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Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls

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Volume 3 Anthropogenic Compounds Part K

Part of the book series: The Handbook of Environmental Chemistry ((HEC3,volume 3K))

Abstract

Methyl sulfone (MeSO2-) and hydroxylated (OH-) metabolites of polychlorinated biphenyls (PCBs) have emerged as important classes of environmental contaminants in wildlife and humans. The detection of persistent MeSO2-PCBs was first shown in tissues of Baltic grey seal in the mid-1970s. In the last decade the detection and quantification of these metabolites in biota has gained momentum. MeSO2-PCBs are one of the major classes of organochlorine contaminants in humans and several marine and a few terrestrial mammal species. A number of studies have demonstrated the toxicological potential of MeSO2-PCBs including tissue selective retention via non-covalent protein binding, induction of cytochrome P450 enzymes, and endocrine-related effects. More recently OH-PCBs have gained greater scientific notoriety in environmental toxicology as a consequence of the capability of certain OH-PCB congeners to bind with the thyroxine transport protein, transthyretin, and their interaction with thyroid and estrogen hormone receptors. Research on environmentally persistent MeSO2-PCBs and OH-PCB metabolites reported in the last two decades is presented, discussed and summarized. Topics include the relative importance and mechanisms of biochemical formation in the context of PCB biotransformation, physico-chemical properties, and chemical synthesis, nomenclature and analysis. The chemical analysis summary encompasses tissue extraction, compound separation and methods of detection. MeSO2-PCB and OH-PCB toxicokinetics are addressed such as species- and congener-specific formation and clearance, persistence in biota and tissue specific retention. The known biological and toxicological activities of these PCB metabolites are also summarized.

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Authors and Affiliations

  1. Environmental Research Group, Research Institute of Toxicology, Utrecht University, P. O. Box 80176, Yalelaan 2, 3508 TD, Utrecht, The Netherlands

    Robert J. Letcher

  2. Department of Environmental Chemistry, Stockholm University, SE-10691, Stockholm, Sweden

    Ake Bergman

  3. Department of Pharmacokinetics and Biopharmaceuticals, AstraZeneca R&D, Södertälje, SE-151 85, Södertälje, Sweden

    Eva Klasson-Wehler

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  1. Robert J. Letcher
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  2. Eva Klasson-Wehler
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  3. Ake Bergman
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Editors and Affiliations

  1. Universität Bayreuth, Postfach 10 12 51, D-95440, Bayreuth, Germany

    Otto Hutzinger

  2. Department of Chemistry, University of Jyväskylä, P. O. Box 35, FIN-40351, Jyväskylä, Finland

    Jaakko Paasivirta

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Letcher, R.J., Klasson-Wehler, E., Bergman, A. (2000). Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls. In: Hutzinger, O., Paasivirta, J. (eds) Volume 3 Anthropogenic Compounds Part K. The Handbook of Environmental Chemistry, vol 3K. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48915-0_11

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