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Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 8
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Research Article

The metabolism of benzo(a)pyrene by English sole (Parophrys vetulus): comparison between isolated hepatocytes in vitro and liver in vivo

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Pages 949-961 | Received 17 Dec 1991, Accepted 30 Apr 1992, Published online: 22 Sep 2008

References

  • Ashurst S. W., Cohen G. M. A benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide is the major metabolite involved in the binding of benzo(a)pyrene to DNA in isolated viable rat hepatocytes. Chemico-Biological Interactions 1980; 29: 117–127
  • Baird W. M., Diamond L. Effect of 7,8-benzoflavone on the formation of benzo(a)pyrene-DNA-bound products in hamster embryo cells. Chemico-Biological Interactions 1977; 13: 67–75
  • Baird W. M., Smolarek T. A., Plakunov I., Hevizi K., Kelley J., Klaunig J. Formation of benzo(a)pyrene-7,8-dihydriol glucuronide is a major pathway of metabolism of benzo(a)pyrene in cell cultures from bluegill fry and brown bullhead. Aquatic Toxicology 1988; 11: 398
  • Bevan D. R., Sadler V. M. Quinol diglucuronides are predominant conjugated metabolites found in bile of rats following intratracheal instillation of benzo(a)pyrene. Carcinogenesis 1992; 13: 403–407
  • Billings R. E., McMahon R. E., Ashmore J., Wagle S. R. The metabolism of drugs in isolated rat hepatocytes. A comparison with in vivo drug metabolism and drug metabolism in subcellular liver fractions. Drug Metabolism and Disposition 1977; 5: 518–526
  • Collier T. K., Stein J. E., Wallace R. J., Varanasi U. Xenobiotic metabolizing enzymes in spawning English sole (Parophrys vetulus) exposed to organic-solvent extracts of marine sediments from contaminated and reference areas. Comparative Biochemistry and Physiology 1986; 84C: 291–298
  • Dipple A., Moschel R. C., Bigger C. A. H. Polynuclear Aromatic Carcinogens. Chemical Carcinogens, C. E. Searle. American Chemical Society, Washington, DC 1984; vol. 1: 41–163
  • Dock L., Cha Y.-N., Jernstrom B., Moldeus P. Effects of 2(3)-tertbutyl-4-hydroxyanisole on benzo(a)pyrene metabolism and DNA-binding of benzo(a)pyrene metabolites in isolated mouse hepatocytes. Chemico-Biological Interactions 1982; 41: 25–37
  • Gmur D. J., Varanasi U. Characterization of benzo(a)pyrene metabolites isolated from muscle, liver, and bile of a juvenile flatfish. Carcinogenesis 1982; 3: 1397–1403
  • Guillouzo A. Liver Cells and Drugs. John Libbey Eurotext, London 1988
  • Gupta R. C., Randerath K. Analysis of DNA adducts by 32P-labeling and thin layer chromatography. DNA Repair, E. C. Friedberg, P. H. Hanawalt. Marcel Dekker, New York 1988; 399–418
  • Jankowiak R., Small Lu P., Nishimoto G. J., Varanasi M. U., Kim S. K., Geacintov N. E. Fluorescence line-narrowing spectrometry: a versatile tool for the study of chemically initiated carcinogenesis. Journal of Pharmaceutical and Biomedical Analysis 1990; 8: 113–121
  • Jones C A., Moore B. P., Cohen G. M., Fry J. R., Bridges J. W. Studies on the metabolism and excretion of benzo(a)pyrene in isolated adult rat hepatocytes. Biochemical Pharmacology 1978; 27: 693–702
  • Layiwola P. J., Linnecar D. F. C., Knights B. The biotransformation of three 14C-labelled phenolic compounds in twelve species of freshwater fish. Xenobiotica 1983; 13: 107–113
  • Malins D. C., Krahn M. M., Myers M. S., Rhodes L. D., Brown D. W., Krone C. A., McCain B. B., Chan S.-L. Toxic chemicals in sediments and biota from a creosote-polluted harbor: relationships with hepatic neoplasms and other hepatic lesions in English sole (Parophrys vetulus). Carcinogenesis 1985; 6: 1463–1469
  • Meerman J. H. N., Sterenborg H. M. J., Mulder G. J. Use of pentachlorophenol as long-term inhibitor of sulfation of phenols and hydroxamic acids in the rat, in vivo. Biochemical Pharmacology 1983; 32: 1587–1593
  • Meerman J. H. N., Nijland C., Mulder G. J. Sex differences in sulfation and glucuronidation of phenol, 4-nitrophenol and N-hydroxy-2-acetylaminofluorene in the rat, in vivo. Biochemical Pharmacology 1987; 36: 2605–2608
  • Moon T. W., Walsh P. J., Mommsen T. P. Fish hepatocytes: a model metabolic system. Canadian Journal of Fisheries and Aquatic Sciences 1985; 42: 1772–1782
  • Myers M. S., Olson O. P., Johnson L. L., Stehr C. S., Hom T., Varanasi U. Hepatic lesions other than neoplasms in subadult flatfish from Puget Sound, WA; relationships with indices of contaminant exposure. Marine Environmental Research 1992, In press
  • Myers M. S., Rhodes L. D., McCain B. B. Pathologic anatomy and patterns of occurrence of hepatic neoplasms, putative preneoplastic lesions, and other idiopathic hepatic conditions in English sole (Parophrys vetulus) from Puget Sound, Washington. Journal of the National Cancer Institute 1987; 78: 333–363
  • Nagel R., Urich K. Quinol sulphate, a new conjugate of phenol in goldfish. Xenobiotica 1983; 13: 97–100
  • Nishimoto M. Metabolism of benzo(a)pyrene by English sole, starry flounder, and rat. University of Washington. 1986, Ph.D. dissertation 1986
  • Nishimoto M., Varanasi U. Benzo(a)pyrene metabolism and DNA adduct formation mediated by English sole liver enzymes. Biochemical Pharmacology 1985; 34: 263–268
  • Nishimoto M., Varanasi U. Metabolism and DNA adduct formation of benzo(a)pyrene and the 7,8-dihydrodiol of benzo(a)pyrene by fish liver enzymes. Polynuclear Aromatic Hydrocarbons: Ninth International Symposium on Chemistry, Characterization and Carcinogenesis. Battelle Press, Columbus, OH 1986; 685–699
  • Nishimoto M., Yanagida G. K., Stein J. E., Varanasi U. The metabolism of benzo(a)pyrene by isolated hepatocytes of English sole (Parophrys vetulus), in. Proceedings of the Puget Sound ′91 Meeting 1991; 2: 774
  • Plakunov I., Smolarek T. A., Fischer D. L., Wiley J. C. J., Baird W. M. Separation by ion-pair high-performance liquid chromatography of the glucuronide, sulfate and glutathione conjugates formed from benzo(a)pyrene in cell cultures from rodents, fish and humans. Carcinogenesis 1987; 8: 59–66
  • Plummer J. L., Smith B. R., Ball L. M., Bend J. R. Metabolism and biliary excretion of benzo(a)pyrene 4,5-oxide in the rat. Drug Metabolism and Disposition 1980; 8: 68–72
  • Rauckman E. J., Padilla G. M. The Isolated Hepatocyte: Use in Toxicology and Xenobiotic Biotransformation. Academic Press, Orlando, FL 1987
  • Reichert W. L., French B. L., Stein J. E., Varanasi U. 32P-Postlabeling analysis of the persistence of bulky hydrophobic xenobiotic-DNA adducts in liver of English sole (Parophrys vetulus), in. Proceedings of the 82nd Annual Meeting of the American Association of Cancer Research 1991; 32: 87
  • Schiewe M. H., Weber D. D., Myers M. S., Jacques F. J., Reichert W. L., Krone C. A., Malins D. C., McCain B. B., Chan S.-L., Varanasi U. Induction of foci of cellular alteration and other hepatic lesions in English sole (Parophrys vetulus) exposed to an extract of an urban marine sediment. Canadian Journal of Fisheries and Aquatic Science 1991; 48: 1750–1760
  • Schwarz L. R., Schwenk M. Sulfation in isolated enterocytes of guinea pig: dependence on inorganic sulfate. Biochemical Pharmacology 1984; 33: 3353–3356
  • Schwenk M., Locher M. 1-Naphthol conjugation in isolated cells from liver, jejunum, ileum, colon and kidney of the guinea pig. Biochemical Pharmacology 1985; 34: 697–701
  • Shen A. L., Fahl W. E., Jefcoate C. R. Metabolism of benzo(a)pyrene by isolated hepatocytes and factors affecting covalent binding of benzo(a)pyrene metabolites to DNA in hepatocytes and microsomal systems. Archives of Biochemistry and Biophysics 1980; 204: 511–523
  • Shugart L., McCarthy J., Jiminez B., Daniels J. Analysis of adduct formation in the bluegill sunfish (Lepomis macrochirus) between benzo(a)pyrene and DNA of the liver and hemoglobin of the erythrocyte. Aquatic Toxicology 1987; 9: 319–325
  • Smolarek T. A., Baird W. M., Morgan S., Ferin M., Nishimoto M., Stein J. E., Varanasi U., Klaunig J. Metabolic activation of benzo(a)pyrene (BaP) to DNA-binding metabolites in primary hepatocyte cultures from fish. Proceedings of the 79th Annual Meeting of the American Association of Cancer Research 1988; 29: 94
  • Smolarek T. A., Morgan S. L., Moynihan C. G., Lee H., Harvez R. G., Baird W. M. Metabolism and DNA adduct formation of benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene in fish cell lines in culture. Carcinogenesis 1987; 8: 1501–1509
  • Stein J. E., Hom T., Casillas E., Friedman A., Varanasi U. Simultaneous exposure of English sole (Parophrys vetulus) to sediment-associated xenobiotics: Part II. Chronic exposure to an urban estuarine sediment with added [3H]benzo(a)pyrene and [14C]polychlorinated biphenyls. Marine Environmental Research 1987; 22: 123–149
  • Stein J. E., Collier T. K., Reichert W. L., Casillas E., Hom T., Varanasi U. Bioindicators of contaminant exposure and sublethal effects: Studies with benthic fish in Puget Sound, WA. Environmental Toxicology and Chemistry 1992; 11: 701–714
  • Steward A. R., Zaleski J., Sikka H. C. Metabolism of benzo(a)pyrene and (-) trans-benzo(a)pyrene-7,8-dihydrodiol by freshly isolated hepatocytes of brown bullheads. Chemico-Biological Interactions 1990; 74: 119–138
  • Varanasi U., Nishimoto M., Reichert W. L., Eberhart B.-T. L. Comparative metabolism of benzo(a)pyrene and covalent binding to hepatic DNA in English sole, starry flounder, and rat. Cancer Research 1986; 46: 3817–3824
  • Varanasi U., Nishimoto M., Baird W. M., Smolarek T. A. Metabolic activation of PAH in subcellular fractions and cell cultures from aquatic and terrestrial species. Metabolism of Polycyclic Aromatic Hydrocarbons in the Aquatic Environment, U. Varanasi. CRC Press, Boca Raton, FL 1989a; 203–251
  • Varanasi U., Reichert W. L., Eberhart B.-T. L., Stein J. E. Formation and persistence of benzo(a)pyrene-diolepoxide-DNA adducts in liver of English sole (Parophrys vetulus). Chemico-Biological Interactions 1989b; 69: 203–216
  • Varanasi U., Stein J. E., Nishimoto M. Biotransformation and disposition of polycyclic aromatic hydrocarbons (PAH) in fish. Metabolism of Polycyclic Aromatic Hydrocarbons in the Aquatic Environment, U. Varanasi. CRC Press, Boca Raton, FL 1989c; 94–149
  • Zaleski J., Bansal S. K., Gessner T. Formation of glucuronide, sulphate and glutathione conjugates of benzo(a)pyrene metabolites in hepatocytes isolated from inbred strains of mice. Carcinogenesis 1983; 4: 1359–1366
  • Zaleski J., Steward A. R., Sikka H. C. Metabolism of benzo(a)pyrene and (-)-trans-benzo(a)pyrene-7,8-dihydrodiol by freshly isolated hepatocytes from mirror carp. Carcinogenesis 1991; 12: 167–174

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