Catalytic roles of CYP2D6.10 and CYP2D6.36 enzymes in mexiletine metabolism: In vitro functional analysis of recombinant proteins expressed in Saccharomyces cerevisiae

Biochemical Pharmacology

Volumn 71, Issue 9, 2006, Pages 1386-1395

  Hanioka, Nobumitsu ^a   Okumura, Yoshihito ^a   Saito, Yoshiro ^b   Hichiya, Hiroyuki ^b   Soyama, Akiko ^b   Saito, Keita ^a   Ueno, Kazuyuki ^c   Sawada, Jun Ichi ^b   Narimatsu, Shizuo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

CYP2D6; CYP2D6*10; CYP2D6*36; Genetic polymorphism; Mexiletine

Indexed keywords

APOPROTEIN; BUFURALOL; CYTOCHROME P450 2D6; MEXILETINE; RECOMBINANT PROTEIN;

AMINO ACID SUBSTITUTION; ARTICLE; DNA POLYMORPHISM; DRUG STRUCTURE; HUMAN; HYDROXYLATION; IN VITRO STUDY; METABOLISM; NONHUMAN; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; YEAST;

ANTI-ARRHYTHMIA AGENTS; ASIAN CONTINENTAL ANCESTRY GROUP; CATALYSIS; CYTOCHROME P-450 CYP2D6; GENE EXPRESSION REGULATION, FUNGAL; HAPLOTYPES; HUMANS; HYDROXYLATION; LIVER; MEXILETINE; MICROSOMES; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE; TRANSFECTION; VARIATION (GENETICS);

EID: 33645129348     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2006.01.019     Document Type: Article

References (38)

1. N.P. Campbell, J.G. Kelly, A.A. Adgey, and R.G. Shanks The clinical pharmacology of mexiletine Br J Clin Pharmacol 6 1978 103 108
2. L. Labbé, and J. Turgeon Clinical pharmacokinetics of mexiletine Clin Pharmacokinet 37 1999 361 384
3. A.H. Beckett, and E.C. Chidomere The identification and analysis of mexiletine and its metabolic products in man J Pharm Pharmacol 29 1977 281 285
4. R.L. Woosley, T. Wang, W. Stone, L. Siddoway, K. Thompson, and H.J. Duff Pharmacology, electrophysiology, and pharmacokinetics of mexiletine Am Heart J 107 1984 1058 1065
5. F. Broly, C. Libersa, and M. Lhermitte Mexiletine metabolism in vitro by human liver Drug Metab Dispos 18 1990 362 368
6. J. Turgeon, C. Fiset, R. Giguere, M. Gilbert, K. Moerike, and J.R. Rouleau Influence of debrisoquine phenotype and of quinidine on mexiletine disposition in man J Pharmacol Exp Ther 259 1991 789 798
7. F. Broly, A. Gaedigk, M. Heim, M. Eichelbaum, K. Morike, and U.A. Meyer Debrisoquine/sparteine hydroxylation genotype and phenotype: analysis of common mutations and alleles of CYP2D6 in a European population DNA Cell Biol 10 1991 545 558
8. Y. Horai, M. Nakano, T. Ishizaki, K. Ishikawa, H.H. Zhou, and B.I. Zhou Metoprolol and mephenytoin oxidation polymorphisms in Far Eastern Oriental subjects: Japanese versus mainland Chinese Clin Pharmacol Ther 46 1989 198 207
9. I. Johansson, M. Oscarson, Q.Y. Yue, L. Bertilsson, F. Sjoqvist, and M. Ingelman-Sundberg Genetic analysis of the Chinese cytochrome P4502D locus: characterization of variant CYP2D6 genes present in subjects with diminished capacity for debrisoquine hydroxylation Mol Pharmacol 46 1994 452 459
10. H. Yokota, S. Tamura, H. Furuya, S. Kimura, M. Watanabe, and I. Kanazawa Evidence for a new variant CYP2D6 allele CYP2D6J in a Japanese population associated with lower in vivo rates of sparteine metabolism Pharmacogenetics 3 1993 256 263
11. T. Kubota, Y. Yamaura, N. Ohkawa, H. Hara, and K. Chiba Frequencies of CYP2D6 mutant alleles in a normal Japanese population and metabolic activity of dextromethorphan O-demethylation in different CYP2D6 genotypes Br J Clin Pharmacol 50 2000 31 34
12. Q.Y. Yue, L. Bertilsson, M.L. Dahl-Puustinen, J. Säwe, F. Sjöqvist, and I. Johansson Disassociation between debrisoquine hydroxylation phenotype and genotype among Chinese Lancet 2 1989 870
13. I. Johansson, Q.Y. Yue, M.L. Dahl, M. Heim, J. Säwe, and L. Bertilsson Genetic analysis of the interethnic difference between Chinese and Caucasians in the polymorphic metabolism of debrisoquine and codeine Eur J Clin Pharmacol 40 1991 553 556
14. M.L. Lai, S.L. Wang, M.D. Lai, E.T. Lin, M. Tse, and J.D. Huang Propranolol disposition in Chinese subjects of different CYP2D6 genotypes Clin Pharmacol Ther 58 1995 264 268
15. T. Fukuda, I. Yamamoto, Y. Nishida, Q. Zhou, M. Ohno, and K. Takada Effect of the CYP2D6*10 genotype on venlafaxine pharmacokinetics in healthy adult volunteers Br J Clin Pharmacol 47 1999 450 453
16. J. Huang, S.K. Chuang, C.L. Cheng, and M.L. Lai Pharmacokinetics of metoprolol enantiomers in Chinese subjects of major CYP2D6 genotypes Clin Pharmacol Ther 65 1999 402 407
17. Y.R. Yoon, I.J. Cha, J.H. Shon, K.A. Kim, Y.N. Cha, and I.J. Jang Relationship of paroxetine disposition to metoprolol metabolic ratio and CYP2D6*10 genotype of Korean subjects Clin Pharmacol Ther 67 2000 567 576
18. M. Otani, T. Fukuda, M. Naohara, H. Maune, C. Senda, and I. Yamamoto Impact of CYP2D6*10 on mexiletine pharmacokinetics in healthy adult volunteers Eur J Clin Pharmacol 59 2003 395 399
19. C. Senda, Y. Yamaura, K. Kobayashi, H. Fujii, H. Minami, and Y. Sasaki Influence of the CYP2D6*10 allele on the metabolism of mexiletine by human liver microsomes Br J Clin Pharmacol 52 2001 100 103
20. T. Sakaki, M. Akiyoshi-Shibata, Y. Yabusaki, and H. Ohkawa Organella-targeted expression of rat liver cytochrome P450c27 in yeast: genetically engineered alteration of mitochondrial P450 into a microsomal form creates a novel functional electron transport chain J Biol Chem 267 1992 16497 16502
21. J. Wan, S. Imaoka, T. Chow, T. Hiroi, Y. Yabusaki, and Y. Funae Expression of four rat CYP2D isoforms in Saccharomyces cerevisiae and their catalytic specificity Arch Biochem Biophys 348 1997 383 390
22. H. Hichiya, C. Takemi, D. Tsuzuki, S. Yamamoto, K. Asaoka, and S. Suzuki Complementary DNA cloning and characterization of cytochrome P450 2D29 from Japanese monkey liver Biochem Pharmacol 64 2002 1101 1110
23. 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
24. M. Nakajima, K. Kobayashi, N. Shimada, S. Tokudome, T. Yamamoto, and Y. Kuroiwa Involvement of CYP1A2 in mexiletine metabolism Br J Clin Pharmacol 46 1998 55 62
25. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the Folin phenol reagent J Biol Chem 193 1951 265 275
26. N. Hanioka, S. Ozawa, H. Jinno, T. Tanaka-Kagawa, T. Nishimura, and M. Ando Interaction of irinotecan (CPT-11) and its active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38) with human cytochrome P450 enzymes Drug Metab Dispos 30 2002 391 396
27. T. Fukuda, Y. Nishida, S. Imaoka, T. Hiroi, M. Naohara, and Y. Funae The decreased in vivo clearance of CYP2D6 substrates by CYP2D6*10 might be caused not only by the low-expression but also by low affinity of CYP2D6 Arch Biochem Biophys 380 2000 303 308
28. D. Tsuzuki, C. Takemi, S. Yamamoto, K. Tamagake, S. Imaoka, and Y. Funae Functional evaluation of cytochrome P450 2D6 with Gly42Arg substitution expressed in Saccharomyces cerevisiae Pharmacogenetics 11 2001 709 718
29. P.A. Williams, J. Cosme, V. Sridhar, E.F. Johnson, and D.E. McRee Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity Mol Cell 5 2000 121 131
30. P.A. Williams, J. Cosme, A. Ward, H.C. Angove, D.M. Vinković, and H. Jhoti Crystal structure of human cytochrome P450 2C9 with bound warfarin Nature 424 2003 464 468
31. P.A. Williams, J. Cosme, D.M. Vinković, A. Ward, H.C. Angove, and P.J. Day Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone Science 305 2004 683 686
32. G.A. Schoch, J.K. Yano, M.R. Wester, K.J. Griffin, C.D. Stout, and E.F. Johnson Structure of human microsomal cytochrome P450 2C8: evidence for a peripheral fatty acid binding site J Biol Chem 279 2004 9497 9503
33. E.E. Scott, M.A. White, Y.A. He, E.F. Johnson, C.D. Stout, and J.R. Halpert Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl)imidazole at 1.9-Å resolution: insight into the range of P450 conformations and the coordination of redox partner binding J Biol Chem 279 2004 27294 27301
34. D.F. Lewis Homology modelling of human CYP2 family enzymes based on the CYP2C5 crystal structure Xenobiotica 32 2002 305 323
35. D.F. Lewis Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes Arch Biochem Biophys 409 2003 32 44
36. J. Venhorst, A.M. ter Laak, J.N. Commandeur, Y. Funae, T. Hiroi, and N.P. Vermeulen Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities J Med Chem 46 2003 74 86
37. B. Kemper Structural basis for the role in protein folding of conserved proline-rich regions in cytochromes P450 Toxicol Appl Pharmacol 19 2004 305 315
38. Rowland P, Blaney FE, Smyth MG, Jones JJ, Leydon VR, Oxbrow AK, et al. Crystal structure of human cytochrome P450 2D6. J Biol Chem, in press.