Structural and mechanistic aspects of transcriptional induction of cytochrome P450 1A1 by benzimidazole derivatives in rat hepatoma H4IIE cells

European Journal of Biochemistry

Volumn 261, Issue 1, 1999, Pages 66-71

  Backlund, Maria ^b   Weidolf, Lars ^a   Ingelman Sundberg, Magnus ^c  

^a ASTRAZENECA R AND D   (Sweden)

^b KAROLINSKA INSTITUTE   (Sweden)

^c NONE

Author keywords

CYP1A1; CYP1A2; Luciferase; Omeprazole; Thiabendazole

Indexed keywords

2 BENZIMIDAZOLETHIOL DERIVATIVE; 2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; AROMATIC HYDROCARBON RECEPTOR; BENZIMIDAZOLE DERIVATIVE; CARBENDAZIM; CARBOXYLIC ACID DERIVATIVE; ETHOXYRESORUFIN DEETHYLASE; MESSENGER RNA; OMEPRAZOLE; PROPIONIC ACID DERIVATIVE; TIABENDAZOLE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; ENZYME MECHANISM; ENZYME STRUCTURE; GENE CONSTRUCT; GENE INDUCTION; HEPATOMA CELL; IMMUNOBLOTTING; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; REPORTER GENE; SIGNAL TRANSDUCTION; TRANSCRIPTION REGULATION;

ANIMALS; BENZIMIDAZOLES; CARBAMATES; CYTOCHROME P-450 CYP1A1; GENE EXPRESSION REGULATION; LIVER NEOPLASMS, EXPERIMENTAL; OMEPRAZOLE; RATS; RNA, MESSENGER; THIABENDAZOLE; TRANSFECTION; TUMOR CELLS, CULTURED;

EID: 0002798481     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1999.00225.x     Document Type: Article

References (38)

1. 1. Diaz, D., Fabre, I., Daujat, M., Saint Aubert, B., Bories, P., Michel, H. & Maurel, P. (1990) Omeprazole is an aryl hydrocarbon-like inducer of human hepatic cytochrome P450. Gastroenterology 99, 737-747.
2. 2. Curi-Pedrosa, R., Daujat, M., Pichard, L., Ourlin, J.C., Clair, P., Gervot, L., Lesca, P., Domergue, J., Joyeux, H., Fourtanier, G. & Maurel, P. (1994) Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J. Pharmacol. Exp. Ther. 269, 384-392.
3. 3. McDonnell, W.M., Scheiman, J.M. & Traber, P.G. (1992) Induction of cytochrome P450IA genes (CYP1A) by omeprazole in the human alimentary tract. Gastroenterology 103, 1509-1516.
4. 4. Buchthal, J., Grund, K.E., Buchmann, A., Schrenk, D., Beaune, P. & Bock, K.W. (1995) Induction of cytochrome P4501A by smoking or omeprazole in comparison with UDP-glucuronosyltransferase in biopsies of human duodenal mucosa. Eur. J. Clin. Pharmacol. 47, 431-435.
5. 5. Souhaili-el Amri, H., Fargetton, X., Benoit, E., Totis, M. & Batt, A.M. (1988) Inducing effect of albendazole on rat liver drug-metabolizing enzymes and metabolite pharmacokinetics. Toxicol. Appl. Pharmacol. 92, 141-149.
6. 6. Gleizes, C., Eeckhoutte, C., Pineau, T., Alvinerie, M. & Galtier, P. (1991) Inducing effect of oxfendazole on cytochrome P450IA2 in rabbit liver. Consequences on cytochrome P450 dependent mono-oxygenases. Biochem. Pharmacol. 41, 1813-1820.
7. 7. Aix, L., Rey-Grobellet, X., Larrieu, G., Lesca, P. & Galtier, P. (1994) Thiabendazole is an inducer of cytochrome P4501A1 in cultured rabbit hepatocytes. Biochem. Biophys. Res. Commun. 202, 1483-1489.
8. 8. Rey-Grobellet, X., Ferre, N., Eeckhoutte, C., Larrieu, G., Pineau, T. & Galtier, P. (1996) Structural requirements for the induction of cytochromes P450 by benzimidazole anthelmintic derivatives in cultured rabbit hepatocytes. Biochem. Biophys. Res. Commun. 220, 789-794.
9. 9. Quattrochi, L.C. & Tukey, R.H. (1993) Nuclear uptake of the Ah (dioxin) receptor in response to omeprazole: transcriptional activation of the human CYP1A1 gene. Mol. Pharmacol. 43, 504-508.
10. 10. Kikuchi, H., Hossain, A., Sagami, I., Ikawa, S. & Watanabe, M. (1995) Different inducibility of cytochrome P-4501A1 mRNA of human and mouse by omeprazole in culture cells. Arch. Biochem. Biophys. 316, 649-652.
11. 11. Daujat, M., Charrasse, S., Fabre, I., Lesca, P., Jounaidi, Y., Larroque, C., Poellinger, L. & Maurel, P. (1996) Induction of CYP1A1 gene by benzimidazole derivatives during Caco-2 cell differentiation. Evidence tor an aryl-hydrocarbon receptor-mediated mechanism. Eur. J. Biochem. 237, 642-652.
12. 12. Backlund, M., Johansson, I., Mkrtehian, S. & Ingelman-Sundberg, M. (1997) Signal transduction-mediated activation of the aryl hydrocarbon receptor in rat hepatoma H4IIE cells. J. Biol. Chem. 272, 31755-31763.
13. 13. Hankinson, O. (1995) The aryl hydrocarbon receptor complex. Annu. Rev. Pharmacol Toxicol. 35, 307-340.
14. 14. Daujat, M., Peryt, B., Lesca, P., Fourtanier, G., Domergue, J. & Maurel, P. (1992) Omeprazole, an inducer of human CYP1A1 and 1A2, is not a ligand for the Ah receptor. Biochem. Biophys. Res. Commun. 188, 820-825.
15. 15. Gleizes-Escala, C., Lesca, P., Larrieu, G., Dupuy, J., Pineau, T. & Galtier, P. (1996) Effect of exposure of rabbit hepatocytes to sulfur-containing anthelmintics (Oxfendazole and Fenbendazole) on cytochrome P4501A1 expression. Toxicology in Vitro 10, 129-139.
16. 16. Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
17. 17. Chomczynski, P. & Sacchi, N. (1987) Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal. Biochem. 162, 156-159.
18. 18. Sogawa, K., Fujisawa-Sehara, A., Yamane, M. & Fujii-Kuriyama, Y. (1986) Location of regulatory elements responsible for drug induction in the rat cytochrome P-450c gene. Proc. Natl Acad. Sci. USA 83, 8044-8048.
19. 19. Carver, L.A. & Bradfield, C.A. (1997) Ligand-dependent interaction of the aryl hydrocarbon receptor with a novel immunophilin homolog in vivo. J. Biol. Chem. 272, 11452-11456.
20. 20. Ma, Q. & Whitlock Jr J.P. (1997) A novel cytoplasmic protein that interacts with the Ah receptor, contains tetratricopeptide repeat motifs, and augments the transcriptional response to 2,3,7,8-tetrachlorodibenzo-p-dioxin. J. Biol. Chem. 272, 8878-8884.
21. 21. Perdew, G.H. & Whitelaw, M.L. (1991) Evidence that the 90-kDa heat shock protein (HSP90) exists in cytosol in heteromeric complexes containing HSP70 and three other proteins with Mr of 63,000, 56,000, and 50,000. J. Biol. Chem. 266, 6708-6713.
22. 22. Enan, E. & Matsumura, F. (1996) Identification of c-Src as the integral component of the cytosolic Ah receptor complex, transducing the signal of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) through the protein phosphorylation pathway. Biochem. Pharmacol. 52, 1599-1612.
23. 23. Poland, A., Glover, E. & Kende, A.S. (1976) Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. J. Biol. Chem. 251, 4936-4946.
24. 24. Poland, A. & Knutson, J.C. (1982) 2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu. Rev. Pharmacol. Toxicol. 22, 517-554.
25. 25. Gillner, M., Bergman, J., Cambillau, C., Fernstrom, B. & Gustafsson, J.A. (1985) Interactions of indoles with specific binding sites for 2,3,7,8-tetrachlorodibenzo-p-dioxin in rat liver. Mol. Pharmacol. 28, 357-363.
26. 26. Gillner, M., Bergman, J., Cambillau, C., Alexandersson, M., Fernstrom, B. & Gustafsson, J.A. (1993) Interactions of indolo[3,2-b]carbazoles and related polycyclic aromatic hydrocarbons with specific binding sites for 2,3,7,8-tetrachlorodibenzo-p-dioxin in rat liver. Mol. Pharmacol. 44, 336-345.
27. 27. Dzeletovic, N., McGuire, J., Daujat, M., Tholander, J., Ema, M., Fujii-Kuriyama, Y., Bergman, J., Maurel, P. & Poellinger, L. (1997) Regulation of dioxin receptor function by omeprazole. J. Biol Chem. 272, 12705-12713.
28. 28. Robertson, R.W., Zhang, L., Pasco, D.S. & Fagan, J.B. (1994) Aryl hydrocarbon-induced interactions at multiple DNA elements of diverse sequence - a multicomponent mechanism for activation of cytochrome P4501A1 (CYP1A1) gene transcription. Nucl. Acids Res. 22, 1741-1749.
29. 29. Houser, W.H., Cunningham, C.K., Hines, R.N., Schaeffer, W.I. & Bresnick, E. (1987) Interaction of the 4 S polycyclic aromatic hydrocarbon-binding protein with the cytochrome P-450c gene. Arch. Biochem. Biophys. 259, 215-223.
30. 30. Sterling, K., Weaver, J., Ho, K.L., Xu, L.C. & Bresnick, E. (1993) Rat CYP1A1 negative regulatory element: biological activity and interaction with a protein from liver and hepatoma cells. Mol. Pharm. 44, 560-568.
31. 31. Walsh, A.A., Tullis, K., Rice, R.H. & Denison, M.S. (1996) Identification of a novel cis-acting negative regulatory element affecting expression of the CYP1A1 gene in rat epidermal cells. J. Biol. Chem. 271, 22746-22753.
32. 32. Lee, I.J., Jeong, K.S., Roberts, B.J., Kallarakal, A.T., Fernandez-Salguero, P., Gonzalez, F.J. & Song, B.J. (1996) Transcriptional induction of the cytochrome P4501A1 gene by a thiazolium compound, YH439. Mol. Pharmacol. 49, 980-988.
33. 33. Gradelet, S., Astorg, P., Pineau, T., Canivenc, M.C., Siess, M.H., Leclerc, J. & Lesca, P. (1997) Ah receptor-dependent CYP1A induction by two carotenoids, canthaxanthin and beta-apo-8′-carotenal, with no affinity for the TCDD binding site. Biochem. Pharmacol. 54, 307-315.
34. 34. Ledirac, N., Delescluse, C., de Sousa, G., Pralavorio, M., Lesca, P., Amichot, M., Berge, J.B. & Rahmani, R. (1997) Carbaryl induces CYP1A1 gene expression in HepG2 and HaCaT cells but is not a ligand of the human hepatic Ah receptor. Toxicol. Appl. Pharmacol. 144, 177-182.
35. 35. Sinai, C.J. & Bend, J.R. (1997) Aryl hydrocarbon receptor-dependent induction of Cyp1a1 by bilirubin in mouse hepatoma Hepa 1c1c7 cells. Mol. Pharmacol. 52, 590-599.
36. 36. Sadek, C.M. & Allen-Hoffmann, B.L. (1994) Suspension-mediated induction of Hepa 1c1c7 Cyp1a-1 expression is dependent on the Ah receptor signal transduction pathway. J. Biol. Chem. 269, 31505-31509.
37. 37. Singh, S.S., Hord, N.G. & Perdew, G.H. (1996) Characterization of the activated form of the aryl hydrocarbon receptor in the nucleus of HeLa cells in the absence of exogenous ligand. Arch. Biochem. Biophys. 329, 47-55.
38. 38. Fernandez-Salguero, P., Pineau, T., Hilbert, D.M., McPhail, T., Lee, S.S., Kimura, S., Nebert, D.W., Rudikoff, S., Ward, J.M. & Gonzalez, F.J. (1995) Immune system impairment and hepatic fibrosis in mice lacking the dioxin-binding Ah receptor. Science 268, 722-726.