Characterization of arsenic compounds formed by Daphnia magna and Tetraselmis chuii from inorganic arsenate.

Irgolic, Kurt J.; Woolson, E. A.; Stockton, R. A.; Newman, Robert D.; Bottino, Nestor R.; Zingaro, Ralph A.; Kearney, Philip C.; Pyles, Robert A.; Miyagawa, Shigeru; McShane, William J.; Cox, Elenor R.

doi:10.1289/ehp.771961

Cited by 95 publications

(16 citation statements)

References 14 publications

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“…In addition methylarsenic compounds may be incorporated by biosynthesis into phospholipids which are found in most marine organisms (16). The volatile species arsine, demethylarsine, and trimethylarsine, will be released into the aerobic environment at the sediment/water, water/air, or soil/air interface.…”

Section: Discussionmentioning

confidence: 99%

Recent Studies on Biomethylation and Demethylation of Toxic Elements

Ridley¹,

Dizikes²,

Cheh³

et al. 1977

Environmental Health Perspectives

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. The National Institute of Environmental Health Sciences (NIEHS) and Brogan & Partners are collaborating with JSTOR to digitize, preserve and extend access to Environmental Health Perspectives.Methylcobalamin (methyl-B12) has been implicated in the biomethylation of the heavy metals (mercury, tin, platinum, gold, and thallium) as well as the metalloids (arsenic, selenium, tellurium and sulfur). In addition, methylcobalamin has been shown to react with lead, but the lead-alkyl product is unstable in water.Details of the kinetics and mechanisms for biomethylation of arsenic are presented, with special emphasis on synergistic reactions between metal and metalloids in different oxidation states. This study explains why synergistic, or antagonistic, processes can occur when one toxic element reacts in the presence of another.The relative importance of biomethylation reactions involving methylcobalamin will be compared to those reactions where S-adenosylmethionine is involved. fore, the biosynthesis of methylarsenic compounds must occur in a reducing environment. However, McBride and Wolfe (3) found that methyl-B12 wascapable of functioning as methyl donor in the biosynthesis of dimethylarsine from arsenate or arsenite in cell extracts of Methanobacillus (M. O.H.). Since the Co-C (r bond has been shown to be susceptible to electrophilic attack (4), nucleophilic attack (5), and homolytic attack by freeradical species (6), it is important to determine how methyl-groups are transferred from methyl-B12 to arsenic. Schrauzer et al. (7) have formulated a mechanism for B12-dependent synthesis of dimethylarsine which involves inorganic arsenic salts functioning as electrophiles. In this communication we review the alternative mechanisms for the biosynthesis of methyl-arsenic compounds with a view to providing a chemical basis for determining which methylated species of arsenic are likely to reach significant concentrations in aqueous systems.

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Section: Discussionmentioning

confidence: 99%

Recent Studies on Biomethylation and Demethylation of Toxic Elements

Ridley¹,

Dizikes²,

Cheh³

et al. 1977

Environmental Health Perspectives

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“…Arsenolipids are believed to be produced in marine algae [88,89], and further transferred, via the food chain, to other organisms [62,[89][90][91] (Figure 1.1) In a study on arsenic transfer in a simple food chain, arsenic from seawater was incorporated in phytoplankton (Dunaliella marina), which biotransformed arsenic into lipid-soluble arsenic, and further transferred the arsenolipids to zooplankton (Artemia salina) and…”

Section: Origin Of Arsenolipidsmentioning

confidence: 99%

Detection of arsenic-containing hydrocarbons in a range of commercial fish oils by GC-ICPMS analysis

Sele

Amlund²,

Berntssen³

et al. 2013

Anal Bioanal Chem

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The present study describes the use of a simple solid-phase extraction procedure for the extraction of arsenic-containing hydrocarbons from fish oil followed by analysis using gas chromatography (GC) coupled to inductively coupled plasma mass spectrometry (ICPMS). The procedure permitted the analysis of a small sample amount, and the method was applied on a range of different commercial fish oils, including oils of anchovy (Engraulis ringens), Atlantic herring (Clupea harengus), sand eel (Ammodytes marinus), blue whiting (Micromesistius poutassou) and a commercial mixed fish oil (mix of oils of Atlantic herring, Atlantic cod (Gadus morhua) and saithe (Pollachius virens)). Total arsenic concentrations in the fish oils and in the extracts of the fish oils were determined by microwave-assisted acid digestion and ICPMS. The arsenic concentrations in the fish oils ranged from 5.9 to 8.7 mg kg(-1). Three dominant arsenic-containing hydrocarbons in addition to one minor unidentified compound were detected in all the oils using GC-ICPMS. The molecular structures of the arsenic-containing hydrocarbons, dimethylarsinoyl hydrocarbons (C17H38AsO, C19H42AsO, C23H38AsO), were verified using GC coupled to tandem mass spectrometry (MS/MS), and the accurate masses of the compounds were verified using quadrupole time-of-flight mass spectrometry (qTOF-MS). Additionally, total arsenic and the arsenic-containing hydrocarbons were studied in decontaminated and in non-decontaminated fish oils, where a reduced arsenic concentration was seen in the decontaminated fish oils. This provided an insight to how a decontamination procedure originally ascribed for the removal of persistent organic pollutants affects the level of arsenolipids present in fish oils.

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“…The methyl donor used for the biological methylation of arsenic by these microorganisms was S-adenosylmethionine (141). The marine alga, Tetraselmis chuii, and Daphnia magna incorporated arsenic from arsenate into the lipid fraction (144). H. (142).…”

Section: Cacodylic Acid Was Not Converted Into Inorganic Arsenic By Rmentioning

confidence: 99%

The Role of Metals in Carcinogenesis: Biochemistry and Metabolism

Jennette¹

1981

Environmental Health Perspectives

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. The National Institute of Environmental Health Sciences (NIEHS) and Brogan & Partners are collaborating with JSTOR to digitize, preserve and extend access to Environmental Health Perspectives.The oxyanions of vanadium, chromium, molybdenum, arsenic, and selenium are stable forms of these elements in high oxidation states which cross cell membranes using the normal phosphate and/or sulfate transport systems of the cell. Once inside the cell, these oxyanions may act as phosphate and/or sulfate analogs, inhibiting enzymes involved in catalyzing phosphoryl or sulfuryl transfer reactions. Often the oxyanions serve as alternate enzyme substrates but form ester products which are hydrolytically unstable compared with the sulfate and phosphate esters and, therefore, decompose readily in aqueous solution. Arsenite and selenite are capable of reacting with sulfhydryl groups in proteins. Some cells are able to metabolize redox active oxyanions to forms of the elements in other stable oxidation states. Specific enzymes may be involved in the metabolic processes. The metabolites of these elements may form complexes with small molecules, proteins and nucleic acids which inhibit their ability to function properly.The divalent ions of beryllium, manganese, cobalt, nickel, cadmium, mercury, and lead are stable forms of these elements which may mimic essential divalent ions such as magnesium, calcium, iron, copper, or zinc. These ions may complex small molecules, enzymes, and nucleic acids in such a way that the normal activity of these species is altered. Free radicals may be produced in the presence of these metal ions which damage critical cellular molecules. across the cell membrane may be transformed into a different form by reaction with cellular components. The transformation may result in a complex which is easily excreted, hence deactivated. Alternatively, the element may be activated and bind to enzymes and/or nucleic acids, altering their ability to function properly in the cell. The ultimate disposition of the element will depend on the chemical properties of the individual inorganic species involved. Oxide ComplexesThe early transition elements have a tendency to exist in high oxidation states as oxy or hydroxy complexes in aqueous solution (1). The nature of the oxy species depends on concentration and pH. For example, in neutral aqueous solution at concentrations less than 10-4M, vanadium (V) exists mainly as H2V04-; chromium (VI) exists as chromate, CrO42-; manganese (VII) exists as permanganate, MnO4; molybdenum (VI) exists as molybdate, MoO42. As the concentration of these species is increased, the mononuclear ions aggregate to form polyanions. August 1981 233This content downloa...

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Characterization of arsenic compounds formed by Daphnia magna and Tetraselmis chuii from inorganic arsenate.

Cited by 95 publications

References 14 publications

Recent Studies on Biomethylation and Demethylation of Toxic Elements

Recent Studies on Biomethylation and Demethylation of Toxic Elements

Detection of arsenic-containing hydrocarbons in a range of commercial fish oils by GC-ICPMS analysis

The Role of Metals in Carcinogenesis: Biochemistry and Metabolism

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