Comparative metabolism of polychlorinated biphenyls and tissue distribution of persistent metabolites in rats, hamsters, and guinea pigs

Drug Metabolism and Disposition

Volumn 33, Issue 3, 2005, Pages 373-380

  Haraguchi, Koichi ^a   Koga, Nobuyuki ^b   Kato, Yoshihisa ^c  

^a DAIICHI UNIVERSITY OF PHARMACY   (Japan)

^b NAKAMURA GAKUEN UNIVERSITY   (Japan)

^c UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; CYTOCHROME P450; KANECHLOR 500; PHENOL DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHLORINATION; CONTROLLED STUDY; ELECTRON CAPTURE DETECTION; EXPOSURE; GAS CHROMATOGRAPHY; GUINEA PIG; HAMSTER; LIVER; MALE; MASS SPECTROMETRY; METABOLISM; NONHUMAN; PRIORITY JOURNAL; RAT; REACTION TIME; SENSITIVITY ANALYSIS; SPECIES COMPARISON; SUBSTITUTION REACTION; TISSUE DISTRIBUTION;

ANIMALS; CRICETINAE; ENVIRONMENTAL POLLUTANTS; GUINEA PIGS; LIVER; MALE; MESOCRICETUS; POLYCHLORINATED BIPHENYLS; RATS; RATS, WISTAR; SPECIES SPECIFICITY; TISSUE DISTRIBUTION;

EID: 14044270107     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.104.002444     Document Type: Article

References (38)

1. Amaro AR, Oakley GG, Bauwer U, Spielmann HP, and Pobertson LW (1996) Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase. Chem Res Toxicol 9:623-629.
2. Ariyoshi N, Koga N, Yoshimura H, and Oguri K (1997) Metabolism of 2,4,5,2′,4′,5′-hexachlorobiphenyl (PCB153) in the guinea pig. Xenobiotica 27:973-983.
3. Bakke JE, Bergman Å, and Larsen GL (1982) Metabolism of 2,4′,5-trichlorobiphenyl by the mercapturic acid pathway. Science (Wash DC) 217:645-647.
4. Bergman Å, Klasson-Wehler E, and Kuroki H (1994a) Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect 102:464-469.
5. Bergman Å, Klasson-Wehler E, Kuroki H, and Nilsson A (1995) Synthesis and mass spectrometry of some methoxylated PCB. Chemosphere 30:1921-1938.
6. Bergman Å, Norstrom RJ, Haraguchi K, Kuroki H, and Béland P (1994b) PCB and DDE methyl sulphones in mammals from Canada and Sweden. Environ Toxicol Chem 13:121-128.
7. Brouwer A, Morse DC, Lans MC, Schuur AG, Murk AJ, Klasson-Wehler E, Bergman Å, and Visser TJ (1998) Interactions of persistent environmental organohalogens with the thyroid hormone system: mechanisms and possible consequences for animal and human health. Toxicol Ind Health 14:59-84.
8. Chu S, Covaci A, Jacobs W, Haraguchi K, and Schepens P (2003) Distribution of methyl sulfone metabolites of polychlorinated biphenyls and p,p′-DDE in human tissues. Environ Health Perspect 111:1222-1227.
9. Connor K, Ramamoorthy K, Moore M, Mustain M, Chen I, Safe S, Zacharewski T, Gillesby B, Joyeux A, and Balaguer P (1997) Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: structure-activity relationships. Toxicol Appl Pharmacol 145:111-123.
10. Garner CE, Jefferson WN, Burka LT, Matthews HB, and Newbold RR (1999) In vitro estrogenicity of the catechol metabolites of selected polychlorinated biphenyls. Toxicol Appl Pharmacol 154:188-197.
11. Haraguchi K, Kato Y, Kimura R, and Masuda Y (1997) Comparative study on formation of hydroxy and sulfur-containing metabolites from different chlorinated biphenyls with 2,5-substitution in rats. Drug Metab Dispos 25:845-852.
12. Haraguchi K, Kato Y, Kimura R, and Masuda Y (1998) Hydroxylation and methylthiolation of mono-ortho-substituted polychlorinated biphneyls in rats: identification of metabolites with tissue affinity. Chem Res Toxicol 11:1508-1515.
13. Haraguchi K, Kato Y, Kimura R and Masuda Y (1999) Tissue distribution of methylsulfonyl metabolites derived from 2,2′,4,5,5′-penta- and 2,2′,3,4′,5′,6-hexachlorobiphenyls in rats. Arch Environ Contam Toxicol 37:135-142.
14. Haraguchi K, Kuroki H, and Masuda Y (1987) Synthesis and characterization of tissue-retainable methylsulfonyl polychlorinated biphenyl isomers. J Agric Food Chem 35:178-182.
15. Ishida C, Koga N, Hanioka N, Saeki HK, and Yoshimura H (1991) Metabolism in vitro of 3,4,3′, 4′- and 2,5,2′,5′- tetrachlorobiphenyl by rat liver microsomes and highly purified cytochrome P-450. J Pharmacobio-Dyn 14:276-284.
16. Kaminsky LS, Kennedy MW, Adams SM, and Guengerich FP (1981) Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry 20:7379-7384.
17. Kato S, McKinney JD, and Matthews HB (1980) Metabolism of symmetrical hexachlorobiphenyl isomers in the rat. Toxcol Appl Pharmacol 53:389-398.
18. Kato Y, Haraguchi K, Shibahara T, Yumoto S, Masuda Y, and Kimura R (1999) Reduction of thyroid hormone levels by methylsulfonyl metabolites of tetra- and pentachlorinated biphenyls in male Sprague-Dawley rats. Toxicol Sci 48:51-54.
19. Kato Y, Haraguchi K, Tomiyasu K, Saito H, Isogai M, Masuda Y, and Kimura R (1997) Structure-dependent induction of CYP2B1/2 by 3-methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Environ Pharmacol Toxocol 3:137-144.
20. Kester MH, Bulduk S, van Toor H, Tibboel D, Neinl W, Glatt H, Falany CN, Coughtrie MW, Schuur AG, Brouwer A, and Visser TJ (2002) Potent inhibition of estrogen sulfotransferase by hydroxylated metabolites of polyhalogenated aromatic hydrocarbons reveals alternative mechanism for estrogenic activity of endocrine disrupters. J Chin Endocrinol Metab 87:1142-1150.
21. Kociba RJ and Cabey O (1985) Comparative toxicology and biologic activity of chlorinated dibenzo-p-dioxins and furans relative to 2,3,7,8- tetrachlorodibenzo-p-dioxin (TCDD). Chemosphere 14:649-660.
22. Koga N, Haraguchi K, Kanamaru T, Kato Y, and Kimura R (2002) Metabolism of 2,3′,4,4′,5-pentachlorobiphenyl (CB118) by guinea pig liver microsomes. Organohalogen Compds 56:17-20.
23. Koga N, Kanamaru T, Kikuichi N, Oishi N, Kato S, and YoshimuraH (1995) Effect of cytochrome P450 inducers on liver microsomal metabolism of tetrachlorobiphenyls in rats, guinea pigs and hamsters. Biol Pharm Bull 18:705-710.
24. Koga N, Kanamaru T, Oishi N, Kato Y, Kimura R, Haraguchi K, and Masuda Y (2001) Species differences in the in vitro metabolism of 2,4,5,2′, 3′,4′-hexachlorobiphenyl. Fukuoka Acta Med 92:167-176.
25. Koga N, Kikuichi N, Kanamaru T, Kuroki H, Matsusue K, Ishida C, Ariyoshi N, Oguri K, and Yoshimura H (1998) Metabolism of 2,3′,4′,5- tetrachlorobiphenyl by cytochrome P450 from rats, guinea pigs and hamsters. Chemosphere 37:1985-1904.
26. Koga N and Yoshimura H (1996) Metabolism of PCBs and related compounds and their toxicity, in Yusho - a Human Disaster Caused by PCBs and Related Compounds (Kuratsune M ed), pp 105-120, Kyushu University Press, Fukuoka.
27. Letcher RJ, Klasson-Wehler E, and Bergman Å (2000) Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls, in The Handbook of Environmental Chemistry Vol 3, Part K (Paasivirta J ed): New Type of Persistent Halogenated Compounds pp 315-319, Springer-Verlag, Berlin, Heidelberg.
28. Letcher RJ, Lemmen JG, van der Berg B, Brouwer A, Bergman Å, Giesy JP, and van den Berg M (2002) In vitro antiestrogenic effects of aryl methyl sulfone metabolites of polychlorinated biphenyls and 2,2-bis(4-chlorophenyl)-1, 1-dichloroethene on 17β-estradiol-induced gene expression in several bioassay systems. Toxicol Sci 69:362-372.
29. Lund BO, Örberg J, Bergman Å, Larsson C, Bergman A, Bäcklin BM, Håkansson H, Madej A, Brouwer A, and Brunström B (1999) Chronic and reproductive toxicity of a mixture of 15 methylsulfonyl- polychlorinated biphenyls and 3-methylsulfonyl-2,2-bis-(4-chlorophenyl)-1,1- dichloroethene in mink (Mustela vison). Environ Toxicol Chem 18:292-298.
30. Mio T and Sumino K (1985) Mechanism of biosynthesis of methylsulfones from PCBs and related compounds. Environ Health Perspect 59:129-135.
31. Morse DC, Wehler EK, Wesseling W, Koeman JH, and Brouwer A (1996) Alterations in rat brain thyroid hormone status following pre- and postnatal exposure to polychlorinated biphenyls (Aroclor 1254). Toxicol Appl Pharmacol 136:269-279.
32. Öberg M, Sjödin A, Casabona H, Nordgren I, Klasson-Wehler E, and Håkansson 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. Toxicol Sci 70:171-182.
33. Olson JR, Gasiewicz TA, and Neal RA (1980) Tissue distribution, excretion, and metabolism of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the Golden Syrian hamster. Toxicol Appl Pharmacol 56:78-85.
34. Safe SH (1994) Polychlorinated biphenyls (PCBs):environmental impact, biochemical and toxic responses, and implications for risk assessment. Crit Rev Toxicol 24:87-149.
35. Sandau CD, Ayotte P, Dewailly E, Duffe J, and Norstrom RJ (2000) Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian Inuit. Environ Health Perspect 108:611-616.
36. Schuetz EG, Brimer C, and Schuetz JD (1998) Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element. Mol Pharmacol 54:1113-1117.
37. Schuetz EG, Wrighton SA, Safe SH, and Guzelian PS (1986) Regulation of cytochrome P-450p by phenobarbital and phenobarbital-like inducers in adult rat hepatocytes in primary monolayer culture and in vivo. Biochemistry 25:1124-1133.
38. Wroblewski VJ and Olson JR (1988) Effect of monooxygenase inducers and inhibitors on the hepatic metabolism of 2,3,7,8-tetrachlorodibenzo-p-dioxin in the rat and hamster. Drug Metab Dispos 16:43-51.