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Xenobiotica
the fate of foreign compounds in biological systems
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Research Article

Metabolism of 2-nitrofluorene, an environmental pollutant, by liver preparations of sea bream, Pagrus major

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Pages 667-682 | Published online: 22 Sep 2008

References

  • BAGNASCO, M., CAMOIRANO, A., DE FLORA, S., MELODIA, F. and ARILLO, A., 1991, Enhanced liver metabolism of mutagens and carcinogens in fish living in polluted seawater. Mutation Research, 262, 129–137.
  • BEND, J. R. and JAMES, M., 1978, Xenobiotic metabolism in marine and freshwater species. In D. C. Malins and J. A. Sargent (eds), Biochemical and Biophysical Perspectives in Marine Biology, vol. 4 (New York: Academic Press), pp. 125–188.
  • BIELSCHOWSKY, F., 1945, A metabolite of 2-acetamidofluorene. Biochemical Journal, 39, 287–289.
  • BEIJE, B. and MOLLER, L., 1988, 2-Nitrofluorene and related compounds: prevalence and biological effects. Mutation Research, 196, 177–209.
  • BINDER, R. L., MELANCON, M. J. and LECH, J. J., 1984, Factors influencing the persistence and metabolism of chemicals in fish. Drug Metabolism Reviews, 15, 697–724.
  • BUHLER, D. R. and RASMUSSON, M. E., 1968, Reduction of p-nitrobenzoic acid by fishes. Archives of Biochemistry Biophysics, 103, 582–595.
  • BUHLER, D. R. and WANG-BUHLER, J. L., 1998, Rainbow trout cytochrome P450: purification, molecular aspects, metabolic activity, induction and role in environmental monitoring. Comparative Biochemistry and Physiology, 121C, 107–138.
  • CAMPBELL, R. M. and MILTON, L. L., 1984, Capillary column gas chromatographic determination of nitro polycyclic aromatic compounds in particulate extracts. Analytical Chemistry, 56, 1026–1030.
  • Cui, X.-S., ERIKSSON, L. C. and MOLLER, L., 1999, Formation and persistence of DNA adducts during and after a long-term administration of 2-nitrofluorene. Mutation Research, 442, 9–18.
  • EL-BAYOUMY, K., HECHT, S. S. and HOFFMANN, D., 1982, Comparative tumor initiating activity on mouse skin of 6-nitrobenzo[a]pyrene, 6-nitrochrysene, 3-nitroperylene, 1-nitropyrene and their parent hydrocarbons. Cancer Letters, 16, 333–337.
  • Fu, P. P., 1990, Metabolism of nitro-polycyclic aromatic hydrocarbons. Drug Metabolism Reviews, 22, 209–268.
  • GOKSOYR, A., 1995, Use of cytochrome P450 1A (CYP1A) in fish as a biomarker of aquatic pollution. Archives of Toxicology Supplement, 17, 80–95.
  • GRONDEL, J. L., Nouws, J. F. M. and HAENEN, L. M., 1986, Fish and antibiotics: Pharmacokinetics of sulphadimidine in carp (Cyprinus carpio). Veterinary Immunology and Immunopathology, 2, 281–286.
  • HAYAKAWA, K., MURAHASHI, T., BUTOH, M. and MIYAZAKI, M., 1995, Determination of 1,3-, 1,6-, and 1,8-dinitropyrenes and 1-nitropyrene in urban air by high-performance liquid chromatography using chemiluminescence detection. Environmental Science and Technology, 29, 928–932.
  • HEYMANN, E. and MENTLEIN, R., 1988, Identification, localization and specificity of detoxifying hydrolases in rat tissues. In J. W. Gorrod, H. Oelschläger and J. Caldwel (eds), Metabolism of Xenobiotics (London: Taylor & Francis), pp. 189–197.
  • HITCHCOCK, M. and MURPHY, S. D., 1966, Reduction of parathion, paraoxon and EPN by tissues of mammals, birds and fishes. Federation Proceedings, 25, 687.
  • HUANG, K. C. and COLLINS, S. F., 1962, Conjugation and excretion of aminobenzoic acid isomers in marine fishes. Journal of Cellular and Comparative Physiology, 60, 49–52.
  • JOHN, D. G., 1967, Human liver aldehyde oxidase: Differential inhibition of oxidation charged and uncharged substrates. Journal of Clinical Investigation, 46, 1492–1505.
  • KITAMURA, S., NARAI, N., HAYASHI, M. and TATSUMI, K., 1983, Rabbit liver enzymes responsible for reduction of nitropolycyclic aromatic hydrocarbons. Chemical and Pharmaceutical Bulletin, 31, 776–779.
  • KITAMURA, S. and TATSUMI, K., 1996, Metabolism in vivo of 1-nitropyrene, an enironmental pollutant, in fish. Biological and Pharmaceutical Bulletin, 19, 1524–1526.
  • KITAMURA, S. and TATSUMI, K., 1997b, 1-Nitropyrene-metabolizing activities of fish liver preparations. Bulletin of Environmental Contamination and Toxicology, 58, 448–455.
  • KITAMURA, S. and TATSUMI, K., 1997a, Purification of NADPH-linked and NADH-linked quinone reductases from liver cytosol of sea bream, Pagrus major. Comparative Biochemistry and Physiology, 118B, 675–680.
  • LEWIS, D. F., 1996, Cytochromes P450: Structure, Function and Mechanism (London: Taylor & Francis). LIVINGSTONE, D. R., 1998, The fate of organic xenobiotics in aquatic ecosystems: quantitative and qualitative differences in biotransformation by invertebrates and fish. Comparative Biochemistry and Physiology, 120A, 43–49.
  • LIVINGSTONE, D. R. and GOLDFAB, P. S., 1998, Aquatic environmental biomonitoring: Use of cytochrome P450 1A and other molecular biomarkers in fish and mussels. In J. Lynch and A. Wiseman (eds), Environmental Biomonitoring, vol. 6: The Biotechnology Ecotoxicology Interface (Cambridge: Cambridge University Press), pp. 101–129.
  • LOTLIKAR, P. D., MILLER, E. C., MILLER, J. A. and HALVER, J. E., 1967, Metabolism of the carcinogen 2-acetylaminofluorene by rainbow trout. Proceedings of the Society for Experimental Biology Medicine, 124, 160–163.
  • LOWRY, H., ROSEBROUGH, N. J., FAR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
  • MANABE, Y., KINOUCHI, Y., WAKISAKA, K., TAHARA, I. and OHNISHI, Y., 1984, Mutagenic 1-nitropyrene in wastewater from oil-water separating tanks of gasoline stations and in used crankcase oil. Environmental Mutagenesis, 6, 669–681.
  • MizmtAmi, M., OKAucm, M., ARIYOSHI, T. and KITO, H., 1994, The isolation and sequence of cDNA encoding a 3-methylcholanthrene-inducible cytochrome P450 from wild red sea bream. Pagrus major. Marine Biology, 120, 343–349.
  • MOLLER, L., RAFTER, J. and GUSTAFSSON, J.-A., 1987, Metabolism of the carcinogenic air pollutant 2-nitrofluorene in the rat. Carcinogenesis, 8, 637–645.
  • MOLLER, L., TORNDAL., U.-B., ERIKSSON, L. C. and GUSTAFSSON, J.-À., 1989, The air pollutant 2-nitrofluorene as initiator and promoter in a liver model for chemical carcinogenesis. Carcinogenesis, 10, 435–440.
  • MOLLER, L., ZEISIG, M., MIDTVED T. and GUSTAFSSON, J.-A., 1994, Intestinal microflora enhances formation of DNA adducts following administration of 2-NF and 2-AAF. Carcinogenesis, 15, 857–861.
  • PUROHIT, V. and Rasu, A. K., 2000, Mutagenicity of nitroaromatic compounds. Chemical Research in Toxicology, 13, 673–692.
  • ROSENKRANZ, H. S. and MERMELSTEIN, R., 1983, Mutagenicity and genotoxicity of nitroarenes. All nitro-containing chemicals were not created equal. Mutation Research, 114, 217–267.
  • SCHLENK, D., 1998, Occurrence of flavin-containing monooxygenases in non-mammalian eukaryotic organisms. Comparative Biochemistry and Physiology, 121C, 185–195.
  • SEN, A. and ARINC, E., 1997, Separation of three P450 isozymes from liver microsomes of gilthead seabrearn treated with fi-NF and partial purification of cytochrome P4501A1. Biochemistry and Molecular Biology International, 41, 131–141.
  • STEGEMAN, J. J. and HAHN, M. E., 1994, Biochemistry and molecular biology of monooxygenases: current perspectives on forms, functions, and regulation of cytochrome P450 in aquatic species. In D. C. Malins and G. K. Ostrander (eds), Aquatic Toxicology: Molecular, Biochemical, and Cellular Perspectves (Florida: Lewis), pp. 87–206.
  • STEGEMAN, J. J., 1981, Polynuclear aromatic hydrocarbons and their metabolism in the marine environment. Polycyclic Hydrocarbons and Cancer, 3, 1–60.
  • TATSUMI, K. and AMANO, H., 1987, Biotransformation of 1-nitropyrene and 2-nitrofluorene to novel metabolites, the corresponding formylamino compounds, in animal bodies. Biochemical and Biophysical Research Communications, 142, 376–382.
  • TATSUMI, K., KITAMURA, S., AMANO, H. and UEDA, K., 1989, Comparative study on metabolic formation of N-arylformamides and N-arylacetamides from carcinogenic arylamines in mammalian species. Cancer Research, 49, 2059–2064.
  • TATSUMI, K., KITAMURA, S., KATo, M. and HIRAOKA, K., 1992, Metabolism of sodium nifurstyrenate, a veterinary antimicrobial nitrofuran, in animals and fish. Drug Metabolism and Disposition, 20, 226–233.
  • TATSUMI, K., KIRAMURA, S. and NARAI, N., 1986, Reductive metabolism of aromatic nitro compounds including carcinogens by rabbit liver preparations. Cancer Research, 46, 1089–1093.
  • UEDA,, KITAMURA, S., HURUSE, Y., SAITO, T., KANZAKI, Y., YANO, Y., KANZAKI, Y., TATSUMI, K. and OHTA, S., 2001b, Metabolism of 2-nitrofluorene, an environmental pollutant, and 2-acetylaminofluorene in fish. Bulletin of Environmental Contamination and Toxicology, 66, 371–378.
  • UEDA,, KITAMURA, S., KUBO, R., Yo, Y., KANZAKI, Y., FUJIMOTO, T. TATSUMI, K. and OHTA, S. 2001a, Metabolism of 2-nitrofluorene, 2-aminofluorene and 2-acylaminofluorenes in rat and dog and the role of intestinal bacteria. Xenobiotica, 31, 33–49.
  • UEDA,, KITAMURA, S. and TATSUMI, K., 1996, Further metabolism of 2-formylaminofluorene, a metabolite of 2-aminofluorene, in rats. Biological and Pharmaceutical Bulletin, 19, 330–333.
  • WANG, C. Y., LEE, M. S., KING, C. M. and WARNER, P., 1980, Evidence for nitroaromatics as directacting mutagens of airborne particulates. Chemosphere, 9, 83–87.
  • WEBER, W. W. and HEIN, D. C., 1985, N-acetylation pharmacogenetics. Pharmacological Reviews, 37, 25–79.
  • WEISBURGER, E. K. and WEISBURGER, J. H., 1955, 2-Acetylamino-5-hydroxyfluorene, a metabolite of the carcinogen 2-acetylaminofluorene. Journal of Organic Chemistry, 20, 1396–1401.

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