Selective mechanism-based inactivation of rat CYP2D by 4-allyloxymethamphetamine

Journal of Pharmacology and Experimental Therapeutics

Volumn 277, Issue 2, 1996, Pages 595-603

  Lin, L Y ^a   Fujimoto, M ^a   Distefano, E W ^a   Schmitz, D A ^a   Jayasinghe, A ^a   Cho, A K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 METHYLENEDIOXYAMPHETAMINE DERIVATIVE; 4 ALLYLOXYMETHAMPHETAMINE; AMINOPHENAZONE; AMPHETAMINE DERIVATIVE; ANILINE; BENZPHETAMINE; BUFURALOL; CYTOCHROME P450 ISOENZYME; ERYTHROMYCIN; METHAMPHETAMINE; QUININE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DEMETHYLATION; DOSE TIME EFFECT RELATION; DRUG DETOXIFICATION; DRUG HYDROXYLATION; ENZYME INACTIVATION; FEMALE; LIVER MICROSOME METABOLISM; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DEALKYLATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ETHANOLAMINES; FEMALE; MALE; METHAMPHETAMINE; PHENCYCLIDINE; PROPRANOLOL; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030430272     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. AL-DABBAGH, S. G., UDLE, J. R. AND SMITH, R. L.: Animal modeling of human polymorphic drug oxidation - The metabolism of debrisoquine and phenacetin in rat inbred strains. J. Pharm. Pharmacol. 33: 161-164, 1981.
2. BARHAM, H M., LENNARD, M. S. AND TUCKER, G. T.: An evaluation of cytochrome P450 isoform activities in the female dark agouti (DA) rat: Relevance to its use as a model of the CYP2D6 poor metaboliser phenotype. Biochem. Pharmacol. 47: 1295-1307, 1994.
3. BOOBIS, A. R., SEDDON, C. E. AND DAVIES, D. S.: Bufuralol 1′-hydroxylase activity of the rat: Strain differences and the effect of inhibitors. Biochem. Pharmacol. 35: 2961-2965, 1986.
4. BRADFORD, M. M.: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254, 1976.
5. BRADY, J. F., DOKKO, J., DISTEFANO, E. W. AND CHO, A. K.: Mechanism-based inhibition of cytochrome P450 by heterocyclic analogues of phencyclidine. Drug Metab Dispos. 15: 648-652, 1987.
6. BRADY, J. F., ISHIZAKI, H., FUKUTO, J. M., LIN, M. C., FADEL, A., GAPAC, J. M. AND YANG, C S.: Inhibition of cytochrome P-450 2E1 by Diallyl sulfide and its metabolites. Chem. Res. Toxicol. 4: 642-647, 1991.
7. BROSEN, K. AND GRAM. L. F.: Clinical significance of the sparteine/debrisoquine oxidation polymorphism. Eur. J. Clin. Pharmacol. 36: 537-547, 1989.
8. COOPER, K. O., WITZ, G. AND WITMER, C.: The effect of α,β-unsaturated aldehydes on hepatic thiols and thiol-containing enzymes. Fundam. Appl. Toxicol. 19: 343-349, 1992.
9. COUTTS, R. T.: Polymorphism in the metabolism of drugs, including antidepressant drugs: Comments on phenotyping. J. Psychol. Neurosci. 19: 30-44, 1994.
10. CROWLEY, J. R. AND HOLLENBERG, P. F.: Mechanism-based inactivation of cytochrome P450 IIB1 by phencyclidine. Fed. Am. Soc. Exp. Biol. J. 6: A1566, 1992.
11. EICHELBAUM, M. AND GROSS, A. S.: The genetic polymorphism of debrisoquine/ sparteine metabolism-clinical aspects. Pharmacol. Ther. 46: 377-394, 1990.
12. ESTERBAUER, H., ZOLLNER, H. AND SCHOLZ, N.: Reaction of glutathione with conjugated carbonyls. Z. Naturforsch. 30: 466-473, 1975.
13. GONZALEZ, F. J. AND MEYER, U. A.: Molecular genetics of the debrisoquine/ sparteine polymorphism. Clin. Pharmacol. Ther. 50: 233-238, 1991.
14. GURTOO, H. L., MARINELLO, A. J., STRUCK, R. F., PAUL, B. AND DAHMS, R. P.: Studies on the mechanism of denaturation of cytochrome P-450 by cyclophosphamide and its metabolites. J. Biol. Chem. 256: 11691-11701, 1981.
15. HIRAMATSU, M., KUMAGAI, Y., UNGER, S. E. AND CHO, A. K: Metabolism of methylenedioxymethamphetamine (MDMA): Formation of dihydroxymethoamphetamine and quinone identified as its glutathione adduct. J. Pharmacol. Exp. Ther. 254: 521-527, 1990.
16. HIRATSUKA, A., CHU, T. Y. Y., DISTEFANO, E. W., LIN, L Y., SCHMITZ, D. A. AND CHO, A. K.: Inactivation of constitutive hepatic cytochromes P450 by phencyclidine in the rat. Drug Metab. Dispos. 23: 201-206, 1995.
17. IMAI, Y., ITO, A. AND SATO, R.: Evidence for biochemically different types of vesicles in the hepatic microsomal fractions. J. Biochem. (Tokyo) 60: 417-428, 1966.
18. KAHN, G. C., RUBENFIELD, M , DAVIES, D. S., MURRAY, S. AND BOOBIS, A. R.: Sex and strain differences in hepatic debrisoquine 4-hydroxylase activity of the rat. Drug Metab. Dispos. 13: 510-516, 1985.
19. KISHI, T., INOUE, T., SUZUKI, S., YASUDA, T., OIKAWA, T. AND NIWAGUCHI, T.: Analysis of impurities in methamphetamine. Eisei Kagaku 29: 400-406, 1983.
20. KITCHEN, I., TREMBLAY, J., ANDRES, J., DRING, L. G., IDLE, J. R., SMITH, R. L. AND WILLIAMS, R. T.: Interindividual and interspecies variation in the metabolism of the hallucinogen 4-methoxyamphetamine. Xenobiotica 9: 397-404, 1979.
21. KUMAGAI, Y., LIN, L. Y., HIRATSUKA, A., NARIMATSU, S., SUZUKI, T., YAMADA, H., OGURI, K., YOSHIMURA, H. AND CHO, A. K.: Participation of cytochrome P450-2B and -2D isoforms in the demethylation of methylenedioxymethamphetamine enantiomers by rats. Mol. Pharmacol. 45: 359-365, 1994.
22. LAW, M. Y. L. AND MOODY, D. E.: Urinary excretion of amphetamine and 4′-hydroxyamphetamine by Sprague Dawley and Dark Agouti rats. Life Sci. 54: 1073-1079, 1994.
23. LEBLANC, G. A. AND WAXMAN, D. J.: Mechanism of cyclophosphamide action on hepatic P450 expression. Cancer Res. 50: 5720-5726, 1990.
24. LENNARD, M. S., TUCKER, G. T., SILAS, J. H. AND WOODS, H. F.: Debrisoquine polymorphism and the metabolism and action of metoprolol, timolol, propranolol and atenolol. Xenobiotica 16: 435-447, 1986
25. LEVIN, W., SERNATINGER, E., JACOBSON, M. AND KUNTZMAN, R.: Destruction of cytochrome P-450 by secobarbital and other barbiturates containing allyl groups Science (Wash. DC) 176: 1341-1343, 1972.
26. LIN, L. Y., KUMAGAI, Y , HIRATSUKA, A., NARIMATSU, S., SUZUKI, T., FUNAE, Y., DISTEFANO, E. W. AND CHO, A. K.: Cytochrome P4502D isozymes catalyze the 4-hydroxylation of methamphetamine enantiomers. Drug Metab. Dispos. 23: 610-614, 1995.
27. MARINELLO, A. J., BANSAL, S. K., PAUL, B., KOSER, P. L., STRUCK, R. F. AND GURTOO, H. L.: Metabolism and binding of cyclophosphamide and its metabolite acrolein to rat hepatic microsomal cytochrome P-450. Cancer Res. 44: 4615-4621, 1984.
28. MASUBUCHI, Y., FUJITA, S., CHIBA, M., KAGIMOTO, N., UMEDA, S. AND SUZUKI, T.: Impairment of debrisoquine 4-hydroxylase and related monooxygenase activities in the rat following treatment with propranolol. Biochem. Pharmacol. 41: 861-865, 1991a.
29. MASUBUCHI, Y., KAGIMOTO, N., NARIMATSU, S., FUJITA, S. AND SUZUKI, T.: Regioselective contribution of the cytochrome P-450 2D subfamily to propranolol metabolism in rat liver microsomes. Drug Metab. Dispos. 21: 1012-1016, 1993.
30. MASUBUCHI, Y., NARIMATSU, S., HOSOKAWA, S. AND SUZUKI, T.: Role of the CYP2D subfamily in metabolism-dependent covalent binding of propranolol to liver microsomal protein in rats. Biochem. Pharmacol. 48: 1891-1898, 1994.
31. MASUBUCHI, Y., UMEDA, S., CHIBA, M., FUJITA, S. AND SUZUKI, T.: Selective 3-hydroxylation deficiency of lidocaine and its metabolite in Dark Agouti rats. Biochem. Pharmacol. 42: 693-695, 1991b.
32. MEYER, U. A., SKODA, R. C. AND ZANGER, U. M.: The genetic polymorphism of debrisoquine/sparteine metabolism-molecular mechanism. Pharmacol. Ther. 46: 297-308, 1990.
33. NASH, T.: The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 55: 416-421, 1953.
34. OMURA, T. AND SATO, R.: The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein. J. Biol. Chem. 239: 2370-2373, 1964.
35. ORTIZ DE MONTELLANO, P. R., STEARNS, R. A. AND LANGRY, K. C.: The allylisopropylacetamide and novonal prosthetic heme adducts. Mol. Pharmacol. 25: 310-317, 1984.
36. OSAWA, Y. AND GOON, M. J.: Selective mechanism-based inactivation of the major phenobarbital-inducible P-450 cytochrome from rabbit liver by phencyclidine and its oxidation product, the iminium compound. Drug Metab. Dispos. 17: 7-13, 1989.
37. OTTON, S V., CREWE, H. K., LENNARD, M. S., TUCKER, G. T. AND WOODS, H. F.: Use of quinidine inhibition to define the role of the sparteine, debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. J. Pharmacol. Exp. Ther. 246: 242-247, 1988.
38. OWENS, S. M., GUNNELL, M., LAURENZANA, E. M. AND VALENTINE, J. L.: Dose- and time-dependent changes in phencyclidine metabolite covalent binding in rats and the possible role of CYP2D1. J. Pharmacol. Exp. Ther. 265:1261-1266, 1993.
39. RYAN, D. E. AND LEVIN, W.: Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol. Ther. 45:153-239, 1990.
40. SMISSMAN, E. E. AND BORCHARDT, R. T.: Conformational study of catecholamine receptor sites. 7. Synthesis of erythro and threo-3-amino-2-(3,4-dihydroxy-phenyl)-2-butanol hydrochlorides and erythro- and threo-2-amino-3-(3,4-dihydroxyphenyl)-2-butane hydrochlorides. J. Med. Chem. 14: 702-707, 1971.
41. SOUCEK, P. AND GUT, I.: Review: Cytochromes P450 in rats: Structures, functions, properties and relevant human forms. Xenobiotica 22: 83-103, 1992.
42. SUZUKI, T., NARIMATSU, S., FUJITA, S., MASUBUCHI, Y. AND UMEDA, S.: Impairment of bunitrolol 4-hydroxylase activity in liver microsomes of Dark Agouti rats. Biochem. Pharmacol. 42: 2241-2244, 1991.
43. SUZUKI, T., NARIMATSU, S., FUJITA, S., MASUBUCHI, Y., UMEDA, S., IMAOKA, S. AND FUNAE, Y.: Purification and characterization of a cytochrome P-450 isozyme catalyzing bunitrolol 4-hydroxylation in liver microsomes of male rats. Drug Metab. Dispos. 20: 367-373, 1992.