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Sources and toxicities of phenolic polychlorinated biphenyls (OH-PCBs)

  • PCBs Risk Evaluation and Environmental Protection
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Abstract

Polychlorinated biphenyls (PCBs), a group of 209 congeners that differ in the number and position of chlorines on the biphenyl ring, are anthropogenic chemicals that belong to the persistent organic pollutants (POPs). For many years, PCBs have been a topic of interest because of their biomagnification in the food chain and their environmental persistence. PCBs with fewer chlorine atoms, however, are less persistent and more susceptible to metabolic attack, giving rise to chemicals characterized by the addition of one or more hydroxyl groups to the chlorinated biphenyl skeleton, collectively known as hydroxylated PCBs (OH-PCBs). In animals and plants, this biotransformation of PCBs to OH-PCBs is primarily carried out by cytochrome P-450-dependent monooxygenases. One of the reasons for infrequent detection of lower chlorinated PCBs in serum and other biological matrices is their shorter half-lives, and their metabolic transformation, resulting in OH-PCBs or their conjugates, such as sulfates and glucuronides, or macromolecule adducts. Recent biomonitoring studies have reported the presence of OH-PCBs in human serum. The occurrence of OH-PCBs, the size of this group (there are 837 mono-hydroxyl PCBs alone), and their wide spectra of physical characteristics (pKa’s and log P’s ranging over 5 to 6 orders of magnitude) give rise to a multiplicity of biological effects. Among those are bioactivation to electrophilic metabolites that can form covalent adducts with DNA and other macromolecules, interference with hormonal signaling, inhibition of enzymes that regulate cellular concentrations of active hormones, and interference with the transport of hormones. This new information creates an urgent need for a new perspective on these often overlooked metabolites.

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Acknowledgments

The authors are supported by a grant from the National Institute of Environmental Health Sciences (P42 ES013661). K.D. and G.S.G. recognize the Training Core of the Iowa Superfund Research Center for training and financial support. Opinions are those of the authors.

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Authors and Affiliations

  1. Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA

    Kiran Dhakal, Gopi S. Gadupudi, Hans-Joachim Lehmler, Gabriele Ludewig, Michael W. Duffel & Larry W. Robertson

  2. Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, 100 Oakdale Campus #219 IREH, Iowa City, IA, 52242-5000, USA

    Kiran Dhakal, Gopi S. Gadupudi, Hans-Joachim Lehmler, Gabriele Ludewig & Larry W. Robertson

  3. Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, IA, USA

    Michael W. Duffel

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  1. Kiran Dhakal
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  2. Gopi S. Gadupudi
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  3. Hans-Joachim Lehmler
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Correspondence to Larry W. Robertson.

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Dhakal, K., Gadupudi, G.S., Lehmler, HJ. et al. Sources and toxicities of phenolic polychlorinated biphenyls (OH-PCBs). Environ Sci Pollut Res 25, 16277–16290 (2018). https://doi.org/10.1007/s11356-017-9694-x

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