Metabolic activation of o-phenylphenol to a major cytotoxic metabolite, phenylhydroquinone: role of human CYP1A2 and rat CYP2C11/CYP2E1

References

• BUTLER, M. A., LANG, N. P., YOUNG, J. F., CAPORASO, N. E., VINEIS, P., HAYES, R. B., TEITEL, C. H., MASSENGILL, J. P., LAWSEN, M. F. and KADLUBAR, F. F., 1992, Determination of CYP1A2 and NAT2 phenotypes in human populations by analysis of caffeine urinary metabolites. Pharmaco-genetics, 2, 116–127.
   PubMedGoogle Scholar
• GOEPTAR, A. R., SCHEERENS, H. and VERMEULEN, N. P. E., 1995, Oxygen and xenobiotic reductase activities of cytochrome P450. Critical Reviews in Toxicology, 25, 25–65.
   PubMed Web of Science ®Google Scholar
• HALPAAP-WOOD, K., HORNING, E. C. and HORNING, M. G., 1981, The effect of phenobarbital and fl-naphthoflavone induction on the metabolism of biphenyl in the rat and mouse. Drug Metabolism and Disposition, 9, 97–102.
   Google Scholar
• HASEGAWA, R., FUKUOKA, M., TAKAHASHI, T., YAMAMOTO, A., YAMAGUCHI, S., SHIBATA, M.-A., TANAKA, A. and FUKUSHIMA, S., 1991, Sex difference in o-phenylphenate rat urinary bladder carcinogenesis : urinary metabolites and electrolytes under conditions of aciduria and alkaliuria. Japanese Journal of Cancer Research, 82, 657–664.
   Google Scholar
• HIRAGA, K. and Fuji', T., 1981, Induction of tumours of the urinary system in F344 rats by dietary administration of sodium o-phenylphenate. Food and Cosmetic Toxicology, 19, 303–310.
   Google Scholar
• HODGE, H. C., MAYNARD, E. A., BLANCHET, H. J., JR, SPENCER, H. C. and ROWE, V. K., 1952, Toxicological studies of orthophenylphenol (Dowcide 1). Journal of Pharmacology and Ex-perimental Therapeutics, 104, 202–210.
   Google Scholar
• ITAGAKI, H., SHIBATA, M., TANI, N., KINOSHITA, S., KAKISHIMA, H., SEYAMA, Y OHUCHI, J., KASAI, Y OKADA, J., KOJIMA, H., OKAMOTO, Y KOTANI, M., OHNO, Y MIYAJIMA, A., TAKANAKA, A., 1995, First-phase inter-laboratory validation of the in vitro eye irritation tests for cosmetic ingredients. X-Evaluation of cytotoxicity tests on SIRC cells. AATEX, 3, 201–209.
   Google Scholar
• LAMBERT, A. C. and EASTMOND, D. A., 1994, Genotoxic effects of the o-phenylphenol metabolites phenylhydroquinone and phenylbenzoquinone in V79 cells. Mutation Research, 322, 243–256.
   PubMed Web of Science ®Google Scholar
• LIGHTFOOT, T., ELLIS, S. W., MAHLING, J., ACKLAND, M. J., BLANEY, F. E., Bipoo, G. J., DE GROOT, M. J., VERMEULEN, N. P., BLACKBURN, G. M., LENNARD, M. S. and TUCKER, G. T., 2000, Regioselective hydroxylation of debrisoquine by cytochrome P4502D6: implications for active site modelling. Xenobiotica, 30, 219–233.
   PubMed Web of Science ®Google Scholar
• LUSTER, M. I., DEAN, J. H., BOORMAN, G. A., ARCHER, D. L., LAUER, L., LAWSON, L. D., MOORE, J. A. and WILSON, R. E., 1981, The effect of orthophenylphenol, tris(2,3-dichloroporpyl)phosphate, and cyclophosphamide on the immune system and host susceptibility of mice following subchronic exposure. Toxicology and Applied Pharmacology, 58, 252–261.
   PubMed Web of Science ®Google Scholar
• MINCHIN, R. F., McMANus, M. E., BOOBIS, A. R., DAVIES, D. S. and THORGEIRSSON, S. S., 1985, Polymorphic metabolism of the carcinogen 2 -acetylaminofluorene in human liver microsomes. Carcinogenesis, 6, 1721–1724.
   PubMed Web of Science ®Google Scholar
• MORIMOTO, K., FUKUOKA, M., HASEGAWA, R., TANAKA, A., TAKAHASHI, A. and HAYASHI, Y .,1987, DNA damage in urinary bladder epithelium of male F344 rats treated with 2-phenyl-1,4-benzoquinone, one of the non-conjugated urinary metabolites of sodium o-phenylphenate. Japanese Journal of Cancer Research (Gann), 78, 1027–1030.
   Google Scholar
• MORIMOTO, K., SATO, M., FUKUOKA, M., HASEGAWA, R., TAKAHASHI, T., TSUCHIYA, T., TANAKA, A., TAKAHASHI, A. and HAYASHI, Y., 1989, Correlation between the DNA damage in urinary bladder epithelium and the urinary 2-phenyl-1,4-benzoquinone levels from F344 rats fed sodium o-phenylphenate in the diet. Carcinogenesis, 10, 1823–1827.
   PubMed Web of Science ®Google Scholar
• MURATA, M., MORIYA, K., INouE, S. and KAWANISHI, S., 1999, Oxidative damage to cellular and isolated DNA by metabolites of a fungecide ortho-phenylphenol. Carcinogenesis, 20, 851–857.
   PubMed Web of Science ®Google Scholar
• NAGAI, F., USHIYAMA, K., SATOH, K. and KANO, I., 1990, DNA cleavage by phenylhydroquinone: the major metabolite of a fungicide o-phenylphenol. Chemico-Biological Interactions, 76, 163–179.
   PubMed Web of Science ®Google Scholar
• NAGAI, F., USHIYAMA, K., SATOH, K., KASAI, H. and KANO, I., 1995, Formation of 8-hydroxy-deoxyguanosine in calf thymus DNA treated in vitro with phenylhydroquinone, the major metabolite of o-phenylphenol. Carcinogenesis, 16, 837–840.
   PubMed Web of Science ®Google Scholar
• NAKAJIMA, M., KOBAYASHI, K., OSHIMA, K., SHIMADA, N., TOKUDOME, S., CHIBA, K. and YOKOI, T., 1999, Activation of phenacetin o-deethylase activity by a -naphthoflavone in human liver microsomes. Xenobiotica, 29, 885–898.
   PubMed Web of Science ®Google Scholar
• NAKAJIMA, M., YOKOI, T., MIZUTANI, M., SHIN, S., KADLUBAR, F. F. and KAMATAKI, T., 1994, Phenotyping of CYP1A2 in Japanese population by analysis of caffeine urinary metabolites: absence of mutation prescribing the phenotype in the CYP1A2 gene. Cancer Epidemiology Biomarkers Prevention, 3, 413–421.
   PubMed Web of Science ®Google Scholar
• OHNO, Y., MIYAJIMA, A. and SUNOUCHI, M., 1998, Alternative methods for mechanistic studies in toxicology. Screening of hepatotoxicity of pesticides using freshly isolated and primary cultured hepatocytes and non-liver-derived cells, SIRC cells. Toxicology Letters, 102–3, 569–573.
   Google Scholar
• ONO, S., HATANAKA, T., HOTTA, H., SATOH, T., GONZALEZ, F. J. and TSUTSUI, M., 1996, Specificity of substrate and inhibitor probes for cytochrome P45 Os: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica, 26, 681–693.
   PubMed Web of Science ®Google Scholar
• RYAN, D. E., THOMA, P. E., LEVIN, W., MAINES, S. L., BANDIERA, S. and REIK, L. M., 1993, Monoclonal antibodies of differentiating specificities as probes of cytochrome P450h (2C11). Archives in Biochemistry and Biophysics, 301, 282–293.
   PubMed Web of Science ®Google Scholar
• SASAKI, Y. F., SAGA, A., AKASAKA, M., YOSHIDA, K., NISHIDATE, E., Su, Y. Q., MATSUSAKA, N. and TSUDA, S., 1997, In vivo genotoxicity of ortho- phenylphenol, biphenyl, and thiabendazole detected in multiple mouse organs by the alkaline single cell gel electrophoresis assay. Mutation Research, 395, 189–198.
   PubMed Web of Science ®Google Scholar
• SHIMADA, T., YAMAZAKI, H., MIMURA, M., WAKAMIYA, N., UENG, Y.-F., GUENGERICH, F. P. and INui, Y., 1996, Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs. Drug Metabolism and Disposition, 24, 515–522.
   Google Scholar
• SUGIHARA, N., Smmomicm, K. and FURUNO, K., 1997, Cytotoxicity of food preservatives in cultured rat hepatocytes loaded with linolenic acid. Toxicology, 120, 29–36.
   PubMed Web of Science ®Google Scholar
• TAYAMA, S. and NAKAGAWA, Y.,1994, Effect of scavengers of active oxygen species on cell damage caused in CHO-K1 cells by phenylhydroquinone, an o-phenylphenol metabolite. Mutation Research, 324, 121–131.
   Google Scholar
• TERAMURA, T., FUKUNAGA, Y., VAN HOOGDALEM, E. J., WATANABE, T. and HIGUCHI, T., 1997, Examin-ation of metabolic pathways and identification of human liver cytochrome P450 isozymes responsible for the metabolism of barnidipine, a calcium channel blocker. Xenobiotica, 27, 885–900.
   PubMed Web of Science ®Google Scholar
• USHIYAMA, K., NAGAI, F., NAKAGAWA, A. and KANO, I., 1992, DNA adduct formation by o-phenylphenol metabolite in vivo and in vitro. Carcinogenesis, 13, 1469–1473.
   PubMed Web of Science ®Google Scholar