The role of 3-methylsulfonyl-2,2',4',5,5'-pentachlorobiphenyl, a metabolite of 2,2',4,5,5'-pentachlorobiphenyl, in the induction of hepatic microsomal drug-metabolizing enzymes by 2,2',4,5,5'-pentachlorobiphenyl in rats

Environmental Toxicology and Pharmacology

Volumn 8, Issue 1, 1999, Pages 39-47

  Kato, Yoshihisa ^a   Haraguchi, Koichi ^b   Tomiyasu, Koichi ^a   Saito, Hiroyuki ^a   Shibahara, Tomoo ^a   Masuda, Yoshito ^b   Kimura, Ryohei ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b DAIICHI UNIVERSITY OF PHARMACY   (Japan)

Author keywords

Drug metabolizing enzyme; Induction; Methylsulfonyl metabolite; PB inducible form; Polychlorinated biphenyl; Rat

Indexed keywords

2,2',4',5,5' PENTACHLOROBIPHENYL; AMINOPYRINE N DEMETHYLASE; CYTOCHROME B5; CYTOCHROME P450; KANAMYCIN; LINCOMYCIN; POLYCHLORINATED BIPHENYL; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME INDUCTION; INTESTINE FLORA; LIVER METABOLISM; MALE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT;

EID: 0032760727     PISSN: 13826689     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1382-6689(99)00028-9     Document Type: Article

References (49)

1. Aimoto T., Ito O., Nozaki K., Harakawa E., Murata T. Metabolism and disposition of bitolterol, a new bronchodilator, in mice. Yakuzaigaku. 37:1977;128-134.
2. Bakke J.E., Rafter J.J., Lindeskog P., Feil V.J., Gustafsson J.-Å., Gustafsson B.E. Metabolism of 2-acetamido-4-(chloromethyl) thiazole in germfree and conventional rats. Biochem. Pharmacol. 30:1981;1839-1844.
3. Bakke J.E., Bergman Å., Larsen G.L. Metabolism of 2,4′,5-trichlorobiphenyl by the mercapturic acid pathway. Science. 217:1982;645-647.
4. Bakke J.E., Feil V.J., Bergman Å. Metabolites of 2,4′,5-trichlorobiphenyl in rats. Xenobiotica. 13:1983;555-564.
5. Bakke J., Struble C., Gustafsson J.-Å., Gustafsson B. Catabolism of premercapturic and pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats. Proc. Natl. Acad. Sci. U.S.A. 82:1985;668-671.
6. Bergman Å., Athanasiadou M., Bergek S., Haraguchi K., Jensen S., Klasson-Wehler E. PCB and PCB methyl sulfones in mink treated with PCB and various PCB fractions. Ambio. 21:1992;570-576.
7. Bergman Å., Norstrom R.J., Haraguchi K., Kuroki H., Béland P. PCB and DDE methyl sulfones in mammals from Canada and Sweden. Environ. Toxicol. Chem. 13:1994;121-128.
8. Cadogan, J.I.G., 1962, A convenient new method of aromatic arylation, J. Chem. Soc. 4257-4258.
9. Dewailly É., Weber J.-P., Gingras S., Laliberté C. Coplanar PCBs in human milk in the province of Québec, Canada: are they more toxic than dioxin for breast fed infants? Bull. Environ. Contam. Toxicol. 47:1991;491-498.
10. Haraguchi K., Kuroki H., Masuda Y. Capillary gas chromatographic analysis of methylsulphone metabolites of polychlorinated biphenyls retained in human tissues. J. Chromatogr. 361:1986;239-252.
11. Haraguchi K., Kuroki H., Masuda Y. Synthesis and characterization of tissue-retainable methylsulfonyl polychlorinated biphenyl isomers. J. Agric. Food Chem. 35:1987;178-182.
12. Haraguchi K., Kuroki H., Masuda Y. Polychlorinated biphenyl methylsulfone congeners in human tissues: Identification of methylsulfonyl dichlorobiphenyls. Chemosphere. 18:1989;477-484.
13. Haraguchi K., Athanasiadou M., Bergman Å., Hovander L., Jensen S. PCB and PCB methyl sulfones in selected groups of seals from Swedish waters. Ambio. 21:1992;546-549.
14. Israili Z.H., Dayton P.G., Kiechel J.R. Novel routes of drug metabolism, a survey. Drug Metab. Dispos. 5:1977;411-415.
15. Jenner P., Testa B. Novel pathways in drug metabolism. Xenobiotica. 8:1978;1-25.
16. Jensen S., Sundström G. Structures and levels of most chlorobiphenyls in two technical PCB products and in human adipose tissue. Ambio. 13:1974;70-76.
17. Kannan N., Tanabe S., Ono M., Tatsukawa R. Critical evaluation of polychlorinated biphenyl toxicity in terrestrial and marine mammals: increasing impact of non-ortho and mono-ortho coplanar polychlorinated biphenyls from land to ocean. Arch. Environ. Contam. Toxicol. 18:1989;850-857.
18. Kato Y., Kimura R. Role of 3,4-dichlorophenyl methyl sulfone, a metabolite of o-dichlorobenzene, in the changes in hepatic microsomal drug-metabolizing enzymes caused by o-dichlorobenzene administration in rats. Toxicol. Appl. Pharmacol. 145:1997;277-284.
19. Kato Y., Kogure T., Sato M., Murata T., Kimura R. Evidence that methylsulfonyl metabolites of m-dichlorobenzene are causative substances of induction of hepatic microsomal drug-metabolizing enzymes by the parent compound in rats. Toxicol. Appl. Pharmacol. 82:1986;505-511.
20. Kato Y., Yamada S., Sato M., Kimura R. Role of 2,3,5-trichlorophenyl methyl sulfone, a metabolite of 1,2,4-trichlorobenzene, in the induction of hepatic microsomal drug-metabolizing enzymes by 1,2,4-trichlorobenzene in rats. Toxicol. Appl. Pharmacol. 122:1993;214-221.
21. Kato Y., Haraguchi K., Kawashima M., Yamada S., Masuda Y., Kimura R. Induction of hepatic microsomal drug-metabolizing enzymes by methylsulphonyl metabolites of polychlorinated biphenyl congeners in rats. Chem.-Biol. Interact. 95:1995a;257-268.
22. Kato Y., Haraguchi K., Kawashima M., Yamada S., Isogai M., Masuda Y., Kimura R. Characterization of hepatic microsomal cytochrome P-450 from rats treated with methylsulphonyl metabolites of polychlorinated biphenyl congeners. Chem.-Biol. Interact. 95:1995b;269-278.
23. Kato Y., Haraguchi K., Tomiyasu K., Saito H., Isogai M., Masuda Y., Kimura R. Structure-dependent induction of CYP2B1/2 by 3-methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Environ. Toxicol. Pharmacol. 3:1997;137-144.
24. Kimura R., Hayashi T., Sato M., Aimoto T., Murata T. Identification of sulfur-containing metabolites of p-dichlorobenzene and their disposition in rats. J. Pharmacobio-Dyn. 2:1979;237-244.
25. Kimura R., Kawai M., Sato M., Aimoto T., Murata T. Induction of hepatic microsomal drug-metabolizing enzymes by sulfur-containing metabolites of chlorinated benzenes in rats. Toxicol. Appl. Pharmacol. 67:1983;338-345.
26. Kimura R., Sano H., Itagaki K., Kogure T., Sato M., Murata T. Indentification of sulfur-containing metabolites of m-dichlorobenzene and their disposition and relationship with glutathione in rats. J. Pharmacobio-Dyn. 7:1984;234-245.
27. Larsen G.L., Bakke J.E. Enterohepatic circulation in formation of propachlor (2-chloro-N-isopropylacetanilide) metabolites in the rat. Xenobiotica. 11:1981;473-480.
28. Letcher R.J., Norstrom R.J., Bergman Å. Geographical distribution and identification of methyl sulphone PCB and DDE metabolites in pooled polar bear (Ursus maritimus) adipose tissue from western hemisphere Arctic and Subarctic regions. Sci. Total Environ. 160/161:1995;409-420.
29. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
30. McFarland V.A., Clarke J.U. Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: Considerations for a congener-specific analysis. Environ. Health Perspect. 81:1989;225-239.
31. Mikov M., Caldwell J., Dolphin C.T., Smith R.L. The role of intestinal microflora in the formation of the methylthio adduct metabolites of paracetamol. Studies in neomycin-pretreated and germ-free mice. Biochem. Pharmacol. 37:1988;1445-1449.
32. Nebert D.W., Gelboin H.V. Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture I. Assay and properties of induced enzyme. J. Biol. Chem. 243:1968;6242-6249.
33. Norén K., Lundén Å., Pettersson E., Bergman Å. Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Environ. Health Perspect. 104:1996;766-772.
34. Olafsson P.G., Bryan A.M., Stone W. PCB congener-specific analysis: a critical evaluation of toxic levels in biota. Chemosphere. 16:1987;2585-2593.
35. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes I. Evidence for its hemoprotein nature. J. Biol. Chem. 239:1964a;2370-2378.
36. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes II. Solubilization, purification, and properties. J. Biol. Chem. 239:1964b;2379-2385.
37. Otsuka M., Kurozumi T., Furuuchi S., Usuki S., Kotera K., Harigaya S. Metabolism of afloqualone, a new centrally acting muscle relaxant, in the rat. Chem. Pharm. Bull. 31:1983a;2438-2450.
38. Otsuka M., Furuuchi S., Harigaya S. Formation route of sulfur-containing metabolites of afloqualone, a new centrally acting muscle relaxant, in rat. Chem. Pharm. Bull. 31:1983b;2799-2809.
39. Parkinson A., Safe S.H., Robertson L.W., Thomas P.E., Ryan D.E., Reik L.M., Levin W. Immunochemical quantitation of cytochrome P-450 isozymes and epoxide hydrolase in liver microsomes from polychlorinated or polybrominated biphenyl-treated rats. A study of structure-activity relationships. J. Biol. Chem. 258:1983;5967-5976.
40. Rafter J.J., Nilsson L. Involvement of the intestinal microflora in the formation of sulphur-containing metabolites of caffeine. Xenobiotica. 11:1981;771-778.
41. Rafter J.J., Bakke J., Larsen G., Gustafsson B., Gustafsson J.-Å. Role of the intestinal microflora in the formation of sulfur-containing conjugates of xenobiotics. Rev. Biochem. Toxicol. 5:1983a;387-408.
42. Rafter J.J., Gustafsson J.-Å., Bakke J.E., Larsen G.L., Norin K.E., Gustafsson B.E. Studies on the re-establishment of the intestinal microflora in germ-free rats with special reference to the metabolism of N-isopropyl-α-chloroacetanilide (propachlor). Xenobiotica. 13:1983b;171-178.
43. Safe S., Safe L., Mullin M. Polychlorinated biphenyls: Congener-specific analysis of a commercial mixture and a human milk extract. J. Agric. Food Chem. 33:1985;24-29.
44. Suzuki S., Tomisawa H., Ichihara S., Fukazawa H., Tateishi M. A C-S bond cleavage enzyme of cysteine conjugates in intestinal microorganisms. Biochem. Pharmacol. 31:1982;2137-2140.
45. Tateishi M., Suzuki S., Shimizu H. Cysteine conjugate β-lyase in rat liver. A novel enzyme catalyzing formation of thiol-containing metabolites of drugs. J. Biol. Chem. 253:1978;8854-8859.
46. Tateishi M. New pathway in drug metabolism: on the attachment of methylthio group. Farumashia. 14:1978;882-887.
47. Weistrand C., Norén K. Methylsulfonyl metabolites of PCBs and DDE in human tissues. Environ. Health Perspect. 105:1997;644-649.
48. Weistrand C., Norén K., Nilsson A. Organochlorine compounds in blood plasma from potentially exposed workers. PCB, PCN, PCDD/PCDF, HCB and methylsulphonyl metabolites of PCB. Environ. Sci. Pollut. Res. 4:1997;2-9.
49. Yamaoka K., Nakagawa T. A nonlinear least squares program based on differential equations, MULTI (RUNGE), for microcomputers. J. Pharmacobio-Dyn. 6:1983;595-606.