Journal article
Chiral polychlorinated biphenyls: absorption, metabolism and excretion—a review
Environmental science and pollution research international, Vol.23(3), pp.2042-2057
02/2016
DOI: 10.1007/s11356-015-4150-2
PMCID: PMC4527964
PMID: 25651810
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.
Details
- Title: Subtitle
- Chiral polychlorinated biphenyls: absorption, metabolism and excretion—a review
- Creators
- Izabela Kania-Korwel - University of Iowa, Occupational and Environmental HealthHans-Joachim Lehmler - University of Iowa, Occupational and Environmental Health
- Resource Type
- Journal article
- Publication Details
- Environmental science and pollution research international, Vol.23(3), pp.2042-2057
- DOI
- 10.1007/s11356-015-4150-2
- PMID
- 25651810
- PMCID
- PMC4527964
- NLM abbreviation
- Environ Sci Pollut Res Int
- ISSN
- 0944-1344
- eISSN
- 1614-7499
- Publisher
- Springer Berlin Heidelberg; Berlin/Heidelberg
- Language
- English
- Date published
- 02/2016
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute; Iowa Superfund Research Program
- Record Identifier
- 9984003796602771
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