2‐Dimethylarsinothioyl Acetic Acid Identified in a Biological Sample: The First Occurrence of a Mammalian Arsinothioyl Metabolite

Hansen, Hanna E.; Pickford, Russell; Thomas‐Oates, Jane; Jaspars, Marcel; Feldmann, Jörg

doi:10.1002/anie.200352740

Cited by 91 publications

(47 citation statements)

References 19 publications

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“…A transformation of DMAE to dimethylarsinothioyl ethanol might be likely in the presence of free sulfide. 22 This means arsenic is highly mobile and arsenic from a massive decay of seaweed would be able to diffuse in the deeper anaerobic zones of a sediment without immobilization. Although sugar-3 and sugar-4 have been identified in marine sediments, 13 DMAE has never been identified to occur in seawater or porewater.…”

Section: Discussionmentioning

confidence: 99%

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Biodegradation of arsenosugars in marine sediment

Pengprecha

Wilson

Raab

et al. 2005

Appl. Organometal. Chem.

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In the marine environment, arsenic accumulates in seaweed and occurs mostly in the form of arsenoribofuranosides (often called arsenosugars). This study investigated the degradation pathways of arsenosugars from decaying seaweed in a mesocosm experiment. Brown seaweed (Laminaria digitata) was placed on top of a marine sediment soaked with seawater. Seawater and porewater samples from different depths were collected and analysed for arsenic species in order to identify the degradation products using high-performance liquid chomatography-inductively coupled plasma mass spectrometry. During the first 10 days most of the arsenic found in the seawater and the shallow sediment is in the form of the arsenosugars released from the seaweed. Dimethylarsenoylethanol (DMAE), dimethylarsinic acid (DMA(V)) and, later, monomethylarsonic acid (MMA(V)) and arsenite and arsenate were also formed. In the deeper anaerobic sediment, the arsenosugars disappear more quickly and DMAE is the main metabolite with 60-80% of the total arsenic for the first 60 days besides a constant DMA(V) contribution of 10-20% of total soluble arsenic. With the degradation of the soluble DMAE the solubility of arsenic decreases in the sediment. The final soluble degradation products (after 106 days) were arsenite, arsenate, MMA(V) and DMA(V). No arsenobetaine or arsenocholine were identified in the porewater.

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Section: Discussionmentioning

confidence: 99%

“…would not elute from the column, and hence would not appear here 22 . However, a significant reduction of chromatographic recovery and an immobilization of arsenic is not obvious, since the concentration of arsenic in the porewater is remarkably constant during the experiment (Fig.…”

Section: Porewatermentioning

confidence: 99%

Biodegradation of arsenosugars in marine sediment

Pengprecha

Wilson

Raab

et al. 2005

Appl. Organometal. Chem.

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“…[26][27][28] In seaweed-eating sheep from Orkney Island, Scotland, daily consumption of arsenic from arsenosugars ranges from 45 to 90 mg. Dimethylarsenic is the major arsenic-containing species in urine in these sheep. [29,30] Other metabolites identified in urine of these sheep are dimethylarsinoyl acetate and dimethylarsinothioyl acetate [31] (Fig. 4) of thioylated metabolites are considered below.)…”

Section: Arsenosugarsmentioning

confidence: 99%

Commonalities in Metabolism of Arsenicals

Adair¹,

Waters²,

Devesa³

et al. 2005

Environ. Chem.

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Abstract. Elucidating the pathway of inorganic arsenic metabolism shows that some of methylated arsenicals formed as intermediates and products are reactive and toxic species. Hence, methylated arsenicals likely mediate at least some of the toxic and carcinogenic effects associated with exposure to arsenic. Trimethylarsonium compounds and arsenosugars are two other classes of arsenicals to which humans are routinely exposed and there is evidence that both classes are metabolized to produce methylated arsenicals. Here, we review evidence for production of methylated metabolism and consider the challenges posed in unraveling a complex web for metabolism of arsenicals in humans.

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“…The main developments in environmental and biological aspects of organoarsenic chemistry over the 1993-2005 period have recently been summarized [1]. Developments since 1993 are large due to improved analytical techniques and includes the discovery of new classes of organoarsenic compounds, such as thioarsenicals found in sheep urine [75] and algae, and arsenolipids found in certain algae and in fish oils [76]. Figure 7.6 shows the structures of a selection of naturally occurring thioarsenicals, the oxo analogues of which been shown to be involved in the synthesis and degradation of the major classes of organoarsenic compounds (Figure 7.7).…”

Section: Arsenic Biomethylation/demethylation and Organoarsenic Compomentioning

confidence: 99%

Biomethylation of Arsenic, Antimony and Bismuth

Jenkins

2010

Biological Chemistry of Arsenic, Antimony and Bismuth

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Biomethylation of metals or metalloids refers to the process whereby living organisms cause direct linkage of methyl groups to the metal(loid)s through enzymatic transfer of a preformed methyl group. The attachment of a methyl group to a metal(loid) changes the chemical and physical properties of the element, which in turn influences its mobility, geological cycling and toxicity. Biomethylation of the following metal(loid)s have been definitively established, although for most very little is known about the biological mechanism involved: Cd, Hg, Tl, Ge, Sn, Pb, As, Sb, Bi, Se and Te. The biological systems responsible for metal(loid) biomethylation are almost exclusively microorganisms. Anaerobic prokaryotes, operating in anoxic environments such as sediments from environmental waters and landfill sites, are major biocatalysts of metal(loid) biomethylation in the natural environment. Methylmetal(loid)s have also been shown to occur in soils from disparate locations and some aerobic and facultatively anaerobic bacteria, fungi and lower algae have been shown to be capable of metal(loid) biomethylation. Although higher organisms have not been shown to biomethylate true metals, methyl derivatives of some metalloids (including those of Se and As) are formed in a wide range of higher animals and plants.Over the past decade there has been a diversification of methods for the detection and measurement of organometallic compounds. Generally, this has been accompanied by improvements in reliability of detection and measurement of organometal(loid)s at low

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2‐Dimethylarsinothioyl Acetic Acid Identified in a Biological Sample: The First Occurrence of a Mammalian Arsinothioyl Metabolite

Cited by 91 publications

References 19 publications

Biodegradation of arsenosugars in marine sediment

Biodegradation of arsenosugars in marine sediment

Commonalities in Metabolism of Arsenicals

Biomethylation of Arsenic, Antimony and Bismuth

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