Formation of a metabolic intermediate complex of cytochrome P4502B1 by clorgyline

Drug Metabolism and Disposition

Volumn 24, Issue 11, 1996, Pages 1247-1253

  Sharma, Uma ^a   Roberts, Elizabeth S ^b   Hollenberg, Paul F ^a,b,c  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c 2301 Med Sci Research Building III ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; 7 ETHOXYCOUMARIN DEETHYLASE; BETA NAPHTHOFLAVONE; CLORGYLINE; CYTOCHROME P450; MONOAMINE OXIDASE INHIBITOR; PHENOBARBITAL; POTASSIUM FERRICYANIDE; PYRIDINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CATALYSIS; CONTROLLED STUDY; DISSOCIATION; DRUG HYDROXYLATION; ENZYME INACTIVATION; INTRAPERITONEAL DRUG ADMINISTRATION; LIVER MICROSOME METABOLISM; MALE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT;

ANIMALS; CARBON MONOXIDE; CATALYSIS; CLORGYLINE; CYTOCHROME P-450 CYP2B1; ISOENZYMES; MALE; MONOAMINE OXIDASE INHIBITORS; RATS; RATS, INBRED F344; SPECTRUM ANALYSIS;

ANIMALIA;

EID: 0030458334     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. T. D. Porter and M. J. Coon: Cytochrome P450: multiplicity of isoforms, substrates and catalytic and regulatory mechanisms. J. Biol. Chem. 266, 13469-13472 (1991).
2. M. A. Leo, J. M. Lasker, J. L. Raucy, C. I. Kim, M. Black, and C. S. Lieber: Metabolism of retinol and retinoic acid by human liver cytochrome P450 IIC8. Arch. Biochem. Biophys. 269, 305-312 (1989).
3. R. A. Prough and M. E. Spearman: Endogenous and dietary chemicals: metabolism and interraction with cytochrome P450. In "Mammalian Cytochrome P450" F.P. Guengerich, ed., vol. II, pp. 153-172. CRC Press, Boca Raton, FL, 1987.
4. J. R. Halpert, F. P. Guengrich, J. R. Bend, and M. A. Correia: Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol. 125, 163-175 (1994).
5. M. Murray and G. F. Reidy: Selectivity in the inhibition of mammalian cytochromes P450 by chemical agents. Pharmacol. Rev. 42, 85-101 (1990).
6. E. F. Johnson: Mapping determinants of the substrate selectivities of P450 enzymes by site-directed mutagenesis. Trends Pharmacol. Sci. 13, 122-126 (1992).
7. J. R. Halpert: Structural basis of cytochrome P450 inhibition. Annu. Rev. Pharmacol. Toxicol. 35 29-53 (1995).
8. M. Murray: Mechanisms of inhibition of cytechrome-P450 mediated drug oxidation by therapeutic agents. Drug Metab. Rev. 18, 55-81 (1987).
9. M. K. Buning and M.R. Franklin: SKF-525A inhibition, induction and 452-nm complex formation. Drug Metab. Dispos. 4, 244-255 (1976).
10. T. Egashira, B. Ekstedt, and L. Oreland: Inhibition by clorgyline and deprenyl of the different forms of monoamine oxidase in rat liver mitochondria. Biochem Pharmacol. 25, 2583-2586 (1976).
11. M. R. Franklin: The formation of cytochrome P450 metabolic intermediate complexes from amines in isolated perfused rat liver. Xenobiotica 4 547-554 (1974).
12. M. Hirata, B. Lindeke, and S. Orrenius: Cytochrome P450 product complexes and glutathione consumption produced in isolated hepatocytes by norbenzphetamine and its N-oxidized congeners. Biochem Pharmacol. 28, 479-484 (1979).
13. J. Werringloer and R. W. Estabrook: Heterogeneity of liver microsomal cytochrome P450: the spectral characterization of reactants with reduced cytochrome P450. Arch. Biochem. Biophys. 167 270-286 (1975).
14. M. R. Franklin: Cytochrome P450 metabolite-intermediate complexes from macrolide antibiotics and related compounds. Methods Enzymol. 206, 559-573 (1991).
15. M. Delaforge, M. Jaouen, and D. Mansuy: The cytochrome P450 metabolite complex dereived from troleandomycin: properties in vitro and stability in vivo. Chem. Biol. Interact. 51, 371-376 (1984).
16. L. K. Pershing and M. R. Franklin: Cytochrome P450 metabolic intermediate complex formation and induction by macrolide antibiotics; a new class of agents. Xenobiotica 12, 687-699 (1982).
17. M. Tinel, V. Descatoire, D. Larrey, J. Leoper, G. Labbe, P. Letteron, and D. Pessayre: Effects of clarithromycin on cytochrome P450. Comparison with other macrolides. J. Pharmacol. Exp. 250, 746-751 (1989).
18. M.R. Franklin: The influence of cytochrome P450 induction on the metabolic formation of 455-nm complexes from amphetamines. Drug Metab. Dispos. 2, 321-326 (1974).
19. J. C. Kawalek, W. Levin, D. Ryan, and A. Y. H. Lu: Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds and endogenous substrates. Drug Metab. Dispos. 4, 190-194 (1976).
20. M. J. Coon, T. A. van der Hoeven, S. B. Dahl, and D. A. Haugen: Two forms of liver microsomal cytochrome P450, P450 LM2 and P450 LM4 (rabbit liver). Methods Enzymol. 52, 109-117 (1978).
21. T. Saito and H. W. Strobel: Purification to homogeneity and characterization of a form of cytochrome P450 with high specificity for benzo[alpha]pyrene from beta-naphthoflavone-pretreated rat liver microsomes. J. Biol. Chem. 256, 984-988 (1981).
22. H. W. Strobel and J. D. Dignam: Purification and properties of NADPH-cytochrome P450 reductase. Methods Enzymol. 52, 89-92 (1978).
23. T. Omura and R. Sato: The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378 (1964).
24. J. T. M. Buters, C. D. Schiller, and R. C. Chou: A highly sensitive tool for the cytochrome P450 enzyme activity in rat, dog and man. Biochem. Pharmacol. 46, 1577-1584 (1993).
25. H. Dupont, D. S. Davies, and M. Strolin-Benedetti: Inhibition of cytochrome P450-dependent oxidation reactions by MAO inhibitors in rat liver microsomes. Biochem Pharmacol. 36, 1651-1657 (1987).
26. U. Sharma, E. S. Roberts, and P. F. Hollenberg: Inactivation of cytochrome P450 2B1 by the monoamine oxidase inhibitors R-(-)-deprenyl and clorgyline. Drug Metab. Dispos. 24, 669-675, 1996.
27. P. B. Watkins: Role of cytochromes P450 in drug metabolism and hepatotoxicity. Semin Liver Dis. 10, 235-250 (1990).
28. B. Testa and P. Jenner: Inhibitors of cytochrome P450s and their mechanism of action. Drug Metab. Rev. 12, 1-117 (1981).
29. E. S. Roberts, N. E. Hopkins, W. L. Alworth, and P. F. Hollenberg: Mechanism-based inactivtion of cytochrome P450 2B1 by 2-ethynylnaphthalene; identification of an active-site peptide. Chem Res. Toxicol. 6, 470-479 (1993).
30. 3H-labeled 2-ethynylnaphtalene-inactivated P450 2B1 and 2B4 using amino acid sequencing and mass spectrometry. Biochemistry 33, 3766-3771 (1994).
31. J. R. Halpert and R. A. Neal: Inactivation of purified rat liver cytochrome P450 by chloramphenicol. Mol. Pharmacol. 17, 427-431 (1980).
32. J. Werringloer and R. W. Estabrook: Evidence for an inhibitory product cytochrome P450 complex generated during benzphetamine metabolism by liver microsomes. Life Sci. 13, 1319-1330 (1973).
33. R. Leurs, D. Donnell, H. Timmerman, and A. Bast: Cytochrome P450 metabolite intermediate complex of nefopam. J. Pharm. Pharmacol. 39, 835-837 (1987).
34. R. B. Silverman: Introduction. In "Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology," vol. 1, pp. 3-23. CRC Press, Boca Raton, FL, 1988.
35. C. J. Sinal and J. R. Bend: Isozyme-selective metabolic intermediate complex formation of guinea pig hepatic cytochrome P450 by N-aralkylated derivatives of 1-aminobenztriazoles. Chem. Res. Toxicol. 8, 82-91 (1995).
36. J. B. Robinson: Steroselectivity and isoenzyme selectivity of monoamine oxidase inhibitors; enantiomers of amphetamine, N-methylamphetamine and deprenyl. Biochem. Pharmacol. 34, 4105-4108 (1985).
37. A. L. Green: The kinetics of inhibition of type-B monoamine oxidase by clorgyline, pargyline and (-)-deprenyl. J. Pharm. Pharmacol. 33, 798-800 (1981).
38. E. S. Roberts, N. E. Hopkins, E. J. Zaluzec, D. A. Gage, W. L. Alworth, and P. F. Hollenberg: Mechanism-based inactivation of cytochrome P450 2B1 by 9-ethynylphenanthrene. Arch Biochem. Biophys. 323, 295-302 (1995).
39. D. R. Koop: Inhibition of ethanol-inducible cytochrome P450 2E1 by 3-amino-1,2,4-triazole. Chem. Res. Toxicol. 3, 377-383 (1990).
40. F. P. Guengerich: Mechanism-based inactivation of human liver microsomal cytochrome P450 IIIA4 by gestodene. Chem. Res. Toxicol. 3, 363-371 (1990).
41. A. Bast and J. Noordhoek: Spectral interaction of orphenadrine and its metabolites with oxidized and reduced hepatic microsomal cytochrome-P450 in the rat. Biochem. Pharmacol. 31, 2745-2753, 1982.
42. U. Paulsen-Sorman, K.-H. Jonsson, and B. Lindeke: Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. IX. A comparative study with enantiomeric 2-nitroso-1-phenylpropane in microsomes and a reconstituted cytochrome P-450 system from rat liver. Chem. Biol. Interact. 67, 49-58 (1988).