Metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats

References

• Burka L. T., Plucinski T. M., Macdonald T. L. Mechanisms of hydroxylation by cytochrome P-450: Metabolism of monohalobenzenes by phenobarbital-induced microsomes. Proceedings of the National Academy of Science of the United States of America 1983; 80: 6680–6684
   PubMed Web of Science ®Google Scholar
• Bush E. D., Trager W. F. Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin. Journal of Medicinal Chemistry 1985; 28: 992–996
   PubMed Web of Science ®Google Scholar
• Chen P. R. S., McKinney J. D., Matthews H. B. Metabilism of 2,4,5,2′,5′-pentachl-orobiphenyl in the rat. Drug Metabolism and Disposition 1976; 4: 362–367
   PubMed Web of Science ®Google Scholar
• Colbert L. C., Lacy R. M. The effect of substituent groups upon the course of the condensation reaction between benzenediazonium salts and phenols. Journal of the American Chemical Society 1946; 68: 270–271
   Google Scholar
• Folch J., Lees M., Sloane-Stanley G. H. A simple method for the isolation and purification of total lipids from animal tissues. Journal of Biological Chemistry 1957; 226: 497–509
   PubMed Web of Science ®Google Scholar
• Gardner A. M., Chen J. T., Roach J. A. G., Ragelis E. P. Polychlorinated biphenyls: hydroxylated urinary metabolites of 2,2′,5,5′-tetrachlorobiphenyl identified in rabbits. Biochemical and Biophysical Research Communications 1973; 55: 1377–1384
   PubMed Web of Science ®Google Scholar
• Goldstein J. A., Hickman P., Bergman H., McKinney J. D., Walker M. P. Separation of pure polychlorinated biphenyl isomers into two types of inducers on the basis of induction of cytochrome P-450 or P-448. Chemico-Biological Interaction 1977; 17: 69–87
   PubMed Web of Science ®Google Scholar
• Jackman L. M., Sternhell S. Applications of the chemical shift. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed. Pergamon Press, Oxford 1969; 159
   Google Scholar
• Jerina D. M., Daly J. W. Arene oxide: A new aspect of drug metabolism. Science 1974; 185: 573–582
   PubMed Web of Science ®Google Scholar
• Johansson I., Ingelman-Sundberg M. Hydroxyl radical-mediated, cytochrome P-450-dependent metabolic activation of benzene in microsomes and reconstituted enzyme systems from rabbit liver. Journal of Biological Chemistry 1983; 258: 7311–7316
   PubMed Web of Science ®Google Scholar
• Kato S., McKinney J. D., Matthews H. B. Metabolism of symmetrical hexachlorobi-phenyl isomers in the rat. Toxicology and Applied Pharmacology 1980; 53: 389–398
   PubMed Web of Science ®Google Scholar
• Kuratsune M., Yoshimura T., Matsuzaka J., Yamaguchi A. Epidemiologic study on Yusho, a poisoning caused by ingestion of rice oil contaminated with a commercial brand of polychlorinated biphenyls. Environmental Health Perspectives 1972; 1: 119–128
   PubMedGoogle Scholar
• Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. T. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Nakatsu K., Brien J. F., Taub H., Racz W. J., Marks G. C. Gram quantity synthesis and chromatographic assessment of 3,3′,4,4′-tetrachlorobiphenyl. Journal of Chromatography 1982; 239: 97–106
   Web of Science ®Google Scholar
• Poland A., Glover E. Chlorinated biphenyl induction of aryl hydrocarbon hydroxylase activity: a study of structure-activity relationship. Molecular Pharmacology 1977; 13: 924–938
   PubMed Web of Science ®Google Scholar
• Preston B. D., Miller J. A., Miller E. C. Non-arene oxide aromatic ring hydroxylation of 2,2′,5,5′-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes. Journal of Biological Chemistry 1983; 258: 8304–8311
   PubMed Web of Science ®Google Scholar
• Saeki S., Yoshihara S., Uchino Y., Yoshimura H. Improved method of the synthesis of 3,4,5,3′,4′-pentachlorobiphenyl. Fukuoka Acta Medica 1979; 70: 85–87
   PubMedGoogle Scholar
• Safe S., Hutzinger O., Jones D. The mechanism of chlorobiphenyl metabolism. Journal of Agricultural and Food Chemistry 1975; 23: 851–853
   PubMed Web of Science ®Google Scholar
• Safe S., Jones D., Hutzinger O. Metabolism of 4,4′-dihalobiphenyls. Journal of the Chemical Society: Perkin Transaction I 1976; 357–359
   Google Scholar
• Safe S., Bandiera S., Sawyer T., Robertson L., Safe L., Parkinson A., Thomas P. E., Ryan D. E., Reik L. M., Levin W., Denomme M. A., Fujita T. PCBs: Structure-function relationships and mechanism of action. Environmental Health Perspectives 1985; 60: 47–56
   PubMed Web of Science ®Google Scholar
• Shimada T., Sawabe Y. Activation of 3,4,3′,4′-tetrachlorobiphenyl to protein-bound metabolites by rat liver microsomal cytochrome P-448-containing monooxygenase system. Toxicology and Applied Pharmacology 1983; 70: 486–493
   PubMed Web of Science ®Google Scholar
• Stadnicki S. S., Allen J. R. Toxicity of 2,2′,5,5′-tetrachlorobiphenyl and its metabolites. 2,2′,5,5′-tetrachlorobiphenyl-3,4-oxide and 2,2′,5,5′-tetrachlorobiphenyl-4-ol to cultured cells, in vitro. Bulletin of Environmental Contamination and Toxicology 1979; 23: 788–796
   PubMed Web of Science ®Google Scholar
• Sundstrom G., Hutzinger O., Safe S. The metabolism of chlorobiphenyls—a review. Chemosphere 1976; 5: 267–298
   Web of Science ®Google Scholar
• Tomaszewski J. E., Jerina D. M., Daly J. W. Deuterium isotope effects during formation of phenols by hepatic monooxygenases. Evidence for an alternative to the arene oxide pathway. Biochemistry 1975; 14: 2024–2031
   PubMed Web of Science ®Google Scholar
• Yamamoto H., Yoshimura H. Metabolic studies on polychlorinated biphenyl. III. Complete structure and acute toxicity of the metabolites of 2,4,3′,4′-tetrachlorobiphenyl. Chemical and Pharmaceutical Bulletin 1973; 21: 2237–2242
   PubMed Web of Science ®Google Scholar
• Yoshihara S., Kawano K., Yoshimcra H. Toxicological assessment of highly chlorinated biphenyl congeners retained in the Yusho patients. Chemosphere 1979; 8: 531–538
   Web of Science ®Google Scholar
• Yoshihara S., Nagata K., Yoshimura H., Kuroki H., Masuda Y. Inductive effect on hepatic enzymes and acute toxicity of individual polychlorinated dibenzofuran congeners in rats. Toxicology and Applied Pharmacology 1981; 59: 580–588
   PubMed Web of Science ®Google Scholar
• Yoshimura H., Ozawa N., Saeki S. Inductive effect of polychlorinated biphenyls mixture and individual isomers on the hepatic microsomal enzymes. Chemical and Pharmaceutical Bulletin 1978; 26: 1215–1221
   PubMed Web of Science ®Google Scholar
• Yoshimura H., Yamamoto H. Metabolic studies on polychlorinated biphenyls. I. Metabolic fate of 3,4,3′,4′-tetrachlorobiphenyl in rats. Chemical and Pharmaceutical Bulletin 1973; 21: 1168–1169
   PubMedGoogle Scholar
• Yoshimura H., Yamamoto H. Metabolic studies on polychlorinated biphenyls. IV. Biotransformation of 3,4,3′,4′-tetrachlorobiphenyl, one of the major components of Kanechlor-400. Fukuoka Acta Medica 1974; 65: 5–11
   Google Scholar
• Yoshimura H., Yoshihara S., Ozawa N., Miki M. Possible correlation between induction modes of hepatic enzymes by PCBs and their toxicity in rats. Annals of the New York Academy of Sciences 1979; 320: 179–192
   PubMedGoogle Scholar