Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6

Molecular Brain Research

Volumn 129, Issue 1-2, 2004, Pages 117-123

  Niwa, Toshiro ^a   Hiroi, Toyoko ^a   Tsuzuki, Daisuke ^b   Yamamoto, Shigeo ^b   Narimatsu, Shizuo ^b   Fukuda, Tsuyoshi ^c   Azuma, Junichi ^c   Funae, Yoshihiko ^a  

^a OSAKA CITY UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

CYP2D6; Dopamine formation from p tyramine; Human brain; Polymorphism; Progesterone hydroxylation

Indexed keywords

CYTOCHROME P450 2D6; DOPAMINE; MUTANT PROTEIN; PROGESTERONE; TYRAMINE;

ALCOHOL METABOLISM; ARTICLE; BRAIN METABOLISM; CATALYSIS; COMPARATIVE STUDY; DOPAMINE METABOLISM; GENETIC POLYMORPHISM; HORMONE METABOLISM; HYDROXYLATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; SACCHAROMYCES CEREVISIAE; WILD TYPE;

ADRENERGIC UPTAKE INHIBITORS; BRAIN; CYTOCHROME P-450 CYP2D6; DOPAMINE; FEMALE; HUMANS; MICROSOMES; MIXED FUNCTION OXYGENASES; POLYMORPHISM, GENETIC; PROGESTERONE; TYRAMINE;

SACCHAROMYCES; SACCHAROMYCES CEREVISIAE;

EID: 4644295005     PISSN: 0169328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molbrainres.2004.06.030     Document Type: Article

References (41)

1. G. Alvan, P. Bechtel, L. Iselius, and U. Gundert-Remy Hydroxylation polymorphisms of debrisoquine and mephenytoin in European populations Eur. J. Clin. Pharmacol. 39 1990 533 537
2. E.E. Baurieu Neurosteroids: a new function of the brain Psychoneuroendocrinology 23 1998 963 987
3. L. Bertilsson, C. Alm, C. De Las Carreras, J. Widen, G. Edman, and D. Schalling Debrisoquine hydroxylation polymorphism and personality Lancet ii 1989 555
4. L. Bertilsson, M.-L. Dahl, P. Dalen, and A. Al-Shurbaji Molecular genetics of CYP2D6: Clinical relevance with focus on psychotropic drugs Br. J. Clin. Pharmacol. 53 2002 111 122
5. S. Cholerton, A.K. Daly, and J.R. Idle The role of individual human cytochromes P450 in drug metabolism and clinical response Trends Pharmacol. Sci. 13 1992 434 439
6. A.K. Daly, J. Brockmoller, F. Broly, M. Elichelbaum, W.E. Evans, F.J. Gonzalez, J.-D. Huang, J.R. Idle, M. Ingelman-Sundberg, T. Ishizaki, E. Jacqz-Aigrain, U.A. Meyer, D.W. Nebert, V.M. Steen, C.R. Wolf, and U.M. Zanger Nomenclature for human CYP2D6 alleles Pharmacogenetics 6 1996 193 201
7. S.W. Ellis, G.P. Hayhurst, G. Smith, T. Lightfoot, M.M.S. Wong, A.P. Simula, M.J. Ackland, M.J.E. Sternberg, M.S. Lennard, G.T. Tucker, and C.R. Wolf Evidence that aspartic acid 301 is a critical substrate-contact residue in the active site of cytochrome P450 2D6 J. Biol. Chem. 270 1995 29055 29058
8. T. Fukuda, Y. Nishida, S. Imaoka, T. Hiroi, M. Naohara, Y. Funae, and J. Azuma 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
9. Y. Funae, W. Kishimoto, T. Cho, T. Niwa, and T. Hiroi CYP2D in the brain Drug Metab. Pharmacokin. 18 2003 337 349
10. F.J. Gonzalez Molecular genetics of the P-450 superfamily Pharmacol. Ther. 45 1990 1 38
11. O. Gotoh Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences J. Biol. Chem. 267 1992 83 90
12. F.P. Guengerich Characterization of human cytochrome P450 enzymes FASEB J. 6 1992 745 748
13. F.P. Guengerich, I.H. Hanna, M.V. Martin, and E.M. Gillam Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis Biochemistry 42 2003 1245 1253
14. T. Hiroi, S. Imaoka, and Y. Funae Dopamine formation from tyramine by CYP2D6 Biochem. Biophys. Res. Commun. 249 1998 838 843
15. T. Hiroi, W. Kishimoto, T. Chow, S. Imaoka, T. Igarashi, and Y. Funae Progesterone oxidation by cytochrome P450 2D isoforms in the brain Endocrinology 142 2001 3901 3908
16. Y. Horai, M. Nakano, T. Ishizaki, K. Ishikawa, H.-H. Zhou, B.-J. Zhou, C.-L. Liao, and L.-M. Zhang Metoprolol and mephenytoin oxidation polymorphisms in Far Eastern Oriental subjects: Japanese versus mainland Chinese Clin. Pharmacol. Ther. 46 1989 198 207
17. S. Imaoka, T. Yamada, T. Hiroi, K. Hayashi, T. Sakaki, Y. Yabusaki, and Y. Funae Multiple forms of human P450 expressed in Saccharomyces cerevisiae. Systemic characterization and comparison with those of rat Biochem. Pharmacol. 51 1996 1041 1050
18. I. Johansson, M. Oscarson, Q.-Y. Yue, L. Bertilsson, F. Sjoqvist, and M. Ingelman-Sndberg Genetic analysis of the Chinese cytochrome P4502D locus: Characterization of variant CYP2D6 genes in subjects with diminished capacity for debrisoquine hydroxylation Mol. Pharmacol. 46 1994 452 459
19. I. Jung-Testas, A. Do Thi, H. Koenig, F. Desarnaud, K. Shazand, M. Schumacher, and E.E. Baulieu Progesterone as a neurosteroid: synthesis and actions in rat glial cells J. Steroid Biochem. Mol. Biol. 69 1999 97 107
20. W. Kishimoto, T. Hiroi, M. Shiraishi, M. Osada, S. Imaoka, S. Kominami, T. Igarashi, and Y. Funae Cytochrome P450 2D catalyze steroid 21-hydroxylation in the brain Endocrinology 145 2004 699 705
21. M. Komori A novel P450 expressed at the high level in rat brain Biochem. Biophys. Res. Commun. 196 1993 721 728
22. 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
23. J.B.S. Leathart, S.J. London, A. Steward, J.D. Adams, J.R. Idle, and A.K. Daly CYP2D6 phenotypeâ€"genotype relationships in African-Americans and Caucasians in Los Angels Pharmacogenetics 8 1998 529 541
24. A. Llerena, G. Edman, J. Cobaleda, J. Benitez, D. Schalling, and L. Bertilsson Relationship between personality and debrisoquine hydroxylation capacity. Suggestion of an endogenous neuroactive substrate or product of the cytochrome P4502D6 Acta Psychiatrica Scandinavica 87 1993 23 28
25. K.A. Marcucci, R.E. Pearce, C. Crespi, D.T. Steimel, J.S. Leeder, and A. Gaedigk Characterization of cytochrome P450 2D6.1 (CYP2D6.1), CYP2D6.2, and CYP2D6.17 activities toward model CYP2D6 substrates dextromethorphan, bufuralol, and debrisoquine Drug Metab. Dispos. 30 2002 595 601
26. D. Marez, M. Legrand, N. Sabbagh, J.-M. Lo Guidice, C. Spire, J.-J. Lafitte, U.A. Meyer, and F. Broly Polymorphism of the cytochrome P450 CYP2D6 gene in a European population: characterization of 48 mutations and 53 alleles, their frequencies and evolution Pharmacogenetics 7 1997 193 202
27. M.C.E. McFadyen, W.T. Melvin, and G.I. Murray Regional distribution of individual forms of cytochrome P450 mRNA in normal adult human brain Biochem. Pharmacol. 55 1998 625 830
28. Y. Nishida, T. Fukuda, I. Yamamoto, and J. Azuma CYP2D6 genotypes in a Japanese population: low frequencies of CYP2D6 gene duplication but high frequency of CYP2D6*10 Pharmacogenetics 10 2000 567 570
29. T. Niwa, Y. Yabusaki, K. Honma, N. Matsuo, K. Tatsuta, F. Ishibashi, and M. Katagiri Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones Xenobiotica 28 1998 539 547
30. T. Niwa, T. Shiraga, Y. Mitani, M. Terakawa, Y. Tokuma, and A. Kagayama Stereoselective metabolism of cibenzoline, an antiarrhythmic drug, by human and rat liver microsomes: Possible involvement of CYP2D and CYP3A Drug Metab. Dispos. 28 2000 1128 1134
31. M. Oscarson, M. Hidestrand, I. Johansson, and M. Ingelman-Sundberg A combination of mutations in the CYP2D6*17 (CYP2D6Z) allele causes alterations in enzyme function Mol. Pharmacol. 52 1997 1034 1040
32. S.M. Paul, and R.H. Purdy Neuroactive steroids FASEB J. 6 1992 2311 2322
33. S.R. Philips, B. Rozdilsky, and A.A. Boulton Evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenylethylamine in the rat brain and several areas of the human brain Biol. Psychiatry 13 1978 51 57
34. Y. Ramamoorthy, R.F. Tyndale, and E.M. Sellers Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates Pharmacogenetics 11 2001 477 487
35. S. Rendic Summary of information on human CYP enzymes: human P450 metabolism data Drug Metab. Rev. 34 2002 83 448
36. T. Shimada, H. Yamazaki, M. Mimura, Y. Inui, and F.P. Guengerich Interindividual variation in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians J. Pharmacol. Exp. Ther. 270 1994 414 423
37. D. Tsuzuki, C. Takemi, S. Yamamoto, K. Tamagake, S. Imaoka, Y. Funae, H. Kataoka, S. Shinoda, and S. Narimatsu Functional evaluation of cytochrome P450 2D6 with Gly42Arg substitution expressed in Saccharomyces cerevisiae Pharmacogenetics 11 2001 709 718
38. J. Venhorst, A.M. ter Laak, J.N.M. Commandeur, Y. Funae, T. Hiroi, and N.P.E. Vermeulen Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding J. Med. Chem. 46 2003 74 86
39. F.S. Wu, T.T. Gtibbs, and D.H. Farb Inverse modulation of gamma-aminobutyric acid- and glycine-induced currents by progesterone Mol. Pharmacol. 37 1990 597 602
40. H. Yokota, S. Tamura, H. Furuya, S. Kimura, M. Watanabe, I. Kanazawa, I. Kondo, and F.J. Gonzalez 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
41. A. Yu, B.M. Kneller, A.E. Rettie, and R.L. Haining Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms J. Pharmacol. Exp. Ther. 303 2002 1291 1300