Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol

Chemico-Biological Interactions

Volumn 197, Issue 2-3, 2012, Pages 87-92

  Kramlinger, Valerie M ^a   Von Weymarn, Linda B ^a   Murphy, Sharon E ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Nicotyrine; CYP2A13; CYP2A6; Cytochrome P450; Inactivation; Inhibition

Indexed keywords

CYTOCHROME P450 2A; CYTOCHROME P450 2A13; CYTOCHROME P450 2A6; ENZYME INHIBITOR; MENTHOFURAN; MENTHOL; NICOTYRINE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME KINETICS; HYDROXYLATION; NONHUMAN; RAT;

ARYL HYDROCARBON HYDROXYLASES; ENZYME ACTIVATION; ENZYME INHIBITORS; HEME; MENTHOL; MONOTERPENES; PYRIDINES; TOBACCO;

NICOTIANA TABACUM;

EID: 84860216857     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.03.009     Document Type: Article

References (37)

1. N.L. Benowitz Pharmacological aspects of cigarette smoking and nicotine addiction N. Engl. J. Med. 319 1988 1318 1330
2. International Agency for Research on Cancer Tobacco Smoke and Involuntary Smoking IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 2004 IARC Lyon, FR 1179 1187
3. N.L. Benowitz, B. Herrera, and P. Jacob III Mentholated cigarette smoking inhibits nicotine metabolism J Pharmacol. Exp. Ther. 310 2004 1208 1215
4. J.M. MacDougall, K. Fandrick, X. Zhang, S.V. Serafin, and J.R. Cashman Inhibition of human liver microsomal (S)-nicotine oxidation by (-)-menthol and analogues Chem. Res. Toxicol. 16 2003 988 993
5. M. Goozner, FDA Finding May Curb Mentholated Cigarette Availability, J. Natl. Cancer Inst. Epub ahead of print 2011 April 7 (2011).
6. J. Hukkanen, P. Jacob III, and N.L. Benowitz Metabolism and disposition kinetics of nicotine Pharmacol. Rev. 57 2005 79 115
7. J.R. Jalas, S.S. Hecht, and S.E. Murphy Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific carcinogen Chem. Res. Toxicol. 18 2005 95 110
8. E.M. Sellers, H.L. Kaplan, and R.F. Tyndale Inhibition of cytochrome P450 2A6 increases nicotine's oral bioavailablity and decreases smoking Clin. Pharmacol. Ther. 68 2000 35 43
9. E.M. Sellers, R.F. Tyndale, and L.C. Fernandes Decreasing smoking behaviour and risk through CYP2A6 inhibition Drug Discovery Today 8 2003 487 493
10. P. Fernandez-Salguero, S. Hoffman, S. Cholerton, H. Mohrenweiser, H. Raunio, H. Rautio, O. Pelkonen, J.D. Huang, W. Evans, J. Idle, and F. Gonzalez A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles Hum. Genet. 57 1995 651 660
11. T. Su, Z. Bao, Q.Y. Zhang, T.J. Smith, J.Y. Hong, and X. Ding Human cytochrome P 450 CYP2A13: predominant expression in the respiratory tract and in high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone Cancer Res. 60 2000 5074 5079
12. X. Zhang, J. D'Agostino, H. Wu, Q.Y. Zhang, L. von Weymarn, S.E. Murphy, and X. Ding CYP2A13: variable expression and role in human lung microsomal metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanone J. Pharmacol. Exp. Ther. 323 2007 570 578
13. J.C. Mwenifumbo, and R.F. Tyndale Genetic variability in CYP2A6 and the pharmacokinetics of nicotine Pharmacogenomics. 8 2007 1385 1402
14. K.E. Schlicht, J. Zinggeler-Berg, and S.E. Murphy Effect of CYP2A13 active site mutation Asn297Ala on metabolism of coumarin and tobacco-specific nitrosamines Drug Metab. Dispos. 37 2009 665 671
15. S.E. Murphy, V. Raulinaitis, and K.M. Brown Nicotine 5′-oxidation and methyl oxidation by P450 2A enzymes Drug Metab. Dispos. 13 2005 1166 1173
16. L.B. von Weymarn, K.M. Brown, and S.E. Murphy Inactivation of CYP2A6 and CYP2A13 during nicotine metabolism J. Pharmacol. Exp. Ther. 316 2006 295 303
17. B.D. Silverman Kinetics of mechanisms-based inactivation Mechanism-based Enzyme Inactivation: Chemistry and Enzymology 1988 CRC Press Boca Raton, FL 3 30
18. S.C. Khojasteh-Bakht, L.L. Koenigs, R.M. Peter, W.F. Trager, and S.D. Nelson (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6 Drug Metab. Dispos. 26 1998 701 704
19. T.T. Denton, X. Zhang, and J.R. Cashman Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6 Biochem. Pharmacol. 67 2004 751 756
20. E. Werle, and A. Meyer Decomposition of tobacco alkaloids in animal tissue Biochem. Z. 321 1950 221 235
21. E. Wada, T. Kisaki, and K. Saito Autoxidation of nicotine Arch. Biochem. Biophys. 79 1959 124 130
22. U.M. Kent, S. Yanev, and P.F. Hollenberg Mechanism-based inactivation of cytochromes P450 2B1 and P450 2B6 by n-propylxanthate Chem. Res. Toxicol. 12 1999 317 322
23. L.B. von Weymarn, Q.Y. Zhang, X. Ding, and P.F. Hollenberg Effects of 8-methoxypsoralen on cytochrome P450 2A13 Carcinogenesis 26 2005 621 629
24. P. Soucek Expression of cytochrome P450 2A6 in Escherichia coli: purification, spectral and catalytic characterization, and preparation of polyclonal antibodies Arch. Biochem. Biophys. 370 1999 190 200
25. L.B. von Weymarn, N.D. Felicia, X. Ding, and S.E. Murphy N-Nitrosobenzylmethylamine α-hydroxylation and coumarin 7-hydroxylation by rat esophageal microsomes and cytochrome P450 2A3 and 2A6 enzymes Chem. Res. Toxicol. 12 1999 1254 1261
26. L.B. von Weymarn, A.L. Blobaum, and P.F. Hollenberg The mechanism-based inactivation of p450 2B4 by tert-butyl 1-methyl-2-propynyl ether: structural determination of the adducts to the p450 heme Arch. Biochem. Biophys. 425 2004 95 105
27. T. Omura, and R. Sato The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J. Biol. Chem. 239 1964 2370 2378
28. L.B. von Weymarn, and S.E. Murphy CYP 2A13-catalyzed coumarin metabolism, comparison to CYP2A5 and CYP2A6 Xenobiotica 33 2003 73 81
29. N.M. DeVore, B.D. Smith, J.L. Wang, G.H. Lushington, and E.E. Scott Key residues controlling binding of diverse ligands to human cytochrome P450 2A enzymes Drug Metab. Dispos. 37 2009 1319 1327
30. B.D. Smith, J.L. Sanders, P.R. Porubsky, G.H. Lushington, C.D. Stout, and E.E. Scott Structure of the human lung cytochrome P450 2A13 J. Biol. Chem. 282 2007 17306 17313
31. U.S. Substance Abuse and Mental Health Services Administration. National Survey on Drug Use & Health, 2009.
32. S. Sidney, I.S. Tekawa, G.D. Friedman, M.C. Sadler, and D.P. Tashkin Mentholated cigarette use and lung cancer Arch. Intern. Med. 155 1995 727 732
33. W.J. Blot, S.S. Cohen, M. Aldrich, J.K. McLaughlin, M.K. Hargreaves, L.B. Signorello, Lung Cancer Risk Among Smokers of Menthol Cigarettes, J. Natl. Cancer Inst. Epub ahead of print 2011 Mar 23 (2011).
34. T. Stalhandske, and P. Slanina Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity Toxicol. Appl. Pharmacol. 65 1982 366 372
35. N. Castagnoli, X. Liu, M.K. Shigenaga, R. Wardrop, and K. Castagnoli Studies on the metabolic fate of (S)-nicotine and its pyrrolic analog beta-nicotyrine N.L. Benowitz, Nicotine Safety and Toxicity 1998 Oxford University Press New York 57 65
36. X. Liu, K. Castagnoli, C.J. Van der Schyf, and N. Castagnoli Studies on the in vivo biotransformation of the tobacco alkaloid β-nicotyrine Chem. Res. Toxicol. 13 2000 336 341
37. S.C. Khojasteh, S. Oishi, and S.D. Nelson Metabolism and toxicity of menthofuran in rat liver slices and in rats Chem. Res. Toxicol. 23 2010 1824 1832