Characterization of cytochrome P450 3a inactivation by cannabidiol: Possible involvement of cannabidiol-hydroxyquinone as a P450 inactivator

Chemical Research in Toxicology

Volumn 11, Issue 10, 1998, Pages 1209-1216

  Bornheim, Lester M ^a   Grillo, Mark P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABIDIOL; CANNABIS; CYTOCHROME P450 INHIBITOR; CYTOCHROME P450 ISOENZYME; GLUTATHIONE; PROTEINASE; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME INACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME METABOLISM; MASS SPECTROMETRY; MOLECULAR WEIGHT; MOUSE; NONHUMAN; OXIDATION; ULTRAVIOLET SPECTROSCOPY;

AMINO ACID SEQUENCE; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BINDING SITES; CANNABIDIOL; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; GLUTATHIONE; HYDROQUINONES; MICE; MOLECULAR SEQUENCE DATA; OXIDOREDUCTASES, N-DEMETHYLATING;

EID: 0031773166     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9800598     Document Type: Article

References (41)

1. Siemens, A. J., Kalant, H., Khanna, J. M., Marshman, J., and Ho, G. (1974) Effect of cannabis on pentobarbital-induced sleeping time and pentobarbital metabolism in the rat. Biochem, Pharmacol. 23, 477-488.
2. Bornheim, L. M., Borys, H. K., and Karler, R. (1981) Effect of cannabidiol on cytochrome P-450 and hexobarbital sleep time. Biochem. Pharmacol. 30, 503-507.
3. Hamajima, K., Watanabe, K., Narimatsu, S., Tateoka, Y., Yamamoto, I., and Yoshimura, H. (1983) Sex difference in the effects of Δ9-tetrahydrocannabinol and cannabidiol on pentobarbital-induced sleeping time and hepatic microsomal drug metabolizing enzyme systems in mice. Yakugaku Zasshi 103, 1289-1297.
4. Watanabe, K., Arai, M., Narimatsu, S., Yamamoto, I., and Yoshimura, H. (1987) Self-catalyzed inactivation of cytochrome P-450 during microsomal metabolism of cannabidiol. Biochem. Pharmacol. 36, 3371-3377.
5. Bornheim, L. M., and Correia, M. A. (1989) Effect of cannabidiol on cytochrome P-450 isozymes. Biochem. Pharmacol. 38, 2789-2794.
6. Bornheim, L. M. (1989) Effect of cannabidiol on drug metabolism. In Biochemistry and Physiology of Substance Abuse (Watson, R., Ed.) Vol. 1, pp 21-35, CRC Press, Boca Raton, FL.
7. Bornheim, L. M., and Correia, M. A. (1990) Selective inactivation of mouse liver cytochrome P-450IIIA by cannabidiol. Mol. Pharmacol. 38, 319-326.
8. Bornheim, L. M., and Correia, M. A. (1991) Purification and characterization of the major hepatic cannabinoid hydroxylase in the mouse: a possible member of the cytochrome P-450IIC subfamily. Mol. Pharmacol. 40, 228-234.
9. Jaeger, W., Benet, L. Z., and Bornheim, L. M. (1996) Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes. Xenobiotica 26 (3), 275-284.
10. 1-tetrahydrocannabinol. Drug Metab. Dispos. 2, 241-246.
11. Guengerich, F. P. (1995) Human cytochrome P450 enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano, P. R., Ed.) pp 473-535, Plenum Press, New York.
12. Hollister, L. E. (1973) Cannabidiol and cannabinol in man. Experientia 29, 825-826.
13. Karniol, I. G., Shirakawa, I., Kasinski, N., Pfeferman, A., and Carlini, E. A. (1974) Cannabidiol interferes with the effects of Δ9-tetrahydrocannabinol in man. Eur. J. Pharmacol. 28, 172-177.
14. Dalton, W. S., Martz, R., Rodda, B. E., Lemberger, L., and Forney, R. B. (1976) Influence of cannabidiol on secobarbital effects and plasma kinetics. Clin. Pharmacol. Ther. 20, 695-700.
15. Zuardi, A. W., Shirakawa, I., Finkelfarb, E., and Karniol, I. G. (1982) Action of cannabidiol on the anxiety and other effects produced by Δ9-THC in normal subjects. Psychopharmacology 76, 245-250.
16. Bornheim, L. M., Kim, K. Y., Li, J., Perotti, B. Y. T., and Benet, L. Z. (1995) Effect of cannabidiol pretreatment on the kinetics of tetrahydrocannabinol metabolites in mouse brain. Drug Metab. Dispos. 23, 825-831.
17. Bornheim, L. M., Everhart, E. T., and Correia, M. A. (1993) Characterization of cannabidiol-mediated cytochrome P-450 inactivation. Biochem. Pharmacol. 45, 1323-1331.
18. Watanabe, K., Narimatsu, S., Gohda, H., Yamamoto, I., and Yoshimura, H. (1988) Formation of similar species to carbon monoxide during hepatic microsomal metabolism of cannabidiol on the basis of spectral interaction with cytochrome P-450. Biochem. Pharmacol 37, 4719-4762.
19. Rolling, M. V., Aoyama, T., Gonzalez, F. J., and Meyer, U. A. (1990) Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. J. Pharmacol. Exp. Ther. 252, 442-447.
20. Pichard, L., Fabre, I., Fabre, G., Domergue, J., St. Aubert, B., Moorad, G., and Maurel, P. (1990) Cyclosporine A drug interactions. Drug Metab. Dispos. 18, 595-606.
21. Watanabe, K., Usami, N., Yamamoto, I., and Yoshimura, H. (1991) Inhibitory effect of cannabidiol hydroxyquinone, an oxidative product of cannabidiol, on the hepatic microsomal drug-metabolizing enzymes of mice. J. Pharmacobio-Dyn. 14, 421-427.
22. Waxman, D. J., and Walsh, C. (1982) Phenobarbital-induced rat liver cytochrome P-450: Purification of two closely related isozymic forms. J. Biol. Chem. 258, 11937.
23. Schagger, H., and Von Jagow, G. (1987) Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal. Biochem. 166, 368-379.
24. Yao, K., Falick, A. M., and Correia, M. A. (1993) Cumene hydroperoxide-mediated inactivation of cytochrome P450 2B1: Identification of an active site heme-modified peptide. J. Biol. Chem. 268, 59-65.
25. Mechoulam, R., Ben-Zvi, Z., and Gaoni, Y. (1968) Hashish-XIII: On the nature of the Beam test. Tetrahedron 24, 5615-5624.
26. Kassahun, K., Hu, P., Grillo, M. P., Davis, M. R., Jin, L., and Baillie, T. A. (1994) Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and independent processes. Chem.-Biol. Interact. 90, 253-275.
27. Gotoh, O. (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 267, 83-90.
28. Hasemann, C. A., Kurumbail, R. G., Boddupali, S. S., Peterson, J. A., and Deisenhofer, J. (1995) Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure 3, 41-62.
29. von Wachenfeldt, C., and Johnson, E. F. (1995) Structures of eukaryotic cytochrome P450 enzymes. In Cytochrome P450; Structure, Function, and Mechanism (Ortiz de Montellano, P. R., Ed.) pp 183-223, Plenum Press, New York.
30. Szklarz, G. D., and Halpert, J. R. (1997) Molecular modeling of cytochrome P450 3A4. J. Comput.-Aided Mol. Des. 11, 265-272.
31. Roberts, E. S., Hopkins, N. E., Alworth, W. L., and Hollenberg, P. F. (1993) Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: Identification of an active-site peptide. Chem. Res. Toxicol. 6, 470-479.
32. 3H-labeled 2-ethynylnaphthalene-inactivated P450 2B1 and 2B4 using amino acid sequencing and mass spectrometry. Biochemistry 33, 3766-3771.
33. 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.
34. He, K., Falick, A. M., Chen, B., Nilsson, F., and Correia, M. A. (1996) Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital. Chem. Res. Toxicol. 9, 614-622.
35. Monks, T. J., Highet, R. J., and Lau, S. S. (1990) Oxidative cyclization, 1,4-benzothiazine formation and dimerization of 2-bromo-3-(glutathion-S-yl)hydroquinone. Mol. Pharmacol. 38, 121-127.
36. Monks, T. J., and Lau, S. S. (1997) Biological reactivity of polyphenolic-glutathione conjugates. Chem. Res. Toxicol. 10, 1296-1313.
37. Finley, K. T. (1974) The addition and substitution chemistry of quinones. In The Chemistry of The Quinonoid Compounds (Patai, S., Ed.) pp 877-1144, John Wiley and Sons, New York.
38. Smith, A. L., and Lester, R. L. (1961) The inhibition of oxidation and phosphorylation in beef-heart mitochondria by benzoquinones. Biochim. Biophys. Acta 48, 547-551.
39. Redfearn, E. R., and Whittaker, P. A. (1962) The inhibitory effects of quinones on the succinic oxidase system of the respiratory chain. Biochim. Biophys. Acta 56, 440-444.
40. Baillie, T. A., and Davis, M. R. (1993) Mass spectrometry in the analysis of glutathione conjugates. Biol. Mass Spectrom. 22, 319325.
41. Finley, K. T. (1988) Quinones as synthones. In The Chemistry of The Quinonoid Compounds (Patai, S., and Rappoport, Z., Eds.) pp 537-717, John Wiley and Sons, New York.