Inhibition of human cytochrome P450 enzymes by 1,2-dithiole-3-thione, oltipraz and its derivatives, and sulforaphane

Chemical Research in Toxicology

Volumn 13, Issue 4, 2000, Pages 245-252

  Langouët, Sophie ^a,c   Furge, Laura Lowe ^d   Kerriguy, Nathalie ^c   Nakamura, Katsunori ^b   Guillouzo, André ^c   Guengerich, F Peter ^b  

^a INSERM   (France)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITÉ DE RENNES 1   (France)

^d KALAMAZOO COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLE 3 THIONE DERIVATIVE; CYTOCHROME P450; ISOTHIOCYANIC ACID DERIVATIVE; OLTIPRAZ; QUINOLINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; COMPETITIVE INHIBITION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; MUTAGENICITY; NONHUMAN; XENOBIOTIC METABOLISM;

ANTICARCINOGENIC AGENTS; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; PYRAZINES; QUINOLINES; THIOCYANATES; THIONES; THIOPHENES;

ESCHERICHIA COLI;

EID: 0034014663     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990189w     Document Type: Article

References (51)

1. Kensler, T. W., Styczynski, P., Groopman, J. D., Helzlsouer, K., Curphey, T. J., Maxuitenko, Y. Y., and Roebuck, B. D. (1992) Mechanisms of chemoprotection by oltipraz. J. Cell Biochem. 161, 167-172.
2. Zhang, Y., Talalay, P., Cho, G. C., and Posner, G. H. (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 89, 2399-2403.
3. Zhang, Y., and Talalay, P. (1994) Anticarcinogenic activities of organic isothiocyanates: Chemistry and mechanisms. Cancer Res. (Suppl.) 54, 1976s-1981s.
4. 1 in the rat. Toxicol. Appl. Pharmacol. 93, 442-451.
5. Kensler, T. W., Groopman, J. D., Eaton, D. L., Curphey, T. J., and Roebuck, B. D. (1992) Potent inhibition of aflatoxin-induced hepatic tumorigenesis by the monofunctional enzyme inducer 1,2-dithiole-3-thione. Carcinogenesis 13, 95-100.
6. Kensler, T. W., Egner, P. A., Dlan, P. M., Groopman, J. D., and Roebuck, B. D. (1987) Mechanism of protection against aflatoxin tumorigenicity in rats fed 5-(2-pyrazinyl)-4-methyl-l,2-dithiole-3-thione (oltipraz) and related 1,2-dithiole-3-thiones and 1,2-dithiole-3-ones. Cancer Res. 47, 4271-4277.
7. Primiano, T., Egner, P. A., Sutter, T. R., Kelloff, G. J., Roebuck, B. D., and Kensler, T. W. (1995) Intermittent dosing with oltipraz: relationship between chemoprevention of aflatoxin-induced tumorigenesis and induction of glutathione S-transferases. Cancer Res. 55, 4319-4324.
8. Egner, P. A., Kensler, T. W., Prestera, T., Talalay, P., Libby, A. H., Joyner, H. H., and Curphey, T. J. (1994) Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones. Carcinogenesis 15, 177-181.
9. 1 metabolism in human hepatocytes in primary culture. Cancer Res. 55, 5574-5579.
10. Langouët, S., Mahéo, K., Berthou, F., Morel, F., Lagadic-Gossman, D., Glaise, D., Coles, B., Ketterer, B., and Guillouzo, A. (1997) Effect of administration of the chemoprotective agent oltipraz on P4501A and P4502B in rat liver and rat hepatocytes in culture. Carcinogenesis 18, 1343-1349.
11. Mahéo, K., Morel, F., Langouët, S., Kramer, H., Le Ferréc, E., Ketterer, B., and Guillouzo, A. (1997) Inhibition of cytochromes P-450 and induction of glutathione S-transferases by sulforaphane in primary human and rat hepatocytes. Cancer Res. 57, 3649-3652.
12. Conaway, C. C., Jiao, D., and Chung, F. L. (1996) Inhibition of rat cytochrome P450 by isothiocyanates and their conjugates: a structure-activity relationship study. Carcinogenesis 17, 2423-2427.
13. Barcelo, S., Gardiner, J. M., Gescher, A., and Chipman, J. K. (1996) P4502E1-mediated mechanism of anti-genotoxicity of the broccoli constituent sulforaphane. Carcinogenesis 17, 277-282.
14. Parikh, A., Gillam, E. M. J., and Guengerich, F. P. (1997) Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol. 15, 784-788.
15. Shimada, T., Yamazaki, H., Foroozesh, M., Hopkins, N. E., Alworth, W. L., and Guengerich, F. P. (1998) Selectivity of polycyclic inhibitors for human cytochrome P450s IA1, 1A2, and IB1. Chem. Res. Toxicol. 11, 1048-1056.
16. Gillam, E. M. J., Baba, T., Kim, B. R., Ohmori, S., and Guengerich, F. P. (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch. Biochem. Biophys. 305, 123-131.
17. Sandhu, P., Guo, Z., Baba, T., Martin, M. V., Tukey, R. H., and Guengerich, F. P. (1994) Expression of modified human cytochrome P450 1A2 in Escherichia coli: stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch. Biochem. Biophys. 309, 168-177.
18. Prough, R. A., Burke, M. D., and Meyer, R. T. (1978) Direct fluorimetric methods for measuring mixed-function oxidases. Methods Enzymol. 52, 372-377.
19. 5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes. Biochem. Pharmacol. 52, 301-309.
20. Halpert, J. R. (1995) Structural basis of selective cytochrome P450 inhibition. Annu. Rev. Pharmacol. Toxicol. 35, 29-53.
21. Guengerich, F. P. (1999) Inhibition of drug metabolizing enzymes: Molecular and biochemical aspects. In Handbook of Drug Metabolism (Wolf, T. F., Ed.) pp 203-227, Marcel Dekker, New York.
22. Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2370-2378.
23. Guengerich, F. P. (1978) Destruction of heme and hemoproteins by liver microsomal reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase. Biochemistry 17, 3633-3639.
24. Josephy, P. D., Evans, D. H., Parikh, A., and Guengerich, F. P. (1998) Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli. Chem. Res. Toxicol. 11, 70-74.
25. Parikh, A., Josephy, P. D., and Guengerich, F. P. (1999) Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties. Biochemistry 38, 5283-5289.
26. Foroozesh, M., Primrose, G., Guo, Z., Bell, L. C., Alworth, W. L., and Guengerich, F. P. (1997) Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem. Res. Toxicol. 10, 91-102.
27. Bieder, A., Decouvelaere, B., Gaillard, C., Depaire, H., Heusse, D., Ledoux, C., Lemar, M., Le Roy, J. P., Raynaud, L., Snozzi, C., and Gregoire, J. (1983) Comparison of the metabolism of oltipraz in the mouse, rat and monkey and in man. Arzneim.-Forsch. 33, 1289-1297.
28. Levin, W., Lu, A. Y. H., Jacobson, M., Kuntzman, R., Poyer, J. L., and McCay, P. B. (1973) Lipid peroxidation and the degradation of cytochrome P-450 heme. Arch. Biochem. Biophys. 158, 842-852.
29. De Matteis, F., Gibbs, A. H., and Unseld, A. (1977) Loss of haem from cytochrome P-450 caused by lipid peroxidation and 2-allyl-2-isopropylacetamide. Biochem. J. 168, 417-422.
30. Schaefer, W. H., Harris, T. M., and Guengerich, F. P. (1985) Characterization of the enzymatic and nonenzymatic peroxidative degradation of iron porphyrins and cytochrome P-450 heme. Biochemistry 24, 3254-3263.
31. Buege, J. A., and Aust, S. D. (1978) Microsomal lipid peroxidation. Methods Enzymol. 52, 302-310.
32. Moreau, N., Martens, T., Fleury, M. B., and Leroy, J. P. (1990) Metabolism of oltipraz and glutathione reductase inhibition. Biochem. Pharmacol. 40, 1299-1305.
33. Shiraki, H., and Guengerich, F. P. (1984) Turnover of membrane proteins: kinetics of induction and degradation of seven forms of rat liver microsomal cytochrome P-450, NADPH-cytochrome P-450 reductase, and epoxide hydrolase. Arch. Biochem. Biophys. 235, 86-96.
34. Halpert, J. R., Guengerich, F. P., Bend, J. R., and Correia, M. A. (1994) Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol. 125, 163-175.
35. Mammons, G. J., Alworth, W. L., Hopkins, N. E., Guengerich, F. P., and Kadlubar, F. F. (1989) 2-Ethynylnaphthalene as a mechanism-based inactivator of the cytochrome P-450 catalyzed N-oxidation of 2-naphthylamine. Chem. Res. Toxicol. 2, 367-374.
36. Yun, C.-H., Hammons, G. J., Jones, G., Martin, M. V., Hopkins, N. E., Alworth, W. L., and Guengerich, F. P. (1992) Modification of cytochrome P450 1A2 enzymes by the mechanism-based inactivator 2-ethynylnaphthalene and the photoaffinity label 4-azidobiphenyl. Biochemistry 31, 10556-10563.
37. Guengerich, F. P. (1990) Mechanism-based inactivation of human liver cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3, 363-371.
38. Bondon, A., Macdonald, T. L., Harris, T. M., and Guengerich, F. P. (1989) Oxidation of cycloalkylamines by cytochrome P-450. Mechanism-based inactivation, adduct formation, ring expansion, and nitrone formation. J. Biol. Chem. 264, 1988-1997.
39. Grimm, S. W., Dyroff, M. C., Philpot, R. M., and Halpert, J. R. (1994) Catalytic selectivity and mechanism-based inactivation of stably expressed and hepatic cytochromes P450 2B4 and 2B5: implications of the cytochrome P450 2B5 polymorphism. Mol. Pharmacol. 46, 1090-1099.
40. Roberts, E. S., Hopkins, N. E., Zaluzec, E. J., Gage, D. A., Alworth, W. L., and Hollenberg, P. F. (1995) Mechanism-based inactivation of cytochrome P450 2B1 by 9-ethynylphenanthrene. Arch. Biochem. Biophys. 323, 295-302.
41. Raner, G. M., Chiang, E. W., Vaz, A. D. N., and Coon, M. J. (1997) Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: relationship to aldehyde deformylation via a peroxyhemiacetal intermediate. Biochemistry 36, 4895-4902.
42. Roberts, E. S., Hopkins, N. E., Foroozesch, M., Alworth, W. L., Halpert, J. R., and Hollenberg, P. F. (1997) Inactivation of cytochrome P450s 2B1, 2B4, 2B6, and 2B11 by arylalkynes. Drug Metab. Dispos. 25, 1242-1248.
43. Roberts, E. S., Alworth, W. L., and Hollenberg, P. F. (1998) Mechanism-based inactivation of cytochromes P450 2E1 and 2B1 by 5-phenyl-1-pentyne. Arch. Biochem. Biophys. 354, 295-302.
44. Maxuitenko, Y. Y., Libby, A. H., Joyner, H. H., Curphey, T. J., MacMillan, D. L., Kensler, T. W., and Roebuck, B. D. (1998) Identification of dithiolethiones with better chemopreventive properties than oltipraz. Carcinogenesis 19, 1609-1615.
45. 1 by oltipraz in residents of Qidong, People's Republic of China. J. Natl. Cancer Inst. 91, 347-354.
46. Wattenberg, L. W. (1987) Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamines or benzo[a]pyrene on pulmonary and forestomach neoplasia in A/J mice. Carcinogenesis 8, 1971-1973.
47. Morse, M. A., Wang, C. G., Stoner, G. D., Mandal, S., Conrad, P. B., Amin, S. G., Hetch, S. S., and Chung, F. L. (1989) Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rat by dietary phenethyl isothiocyanate. Cancer Res. 49, 549-553.
48. Stoner, G. D., Morrissey, D. T., Heur, Y. H., Daniel, E. M., Galati, A. J., and Wagner, S. A. (1991) Inhibitory effects of phenyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res. 51, 2063-2068.
49. Prestera, T., Holtzclaw, W. D., Zhang, Y., and Talalay, P. (1993) Chemical and molecular regulation of enzymes that detoxify carcinogens. Proc. Natl. Acad. Sci. U.S.A. 90, 2965-2969.
50. Guo, Z., Smith, T. J., Wang, E., Eklind, K. I., Chung, F. L., and Yang, C. S. (1993) Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis 14, 1167-1173.
51. Kassahun, K., Davis, M., Hu, P., Martin, B., and Baillie, T. (1997) Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: Identification of phase I metabolites and glutathione conjugates. Chem. Res. Toxicol. 10, 1228-1233.