Exploring the in vitro formation of trimethylarsine sulfide from dimethylthioarsinic acid in anaerobic microflora of mouse cecum using HPLC–ICP-MS and HPLC–ESI-MS

Kubachka, Kevin M.; Kohan, Michael C.; Herbin-Davis, Karen; Creed, John T.; Thomas, David J.

doi:10.1016/j.taap.2008.12.008

Cited by 64 publications

(46 citation statements)

References 30 publications

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“…The authors suggest that the high cellular toxicity induced by arsenolipids may be related to their ability to easily pass cell membranes, possibly by passive diffusion. Thio-arsenicals are probably produced by the colon microbiota [95][96][97], and one recent study found that sulfatereducing bacteria present in the human gut was necessary for conversion of MA (V) into the thiolated monomethyl monothioarsonate [98]. Thio-arsenicals have been recognized as toxic in studies on human cells [132,133].…”

Section: Mechanisms and Toxicity Of Arsenic Compounds Occurring In Sementioning

confidence: 99%

“…It is also possible that the microbiome of the GI-tract can play a role in the (pre-absorptive) metabolism of arsenicals. In vitro studies have shown that the microbiome in mouse coecum and human colon microbiota converts As (V) and methylated arsenicals into oxo-arsenicals and thio-arsenicals [95][96][97][98]. In our previous study, a multitude of urinary arsenicals excreted after volunteers ingested an identical meal consisting of 150 g blue mussels were identified;…”

mentioning

confidence: 98%

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Arsenic in the human food chain, biotransformation and toxicology – Review focusing on seafood arsenic

Molin

Ulven

Meltzer

et al. 2015

Journal of Trace Elements in Medicine and Biology

196

105

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Section: Mechanisms and Toxicity Of Arsenic Compounds Occurring In Sementioning

confidence: 99%

mentioning

confidence: 98%

Arsenic in the human food chain, biotransformation and toxicology – Review focusing on seafood arsenic

Molin

Ulven

Meltzer

et al. 2015

Journal of Trace Elements in Medicine and Biology

196

105

View full text Add to dashboard Cite

show abstract

“…TMAsO was almost quantitatively converted to TMAsS within 1 h. Three chromatographic separations were utilized to verify the lack of co-elution prior to quantification by ICP-MS, and the identities of all three thiolated metabolites were confirmed with HPLC-ESI-MS/MS. Furthermore, in a R. A. DIAZ-BONE AND T. VAN DE WIELE follow-up study, incubation of 34 S labeled DMMTAs V ( 34 S-DMMTAs V ) with anaerobic microbiota of mouse cecum yielded 34 S-TMAsS, thereby indicating that thiolated compounds can be methylated directly without the need of intermediate conversion toward the oxoforms [33].…”

Section: Thiolation Of As Compounds By Intestinal Microorganismsmentioning

confidence: 98%

Biotransformation of metal(loid)s by intestinal microorganisms

Diaz-Bone

Wiele

2010

Pure and Applied Chemistry

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Many metals and metalloids undergo complex biotransformation processes by micro organisms in the environment, namely, Ge, As, Se, Cd, In, Sn, Sb, Te, Hg, Tl, Pb, Bi, and Po. Though the human intestine harbors a highly diverse and metabolically active microbial community, the knowledge on metal(loid) biotransformation by gut microbiota is limited. Microbial metal(loid) metabolism in the gut is highly relevant when assessing health risks from oral exposure, as both the bioavailability and the toxicity of the ingested compound can be modulated. This review gathers and compares a broad selection of scientific studies on the intestinal biotransformation of metal(loid)s.It can be inferred that metal(loid) biotransformation by intestinal microbiota is a common process, resulting in both beneficial and adverse toxicological effects. Whereas for Hg the intestinal demethylation of methylmercury results in enhanced elimination, highly bioavailable and toxic arsenic and Bi species are formed by intestinal microorganisms. In either case, we conclude that the gut microbial potency should be considered to be taken up in toxicokinetic studies and models for assessing the health risks of oral metal(loid) exposure. This will allow the relevance of intestinal metal(loid) biotransformation to be assessed for human health risks.

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“…The also identified organic thioarsenic compounds methylthioarsonic acid, dimethylthioarsinic acid, dimethyldithioarsinic acid or trimethylarsine sulfide (Adair et al 2007) can be formed in erythrocytes or other cells (Naranmandura and Suzuki 2008; and in the gastrointestinal tract by hydrogen sulfide-producing micro-organisms that replace the oxygen of the methylarsenic compounds with sulfur (Kubachka et al 2009;Pinyayev et al 2011). Organic thioarsenic compounds were found in the urine of humans (Chilakapati et al 2010;Raml et al 2007), sheep (Hansen et al 2004), hamsters (Naranmandura et al 2007 b) and rats (Naranmandura et al 2007 b;Suzuki et al 2010;Yoshida et al 1997) after exposure to inorganic arsenic compounds.…”

Section: Thiomethylarsenic Compoundsmentioning

confidence: 99%

Methylarsenic compounds [MAK Value Documentation, 2014]

Hartwig

2018

The MAK‐Collection for Occupational Health and Safety

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The German Commission for the Investigation of Health Hazards of Chemical Compounds in the Work Area has evaluated methylarsenic compounds considering all toxicological endpoints. Available publications and unpublished study reports are described in detail. Methylarsenic compounds are the carcinogenic metabolites of arsenic and its inorganic compounds, which are proven human carcinogens. Methylated arsenic compounds are able to interfere with all important cellular processes. In mice and rats, dimethylarsinic acid was clearly carcinogenic. Trimethylarsine oxide caused liver adenomas in F344 rats and with methylarsenic acid, preneoplastic liver effects were found. If all aspects are considered, methylarsenic compounds are classified in Carcinogen Category 1. Methylarsenic compounds are genotoxic in vitro and in vivo. As they are bioavailable and can reach the germ cells, they are classified in Category 3 A for Germ Cell Mutagens. Methylarsenic compounds are genotoxic carcinogens, for which no safe systemic exposure can be estimated. It must be assumed that even small amounts absorbed percutaneously increase the carcinogenic risk. Therefore, methylarsenic compounds are designated with an “H” (for substances that can be absorbed through the skin in toxicologically relevant amounts). Dimethylarsinic acid induced developmental toxicity in rats. Apart from a well‐documented case report, there are no clear findings available to conclude a skin‐sensitizing potential in humans.

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Exploring the in vitro formation of trimethylarsine sulfide from dimethylthioarsinic acid in anaerobic microflora of mouse cecum using HPLC–ICP-MS and HPLC–ESI-MS

Cited by 64 publications

References 30 publications

Arsenic in the human food chain, biotransformation and toxicology – Review focusing on seafood arsenic

Arsenic in the human food chain, biotransformation and toxicology – Review focusing on seafood arsenic

Biotransformation of metal(loid)s by intestinal microorganisms

Methylarsenic compounds [MAK Value Documentation, 2014]

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