Induction of cytochrome P450 1A1 by ketoconazole and itraconazole but not fluconazole in murine and human hepatoma cell lines

Toxicological Sciences

Volumn 97, Issue 1, 2007, Pages 32-43

  Korashy, Hesham M ^a   Shayeganpour, Anooshirvan ^a   Brocks, Dion R ^a   El Kadi, Ayman O S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Antifungal drugs; Aryl hydrocarbon receptor; Carcinogenesis; CYP1A1; Hepatotoxicity; Transcription

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 1A1; DACTINOMYCIN; FLUCONAZOLE; ITRACONAZOLE; KETOCONAZOLE; LUCIFERASE; MESSENGER RNA; XENOBIOTIC AGENT; AHR PROTEIN, HUMAN; AHR PROTEIN, MOUSE; ANTIFUNGAL AGENT; ENZYME INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL STRAIN HEPG2; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG STRUCTURE; ENZYME INDUCTION; ENZYME SUBSTRATE; GENE EXPRESSION REGULATION; HUMAN; HUMAN CELL; LIVER TOXICITY; MOUSE; NONHUMAN; RNA SYNTHESIS; RNA TRANSCRIPTION; ANIMAL; BIOSYNTHESIS; CELL SURVIVAL; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; GENETIC TRANSCRIPTION; GENETICS; LIVER CELL CARCINOMA; LIVER TUMOR; PATHOLOGY; PROMOTER REGION; REPORTER GENE; TIME; TUMOR CELL LINE;

MURINAE;

ANIMALS; ANTIFUNGAL AGENTS; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CELL SURVIVAL; CYTOCHROME P-450 CYP1A1; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INDUCTION; ENZYME INHIBITORS; FLUCONAZOLE; GENES, REPORTER; HUMANS; ITRACONAZOLE; KETOCONAZOLE; LIVER NEOPLASMS; LUCIFERASES; MICE; PROMOTER REGIONS (GENETICS); RECEPTORS, ARYL HYDROCARBON; RNA, MESSENGER; TIME FACTORS; TRANSCRIPTION, GENETIC;

EID: 34347231660     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfm012     Document Type: Article

References (44)

1. Amin, A., and Hamza, A. A. (2005). Oxidative stress mediates drug-induced hepatotoxicity in rats: A possible role of DNA fragmentation. Toxicology 208, 367-375.
2. Babin, M., Casado, S., Chana, A., Herradon, B., Segner, H., Tarazona, J. V., and Navas, J. M. (2005). Cytochrome P4501A induction caused by the imidazole derivative Prochloraz in a rainbow trout cell line. Toxicol. In Vitro 19, 899-902.
3. Brass, C., Galgiani, J. N., Blaschke, T. F., Defelice, R., O'Reilly, R. A., and Stevens, D. A. (1982). Disposition of ketoconazole, an oral antifungal, in humans. Antimicrob. Agents Chemother. 21, 151-158.
4. Caillot, D., Bassaris, H., McGeer, A., Arthur, C., Prentice, H. G., Seifert, W., and De Beule, K. (2001). Intravenous itraconazole followed by oral itraconazole in the treatment of invasive pulmonary aspergillosis in patients with hematologic malignancies, chronic granulomatous disease, or AIDS. Clin. Infect. Dis. 33, e83-e90.
5. Chan, P. K., Lu, S. Y., Liao, J. W., Wei, C. F., Tsai, Y., and Ueng, T. H. (2006). Induction and inhibition of cytochrome P450-dependent monooxygenases of rats by fungicide bitertanol. Food Chem. Toxicol. 44, 2047-2057.
6. Ciolino, H. P., Macdonald, C. J., Memon, O. S., Bass, S. E., and Yeh, G. C. (2006). Sulindac regulates the aryl hydrocarbon receptor-mediated expression of Phase 1 metabolic enzymes in vivo and in vitro. Carcinogenesis. 27, 1586-1592.
7. Denison, M. S., Fisher, J. M., and Whitlock, J. P., Jr (1989). Protein-DNA interactions at recognition sites for the dioxin-Ah receptor complex. J. Biol. Chem. 264, 16478-16482.
8. Denison, M. S., and Nagy, S. R. (2003). Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 43, 309-334.
9. Elbekai, R. H., Korashy, H. M., Wills, K., Gharavi, N., and El-Kadi, A. O. (2004). Benzo[a]pyrene, 3-methylcholanthrene and beta-naphthoflavone induce oxidative stress in hepatoma hepa 1c1c7 Cells by an AHR-dependent pathway. Free Radic. Res. 38, 1191-1200.
10. Gharavi, N., and El-Kadi, A. O. (2005). tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand. Drug Metab. Dispos. 33 365-372.
11. Girois, S. B., Chapuis, F., Decullier, E., and Revol, B. G. (2005). Adverse effects of antifungal therapies in invasive fungal infections: Review and meta-analysis. Eur. J. Clin. Microbiol. Infect. Dis. 24, 119-130.
12. Hankinson, O., (1995). The aryl hydrocarbon receptor complex. Annu. Rev. Pharmacol. Toxicol. 35, 307-340.
13. Hardin, T. C., Graybill, J. R., Fetchick, R., Woestenborghs, R., Rinaldi, M. G., and Kuhn, J. G. (1988). Pharmacokinetics of itraconazole following oral administration to normal volunteers. Antimicrob. Agents Chemother. 32, 1310-1313.
14. Hasselberg, L., Grosvik, B. E., Goksoyr, A., and Celander, M. C. (2005). Interactions between xenoestrogens and ketoconazole on hepatic CYP1A and CYP3A, in juvenile Atlantic cod (Gadus morhua). Comp. Hepatol. 4, 2.
15. Hegelund, T., Ottosson, K., Radinger, M., Tomberg, P., and Celander, M. C. (2004). Effects of the antifungal imidazole ketoconazole on CYP1A and CYP3A in rainbow trout and killifish. Environ. Toxicol. Chem. 23, 1326-1334.
16. Jaeschke, H., Gores, G. J., Cederbaum, A. I., Hinson, J. A., Pessayre, D., and Lemasters, J. J. (2002). Mechanisms of hepatotoxicity. Toxicol. Sci. 65, 166-176.
17. Jeuken, A., Keser, B. J., Khan, E., Brouwer, A., Koeman, J., and Denison, M. S. (2003). Activation of the Ah receptor by extracts of dietary herbal supplements, vegetables, and fruits. J. Agric. Food Chem. 51, 5478-5487.
18. Juberg, D. R., Mudra, D. R., Hazelton, G. A., and Parkinson, A. (2006). The effect of fenbuconazole on cell proliferation and enzyme induction in the liver of female CD1 mice. Toxicol. Appl. Pharmacol. 214 178-187.
19. Kim,W. K., In, Y. J., Kim, J. H., Cho, H. J., Kim, J. H., Kang, S., Lee, C. Y., and Lee, S. C. (2006). Quantitative relationship of dioxin-responsive gene expression to dioxin response element in Hep3B and HepG2 human hepatocarcinoma cell lines. Toxicol. Lett. 165 174-181.
20. Korashy, H. M., and El-Kadi, A. O. (2004). Differential effects of mercury, lead and copper on the constitutive and inducible expression of aryl hydrocarbon receptor (AHR)-regulated genes in cultured hepatoma Hepa 1c1c7 cells. Toxicology 201, 153-172.
21. Korashy, H. M., and El-Kadi, A. O. (2005). Regulatory mechanisms modulating the expression of cytochrome P450 1A1 gene by heavy metals. Toxicol. Sci. 88, 39-51.
22. Korashy, H. M., and El-Kadi, A. O. (2006a). The role of aryl hydrocarbon receptor in the pathogenesis of cardiovascular diseases. Drug Metab. Rev. 38, 411-450.
23. Korashy, H. M., and El-Kadi, A. O. (2006b). The role of aryl hydrocarbon receptor and the reactive oxygen species in the modulation of glutathione transferase by heavy metals in murine hepatoma cell lines. Chem. Biol. Interact. 162, 237-248.
24. Lemaire, G., Delescluse, C., Pralavorio, M., Ledirac, N., Lesca, P., and Rahmani, R. (2004). The role of protein tyrosine kinases in CYP1A1 induction by omeprazole and thiabendazole in rat hepatocytes. Life Sci. 74, 2265-2278.
25. Liu, N., Zhang, Q. Y., Vakharia, D., Dunbar, D., and Kaminsky, L. S. (2001). Induction of CYP1A by benzo[k]fluoranthene in human hepatocytes: CYP1A1 or CYP1A2? Arch. Biochem. Biophys. 389, 130-134.
26. Lorenzen, A., and Kennedy, S. W. (1993). A fluorescence-based protein assay for use with a microplate reader. Anal. Biochem. 214, 346-348.
27. Nebert, D. W., Dalton, T. P., Okey, A. B., and Gonzalez, F. J. (2004). Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer. J. Biol. Chem. 279, 23847-23850.
28. Paine, M. F., Schmiedlin-Ren, P., andWatkins, P. B. (1999). Cytochrome P-450 1A1 expression in human small bowel: Interindividual variation and inhibition by ketoconazole. Drug Metab. Dispos. 27, 360-364.
29. Pasco, D. S., Boyum, K. W., Merchant, S. N., Chalberg, S. C., and Fagan, J. B. (1988). Transcriptional and post-transcriptional regulation of the genes encoding cytochromes P-450c and P-450d in vivo and in primary hepatocyte cultures. J. Biol. Chem. 263, 8671-8676.
30. Prentice, A. G., and Glasmacher, A. (2005). Making sense of itraconazole pharmacokinetics. J. Antimicrob. Chemother. 56(Suppl. 1), i17-i22.
31. Rodriguez, R. J., and Acosta, D., Jr (1997). Metabolism of ketoconazole and deacetylated ketoconazole by rat hepatic microsomes and flavin-containing monooxygenases. Drug Metab. Dispos. 25, 772-777.
32. Rodriguez, R. J., and Buckholz, C. J. (2003). Hepatotoxicity of ketoconazole in Sprague-Dawley rats: Glutathione depletion, flavin-containing monooxygenases-mediated bioactivation and hepatic covalent binding. Xenobiotica 33, 429-441.
33. Rodriguez, R. J., Proteau, P. J., Marquez, B. L., Hetherington, C. L., Buckholz, C. J., and O'Connell, K. L. (1999). Flavin-containing monooxygenasemediated metabolism of N-deacetyl ketoconazole by rat hepatic microsomes. Drug Metab. Dispos. 27, 880-886.
34. Rogers, J. M., and Denison, M. S. (2002). Analysis of the antiestrogenic activity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in human ovarian carcinoma BG-1 cells. Mol. Pharmacol. 61, 1393-1403.
35. Seidel, S. D., Li, V.,Winter, G. M., Rogers,W. J., Martinez, E. I., and Denison, M. S. (2000). Ah receptor-based chemical screening bioassays: Application and limitations for the detection of Ah receptor agonists. Toxicol. Sci. 55, 107-115.
36. Shayeganpour, A., El-Kadi, A. O., and Brocks, D. R. (2006). Determination of the enzyme(s) involved in the metabolism of amiodarone in liver and intestine of rat: The contribution of cytochrome P450 3A isoforms. Drug Metab. Dispos. 34, 43-50.
37. Silkworth, J. B., Koganti, A., Illouz, K., Possolo, A., Zhao, M., and Hamilton, S. B. (2005). Comparison of TCDD and PCB CYP1A induction sensitivities in fresh hepatocytes from human donors, Sprague-Dawley rats, and rhesus monkeys and HepG2 cells. Toxicol. Sci. 87, 508-519.
38. Stricker, B. H., Blok, A. P., Bronkhorst, F. B., Van Parys, G. E., and Desmet, V. J. (1986). Ketoconazole-associated hepatic injury. A clinicopathological study of 55 cases. J. Hepatol. 3, 399-406.
39. Sun, G., Thai, S. F., Tully, D. B., Lambert, G. R., Goetz, A. K.,Wolf, D. C., Dix, D. J., and Nesnow, S. (2005). Propiconazole-induced cytochrome P450 gene expression and enzymatic activities in rat and mouse liver. Toxicol. Lett. 155, 277-287.
40. Venkatakrishnan, K., von Moltke, L. L., and Greenblatt, D. J. (2000). Effects of the antifungal agents on oxidative drug metabolism: Clinical relevance. Clin. Pharmacokinet. 38, 111-180.
41. Walisser, J. A., Glover, E., Pande, K., Liss, A. L., and Bradfield, C. A. (2005). Aryl hydrocarbon receptor-dependent liver development and hepatotoxicity are mediated by different cell types. Proc. Natl. Acad. Sci. U.S.A. 102, 17858-17863.
42. Werlinder, V., Backlund, M., Zhukov, A., and Ingelman-Sundberg, M. (2001). Transcriptional and post-translational regulation of CYP1A1 by primaquine. J. Pharmacol. Exp. Ther. 297, 206-214.
43. Whitelaw, M. L., Gustafsson, J. A., and Poellinger, L. (1994). Identification of transactivation and repression functions of the dioxin receptor and its basic helix-loop-helix/PAS partner factor Arnt: Inducible versus constitutive modes of regulation. Mol. Cell. Biol. 14, 8343-8355.
44. Zhang, Z. Y., Pelletier, R. D., Wong, Y. N., Sugawara, M., Zhao, N., and Littlefield, B. A. (2006). Preferential inducibility of CYP1A1 and CYP1A2 by TCDD: Differential regulation in primary human hepatocytes versus transformed human cells. Biochem. Biophys. Res. Commun. 341, 399-407.