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Project Publications: University of Iowa: PCBs and Cytosolic Phenol and Steroid Sulfotransferases

Superfund Research Program

PCBs and Cytosolic Phenol and Steroid Sulfotransferases

Project Leader: Michael W. Duffel
Grant Number: P42ES013661
Funding Period: 2006-2020
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  • Li X, Wu X, Kelly KM, Veng-Pedersen P, Lehmler H. 2019. Toxicokinetics of chiral PCB 136 and its hydroxylated metabolites in mice with a liver-specific deletion of cytochrome P450 reductase. Chem Res Toxicol 32:727-736. doi:10.1021/acs.chemrestox.8b00389 PMID:30729780 PMCID:PMC6465157
  • Sethi S, Morgan RK, Feng W, Lin Y, Li X, Luna C, Koch M, Bansal R, Duffel MW, Puschner B, Zoeller RT, Lehmler H, Pessah IN, Lein PJ. 2019. Comparative analyses of the 12 most abundant PCB congeners detected in human maternal serum for activity at the thyroid hormone receptor and ryanodine receptor. Environ Sci Technol 53:3948-3958. doi:10.1021/acs.est.9b00535 PMID:30821444 PMCID:PMC6457253
  • Uwimana E, Cagle B, Yeung C, Li X, Patterson EV, Doorn JA, Lehmler H. 2019. Atropselective oxidation of 2,2 ,3,3 ,4,6 -hexachlorobiphenyl (PCB 132) to hydroxylated metabolites by human liver microsomes and its implications for pcb 132 neurotoxicity. Toxicology 171:406-420. doi:10.1093/toxsci/kfz150 PMID:31268529 PMCID:PMC6760323
  • Uwimana E, Ruiz P, Li X, Lehmler H. 2019. Human CYP2A6, CYP2B6, and CYP2E1 atropselectively metabolize polychlorinated biphenyls to hydroxylated metabolites. Environ Sci Technol 53(4):2114-2123. doi:10.1021/acs.est.8b05250 PMID:30576102 PMCID:PMC6380921


  • Alam S, Carter GS, Krager KJ, Li X, Lehmler H, Aykin-Burns N. 2018. PCB11 metabolite, 3,3-dichlorobiphenyl-4-ol, exposure alters the expression of genes governing fatty acid metabolism in the absence of functional sirtuin 3: examining the contribution of MnSOD. Antioxidants (Basel) 7(9):121. doi:10.3390/antiox7090121 PMID:30223548
  • Cheng SL, Li X, Lehmler H, Phillips B, Shen D, Cui JY. 2018. Gut microbiota modulates interactions between polychlorinated biphenyls and bile acid homeostasis. Toxicol Sci 166:269-287. doi:10.1093/toxsci/kfy208 PMID:30496569 PMCID:PMC6260149
  • Dhakal K, Gadupudi GS, Lehmler H, Ludewig G, Duffel MW, Robertson LW. 2018. Sources and toxicities of phenolic polychlorinated biphenyls (OH-PCBs). Environ Sci Pollut Res Int 25:16277-16290. doi:10.1007/s11356-017-9694-x PMID:28744683 PMCID:PMC5785587
  • Li X, Holland EB, Feng W, Zheng J, Dong Y, Pessah IN, Duffel MW, Robertson LW, Lehmler H. 2018. Authentication of synthetic environmental contaminants and their (bio)transformation products in toxicology: polychlorinated biphenyls as an example. Environ Sci Pollut Res Int 25(17):1-14. doi:10.1007/s11356-017-1162-0 PMID:29322390 PMCID:PMC6015536
  • Li X, Parkin S, Lehmler H. 2018. Absolute configuration of 2,2',3,3',6-pentachlorinatedbiphenyl (PCB 84) atropisomers. Environ Sci Pollut Res Int 25:16402-16410. doi:10.1007/s11356-017-9259-z PMID:28537024 PMCID:PMC5823790
  • Parker VS, Squirewell EJ, Lehmler H, Robertson LW, Duffel MW. 2018. Hydroxylated and sulfated metabolites of commonly occurring airborne polychlorinated biphenyls inhibit human steroid sulfotransferases SULT1E1 and SULT2A1. Environ Toxicol Pharmacol 58:196-201. doi:10.1016/j.etap.2018.01.010 PMID:29408762 PMCID:PMC6078096
  • Pencikova K, Svrzkova L, Strapacova S, Neca J, Bartonkova I, Dvorak Z, Hyzdalova M, Pivnicka J, Palkova L, Lehmler H, Li X, Vondracek J, Machala M. 2018. In vitro profiling of toxic effects of prominent environmental lower-chlorinated PCB congeners linked with endocrine disruption and tumor promotion. Environ Pollut 237:473-486. doi:10.1016/j.envpol.2018.02.067 PMID:29518658 PMCID:PMC5908724
  • Rodriguez EA, Vanle BC, Doorn JA, Lehmler H, Robertson LW, Duffel MW. 2018. Hydroxylated and sulfated metabolites of commonly observed airborne polychlorinated biphenyls display selective uptake and toxicity in N27, SH-SY5Y, and HepG2 cells. Environ Toxicol Pharmacol 62:69-78. doi:10.1016/j.etap.2018.06.010 PMID:29986280 PMCID:PMC609219
  • Uwimana E, Li X, Lehmler H. 2018. Human liver microsomes atropselectively metabolize 2,2 ',3,4 ',6-pentachlorobiphenyl (PCB 91) to a 1,2-shift product as the major metabolite. Environ Sci Technol 52:6000-6008. doi:10.1021/acs.est.8b00612 PMID:29659268 PMCID:PMC5966832


  • Grimm FA, Lehmler H, Koh W, DeWall J, Teesch LM, Hornbuckle KC, Thorne PS, Robertson LW, Duffel MW. 2017. Identification of a sulfate metabolite of PCB 11 in human serum. Environ Int 98:120-128. doi:10.1016/j.envint.2016.10.023 PMID:27816204 PMCID:PMC5127762
  • Klinefelter K, Hoover MK, Bates C, Colter BT, Dailey A, Infante SK, Kania-Korwel I, Lehmler H, Lopez-Juarez A, Ludwig CP, Curran CP. 2017. Genetic differences in the aryl hydrocarbon receptor and CYP1A2 affect sensitivity to developmental polychlorinated biphenyl exposure in mice: relevance to studies of human neurological disorders. Mamm Genome 1-16. doi:10.1007/s00335-017-9728-1 PMID:29197979
  • . 2017. Atropisomers of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) exhibit stereoselective effects on activation of nuclear receptors in vitro. Environ Sci Pollut Res Int 25(17):1-9. doi:10.1007/s11356-017-0683-x PMID:29124635 PMCID:PMC5943194


  • Ekuase EJ, van't Erve TJ, Rahaman A, Robertson LW, Duffel MW, Luthe G. 2016. Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes. Environ Sci Pollut Res Int 23(3):2119-2127. doi:10.1007/s11356-015-4886-8 PMID:26165989 PMCID:PMC4713379
  • Kania-Korwel I, Lehmler H. 2016. Chiral polychlorinated biphenyls: absorption, metabolism and excretion--a review. Environ Sci Pollut Res Int 23(3):2042-2057. doi:10.1007/s11356-015-4150-2 PMID:25651810 PMCID:PMC4527964
  • Rodriguez EA, Li X, Lehmler H, Robertson LW, Duffel MW. 2016. Sulfation of lower chlorinated polychlorinated biphenyls increases their affinity for the major drug-binding sites of human serum albumin. Environ Sci Technol 50(10):5320-5327. doi:10.1021/acs.est.6b00484 PMID:27116425 PMCID:PMC4883002



  • Ekuase EJ, Lehmler H, Robertson LW, Duffel MW. 2014. Binding interactions of hydroxylated polychlorinated biphenyls (OHPCBs) with human hydroxysteroid sulfotransferase hSULT2A1. Chem Biol Interact 212:56-64. doi:10.1016/j.cbi.2014.01.018 PMID:24508592 PMCID:PMC3994546
  • Sueyoshi T, Li L, Wang H, Moore R, Kodavanti PS, Lehmler H, Negishi M, Birnbaum LS. 2014. Flame retardant BDE-47 effectively activates nuclear receptor CAR in human primary hepatocytes. Toxicol Sci 137(2):292-302. doi:10.1093/toxsci/kft243 PMID:24218150 PMCID:PMC3908718
  • Wu X, Kammerer A, Lehmler H. 2014. Microsomal oxidation of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) results in species-dependent chiral signatures of the hydroxylated metabolites. Environ Sci Technol 48(4):2436-2444. doi:10.1021/es405433t PMID:24467194 PMCID:PMC3983324
  • Yang DR, Kania-Korwel I, Ghogha A, Chen H, Stamou M, Bose DD, Pessah IN, Lehmler H, Lein PJ. 2014. PCB 136 atropselectively alters morphometric and functional parameters of neuronal connectivity in cultured rat hippocampal neurons via ryanodine receptor-dependent mechanisms. Toxicol Sci 138(2):379-392. doi:10.1093/toxsci/kft334 PMID:24385416 PMCID:PMC4007107



  • Ambati J, Song Y, Rankin S, Lehmler H. 2012. Density functional theory study of semiquinone radical anions of polychlorinated biphenyls in the syn- and anti-like conformation. J Phys Chem A 116:1586-1595. doi:10.1021/jp2077193 PMID:22257259 PMCID:PMC3417754
  • Dhakal K, He X, Lehmler H, Teesch LM, Duffel MW, Robertson LW. 2012. Identification of sulfated metabolites of 4-chlorobiphenyl (PCB3) in the serum and urine of male rats. Chem Res Toxicol 25(12):2796-2804. doi:10.1021/tx300416v PMID:23137097 PMCID:PMC3524396
  • Kania-Korwel I, Barnhart CD, Stamou M, Truong KM, El-Komy MH, Lein PJ, Veng-Pedersen P, Lehmler H. 2012. 2,2',3,5',6-Pentachlorobiphenyl (PCB 95) and its hydroxylated metabolites are enantiomerically enriched in female mice. Environ Sci Technol 46(20):11393-11401. doi:10.1021/es302810t PMID:22974126 PMCID:PMC3475189
  • Oldham E, Xie W, Farnoud AM, Fiegel J, Lehmler H. 2012. Disruption of phosphatidylcholine mono layers and bilayers by perfluorobutane sulfonate. Journal of Physical Chemistry B 116:9999-10007. doi:10.1021/jp304412p PMID:22834732 PMCID:PMC3464004


  • Bunaciu RP, Tharappel JC, Lehmler H, Lee EY, Robertson LW, Bruckner GG, Spear BT, Glauert HP. 2011. Role of oil vehicle on hepatic cell proliferation in PCB-treated rats. J Environ Pathol Toxicol Oncol 30(4):273-282. PMID:22181977 PMCID:PMC3522147
  • Ekuase EJ, Liu Y, Lehmler H, Robertson LW, Duffel MW. 2011. Structure-activity relationships for hydroxylated polychlorinated biphenyls as inhibitors of the sulfation of dehydroepiandrosterone catalyzed by human hydroxysteroid sulfotransferase SULT2A1. Chem Res Toxicol 24:1720-1728. doi:10.1021/tx200260h PMID:21913674 PMCID:PMC3196794
  • Gulcan HO, Duffel MW. 2011. Substrate inhibition in human hydroxysteroid sulfotransferase SULT2A1: studies on the formation of catalytically non-productive enzyme complexes. Arch Biochem Biophys 507:232-240. doi:10.1016/ PMID:21187059 PMCID:PMC3058861
  • Joshi SN, Vyas SM, Duffel MW, Parkin S, Lehmler H. 2011. Synthesis of sterically hindered polychlorinated biphenyl derivatives. Synthesis 7:1045-1054. doi:10.1055/s-0030-1258454 PMID:21516177 PMCID:PMC3080045
  • Joshi SN, Vyas SM, Wu H, Duffel MW, Parkin S, Lehmler H. 2011. Regioselective iodination of chlorinated aromatic compounds using silver salts. Tetrahedron 67(39):7461-7469. doi:10.1016/j.tet.2011.07.064 PMID:21918585 PMCID:PMC3170769
  • Kania-Korwel I, Duffel MW, Lehmler H. 2011. Gas chromatographic analysis with chiral cyclodextrin phases reveals the enantioselective formation of hydroxylated polychlorinated biphenyls by rat liver microsomes. Environ Sci Technol 45:9590-9596. doi:10.1021/es2014727 PMID:21966948 PMCID:PMC3216237
  • Liu Y, Lehmler H, Robertson LW, Duffel MW. 2011. Physicochemical properties of hydroxylated polychlorinated biphenyls aid in predicting their interactions with rat sulfotransferase 1A1 (rSULT1A1). Chem Biol Interact 189:153-160. doi:10.1016/j.cbi.2010.11.009 PMID:21130751 PMCID:PMC3032042
  • Senthilkumar PK, Klingelhutz AJ, Jacobus JA, Lehmler H, Robertson LW, Ludewig G. 2011. Airborne polychlorinated biphenyls (PCBs) reduce telomerase activity and shorten telomere length in immortal human skin keratinocytes (HaCat). Toxicol Lett 204:64-70. doi:10.1016/j.toxlet.2011.04.012 PMID:21530622 PMCID:PMC3109099
  • Song Y, Ambati J, Parkin S, Rankin S, Robertson LW, Lehmler H. 2011. Crystal structure and density functional theory studies of toxic quinone metabolites of polychlorinated biphenyls. Chemosphere 85:386-392. doi:10.1016/j.chemosphere.2011.07.004 PMID:21824639 PMCID:PMC3206982
  • Wu X, Pramanik A, Duffel MW, Hrycay EG, Bandiera SM, Lehmler H, Kania-Korwel I. 2011. 2,2',3,3',6,6'-Hexachlorobiphenyl (PCB 136) is enantioselectively oxidized to hydroxylated metabolites by rat liver microsomes. Chem Res Toxicol 24(12):2249-2257. doi:10.1021/tx200360m PMID:22026639 PMCID:PMC3243785




  • Luthe G, Swenson DC, Robertson LW. 2007. Influence of fluoro-substitution on the planarity of 4-chlorobiphenyl (PCB 3). Acta Crystallogr B 63:319-327. PMID:17374943
  • Sadeghi-aliabadi H, Chan K, Lehmler H, Robertson LW, O-Brian PJ. 2007. Molecular cytotoxic mechanisms of catecholic polychlorinated biphenyl metabolites in isolated rat hepatocytes. Chem Biol Interact 167:184-192. PMID:17408604
  • Zettner M, Flor S, Ludewig G, Wagner J, Robertson LW, Lehmann L. 2007. Quinoid metabolites of 4-monochlorobiphenyl (PCB3) induce gene mutations in cultured Chinese hamster V79 Cells. Toxicol Sci 100:88-98. PMID:17686921


  • Duffel MW. 1997. Sulfotransferases. Chapter 18 in: Comprehensive Toxicology, 3rd Edition. Vol. 10. Elsevier, NY. pp.407-428.
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