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Chiral polychlorinated biphenyls: absorption, metabolism and excretion—a review

  • PCBs: Exposures, Effects, Remediation and Regulation with special reference to PCBs in Schools
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Abstract

Seventy eight out of the 209 possible polychlorinated biphenyl (PCB) congeners are chiral, 19 of which exist under ambient conditions as stable rotational isomers that are non-superimposable mirror images of each other. These congeners (C-PCBs) represent up to 6 % by weight of technical PCB mixtures and undergo considerable atropisomeric enrichment in wildlife, laboratory animals, and humans. The objective of this review is to summarize our current knowledge of the processes involved in the absorption, metabolism, and excretion of C-PCBs and their metabolites in laboratory animals and humans. C-PCBs are absorbed and excreted by passive diffusion, a process that, like other physicochemical processes, is inherently not atropselective. In mammals, metabolism by cytochrome P450 (P450) enzymes represents a major route of elimination for many C-PCBs. In vitro studies demonstrate that C-PCBs with a 2,3,6-trichlorosubstitution pattern in one phenyl ring are readily oxidized to hydroxylated PCB metabolites (HO-PCBs) by P450 enzymes, such as rat CYP2B1, human CYP2B6, and dog CYP2B11. The oxidation of C-PCBs is atropselective, thus resulting in a species- and congener-dependent atropisomeric enrichment of C-PCBs and their metabolites. This atropisomeric enrichment of C-PCBs and their metabolites likely plays a poorly understood role in the atropselective toxicity of C-PCBs and, therefore, warrants further investigation.

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Acknowledgments

The authors would like to acknowledge the support through grants from the National Institute for Environmental Health Sciences/National Institutes of Health (ES05605, ES012475, ES013661 and ES017425) where their own work is cited.

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  1. Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, UI Research Park, Iowa City, IA, 52242, USA

    Izabela Kania-Korwel & Hans-Joachim Lehmler

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  1. Izabela Kania-Korwel
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Correspondence to Hans-Joachim Lehmler.

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Kania-Korwel, I., Lehmler, HJ. Chiral polychlorinated biphenyls: absorption, metabolism and excretion—a review. Environ Sci Pollut Res 23, 2042–2057 (2016). https://doi.org/10.1007/s11356-015-4150-2

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