muscle tissue [7].
  • The determination of urinary arsenobetaine proved to determine specifically the seafood-derived arsenic, allowing this arsenic to be distinguished clearly from the arsenic from occupational exposure [8].
 

Anatomical context of carboxymethyl-trimethyl-arsanium

  • Arsenobetaine formation may then occur in the lumen of the digestive tract (i.e., mediated by microorganisms) or in the liver catalyzed by enzymes [9].
  • Isolation and preliminary toxicological evaluation of arsenobetaine - the water-soluble arsenical constituent from the hepatopancreas of the western rock lobster [2].
  • Since the metabolism of arsenic species varies with the arsenite and arsenate being the most toxic, and organoarsenic compounds such as arsenobetaine the least toxic compounds, the determination of the arsenic species in the diet and their body fluids are important [10].
 

Associations of carboxymethyl-trimethyl-arsanium with other chemical compounds

  • The total As concentrations (less arsenobetaine) in the 'exposed' population were in the range 2.7-58.9 micrograms g-1 creatinine (mean 13.4, median 9.2 micrograms g-1) compared with the control group data range 2.5-5.3 micrograms g-1 (mean 4.2, median 4.7 micrograms g-1) [11].
  • Extraction efficiencies for organoarsenic species ranged from 80% (dimethylarsinic acid, DMA) to 99% for arsenobetaine (AsB) [12].
  • The extracted species were analysed by gas chromatography/inductively coupled plasma mass spectrometry (GC/ICPMS; DBT, TBT and MeHg) and liquid chromatography/inductively coupled plasma mass spectrometry (LC/ICPMS; MMA, DMA, AsB) after ethylation with sodium tetraethylborate or dilution with water, respectively [12].
  • To investigate the properties of arsenobetaine and its likely immediate biogenic precursor, dimethylarsinoylacetic acid, we studied the exchanges of the C-2 methylene protons of these compounds in D2O solution and showed them to be pH dependent first-order reactions [13].
  • The water soluble arsenic compound present in the hepatopancreas of the western rock lobster (Panulirus cygnus George) has been isolated as the reineckate salt and has been identified as arsenobetaine [2].
 

Gene context of carboxymethyl-trimethyl-arsanium

  • Anion-exchange chromatography was optimized to produce a chromatographically pure peak of arsenobetaine (accounting for ca. 64% of all water-soluble As present) that was used to quantify this compound [14].
  • Using fast atom bombardment (FAB) ionization combined with tandem mass spectrometry (MS/MS), the identity of arsenobetaine (AB) in extracts of sole, haddock, lobster and shrimp was unequivocally confirmed [15].
 

Analytical, diagnostic and therapeutic context of carboxymethyl-trimethyl-arsanium

References

  1. Cellular retention, toxicity and carcinogenic potential of seafood arsenic. I. Lack of cytotoxicity and transforming activity of arsenobetaine in the BALB/3T3 cell line. Sabbioni, E., Fischbach, M., Pozzi, G., Pietra, R., Gallorini, M., Piette, J.L. Carcinogenesis (1991) [Pubmed]
  2. Isolation and preliminary toxicological evaluation of arsenobetaine - the water-soluble arsenical constituent from the hepatopancreas of the western rock lobster. Cannon, J.R., Saunders, J.B., Toia, R.F. Sci. Total Environ. (1983) [Pubmed]
  3. Total arsenic in urine: palladium-persulfate vs nickel as a matrix modifier for graphite furnace atomic absorption spectrophotometry. Nixon, D.E., Mussmann, G.V., Eckdahl, S.J., Moyer, T.P. Clin. Chem. (1991) [Pubmed]
  4. Modulation of cell adhesion and viability of cultured murine bone marrow cells by arsenobetaine, a major organic arsenic compound in marine animals. Sakurai, T., Fujiwara, K. Br. J. Pharmacol. (2001) [Pubmed]
  5. Metabolism of arsenobetaine in mice, rats and rabbits. Vahter, M., Marafante, E., Dencker, L. Sci. Total Environ. (1983) [Pubmed]
  6. Arsenic-speciation in arsenate-resistant and non-resistant populations of the earthworm, Lumbricus rubellus. Langdon, C.J., Meharg, A.A., Feldmann, J., Balgar, T., Charnock, J., Farquhar, M., Piearce, T.G., Semple, K.T., Cotter-Howells, J. Journal of environmental monitoring : JEM. (2002) [Pubmed]
  7. Arsenobetaine in Atlantic salmon (Salmo salar L.): influence of seawater adaptation. Amlund, H., Berntssen, M.H. Comp. Biochem. Physiol. C Toxicol. Pharmacol. (2004) [Pubmed]
  8. Biological monitoring of arsenic exposure of gallium arsenide- and inorganic arsenic-exposed workers by determination of inorganic arsenic and its metabolites in urine and hair. Yamauchi, H., Takahashi, K., Mashiko, M., Yamamura, Y. American Industrial Hygiene Association journal. (1989) [Pubmed]
  9. Arsenic occurrence and species in near-shore macroalgae-feeding marine animals. Kirby, J., Maher, W., Spooner, D. Environ. Sci. Technol. (2005) [Pubmed]
  10. Arsenic metabolism in seaweed-eating sheep from Northern Scotland. Feldmann, J., John, K., Pengprecha, P. Fresenius' journal of analytical chemistry. (2000) [Pubmed]
  11. Urinary arsenic species in Devon and Cornwall residents, UK. A pilot study. Kavanagh, P., Farago, M.E., Thornton, I., Goessler, W., Kuehnelt, D., Schlagenhaufen, C., Irgolic, K.J. The Analyst. (1998) [Pubmed]
  12. Simultaneous co-extraction of organometallic species of different elements by accelerated solvent extraction and analysis by inductively coupled plasma mass spectrometry coupled to liquid and gas chromatography. Wahlen, R., Catterick, T. Rapid Commun. Mass Spectrom. (2004) [Pubmed]
  13. Deuterium exchange in arsenobetaine and dimethylarsinoylacetic acid. Edmonds, J.S., Nomachi, M., Morita, M. J. Inorg. Biochem. (2005) [Pubmed]
  14. Investigation of arsenic speciation in oyster test reference material by multidimensional HPLC-ICP-MS and electrospray tandem mass spectrometry (ES-MS-MS). McSheehy, S., Pohl, P., Lobiński, R., Szpunar, J. The Analyst. (2001) [Pubmed]
  15. Identification and confirmation of arsenobetaine and arsenocholine in fish, lobster and shrimp by a combination of fast atom bombardment and tandem mass spectrometry. Lau, B.P., Michalik, P., Porter, C.J., Krolik, S. Biomed. Environ. Mass Spectrom. (1987) [Pubmed]
  16. First report on the detection and quantification of arsenobetaine in extracts of marine algae using HPLC-ES-MS/MS. Nischwitz, V., Pergantis, S.A. The Analyst. (2005) [Pubmed]
  17. Arsenic species contents at aquaculture farm and in farmed mouthbreeder (Oreochromis mossambicus) in blackfoot disease hyperendemic areas. Huang, Y.K., Lin, K.H., Chen, H.W., Chang, C.C., Liu, C.W., Yang, M.H., Hsueh, Y.M. Food Chem. Toxicol. (2003) [Pubmed]
  18. Disposition of arsenobetaine in two marine fish species following administration of a single oral dose of [(14)C]arsenobetaine. Amlund, H., Ingebrigtsen, K., Hylland, K., Ruus, A., Eriksen, D.Ø., Berntssen, M.H. Comp. Biochem. Physiol. C Toxicol. Pharmacol. (2006) [Pubmed]
 
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