A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes

Journal of Pharmacology and Experimental Therapeutics

Volumn 282, Issue 3, 1997, Pages 1608-1614

  Messina, E S ^a   Tyndale, R F ^a   Sellers, E M ^a,b  

^a CENTRE FOR ADDICTION AND MENTAL HEALTH   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COTININE; CYTOCHROME P450; DEXTROMETHORPHAN; NICOTINE;

ARTICLE; DRUG OXIDATION; DRUG PROTEIN BINDING; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; LIVER MICROSOME METABOLISM; PRIORITY JOURNAL;

ADOLESCENT; ADULT; ARYL HYDROCARBON HYDROXYLASES; CHILD; CHILD, PRESCHOOL; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 ENZYME SYSTEM; FEMALE; HUMANS; MALE; MICROSOMES, LIVER; MIDDLE AGED; MIXED FUNCTION OXYGENASES; NICOTINE; OXIDATION-REDUCTION;

EID: 0030885491     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. AGUNDEZ, J. A. AND BENITEZ, J.: Debrisoquine polymorphism: Mechanism for very rapid oxidative phenotype (Letter; Comment). Lancet 341: 689, 1993.
2. AYESH, R., IDLE, J. R., RITCHIE, J. C., CROTHERS, M. J. AND HETZEL, M. R.: Metabolic oxidation phenotypes as markers for susceptibility to lung cancer. Nature 312: 169-171, 1984.
3. BECKETT, A. H., GORROD, J. W. AND JENNER, P.: The effect of smoking on nicotine metabolism in vivo in man. J Pharm. Pharmacol. 23: 62S-67S, 1971.
4. BENITEZ, J., LADERO, J. M., JARA, C., CARRILLO, J. A., COBALEDA, J., LLERENA, A., VARGAS, E. AND MUNOZ, J. J.: Polymorphic oxidation of debrisoquine in lung cancer patients. Eur. J. Cancer 27: 158-161, 1991.
5. BENOWITZ, N. L. AND JACOB, P. D.: Daily intake of nicotine during cigarette smoking. Clin. Pharmacol. Ther. 35: 499-504, 1984.
6. BENOWITZ, N. L., JACOB, P. D., JONES, R. T. AND ROSENBERG, J.: Interindividual variability in the metabolism and cardiovascular effects of nicotine in man. J. Pharmacol. Exp. Ther. 221: 368-372, 1982.
7. BENOWITZ, N. L., JACOB, P. D. AND PEREZ-STABLE, E.: CYP2D6 phenotype and the metabolism of nicotine and cotinine. Pharmacogenetics 6: 239-242, 1996.
8. BENOWITZ, N. L., JACOB, P. D. AND SACHS, D. P. L.: Deficient C-oxidation of nicotine. Clin. Pharmacol. Ther. 57: 590-594, 1995.
9. BERTILSSON, L., LOU, Y. Q., DU, Y. L., LIU, Y., KUANG, T. Y., LIAO, X. M., WANG, K. Y., REVIRIEGO, J., ISELIUS, L. AND SJOQVIST, F.: Pronounced differences between native Chinese and Swedish populations in the polymorphic hydroxylations of debrisoquin and S-mephenytoin [Published erratum appears in Clin. Pharmacol. Ther. 55: 648 (1994)]. Clin. Pharmacol. Ther. 51: 388-397, 1992.
10. BRANDAGE, S. AND LINDBLOM, L.: The enzyme 'aldedyde oxidase' is an iminium oxidase: Reaction with nicotine-delta-1′(5′) iminium ion. Biochem. Biophys. Res. Commun. 91: 991-996, 1979.
11. BROLEY, F., LIBERSA, C., LHERMITTE, M., BECHTEL, P. AND DUPUIS, B.: Effect of quinidine on the dextromethorphan O-demethylase activity of microsomal fractions from human liver. Br. J. Clin. Pharmacol. 28: 29-36, 1989.
12. CAMPBELL, M. E., GRANT, D. M., INABA, T. AND KALOW, W.: Biotransformation of caffeine, paraxanthine, theophylline, and theobromine by polycyclic aromatic hydrocarbon-inducible cytochrome(s) P-450 in human liver microsomes. Drug Metab. Dispos. 15: 237-249, 1987.
13. CASHMAN, J. R., PARK, S. B., YANG, Z. C., WRIGHTON, S. A., JACOB, P. D. AND BENOWITZ, N. L.: Metabolism of nicotine by human liver microsomes: Stereoselective formation of trans-nicotine N′-oxide. Chem. Res. Toxicol. 5: 639-646, 1992.
14. CHANG, T. K., WEBER, G. F., CRESPI, C. L. AND WAXMAN, D. J.: Differential activation of cyclosphosphamide and ifosphamide by cytochrome P-450 2B and 3A in human liver microsomes. Cancer Res. 53: 5629-5637, 1993.
15. CHING, M. S., BLAKE, C. L., GHABRIAL, H., ELLIS, S. W., LENNARD, M. S., TUCKER, G. T. AND SMALLWOOD, R. A.: Potent inhibition of yeast-expressed CYP2D6 by dihydroquinidine, quinidine, and its metabolites. Biochem. Pharmacol. 50: 833-837, 1995.
16. CHOLERTON, S., ARPANAHI, A., MCCRACKEN, N., BOUSTEAD, C., TABER, H., JOHNSTONE, E.. LEATHART, J., DALY, A. K. AND IDLE, J. R.: Poor metabolisers of nicotine and CYP2D6 polymorphism (Letter). Lancet 343: 62-63, 1994.
17. COUTTS, R. T.: Polymorphism in the metabolism of drugs, including antidepressant drugs: Comments on phenotyping. J. Psychiatry Neurosci. 19: 30-44, 1994.
18. CRESPI, C. L., PENMAN, B. W., GELBOIN, H. V. AND GONZALEZ, F. J.: A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis 12: 1197-1201, 1991.
19. DAVIES, R. L., CRESPI, C. L., RUDO, K., TURNER, T. R. AND LANGENBACH, R.: Development of a human cell line by selection and drug-metabolizing gene transfection with increased capacity to activate promutagens. Carcinogenesis 10: 885-891, 1989.
20. DING, X. AND COON, M. J.: Purification and characterization of two unique forms of cytochrome P-450 from rabbit nasal microsomes. Biochemistry 29: 1322-1329, 1988.
21. EVANS, W. E. AND RELLING, M. V.: Concordance of P450 2D6 phenotype and genotype: Inability of dextromethorphan metabolic ratio to discriminate reliably heterozygous and homozygous extensive metabolizers. Pharmacogenetics 1: 143-148, 1991.
22. FERNANDEZ-SALGUERO, P., HOFFMAN, S. M., CHOLERTON, S., MOHRENWEISER, H., RAUNIO, H., RAUTIO, A., PELKONEN, O., HUANG, J. D., EVANS, W. E., IDLE, J. R. AND GONZALEZ, F. J.: A genetic polymorphism in coumarin 7-hydroxylation: Sequence of the human CYP2A genes and identification of variant CYP2A6 alleles. Am. J. Hum. Genet. 57: 651-660, 1995.
23. FLAMMANG, A. M., GELBOIN, H. V., AOYAMA, T., GONZALEZ, F. J. AND MCCOY, G. D.: Nicotine metabolism by cDNA-expressed human cytochrome P-450s. Biochem. Arch. 8: 1-8, 1992.
24. GORROD, J. W. AND HIBBERD, A. R.: The metabolism of nicotine-delta 1′(5′)-iminium ion, in vivo and in vitro. Eur. J. Drug Metab. Pharmacokinet. 7: 293-298, 1982.
25. HENNINGFIELD, J. E., MIYASATO, K. AND JASINKI, D. R.: Abuse liability and pharmacodynamic characteristics of intravenous and inhaled nicotine. J. Pharmacol. Exp. Ther. 234: 1-12, 1985.
26. HIRVONEN, A., HUSGAFVEL-PURSIAINEN, K., ANTTILA, S., KARJALAINEN, A., PELKONEN, O. AND VAINIO, H.: PCR-based CYP2D6 genotyping for Finnish lung cancer patients. Pharmacogenetics 3: 19-27, 1993.
27. KALOW, W.: Genetic variation in the human hepatic cytochrome P-450 system. Eur. J. Clin. Pharmacol. 31: 633-641, 1987.
28. KAPITULNIK, J., POPPER, P. J. AND CONNEY, A. H.: Comparative metabolism of benzo
29. KERRY, N. L., SOMOGYI, A. A., BOCHNER, F. AND MIKUS, G.: The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: In vitro studies using human liver microsomes. Br. J. Clin. Pharmacol. 38: 243-248, 1994.
30. LENNARD, M. S.: Genetic polymorphism of sparteine/debrisoquine oxidation: A reappraisal. Pharmacol. Toxicol. 67: 273-283, 1990.
31. LOU, Y. C., YING, L., BERTILSSON, L. AND SJOQVIST, F.: Low frequency of slow debrisoquine hydroxylation in a native Chinese population (Letter). Lancet. 2: 852-853, 1987.
32. MCCRACKEN, N. W., CHOLERTON, S. AND IDLE, J. R.: Cotinine formation by cDNA-expressed human cytochromes P450. Med. Sci. Res. 20: 877-878, 1992.
33. MCMORROW, M. J. AND FOXX, R. M.: Nicotine's role in smoking: An analysis of nicotine regulation. Psychol. Bull. 93: 302-327, 1983.
34. MILES, J. S., MOSS, J. E., MEEHAN, R. R. AND WOLF, C. R.: Close linkage of the cytochrome P450IIA gene subfamily (Cyp2a) to Cyp2b and Coh on mouse chromosome 7. Genomics 7: 445-448, 1990.
35. MURPHY, P. J.: Enzymatic oxidation of nicotine to nicotine 1′(5′) iminium ion: A newly discovered intermediate in the metabolism of nicotine. J. Biol. Chem. 248: 2796-2800, 1973.
36. NAKAJIMA, M., YAMAMOTO, T., NUNOYA, K., YOKOI, T., NAGASHIMA, K., INOUE, K., FUNAE, Y., SHIMADA, N., KMATAKI, T. AND KUROIWA, Y.: Characterization of CYP2A6 involved in 3′-hydroxylation of cotinine in human liver microsomes. J. Pharmacol. Exp. Ther. 277: 1010-1015, 1996.
37. OTTON, S. V., INABA, T. AND KALOW, W.: Inhibition of sparteine oxidation in human liver by tricyclic antidepressants and other drugs. Life Sci. 32: 795-800, 1983.
38. PEARCE, R., GREENWAY, D. AND PARKINSON, A.: Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: Effects on coumarin, dicumarol, and testosterone oxidation. Arch. Biochem. Biophys. 298: 211-225, 1992.
39. PELKONEN, O., SOTANIEMI, E. A. AND AHOKAS, J. T.: Coumarin 7-hydroxylase activity in human liver microsomes: Properties of the enzyme and interspecies comparisons. Br. J. Clin. Pharmacol. 19: 59-66, 1985.
40. PETERSON, L. A., TREVOR, A. AND CASTAGNOLI, N., JR.: Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the (S)-nicotine delta 1′(5′)-iminium species. J. Med. Chem. 30: 249-254, 1987.
41. RUDELL, U., FOTH, H. AND KAHL, G. F.: Eightfold induction of nicotine elimination in perfused rat liver by pretreatment with phenobarbital. Biochem. Biophys. Res. Commun. 148: 192-198, 1987.
42. RUSSEL, M. S. H.: Nicotine intake and its regulation by smokers: Tobacco smoking and nicotine. In Advances in Behavioral Biology, ed. by Martin, W. R., Vauhon, G. R., Iwamoto, E. T. and David, L., pp. 25-50, New York, Plenum Press (1987).
43. SPEIRS, C., MURRAY, S., DAVIES, D., MABADEJE, A. AND BOOBIS, A.: Debrisoquine oxidation phenotype and susceptibility to lung cancer. Br. J. Clin. Pharmacol. 29: 101-109, 1990.
44. TYNDALE, R. F., INABA, T. AND KALOW, W.: Evidence in humans for variant allozymes of the nondeficient sparteine/debrisoquine monooxygenase (P450IID 1) in vitro. Drug Metab. Dispos. 17: 334-340, 1989.
45. VERONESE, M. E. AND MCLEAN, S.: Debrisoquine oxidation polymorphism in a Tasmanian population. Eur. J. Clin. Pharmacol. 40: 529-532, 1991.
46. WANWIMOLRUK, S., PATAMASUCON, P. AND LEE, E. J.: Evidence for the polymorphic oxidation of debrisoquine in the Thai population. Br. J. Clin. Pharmacol. 29: 244-247, 1990.
47. WILLIAMS, D. E., SHIGENAGA, M. K. AND CASTAGNOLI, N., JR.: The role of cytochromes P-450 and flavin-containing monooxygenase in the metabolism of (S)-nicotine by rabbit lung. Drug Metab. Dispos. 18: 418-428, 1990a.
48. WILLIAMS, D. E., DING, X. X. AND COON, M. J.: Rabbit nasal cytochrome P-450 NMa has high activity as a nicotine oxidase. Biochem. Biophys. Res. Commun. 166: 945-952, 1990b.
49. WOLF, C. R., SMITH, C. A., GOUGH, A. C., MOSS, J. E., VALLIS, K. A., HOWARD, G., CAREY, F. J., MILLS, K., MCNEE, W., CARMICHAEL, J. AND SPURR, N. K.: Relationship between the debrisoquine hydroxylase polymorphism and cancer susceptibility. Carcinogenesis 13: 1035-1038, 1992.
50. YAMANO, S., TATSUNO, J. AND GONZALEZ, F. J.: The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 29: 1322-1329, 1990.
51. YUN, C. H., SHIMADA, T. AND GUENGERICH, F. P.: Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol. Pharmacol. 40: 679-685, 1991.