Drug toxicity mechanisms in human hepatoma HepG2 cells: cyclosporin A and tamoxifen

References

• Anderson R., Van Rensburg C. E. J., Myer M. S. α-Tocopherol prevents cyclosporin A-mediated activation of phospholipase A2 and inhibition of Na+K+ -adenosine triphosphatase activity in cultured hamster renal tubular cells. Toxicology Applied Pharmacology 1994; 125: 176–183
   PubMedGoogle Scholar
• Anuforo D. C., Acosta D., Smith R. V. Hepatotoxicity studies with primary cultures of rat liver cells. In Vitro 1978; 14: 981–988
   PubMedGoogle Scholar
• APBI Data Sheet Compendium. Datapharm Publications Ltd, London 1994
   Google Scholar
• Archakov A. I., Bachmanova G. I. Cytochrome P450 and active oxygen. Taylor & Francis, London 1990
   Google Scholar
• Aust S. D., Roerig D. L., Pedersen T. C. evidence for superoxide generation by NADPH-cytochrome P450 reductase of rat liver microsomes. Biochemical and Biophysical Research Communications 1972; 47: 1133–1137
   PubMed Web of Science ®Google Scholar
• Bäckman L., Appelkvist E. L., Sundberg A., Teclebrhan H., Brunk U. Modulation of metabolism in HepG2 cells upon treatment with cyclosporin A and NVa2-cyclosporin. Experimental and Molecular Pathology 1991; 54: 242–254
   PubMed Web of Science ®Google Scholar
• Barth S. A., Inselmann G., Engemann R., Heidemann H. T. Influences of Ginkgo biloba on cyclosporin A-induced lipid peroxidation in human liver microsomes in comparison to vitamin E, glutathione and N-acetylcysteine. Biochemical Pharmacology 1991; 41: 1521–1526
   PubMed Web of Science ®Google Scholar
• Bernheim F., Bernheim M. L. C., Wilburn K. M. The reaction between thiobarbituric acid and the oxidation products of certain lipids. Journal of Biological Chemistry 1948; 174: 257–264
   PubMed Web of Science ®Google Scholar
• Blackburn A. M., Amiel S. A., Millis R. R., Rubens R. D. Tamoxifen and liver damage. British Medical Journal 1984; 289: 288
   PubMed Web of Science ®Google Scholar
• Bouis P., Brouillard J. F., Fischer V., Donatsch P., Bolsterli U. A. Effect of enzyme induction on Sandimmun (cyclosporin A) biotransformation and hepatotoxicity in cultured rat hepatocytes and. in vivo. Biochemical Pharmacology 1990; 39: 257–266
   PubMed Web of Science ®Google Scholar
• Breast Committee Cancer Trials. Adjuvant tamoxifen in the management of operable breast cancer: the Scottish trial. Lancet 1987; i: 171–175
   Google Scholar
• Brown M. W., Maldonado A. L., Meredith C. G., Speeg K. V. Effect of ketoconazole on hepatic oxidative drug metabolism. Clinical Pharmacology and Therapeutics 1985; 37: 290–297
   PubMed Web of Science ®Google Scholar
• Burke M. D., MacIntyre F., Cameron D., Whiting P. H. Cyclosporin A metabolism and drug interactions. Cyclosporin: Mode of Action and Clinical Applications, A. W. Thompson. Kluwer, Dordrecht 1989; 207–302
   Google Scholar
• Burke M. D., Vadi H., Jernstrom B., Orrenius S. Metabolism of benzopyrene with isolated hepatocytes and the formation and degradation of DNA-binding derivatives. Journal of Biological Chemistry 1977; 252: 6424–6431
   PubMed Web of Science ®Google Scholar
• Cadranel J. F., Erlinger S., Desruenue M., Luciani J., Lunel F., Grippoc P., Cabrol A., Opolou P. Chronic administration of cyclosporin A induces a decrease in hepatic excretory function in men. Digestive Diseases Science 1992; 37: 1473–1476
   PubMedGoogle Scholar
• Casini A. G. M., Hyland R. J., Serroni A., Gilfor D., Farber J. L. Mechanisms of cell injury in the killing of cultured hepatocytes by bromobenzene. Journal of Biological Chemistry 1982; 257: 6721–6728
   PubMed Web of Science ®Google Scholar
• Cavagnaro J., Rauckman E. J., Rosen G. M. Estimation of FAD-monooxygenase in microsomal preparations. Analytical Biochemistry 1981; 118: 204–211
   PubMedGoogle Scholar
• Ching C. K., Smith P. G., Long R. L. Tamoxifen associated hepatocellular damage and agranulocytosis. Lancet 1992; 339: 940
   PubMedGoogle Scholar
• Comporti M. Three models of free-radical-induced cell injury. Chemico-Biological Interactions 1989; 72: 1–56
   PubMed Web of Science ®Google Scholar
• Dawson J. R., Adams D. J., Wolf C. R. Induction of drug metabolising enzymes in human cell line Hep G2. FEBS Letters 1985; 183: 219–222
   PubMed Web of Science ®Google Scholar
• Dierickx P. J. Cytotoxicity testing of 114 compounds by the determination of the protein content in HepG2 cell cultures. Toxicology in Vitro 1989; 3: 189–193
   PubMedGoogle Scholar
• Doostdar H., Grant M. H., Melvin W. T., Wolf C. R., Burke M. D. The effects of inducing agents on cytochrome P450 and UDP-glucuronyltransferase activities in human HepG2 hepatoma cells. Biochemical Pharmacology 1993; 46: 629–635
   PubMed Web of Science ®Google Scholar
• Duthie S. J., Coleman C. S., Grant M. H. Status of reduced glutathione in the human hepatoma cell line HepG2. Biochemical Pharmacology 1988; 37: 3365–3368
   PubMedGoogle Scholar
• Duthie S. J., Grant M. H. The toxicity of menadione and mitoxantrone in human liver-derived HepG2 hepatoma cells. Biochemical Pharmacology 1989b; 38: 1247–1255
   PubMedGoogle Scholar
• Duthie S. J., Grant M. J. The role of reductive and oxidative metabolism in the toxicity of mitoxantrone, adriamycin and menadione in human liver-derived HepG2 hepatoma cells. British Journal of Cancer 1989a; 60: 566–571
   PubMed Web of Science ®Google Scholar
• Duthie S. J., Melvin W. T., Burke M. D. Bromobenzene detoxification in the human liver-derived HepG2 cell line. Xenobiotica 1994; 24: 265–279
   PubMed Web of Science ®Google Scholar
• Erickson S. K., Fielding P. E. Parameters of cholesterol metabolism in the human hepatoma cell line HepG2. Journal of Lipid Research 1986; 27: 875–883
   PubMedGoogle Scholar
• Everson G. T., Polokoff M. A. HepG2 a human hepatoblastoma cell line exhibiting defects in bile acid synthesis and conjugation. Journal of Biological Chemistry 1986; 261: 2197–2201
   PubMed Web of Science ®Google Scholar
• Faulds D., Goa K. L., Benfield P. Cyclosporin—a review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in immunoregulatory disorders. Drugs 1993; 45: 953–1040
   PubMed Web of Science ®Google Scholar
• First M. R., Schroeder T. J., Alexander J. W., Stephens G. W., Weiskittel P., Myre S. A., Pesce A. J. Cyclosporine dose reduction by ketoconazole administration in renal transplantation recipients. Transplantation 1991; 51: 365–370
   PubMedGoogle Scholar
• Goldberger G., Arnaout M. A., Aden D., Kay R., Rits M., Colten H. R. Biosynthesis and postsynthetic processing of human C3b/C4b inactivator (Factor I) in three hepatoma cell lines. Journal of Biological Chemistry 1984; 259: 6492–6497
   PubMed Web of Science ®Google Scholar
• Grant M. H., Doostdar H., Maley M., Melvin W. T., Engeset J., Burke M. D. Glucuronidation in rat and human hepatocyte cultures and in human HepG2 hepatoma cells. Cellular and Molecular Aspects of Glucuronidation, G. Siest, J. Magdalou, B. Burchell. INSERM/Jouhn Libbey Eurotext, Paris 1988b; 129–136
   Google Scholar
• Grant M. H., Duthie S. J., Gray A. G., Burke M. D. Mixed-function-oxidase and UDP-glucuronyl-transferase activities in the human HepG2 hepatoma cell line. Biochemical Pharmacology 1988a; 37: 4111–4116
   PubMed Web of Science ®Google Scholar
• Guarner F., Fremont-Smith M., Prieto J. Cytoprotective effect of prostaglandins on isolated rat liver cells. Liver 1985; 5: 35–39
   PubMedGoogle Scholar
• Hall T. J., James P. R., Cambridge G. Development of an in vitro hepatotoxicity assay for assessing the effects of chronic drug exposure. Research Communications in Chemical Pathology and Pharmacology 1993; 79: 249–256
   PubMedGoogle Scholar
• Holt D. W., Johnston A. Cyclosporin and vitamin E. Lancet 1991; 338: 697
   PubMedGoogle Scholar
• Inselmann G., Hannemann J., Baumann K. Cyclosporin A-induced lipid peroxidation and influence on glucose-6-phosphatase in rat hepatic and renal microsomes. Research Communications in Chemical Pathology and Pharmacology 1990; 68: 189–204
   PubMedGoogle Scholar
• Iwasa F., Galbraith R. A., Sassa S. Phenotypic variation in human HepG2 hepatoma cells: alterations in cell growth, plasma protein synthesis and heme pathway enzymes. International Journal of Biochemistry 1990; 22: 303–310
   PubMedGoogle Scholar
• Jacolot F., Simon Y., Dreano Y., Beaune P., Riche C., Berthou F. Identification of the cytochrome P-450IIIA family as the enzymes involved in the N-demethylation of tamoxifen in human liver microsomes. Biochemical Pharmacology 1991; 41: 1911–1919
   PubMed Web of Science ®Google Scholar
• Kassianides C., Nussenblatt R., Palestine A. J., Mellow S. D., Hoofnagle J. H. Liver injury from cyclosporin A. Digestive Diseases Science 1990; 35: 693–697
   PubMed Web of Science ®Google Scholar
• Klintmalm G. B. G., Iwatsuki S., Starzl T. E. Cyclosporin A hepatoxicity in 66 renal allograft recipients. Transplantation 1981; 32: 488–489
   PubMed Web of Science ®Google Scholar
• Knowles B. B., Howe C. C., Aden D. P. Human hepatocellular carcinoma lines secrete the major plasma proteins and hepatitis B surface antigen. Science 1980; 209: 497–499
   PubMed Web of Science ®Google Scholar
• Kronbach T., Fischer V., Meyer U. A. Cyclosporine metabolism in human liver: identification of a cytochrome P450III gene family as the major cyclosporine-metabolizing enzyme explains interactions of cyclosporine with other drugs. Clinical Pharmacology and Therapeutics 1988; 43: 630–635
   PubMed Web of Science ®Google Scholar
• Liebman K. C. Effects of metyrapone on liver microsomal drug oxidations. Molecular Pharmacology 1969; 5: 1–9
   PubMedGoogle Scholar
• Lien E. A., Solheim E., Lea O. A., Lundgren S., Kvinnsland S., Veland P. M. Distribution of 4-hydroxy-N-desmethyl tamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Research 1989; 49: 2175–2183
   PubMed Web of Science ®Google Scholar
• Lind C., Hochstein P., Frnster L. DT-diaphorase as a quinone reductase: a cellular control device against a semiquinone and superoxide radical formation. Archives of Biochemistry and Biophysics 1982; 216: 178–185
   PubMed Web of Science ®Google Scholar
• Mani C., Gelboin H. V., Park S. S., Pearce R., Parkinson A., Kupfer D. Metabolism of the antimammary cancer antiestrogenic agent tamoxifen: I. cytochrome P-450-catalyzed N-demethylation and 4-hydroxylation. Drug Metabolism and Disposition 1993a; 21: 645–656
   PubMed Web of Science ®Google Scholar
• Mani C., Hodgson E., Kupfer D. Metabolism of the antimammary cancer antiestrognic agent tamoxifen: II. flavin-containing monooxygenase-mediated N-oxidation. Drug Metabolism and Disposition 1993b; 21: 657–661
   PubMed Web of Science ®Google Scholar
• Mani C., Kupfer D. Cytochrome P450-mediated activation and irreversible binding of the antiestrogen tamoxifen to proteins in rat and human liver: possible involvement of flavin-containing monooxygenases in tamoxifen activation. Cancer Research 1991; 51: 6052–6058
   PubMed Web of Science ®Google Scholar
• Maurice M., Pichard L., Daujat M., Fabre I., Joyeux H., Domergue J., Maurel P. Effects of imidazole derivatives on cytochrome P450 from human hepatocytes in primary culture. FASEB Journal 1992; 6: 752–758
   PubMed Web of Science ®Google Scholar
• Mayer R. D., Cockett A. T. K. Cyclosporin-mediated increase in kidney glutathione and effects on gammaglutamyl cyclic enzymes. Journal of Biochemical Toxicology 1988; 3: 213–221
   PubMedGoogle Scholar
• McCord J., Fridovich I. The reduction of cytochrome c by milk xanthine oxidase. Journal of Biological Chemistry 1968; 243: 5753–5760
   PubMed Web of Science ®Google Scholar
• McLachlan G., Smart L. M., Wallace H. M., Thomson A. W. The potential of cyclosporin A as an antitumour agent. International Journal of Immunopharmacology 1990; 12: 469–479
   PubMedGoogle Scholar
• Nisimoto Y. Localisation of cytochrome c binding domain on NADPH-cytochrome P450 reductase. Journal of Biological Chemistry 1986; 261: 14232–14239
   PubMedGoogle Scholar
• Nolvadex Adjuvant Trial Organisation. Controlled trial of tamoxifen as single adjuvant agent in management of early breast cancer. Lancet 1985; ii: 836–839
   Google Scholar
• Olshan A. F., Mattison D. R., Zwanenburg T. S. Cyclosporine A: a review of genotoxicity and potential for adverse human reproductive and developmental effects. Mutation Research 1994; 317: 163–173
   PubMed Web of Science ®Google Scholar
• Palozza P., Moualla S., Krinsky N. I. Effects of β-carotene and α-tocopherol on radical initiated peroxidation of microsomes. Free Radicals in Biology & Medicine 1992; 13: 127–136
   PubMed Web of Science ®Google Scholar
• Powles T. J., Hardy J. R., Ashley S. E., Farrington G. M., Cosgrove D., Davey J. B., Dowsett M., McKinna J. A., Nash A. G., Sinnett H. D., Tillyer C. R., Treleaven J. G. A pilot trial to evaluate the acute toxicity and feasibility of tamoxifen for prevention of breast cancer. British Journal of Cancer 1989; 60: 126–131
   PubMed Web of Science ®Google Scholar
• Roy D., Liehr J. G. Temporary decrease in renal quinone reductase activity by chronic administration of estradiol to male syrian hamsters. Journal of Biological Chemistry 1988; 263: 3646–3651
   PubMed Web of Science ®Google Scholar
• Rush D. N. Cyclosporine toxicity to organs other than the kidney. Clinical Biochemistry 1991; 24: 101–105
   PubMed Web of Science ®Google Scholar
• Sassa S., Sugita O., Galbraith R. A., Kappas A. Drug metabolism by the human hepatoma cell Hep G2. Biochemical and Biophysical Research Communications 1987; 143: 52–57
   PubMed Web of Science ®Google Scholar
• Saville B. A scheme for the colorimetic determination of microgram amounts of thiols. Analyst 1958; 83: 670–672
   Web of Science ®Google Scholar
• Schade R. R., Guglielmi A., van Theil D. H., Thompson M. E., Warty V., Griffith B., Sanghv A., Bahnson H., Hardesty R. Cholestasis in heart transplant recipients treated with cyclosporine. Transplantation Proceedings 1983; 15(Suppl. 1)2757–2760
   Google Scholar
• Shaw P., Barnes T., Cameron D., Engeset J., Melyin W., Omar G., Petrie J., Rush R., Snyder C., Whiting P., Wolf C., Burke M. Purification and characterisation of an anticonvulsant-induced human cytochrome P450 catalysing cyclosporiin metabolism. Biochemical Journal 1989; 263: 653–663
   PubMed Web of Science ®Google Scholar
• Starke P. E., Farber J. L. Endogenous defences against the cytotoxicity of hydrogen peroxide in cultured rat hepatocytes. Journal of Biological Chemistry 1985; 260: 860–892
   PubMedGoogle Scholar
• Styles J. A., Davies A., Lim C. K., De Matteis F., Stanley L. A., White I. N. H., Yuan Z., Smith L. L. Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis 1994; 15: 5–9
   PubMed Web of Science ®Google Scholar
• Thor H., Smith M. T., Hartzell P., Bellomo G., Jewell S. The metabolism of menadione (2-methyl-1,4-naphthoquinone) by isolated hepatocytes. Journal of Biological Chemistry 1982; 257: 12419–12425
   PubMed Web of Science ®Google Scholar
• Turner M. J., Fields C. E., Everman D. B. Evidence for superoxide formation during hepatic metabolism of tamoxifen. Biochemical Pharmacology 1991; 41: 1701–1705
   PubMed Web of Science ®Google Scholar
• Weaver R. J., Dickins M., Burke M. D. Cytochrome P450 2C9 is responsible for hydroxylation of the naphthoquinone antimalarial drug 58C80 in human liver. Biochemical Pharmacology 1993; 46: 1183–1197
   PubMed Web of Science ®Google Scholar
• Williams G. M., Iatropoulos M. J., Hard G. C. Long-term prophylactic use of tamoxifen: is it safe. European Journal of Cancer Prevention 1992; 1: 386–387
   PubMedGoogle Scholar
• Wiseman H., Laughton M. J., Arnstein H. R. V., Cannon M., Haliwell B. The antioxidant action of tamoxifen and its metabolites: inhibition of lipid peroxidation. FEBS Letters 1990; 263: 192–194
   PubMed Web of Science ®Google Scholar
• Zannus V. I., Breslow J. L., SanGiacomo T. R., Aden D. P., Knowles B. B. Characterization of the major apolipoproteins secreted by two human hepatoma cell lines. Biochemistry 1981; 20: 7089–7096
   PubMedGoogle Scholar