PMID- 28744683 OWN - NLM STAT- MEDLINE DCOM- 20190422 LR - 20240326 IS - 1614-7499 (Electronic) IS - 0944-1344 (Print) IS - 0944-1344 (Linking) VI - 25 IP - 17 DP - 2018 Jun TI - Sources and toxicities of phenolic polychlorinated biphenyls (OH-PCBs). PG - 16277-16290 LID - 10.1007/s11356-017-9694-x [doi] AB - 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. FAU - Dhakal, Kiran AU - Dhakal K AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. AD - 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. FAU - Gadupudi, Gopi S AU - Gadupudi GS AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. AD - 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. FAU - Lehmler, Hans-Joachim AU - Lehmler HJ AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. AD - 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. FAU - Ludewig, Gabriele AU - Ludewig G AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. AD - 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. FAU - Duffel, Michael W AU - Duffel MW AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. AD - Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, IA, USA. FAU - Robertson, Larry W AU - Robertson LW AD - Interdisciplinary Graduate Program in Human Toxicology, Graduate College, The University of Iowa, Iowa City, IA, USA. larry-robertson@uiowa.edu. AD - 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. larry-robertson@uiowa.edu. LA - eng GR - P30 CA086862/CA/NCI NIH HHS/United States GR - P30 ES005605/ES/NIEHS NIH HHS/United States GR - P42 ES013661/ES/NIEHS NIH HHS/United States GR - P42 ES013661/National Institute of Environmental Health Sciences/ PT - Journal Article DEP - 20170725 PL - Germany TA - Environ Sci Pollut Res Int JT - Environmental science and pollution research international JID - 9441769 RN - 0 (Environmental Pollutants) RN - 0 (Hydrocarbons, Chlorinated) RN - 0 (Sulfates) RN - 9035-51-2 (Cytochrome P-450 Enzyme System) RN - DFC2HB4I0K (Polychlorinated Biphenyls) SB - IM MH - Animals MH - Cytochrome P-450 Enzyme System/chemistry/*metabolism MH - Environmental Pollutants MH - Humans MH - Hydrocarbons, Chlorinated/*chemistry MH - Polychlorinated Biphenyls/chemistry/*toxicity MH - Sulfates/*chemistry PMC - PMC5785587 MID - NIHMS895524 OTO - NOTNLM OT - Biotransformation OT - Endocrine disruption OT - Hydroxylated PCBs OT - Metabolites OT - PCBs OT - Persistent organic pollutants OT - Phenolic PCBs EDAT- 2017/07/27 06:00 MHDA- 2019/04/23 06:00 PMCR- 2019/06/01 CRDT- 2017/07/27 06:00 PHST- 2017/05/14 00:00 [received] PHST- 2017/06/30 00:00 [accepted] PHST- 2017/07/27 06:00 [pubmed] PHST- 2019/04/23 06:00 [medline] PHST- 2017/07/27 06:00 [entrez] PHST- 2019/06/01 00:00 [pmc-release] AID - 10.1007/s11356-017-9694-x [pii] AID - 10.1007/s11356-017-9694-x [doi] PST - ppublish SO - Environ Sci Pollut Res Int. 2018 Jun;25(17):16277-16290. doi: 10.1007/s11356-017-9694-x. Epub 2017 Jul 25.