Pharmacokinetics of two major hydroxylated polychlorinated biphenyl metabolites with specific retention in rat blood

Reference

• BAKKE, J. E., BERGMAN, A. L. and LARSEN, G. L., 1982, Metabolism of 2,4',5-trichlorobiphenyl by the mercapturic acid pathway. Science, 217, 645–647.
   PubMed Web of Science ®Google Scholar
• BAKKE, J. E., FEIL, V. J. and BERGMAN, A., 1983, Metabolites of 2,4',5-trichlorobiphenyl in rats. Xenabiotica, 13, 555–564.
   PubMed Web of Science ®Google Scholar
• BERGMAN, A., ATHANASIADOU, M., BERGEK, S., HARAGUCHI, K., JENSEN, S. and KLASSON WEHLER, E., 1992, PCB and PCB methyl sulfones in mink treated with PCB and various PCB fractions. Ambfo, 21, 570–576.
   Web of Science ®Google Scholar
• BERGMAN, A., KLASSON WEHLER, E. and KUROKI, H., 1994, Selective retention of hydroxylated PCB metabolites in blood. Environmental Health Perspectives, 102, 464–469.
   PubMed Web of Science ®Google Scholar
• BERGMAN, A., KLASSON WEHLER, E., KUROKI, H. and NILSSON, A., 1995, Synthesis and mass spectrometry of some methoxylated PCBs. Chemosphere, 30, 1921–1938.
   Web of Science ®Google Scholar
• BERGMAN, A., LARSEN, G. L. and BAKKE, J. E., 1982, Biliary secretion, retention and excretion of five 14C-labelled polychlorinated biphenyls in the rat. Chemosphere, 11, 249–253.
   Web of Science ®Google Scholar
• BRAUN, W. H., YOUNG, J. D., BLAU, G. E. and GEHRING, P. J., 1977, The pharmacokinetics and metabolism of pentachlorophenol in rats. Toxicology and Applied Pharmacology, 41, 395–406.
   PubMed Web of Science ®Google Scholar
• BROUWER, A., MORSE, D. C., LANS, M. C., SCHUUR, G., MURK, A. J., KLASSON-WEHLER, E., BERGMAN, A. and VISSER, T. J., 1998, Interactions of persistent environmental organohalogens with the thyroid hormone system: mechanisms and possible consequences for animal and human health. Toxicology and Industrial Health, 14, 59–84.
   Google Scholar
• CADOGAN, J. I. G., 1962, A convenient new method of aromatic arylation. Journal of Chemical Society, 4257–4258.
   Google Scholar
• CAMPBELL, L. M., MUIR, D. C. G., WHITTLE, D. M., BACKUS, S., NORSTROM, R. J. and FISK, A. T., 2003, Hydroxylated PCBs and other chlorinated phenolic compounds in Lake Trout (Salvelinus namaycush) blood plasma from the Great Lakes region. Environmental Science and Technology, 37, 1720–1725.
   Google Scholar
• DARNERUD, P. 0., BRANDT, I., KLASSON-WEHLER, E., BERGMAN, A., D'ARGY, R., DENCKER, L. and SPOERBER, G. 0., 1986, 3,3',4,4'-Tetrachloro-[14C]-biphenyl in pregnant mice: Enrichment of phenol and methyl sulphone metabolites in late gestational fetuses. Xenobiotica, 16, 295–306.
   Google Scholar
• FANGsTRöm, B., ATHANASIADOU, M., GRANDJEAN, P., WEIHE, P. and BERGMAN, A., 2002, Hydroxylated PCB metabolites and PCBs in serum from pregnant Faroese women. Environmental Health Perspectives, 110, 895–899.
   PubMed Web of Science ®Google Scholar
• FANGsTRöm, B., GRANDJEAN, P., WEIHE, P., ATHANASIADOU, M. and BERGMAN, A., 2004, Organohalogen contaminants in fulmar and fulmar eggs from the Faroe Islands area. Ambio (in press).
   Google Scholar
• FANTA, P. E., 1964, The Ullman synthesis of biaryls, 1945–1963. Chemistry Reviews, 64, 613–632. FIESER, L. F. and FIESER, M., 1967, Reagents for Organic Synthesis, Vol. 1 (New York: John Wiley and Sons, Inc.).
   Google Scholar
• HARAGUCHI, K., KATO, Y., KIMURA, R. and MASUDA, Y., 1998, Hydroxylation and methylthiolation of mono-ortho-substituted polychlorinated biphenyls in rats: identification of metabolites with tissue affinity. Chemical Research in Toxicology, 11, 1508–1515.
   PubMed Web of Science ®Google Scholar
• HOVANDER, L., ATHANASIADOU, M., ASPLUND, L., JENSEN, S. and KLASSON WEHLER, E., 2000, Extraction and cleanup methods for analysis of phenolic and neutral organohalogens in plasma. Journal of Analytical Toxicology, 24, 696–703.
   PubMed Web of Science ®Google Scholar
• HOVANDER, L., MALMBERG, T., ATHANASIADOU, M., ATHANASSIADIS, I., RAHM, S., BERGMAN, A. and KLASSON WEHLER, E., 2002, Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma. Archives of Environmental Contamination and Toxicology, 42, 105–117.
   PubMed Web of Science ®Google Scholar
• KLASSON WEHLER, E., BERGMAN, A., ATHANASIADOU, M., LUDWIG, J. P., AUMAN, H. J., KANNAN, K., VAN DEN BERG, M., MURK, A., FEYK, L. A. and GIESY, J. P., 1998, Hydroxylated and methylsulfonyl polychlorinated biphenyl metabolites in albatrosses from Midway atoll, North Pacific Ocean. Environmental Toxicology and Chemistry, 17, 1620–1625.
   Web of Science ®Google Scholar
• KLASSON WEHLER, E., BERGMAN, A., BRANDT, I., DARNERUD, P. 0. and WACHTMEISTER, C. A., 1989, 3,3',4,4'-Tetrachlorobiphenyl. Excretion and tissue retention of hydroxylated metabolites in the mouse. Drug Metabolism and Disposition, 17, 441–448.
   Google Scholar
• KLASSON WEHLER, E., LINDBERG, L., JöNssoN, C.-L. and BERGMAN, A., 1993, Tissue retention and metabolism of 2,3,4,3',4'-pentachlorobiphenyl in mink and mouse. Chemosphere, 27, 2397–2412.
   Google Scholar
• LANS, M. C., SPIERTZ, C., BROUWER, A. and KOEMAN, J. H., 1994, Different competition of thyroxine binding to transthyretin and thyroxine-binding globulin by hydroxy-PCBs, PCDDs and PCDFs. European Journal of Pharmacology, 270, 129–136.
   PubMed Web of Science ®Google Scholar
• LEGLER, J., CENIJN, P. H., MALMBERG, T., BERGMAN, A. and BROUWER, A., 2002, Determination of the endocrine disrupting potency of hydroxylated PCBs and flame retardants with in vitro bioassays. Organohalogen Compounds (Barcelona), 56, 53–56..
   Google Scholar
• LETCHER, R. J., KLASSON-WEHLER, E. and BERGMAN, A., 2000, Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls (Berlin: Heidelberg), pp. 315–359.
   Google Scholar
• Li, H., DROUILLARD, K. G., BENNETT, E., HAFFNER, G. D. and LETCHER, R. J., 2003, Plasma-associated halogenated phenolic contaminants in benthic and pelagic fish species from the Detroit river. Environmental Science and Technology, 37, 832–839.
   PubMed Web of Science ®Google Scholar
• MEIRONYTE GUVENIUS, D., HASSANZADEH, P., BERGMAN, A. and NOREN, K., 2002, Metabolites of polychlorinated biphenyls in human liver and adipose tissue. Environmental Toxicology and Chemistry, 21, 2264–2269.
   PubMed Web of Science ®Google Scholar
• BERG, M., SJ6DIN, A., CASABONA, H., NORDGREN, I., KLASSON WEHLER, E. and HAKANSSON, H., 2002, Tissue distribution and half-lives of individual polychlorinated biphenyls and serum levels of 4-hydroxy-2,3,3',4',5-pentachlorobiphenyl in the rat. Toxicological Sciences, 70, 171–182.
   Google Scholar
• POWER, D. M., ELIAS, N. P., RICHARDSON, S. J., MENDES, J., SOARES, C. M. and SANTOS, C. R. A., 2000, Evolution of the thyroid hormone-binding protein, transthyretin. General and Comparative Endocrinology, 119, 241–255.
   PubMed Web of Science ®Google Scholar
• SANDAU, C. D., 2001, Analytical Chemistry of Hydroxylated Metabolites of PCBs and Other Halogenated Phenolic Compounds in Blood and Their Relationship to Thyroid Hormone and Retinol Homeostasis in Humans and Polar Bears (Ottawa: Carlton University).
   Google Scholar
• SANDAU, C. D., AYOTTE, P., DEWAILLY, E., DUFFE, J. and NORSTROM, R. J., 2000, Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian Inuit. Environmental Health Perspectives, 108, 611–616.
   PubMed Web of Science ®Google Scholar
• SCHUUR, A. G., BROUWER, A., BERGMAN, A., COUGHTRIE, M. W. H. and VISSER, T. J., 1998a, Inhibi-tion of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls. Chemico-Biological Interactions, 109, 293–297.
   Google Scholar
• SCHUUR, A. G., L,EGGER, F. F., VAN MEETEREN, M. E., MOONEN, M. J. H., VAN LEEUWEN-BOL, I., BERGMAN, A., VISSER, T. J. and BROUWER, A., 1998b, In vitro inhibition of thyroid hormone sulfation by hydroxylated metabolites of halogenated aromatic hydrocarbons. Chemical Research in Toxicology, 11, 1075–1081.
   Google Scholar
• SCHUUR, A. G., VAN LEEUWEN-BOL, I., JONG, W. M. C., BERGMAN, A., COUGHTRIE, M. W. H., BROUWER, A. and VISSER, T. J., 1998c, In vitro inhibition of thyroid hormone sulfation by polychlorobiphenylols: isozyme specificity and inhibition kinetics. Toxicological Sciences, 45, 188–194.
   Google Scholar
• SJGDIN, A., HAGMAR, L., KLASSON WEHLER, E., Bi0RE, J. and BERGMAN, A., 2000, Influence of the consumption of fatty Baltic Sea fish on plasma levels of halogenated environmental contaminants in Latvian and Swedish men. Environmental Health Perspectives, 108, 1035–1041.
   Google Scholar
• SJGDIN, A., TULLSTEN, A. K. and KLASSON-WEHLER, E., 1998, Identification of the parent compounds to selectively retained hydroxylated PCB metabolites in rat blood plasma. Organohalogen Compounds ( Stockholm), 37, 365–368.
   Google Scholar
• SUNDSTRöM, G., JANSSON, B. and JENSEN, S., 1975, Structure of phenolic metabolites of p,p'-DDE in rat, wild and guillemot. Nature, 255, 627–628.
   PubMed Web of Science ®Google Scholar
• TAMPAL, N., LEHMLER, H.-J., ESPANDIARI, P., MALMBERG, T. and ROBERTSON, L. W., 2002, Glucuronidation of hydroxylated polychlorinated biphenyls (PCBs). Chemical Research in Toxicology, 15, 1259–1266.
   Google Scholar
• VAN DEN BERG, K. J., 1990, Interaction of chlorinated phenols with thyroxine binding sites of human transthyretin, albumin and thyroid binding globulin. Chemico-Biological Interactions, 76, 63–75.
   PubMed Web of Science ®Google Scholar
• VAN DEN HURK, P., KUBICZAK, G. A., LEHMLER, H.-J. and JAMES, M. 0., 2002, Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo(a)pyrene. Environmental Health Perspectives, 110, 343–348.
   Google Scholar
• WYSS, P. A., MÜHLEBACH, S. and BICKEL, M. H., 1986, Long-term pharmaco-kinetics of 2,2',4,4',5,5'-hexachlorobiphenyl (6-CB) in rats with constant adipose tissue mass. Drug Metabolism and Disposition, 14, 361–365.
   Google Scholar