Comparative study on formation of hydroxy and sulfur-containing metabolites from different chlorinated biphenyls with 2,5-substitution in rats

Drug Metabolism and Disposition

Volumn 25, Issue 7, 1997, Pages 845-852

  Haraguchi, Koichi ^a   Kato, Yoshihisa ^b   Kimura, Ryohei ^b   Masuda, Yoshito ^b  

^a DAIICHI UNIVERSITY OF PHARMACY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

POLYCHLORINATED BIPHENYL;

ANIMAL EXPERIMENT; ARTICLE; CHLORINATION; CONFORMATIONAL TRANSITION; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG CONFORMATION; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG FECES LEVEL; DRUG METABOLISM; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; TISSUE DISTRIBUTION; TISSUE SPECIFICITY;

ANIMALS; BIOTRANSFORMATION; CHEMISTRY, PHYSICAL; FECES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROXYLATION; MALE; POLYCHLORINATED BIPHENYLS; RATS; RATS, WISTAR; SULFUR; TISSUE DISTRIBUTION;

ANIMALIA;

EID: 0030746349     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. P. de Voogt, D. E. Wells, L. Reutergårdh, and U. A. Th. Brinkman: Biological activity, determination and occurrence of planar, mono- and di-ortho PCBs. Int. J. Anal. Chem. 40, 1-46 (1990).
2. H. B. Matthews and R. L. Dedrick: Pharmacokinetics of PCBs. Ann. Rev. Pharmacol. Toxicol. 24, 85-103 (1984).
3. S. Safe: Polyhalogenated aromatics: uptake, disposition and metabolism. In: "Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products" (R. D. Kimbrough and A. A. Jensen, eds.), chap. 5, 2nd ed., pp. 131-159. Elsevier Science Publishers, Amsterdam, The Netherlands, 1989.
4. B. D. Preston, J. A. Miller, and E. C. Miller: Reactions of 2,2′,5,5′-tetrachlorobiphenyl 3,4-oxide with methionine, cysteine and glutathione in relation to the formation of methylthio-metabolites of 2,2′,5,5′-tetrachlorobiphenyl in the rat and mouse. Chem.-Biol. Interact. 50, 289-312 (1984).
5. B. D. Preston, J. A. Miller, and E. C. Miller: 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, 8304-8311 (1983).
6. J. E. Bakke, Å. L. Bergman, and G. L. Larsen: Metabolism of 2,4′,5-trichlorobiphenyl by the mercapturic acid pathway. Science 217, 645-647 (1982).
7. J. E. Bakke, V. J. Feil, and Å. Bergman: Metabolites of 2,4′,5-trichlorobiphenyl in rats. Xenobiotica 13, 555-564 (1983).
8. K. Haraguchi, M. Athanasiadou, Å. Bergman, L. Hovander, and S. Jensen: PCB and PCB methyl sulfones in selected groups of seals from Swedish waters. Ambio 21, 546-549 (1992).
9. Å. Bergman, R. J. Norstrom, K. Haraguchi, H. Kuroki, and P. Béland: PCB and DDE methyl sulfones in mammals from Canada and Sweden. Environ. Toxicol. Chem. 13, 121-128 (1994).
10. K. Haraguchi, H. Kuroki, and Y. Masuda: Capillary gas chromatographic analysis of methylsulphone metabolites of polychlorinated biphenyls retained in human tissues. J. Chromatogr. 361, 239-252 (1986).
11. K. Norén, Å. Lundén, E. Pettersson, and Å. Bergman: Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Environ. Health Perspect. 104, 766-772 (1996).
12. I. Brandt and Å. Bergman: PCB methyl sulphones and related compounds: identification of target cells and tissues in different species. Chemosphere 16, 1671-1676 (1987).
13. J. Lund, I. Brandt, L. Poellinger, Å. Bergman, E. Klasson-Wehler, and J.-Å. Gustafsson: Target cells for the polychlorinated biphenyl metabolite 4,4′-bis(methylsulfonyl)-2,2′,5,5′-tetrachlorobiphenyl. Mol. Pharmacol. 27, 314-323 (1985).
14. M. Gillner, J. Lund, C. Cambillau, M. Alexandersson, U. Hurtig, Å. Bergman, E. Klasson-Wehler, and J.-Å. Gustafsson: The binding of methylsulfonyl-polychlorobiphenyls to uteroglobin. J. Steroid Biochem. 31, 27-33 (1988).
15. T. Härd, H. J. Barnes, C. Larsson, J.-Å. Gustafsson and J. Lund: Solution structure of a mammalian PCB-binding protein in complex with a PCB. Nature Struct. Biol. 2, 983-989 (1995).
16. Y. Kato, K. Haraguchi, M. Kawashima, S. Yamada, Y. Masuda, and R. Kimura: Induction of hepatic microsomal drug-metabolizing enzymes by methylsulphonyl metabolites of polychlorinated biphenyl congeners in rats. Chem.-Biol. Interact. 95, 257-268 (1995).
17. Å. Bergman, E. Klasson-Wehler, and H. Kuroki: Selective retention of hydroxylated PCB metabolites in blood from mammals. Environ. Health Perspect. 102, 464-469 (1994).
18. P. O. Darnerud, D. Morse, E. Klasson-Wehler, and A. Brouwer: Binding of a 3,3′,4,4′-tetrachlorobiphenyl (CB-77) metabolite to fetal transthyretin and effects on fetal thyroid hormone levels in mice. Toxicology 106, 105-114 (1996).
19. J. I. G. Cadogan: A convenient new method of aromatic arylation. J. Chem. Soc. 4257-4258 (1962).
20. K. Haraguchi, H. Kuroki and Y. Masuda: Synthesis and characterization of tissue-retainable methylsulfonyl polychlorinated biphenyl isomers. J. Agricul. Food Chem. 35, 178-182 (1987).
21. Å. Bergman, B. Jansson, and I. Bamford: Methylthio- and methylsulfonylpolychlorobiphenyls: synthesis and studies of correlations between structure and fragmentation pattern on electron impact. Biomed. Mass Spectrom. 7, 20-27 (1980).
22. 14C-labelled PCB methyl sulphones. Chemosphere 23, 1837-1843 (1991).
23. Å. Bergman, E. Klasson-Wehler, H. Kuroki, and A. Nilsson: Synthesis and mass spectrometry of some methoxylated PCB. Chemosphere 30, 1921-1938 (1995).
24. I. Brandt, P. O. Darnerud, Å. Bergman, and Y. Larsson: Metabolism of 2,4′,5-trichlorobiphenyl: enrichment of hydroxylated and methyl sulphone metabolites in the uterine luminal fluid of pregnant mice. Chem.-Biol. Interact. 40, 45-56 (1982).
25. T. Mio, K. Sumino, and T. Mizutani: Sulfur-containing metabolites of 2,5,2′.5′-tetrachlorobiphenyl, a major component of commercial PCB's. Chem. Pharmn. Bull. 24, 1958-1960 (1976).
26. T. Mizutani, K. Yamamoto, and K. Tajima: Sulfur-containing metabolites of chlorobiphenyl isomers, a comparative study. J. Agricul. Food Chem. 26, 862-866 (1978).
27. M. Berlin, J. Gage, and S. Holm: Distribution and metabolism of 2,4,5,2′,5′-pentachlorobiphenyl. Arch. Environ. Health 30, 141-147 (1975).
28. E. Klasson-Wehler, L. Hovander, and B.-O. Lund: 2,2′,4,5,5′-Pentachlorobiphenyl: comparative metabolism in mink (Mustela vison) and mouse. Chem. Res. Toxicol. 9, 1340-1349 (1996).
29. Y. Kato, K. Haraguchi, M. Kawashima, S. Yamada, M. Isogai, Y. Masuda, and R. Kimura: Characterization of hepatic microsomal cytochrome P-450 from rats treated with methylsulfonyl metabolites of polychlorinated biphenyl congeners. Chem.-Biol. Interact. 95, 269-278 (1995).
30. Å. Bergman, I. Brandt, and B. Jansson: Accumulation of methylsulfonyl derivatives of some bronchial-seeking polychlorinated biphenyls in the respiratory tract of mice. Toxicol. Appl. Pharmacol. 48, 213-220 (1979).
31. G. L. Larsen, Å. Bergman, E. Klasson-Wehler, and N. M. Bass: A methylsulfonyl metabolite of a polychlorinated biphenyl can serve as a ligand for liver fatty acid binding protein in rat intestinal mucosa. Chem.-Biol. Interact. 77, 315-323 (1991).
32. G. L. Larsen, J. K. Huwe, Å. Bergman, E. Klasson-Wehler, and P. Hargis: Methylsulfonyl metabolites of xenobiotics can serve as ligands for fatty acid binding proteins in chicken liver and intestinal mucosa. Chemosphere 25, 1189-1194 (1992).
33. T. Mizutani: Identification of sulfur-containing metabolites of 2,4,2′,4′-tetrachlorobiphenyl in mice. Bull. Environ. Contam. Toxicol. 20, 219-226 (1978).
34. 14C]biphenyl in pregnant mice: enrichment of phenol and methyl sulphone metabolites in late gestational fetuses. Xenobiotica 16, 295-306 (1986).