2,2′,3,3′,6,6′-hexachlorobiphenyl (PCB 136) is enantioselectively oxidized to hydroxylated metabolites by rat liver microsomes

Chemical Research in Toxicology

Volumn 24, Issue 12, 2011, Pages 2249-2257

  Wu, Xianai ^a   Pramanik, Ananya ^a   Duffel, Michael W ^a   Hrycay, Eugene G ^b   Bandiera, Stelvio M ^b   Lehmler, Hans Joachim ^a   Kania Korwel, Izabela ^a  

^a UNIVERSITY OF IOWA   (United States)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2,2',3,3',6,6' HEXACHLOROBIPHENYL 5 OL; CORN OIL; CYTOCHROME P450; CYTOCHROME P450 2B; CYTOCHROME P450 2B1; DEXAMETHASONE; DRUG METABOLITE; HEXACHLOROBIPHENYL; PHENOBARBITAL; UNCLASSIFIED DRUG; 2,3,6,2',3',6' HEXACHLOROBIPHENYL; 2,3,6,2',3',6'-HEXACHLOROBIPHENYL; POLYCHLORINATED BIPHENYL;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HUMAN; HYPOTHESIS; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; RAT; ANIMAL; CHEMISTRY; DRUG EFFECT; HYDROXYLATION; METABOLISM; OXIDATION REDUCTION REACTION; POLLUTANT; SPRAGUE DAWLEY RAT; STEREOISOMERISM;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; ENVIRONMENTAL POLLUTANTS; HYDROXYLATION; MALE; MICROSOMES, LIVER; OXIDATION-REDUCTION; POLYCHLORINATED BIPHENYLS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM;

EID: 84055213091     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200360m     Document Type: Article

References (44)

1. Robertson, L. W. and Hansen, L. G. (2001) PCBs: Recent Advances in Environmental Toxicology and Health Effects, University Press of Kentucky, Lexington, KY.
2. Erickson, M. D. and Kaley, R. G. (2011) Applications of polychlorinated biphenyls Environ. Sci. Pollut. Res. 18, 135-151
3. Agency for Toxic Substances and Disease Registry (2000) Toxicological Profile for Polychlorinated Biphenyls (PCBs), Department of Health and Human Services, Public Health Service, Atlanta, GA.
4. Schantz, S. L., Widholm, J. J., and Rice, D. C. (2003) Effects of PCB exposure on neuropsychological function in children Environ. Health Perspect. 111, 357-376 (Pubitemid 36395204)
5. Mariussen, E. and Fonnum, F. (2006) Neurochemical targets and behavioral effects of organohalogen compounds: An update Crit. Rev. Toxicol. 36, 253-89
6. Kodavanti, P. R. S. (2004) Intracellular signaling and developmental neurotoxicity, in Molecular Neurotoxicology: Environmental Agents and Transcription-Transduction Coupling (Zawia, N. H., Ed.) pp 151-182, CRC Press, Boca Raton, FL.
7. 2+ channel complex type 1 (RyR1) Chem. Res. Toxicol. 19, 92-101 (Pubitemid 43185466)
8. Letcher, R. J., Klasson-Wehler, E., and Bergman, A. (2000) Methyl sulfone and hydroxylated metabolite of polychlorinated biphenyls, in The Handbook of Environmental Chemistry: New Types of Persistent Halogenated Compounds (Passivirta, J., Ed.) Vol. 3K, pp 315-359, Springer-Verlag, Berlin, Germany.
9. Nezel, T., Müller-Plathe, F., D., M., Müller, D. M., and Buser, H. R. (1997) Theoretical considerations about chiral PCBs and their methylthio and methylsulfonyl metabolites being possibly present as stable enantiomers Chemosphere 35, 1895-1906 (Pubitemid 27462343)
10. Buckman, A. H., Wong, C. S., Chow, E. A., Brown, S. B., Solomon, K. R., and Fisk, A. T. (2006) Biotransformation of polychlorinated biphenyls (PCBs) and bioformation of hydroxylated PCBs in fish Aquat. Toxicol. 78, 176-185
11. Kunisue, T. and Tanabe, S. (2009) Hydroxylated polychlorinated biphenyls (OH-PCBs) in the blood of mammals and birds from Japan: Lower chlorinated OH-PCBs and profiles Chemosphere 74, 950-61
12. Nomiyama, K., Murata, S., Kunisue, T., Yamada, K. T., Mizukawa, H., Takahashi, S., and Tanabe, S. (2010) Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBs) in the blood of toothed and baleen whales stranded along Japanese coastal watrs Environ. Sci. Technol. 44, 3732-3738
13. Guvenius, D. M., Aronsson, A., Ekman-Ordeberg, G., Bergman, A., and Norén, K. (2003) Human prenatal and postnatal exposure to polybrominated diphenyl ethers, polychlorinated biphenyls, polychlorobiphenylols, and pentachlorophenol Environ. Health Perspect. 111, 1235-1241 (Pubitemid 36939407)
14. Soechitram, S. D., Athanasiadou, M., Hovander, L., Bergman, A., and Sauer, P. J. J. (2004) Fetal exposure to PCBs and their hydroxylated metabolites in a Dutch cohort Environ. Health Perspect. 112, 1208-12 (Pubitemid 39157625)
15. Glynn, A., Larsdotter, M., Aune, M., Darnerud, P. O., Bjerselius, R., and Bergman, A. (2011) Changes in serum concentrations of polychlorinated biphenyls (PCBs), hydroxylated PCB metabolites and pentachlorophenol during pregnancy Chemosphere 83, 144-151
16. Dirtu, A. C., Jaspers, V. L. B., Cernat, R., Neels, H., and Covaci, A. (2010) Distribution of PCBs, their hydroxylated metabolites, and other phenolic contaminants in human serum from two European countries Environ. Sci. Technol. 44, 2876-2883
17. Wong, P., Brackney, W., and Pessah, I. (1997) Ortho-substituted polychlorinated biphenyls alter microsomal calcium transport by direct interaction with ryanodine receptors of mammalian brain J. Biol. Chem. 272, 15145-15153 (Pubitemid 27255529)
18. Wong, P., Joy, R., Albertson, T., Schantz, S., and Pessah, I. (1997) Ortho-substituted 2,2′,3,5′,6-pentachlorobiphenyl (PCB 95) alters rat hippocampal ryanodine receptors and neuroplasticity in vitro: evidence for altered hippocampal function Neurotoxicology 18, 443-456 (Pubitemid 27392653)
19. Wong, P. W. and Pessah, I. N. (1996) Ortho-substituted polychlorinated biphenyls alter calcium regulation by a ryanodine receptor-mediated mechanism: structural specificity toward skeletal- and cardiac-type microsomal calcium release channels Mol. Pharmacol. 49, 740-51
20. Lehmler, H. J., Harrad, S. J., Hühnerfuss, H., Kania-Korwel, I., Lee, C. M., Lu, Z., and Wong, C. S. (2010) Chiral polychlorinated biphenyl transport, metabolism, and distribution: A review Environ. Sci. Technol. 44, 2757-66
21. Pessah, I. N., Lehmler, H.-J., Robertson, L. W., Perez, C. F., Cabrales, E., Bose, D. D., and Feng, W. (2009) Enantiomeric specificity of (-)-2,2′,3,3′,6,6′-hexachlorobiphenyl toward ryanodine receptor types 1 and 2 Chem. Res. Toxicol. 22, 201-207
22. Warner, N. A., Martin, J. W., and Wong, C. S. (2009) Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian cytochrome P-450 isozymes to form hydroxylated metabolites Environ. Sci. Technol. 43, 114-121
23. Kania-Korwel, I., Vyas, S. M., Song, Y., and Lehmler, H.-J. (2008) Gas chromatographic separation of methoxylated polychlorinated biphenyl atropisomers J. Chromatogr., A 1207, 146-154
24. Norstrom, K., Eriksson, J., Haglund, J., Silvari, V., and Bergman, A. (2006) Enantioselective formation of methyl sulfone metabolites of 2,2′,3,3′,4,6′-hexachlorobiphenyl in rat Environ. Sci. Technol. 40, 7649-7655 (Pubitemid 46016071)
25. Larsson, C., Ellerichmann, T., Huehnerfuss, H., and Bergman, A. (2002) Chiral PCB methyl sulfones in rat tissues after exposure to technical PCBs Environ. Sci. Technol. 36, 2833-2838 (Pubitemid 34752168)
26. Shaikh, N., Parkin, S., and Lehmler, H. J. (2006) The Ullmann coupling reaction: A new approach to tetraarylstannanes Organometallics 25, 4207-4214 (Pubitemid 44325172)
27. Kania-Korwel, I., Hrycay, E. G., Bandiera, S. M., and Lehmler, H. J. (2008) 2,2′,3,3′,6,6′-Hexachlorobiphenyl (PCB 136) atropisomers interact enantioselectively with hepatic microsomal cytochrome P450 enzymes Chem. Res. Toxicol. 21, 1295-1303 (Pubitemid 351967395)
28. Waller, S. C., He, Y. A., Harlow, G. R., He, Y. Q., Mash, E. A., and Halpert, J. R. (1999) 2,2′,3,3′,6,6′-Hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11 Chem. Res. Toxicol. 12, 690-699 (Pubitemid 29398531)
29. Blomquist, C. H., Kotts, C. E., and Hakanson, E. Y. (1978) A simple method for detecting steroid aggregation and estimating solubility in aqueous solutions Anal. Biochem. 87, 631-635 (Pubitemid 9066634)
30. Thomas, P. E., Reik, L. M., Ryan, D. E., and Levin, W. (1983) Induction of two immunochemically related rat liver cytochrome P-450 isozymes, cytochromes P-450c and P-450d, by structurally diverse xenobiotics J. Biol. Chem. 258, 4590-4598 (Pubitemid 13080685)
31. Lowry, O. H., Rosenbrough, N. J., Rarr, A. L., and Randall, R. J. (1951) Protein measurement with Folin Phenol reagent J. Biol. Chem. 193, 265-275
32. Weisbrod, A. V., Shea, D., Moore, M. J., and Stegeman, J. J. (2000) Bioaccumulation patterns of polychlorinated biphenyls and chlorinated pesticides in Northwest Atlantic pilot whales Environ. Toxicol. Chem. 19, 667-677 (Pubitemid 30112362)
33. Lagueux, J., Affar, E. B., Adeau, D., Ayotte, P., Dewailly, D., and Poirer, G. G. (1997) A microassay for the detection of low levels of cytochrome P450 O-deethylation activities with alkoxyresorufin substrates Mol. Cell. Biochem. 175, 125-129 (Pubitemid 27453344)
34. Renwick, A. B., Lavignette, G., Worboys, P. D., Williams, B., Surry, D., Lewis, D. F. V., Price, R. J., Lake, B. G., and Evans, D. C. (2001) Evaluation of 7-benzyloxy-4-trifluoromethyl-coumarin, some other 7-hydroxy-4-trifluoro- methylcoumarin derivatives and 7-benzyloxyquinoline as fluorescent substrates for rat hepatic cytochrome P450 enzymes Xenobiotica 31, 861-878 (Pubitemid 34074789)
35. Schnellmann, R., Putnam, C., and Sipes, I. (1983) Metabolism of 2,2′,3,3′,6,6′-hexachlorobiphenyl and 2,2′,4,4′,5, 5′-hexachlorobiphenyl by human hepatic microsomes Biochem. Pharmacol. 32, 3233-3239 (Pubitemid 14209644)
36. Kania-Korwel, I., Hornbuckle, K. C., Peck, A., Ludewig, G., Robertson, L. W., Sulkowski, W. W., Espandiari, P., Gairola, C. G., and Lehmler, H. J. (2005) Congener specific tissue distribution of Aroclor 1254 and a highly chlorinated environmental PCB mixture in rats Environ. Sci. Technol. 39, 3513-3520 (Pubitemid 40705472)
37. Kania-Korwel, I., Zhao, H., Norstrom, K., Li, X., Hornbuckle, K. C., and Lehmler, H. J. (2008) Simultaneous extraction and clean-up of polychlorinated biphenyls and their metabolites from small tissue samples using pressurized liquid extraction J. Chromatogr., A 1214, 37-46
38. Kania-Korwel, I., Vyas, S., Song, Y., and Lehmler, H. J. (2008) Gas chromatographic separation of methoxylated polychlorinated biphenyl atropisomer J. Chromatogr., A 1207, 146-154
39. Preston, B. D., Miller, J. A., and Miller, E. C. (1983) Non-arene oxide aromatic ring hydroxylation of 2,2′,5,5′-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes J. Biol. Chem. 258, 8304-11 (Pubitemid 13074112)
40. Haglund, P. and Wiberg, K. (1996) Determination of the gas chromatographic elution sequences of the (+)- and (-)- enantiomers of stable enantiomeric PCBs on Chirasil-Dex J. High Resol. Chromatogr. 19, 373-376 (Pubitemid 126414451)
41. Kania-Korwel, I., El-Komy, M. H., Veng-Pedersen, P., and Lehmler, H. J. (2010) Clearance of polychlorinated biphenyl atropisomers is enantioselective in female C57Bl/6 mice Environ. Sci. Technol. 44, 2828-35
42. Kania-Korwel, I., Shaikh, N., Hornbuckle, K. C., Robertson, L. W., and Lehmler, H.-J. (2007) Enantioselective disposition of PCB 136 (2,2′,3,3′,6,6′-hexachlorobiphenyl) in C57BL/6 mice after oral and intraperitoneal administration Chirality 19, 56-66 (Pubitemid 44936483)
43. Lehmler, H.-J., Price, D. J., Garrison, A. W., Birge, W. J., and Robertson, L. W. (2003) Distribution of PCB 84 enantiomers in C57Bl/6 mice Fresenius Environ. Bull. 12, 254-260 (Pubitemid 36639364)
44. Larsson, C., Ellerichmann, T., Hühnerfuss, H., and Bergman, A. (2002) Chiral PCB methyl sulfones in rat tissues after exposure to technical PCBs Environ. Sci. Technol. 36, 2833-8 (Pubitemid 34752168)