Further studies on metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl in rats: Identification of minor metabolites in rat faeces

References

• Bergman A., Brandt I., Jansson B. Accumulation of methylsulfonyl derivatives of some bronchial-seeking polychlorinated biphenyls in the tract of mice. Toxicology and Applied Pharmacology 1979; 48: 213–220
   PubMed Web of Science ®Google Scholar
• Boyd D. R. Oxepanes, oxepins, thiepanes and thiepins. Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. W. Rees. Pergamon Press, New York 1984; vol. 7: 547–592
   Google Scholar
• Brandt I., Darnerud P. O., Bergman A., Larsson Y. Metabolism of 2,4′,5-trichlorobiphenyl: enrichment of hydroxylated and methylsulphone metabolites in the uterine luminal fluid of pregnant mice. Chemico-Biological Interactions 1982; 40: 45–56
   PubMed Web of Science ®Google Scholar
• Darnerud P. O., Brandt I., Klasson-Wehler E., Bergman A., D'Argy R., Dencker L., Sperber G. O. 3,3′,4,4′-Tetrachloro‘14C’biphenyl in pregnant mice: enrichment of phenol and methyl sulphone metabolites in late gestational fetuses. Xenobiotica 1986; 16: 295–306
   PubMed Web of Science ®Google Scholar
• Forgue S. T., Allen J. R. Identification of an arene oxide metabolite of 2,2′,5,5′-tetrachlorobiphenyl by gas chromatography-mass spectroscopy. Chemico-Biological Interactions 1982; 40: 233–245
   PubMedGoogle Scholar
• Goldstein J. A. Structure-activity relationships for the biochemical effects and the relationship to toxicity. Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products, R. D. Kimbrough. Elsevier/North-Holland Biomedical Press. 1980; 152–190
   Google Scholar
• Haraguchi K., Kuroki H., Masuda Y. Capillary gas chromatographic analysis of methylsulphone metabolites of polychlorinated biphenyls retained in human tissues. Journal of Chromatography 1986; 361: 239–252
   PubMedGoogle Scholar
• Jansson B., Sundström G. Mass spectrometry of the methyl ethers of isomeric hydroxychlorobiphenyls—potential metabolites of chlorobiphenyls. Biomedical Mass Spectrometry 1974; 1: 386–392
   PubMedGoogle Scholar
• Kaminsky L. S., Kennedy M. W., Adams S. M., Guengerich F. P. Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry 1981; 20: 7379–7384
   PubMed Web of Science ®Google Scholar
• Kato S., McKinney J. D., Matthews H. B. Metabolism of symmetrical hexachlorobiphenyl 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
• Mills R. A., Mills C. D., Dannan G. A., Guengerich F. P., Aust S. D. Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes. Toxicology and Applied Pharmacology 1985; 78: 96–104
   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
• Pluess H., Poiger H., Schlatter C., Buser H. R. The metabolism of some pentachlorodibenzofurans in the rat. Xenobiotica 1987; 17: 209–216
   PubMed Web of Science ®Google Scholar
• Poiger H., Buser H. R., Schlatter Ch. The metabolism of 2,3,7,8-tetrachlorodibenzofuran in the rat. Chemosphere 1984; 13: 351–357
   Google Scholar
• Preston B. D., Miller J. A., Miller E. C. Non-arene oxide aromatic ring hydroxylation of 2,5,2′,5′-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microcomes. Journal of Biological Chemistry 1983; 258: 8304–8311
   PubMed Web of Science ®Google Scholar
• Reich H. J., Reich I. L., Wollowitz S. Conversion of allyl alcohols to dienes by sulfoxide and selenoxide elimination. Synthesis of PCB arene oxides. Journal of the American Chemical Society 1978; 100: 5981–5982
   Google Scholar
• Safe S. Metabolism, uptake, storage and bioaccumulation. Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products, R. D. Kimbrough. Elsevier/North-Holland Biomedical Press. 1980; 82–107
   Google 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 Transactions 1976; 1: 357–359
   Google Scholar
• Sawahata T., Olson J. R., Neal R. A. Identification of metabolites of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) formed on incubation with isolated rat hepatocytes. Biochemical and Biophysical Research Communications 1982; 105: 341–346
   PubMedGoogle 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
• Shimada T., Sawabe Y., Nakano Y. Interaction of 3,4,3′,4′-tetrachlorobiphenyl metabolites formed by cytochrome P-450 in vitro with rat erythrocytes. Archives of Toxicology 1985; 58: 20–26
   PubMedGoogle Scholar
• Stadnicki S. S., Allen J. R. Toxicity of 2,2′,5,5′-tetrachlorobiphenyl and its metabolites, 2,2′,5,5′-tetrachlorobipheyl-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
• Sundström G., Hutzinger O., Safe S. The metabolism of chlorobiphenyls—a review. Chemosphere 1976; 5: 267–298
   Web of Science ®Google Scholar
• Tulp M. Th. M., Olie K., Hutzinger O. Identification of hydroxyhalobiphenyls as their methyl ethers by gas chromatography mass spectrometry. Biomedical Mass Spectrometry 1977; 4: 310–316
   PubMedGoogle 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
• 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 Kanechior-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 Science 1979; 320: 179–192
   PubMedGoogle Scholar
• Yoshimura H., Yonemoto Y., Yamada H., Koga N., Oguri K., Saeki S. Metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats. Xenobiotica 1987; 17: 897–910
   PubMed Web of Science ®Google Scholar