title: Methylated and thiolated arsenic species for environmental and health research - A review on synthesis and characterization.
abstract: Hundreds of millions of people around the world are exposed to elevated concentrations of inorganic and organic arsenic compounds, increasing the risk of a wide range of health effects. Studies of the environmental fate and human health effects of arsenic require authentic arsenic compounds. We summarize here the synthesis and characterization of more than a dozen methylated and thiolated arsenic compounds that are not commercially available. We discuss the methods of synthesis for the following 14 trivalent (III) and pentavalent (V) arsenic compounds: monomethylarsonous acid (MMAIII), dicysteinylmethyldithioarsenite (MMAIII(Cys)2), monomethylarsonic acid (MMAV), monomethylmonothioarsonic acid (MMMTAV) or monothio-MMAV, monomethyldithioarsonic acid (MMDTAV) or dithio-MMAV, monomethyltrithioarsonate (MMTTAV) or trithio-MMAV, dimethylarsinous acid (DMAIII), dimethylarsino-glutathione (DMAIII(SG)), dimethylarsinic acid (DMAV), dimethylmonothioarsinic acid (DMMTAV) or monothio-DMAV, dimethyldithioarsinic acid (DMDTAV) or dithio-DMAV, trimethylarsine oxide (TMAOV), arsenobetaine (AsB), and an arsenicin-A model compound. We have reviewed and compared the available methods, synthesized the arsenic compounds in our laboratories, and provided characterization information. On the basis of reaction yield, ease of synthesis and purification of product, safety considerations, and our experience, we recommend a method for the synthesis of each of these arsenic compounds.
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, BC V6T 1Z1, Canada.
authors.forename: William R
authors.initials: WR
authors.lastname: Cullen
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Qingqing
authors.initials: Q
authors.lastname: Liu
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Xiufen
authors.initials: X
authors.lastname: Lu
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Anthony
authors.initials: A
authors.lastname: McKnight-Whitford
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Hanyong
authors.initials: H
authors.lastname: Peng
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Popowich
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Xiaowen
authors.initials: X
authors.lastname: Yan
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, BC V6T 1Z1, Canada.
authors.forename: Michael
authors.initials: M
authors.lastname: Fricke
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada.
authors.forename: Hongsui
authors.initials: H
authors.lastname: Sun
authors.affiliation: Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta T6G 2G3, Canada; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G3, Canada. Electronic address: xc.le@ualberta.ca.
authors.forename: X Chris
authors.initials: XC
authors.lastname: Le
mesh_terms: D001151:Arsenic / Q000737:chemistry*; D001152:Arsenicals / Q000737:chemistry*; D062067:Chemical Safety; D004463:Ecology; D004782:Environmental Health; D015386:Hazardous Substances / Q000737:chemistry*
chemical_list: D001152:Arsenicals; D015386:Hazardous Substances; D001151:Arsenic
keywords: Arsenic metabolites; Arsenic standards; Pentavalent and trivalent methylarsenicals; Speciation analysis; Sulphur-containing arsenic species; Synthetic chemistry of arsenic