The prototypic pharmacogenetic drug debrisoquine is a substrate of the genetically polymorphic organic cation transporter OCT1

Biochemical Pharmacology

Volumn 83, Issue 10, 2012, Pages 1427-1434

  Saadatmand, Ali R ^a   Tadjerpisheh, Sina ^a   Brockmöller, Jürgen ^a   Tzvetkov, Mladen V ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Debrisoquine; Drug drug interactions; OCT1; Organic cation transporter 1; Polymorphisms; SLC22A1

Indexed keywords

DEBRISOQUINE; ORGANIC ANION TRANSPORTER; ORGANIC ANION TRANSPORTER OCT1; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA POLYMORPHISM; DRUG MECHANISM; DRUG UPTAKE; GENE DELETION; GENE FUNCTION; GENETIC ANALYSIS; HUMAN; HUMAN CELL; MEMBRANE PERMEABILITY; MICHAELIS MENTEN KINETICS; PHARMACOGENETICS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

ANTIHYPERTENSIVE AGENTS; BASE SEQUENCE; DEBRISOQUIN; DNA PRIMERS; ORGANIC CATION TRANSPORTER 1; PHARMACOGENETICS; POLYMERASE CHAIN REACTION;

EID: 84859107661     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.01.032     Document Type: Article

References (51)

1. M. Angelo, L.G. Dring, R. Lancaster, A. Latham, and R.L. Smith Proceedings: a correlation between the response to debrisoquine and the amount of unchanged drug excreted in the urine Br J Pharmacol 55 1975 264P
2. D.A. Evans, A. Mahgoub, T.P. Sloan, J.R. Idle, and R.L. Smith A family and population study of the genetic polymorphism of debrisoquine oxidation in a white British population J Med Genet 17 1980 102 105 (Pubitemid 10107632)
3. A. Mahgoub, J.R. Idle, L.G. Dring, R. Lancaster, and R.L. Smith Polymorphic hydroxylation of debrisoquine in man Lancet 2 1977 584 586 (Pubitemid 8176607)
4. F.J. Gonzalez, R.C. Skoda, S. Kimura, M. Umeno, U.M. Zanger, and D.W. Nebert Characterization of the common genetic defect in humans deficient in debrisoquine metabolism Nature 331 1988 442 446 (Pubitemid 18064368)
5. S. Kimura, M. Umeno, R.C. Skoda, U.A. Meyer, and F.J. Gonzalez The human debrisoquine 4-hydroxylase (CYP2D) locus: sequence and identification of the polymorphic CYP2D6 gene, a related gene, and a pseudogene Am J Hum Genet 45 1989 889 904 (Pubitemid 20045231)
6. A. Gaedigk, M. Blum, R. Gaedigk, M. Eichelbaum, and U.A. Meyer Deletion of the entire cytochrome P450 CYP2D6 gene as a cause of impaired drug metabolism in poor metabolizers of the debrisoquine/sparteine polymorphism Am J Hum Genet 48 1991 943 950 (Pubitemid 21891638)
7. I. Johansson, E. Lundqvist, L. Bertilsson, M.L. Dahl, F. Sjoqvist, and M. Ingelman-Sundberg Inherited amplification of an active gene in the cytochrome P450 CYP2D locus as a cause of ultrarapid metabolism of debrisoquine Proc Natl Acad Sci USA 90 1993 11825 11829 (Pubitemid 24008732)
8. R.C. Skoda, F.J. Gonzalez, A. Demierre, and U.A. Meyer Two mutant alleles of the human cytochrome P-450db1 gene (P450C2D1) associated with genetically deficient metabolism of debrisoquine and other drugs Proc Natl Acad Sci USA 85 1988 5240 5243
9. M. Kagimoto, M. Heim, K. Kagimoto, T. Zeugin, and U.A. Meyer Multiple mutations of the human cytochrome P450IID6 gene (CYP2D6) in poor metabolizers of debrisoquine. Study of the functional significance of individual mutations by expression of chimeric genes J Biol Chem 265 1990 17209 17214
10. M. Eichelbaum, N. Spannbrucker, B. Steincke, and H.J. Dengler Defective N-oxidation of sparteine in man: a new pharmacogenetic defect Eur J Clin Pharmacol 16 1979 183 187 (Pubitemid 10194487)
11. A.C. Gough, J.S. Miles, N.K. Spurr, J.E. Moss, A. Gaedigk, and M. Eichelbaum Identification of the primary gene defect at the cytochrome P450 CYP2D locus Nature 347 1990 773 776
12. G.E. Blakey, J.A. Lockton, J. Perrett, P. Norwood, M. Russell, and Z. Aherne Pharmacokinetic and pharmacodynamic assessment of a five-probe metabolic cocktail for CYPs 1A2, 3A4, 2C9, 2D6 and 2E1 Br J Clin Pharmacol 57 2004 162 169 (Pubitemid 38223528)
13. M. Christensen, K. Andersson, P. Dalen, R.A. Mirghani, G.J. Muirhead, and A. Nordmark The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes Clin Pharmacol Ther 73 2003 517 528 (Pubitemid 37249122)
14. E. Tanaka, N. Kurata, and H. Yasuhara How useful is the "cocktail approach" for evaluating human hepatic drug metabolizing capacity using cytochrome P450 phenotyping probes in vivo? J Clin Pharm Ther 28 2003 157 165 (Pubitemid 36783091)
15. N.K. Zgheib, R.F. Frye, T.S. Tracy, M. Romkes, and R.A. Branch Validation of incorporating flurbiprofen into the Pittsburgh cocktail Clin Pharmacol Ther 80 2006 257 263 (Pubitemid 44313908)
16. U. Fuhr, A. Jetter, and J. Kirchheiner Appropriate phenotyping procedures for drug metabolizing enzymes and transporters in humans and their simultaneous use in the "cocktail" approach Clin Pharmacol Ther 81 2007 270 283 (Pubitemid 46174825)
17. C. Sachse, J. Brockmoller, S. Bauer, and I. Roots Cytochrome P450 2D6 variants in a Caucasian population: allele frequencies and phenotypic consequences Am J Hum Genet 60 1997 284 295 (Pubitemid 27058401)
18. Y. Zhen, O. Slanar, K.W. Krausz, C. Chen, J. Slavik, and K.L. McPhail 3,4-Dehydrodebrisoquine, a novel debrisoquine metabolite formed from 4-hydroxydebrisoquine that affects the CYP2D6 metabolic ratio Drug Metab Dispos 34 2006 1563 1574 (Pubitemid 44285399)
19. R. Ayesh, J.R. Idle, J.C. Ritchie, M.J. Crothers, and M.R. Hetzel Metabolic oxidation phenotypes as markers for susceptibility to lung cancer Nature 312 1984 169 170 (Pubitemid 14000084)
20. A. Rostami-Hodjegan, M.S. Lennard, H.F. Woods, and G.T. Tucker Meta-analysis of studies of the CYP2D6 polymorphism in relation to lung cancer and Parkinson's disease Pharmacogenetics 8 1998 227 238 (Pubitemid 28282879)
21. A.T. Nies, H. Koepsell, S. Winter, O. Burk, K. Klein, and R. Kerb Expression of organic cation transporters OCT1 (SLC22A1) and OCT3 (SLC22A3) is affected by genetic factors and cholestasis in human liver Hepatology 50 2009 1227 1240
22. Y. Shu, S.A. Sheardown, C. Brown, R.P. Owen, S. Zhang, and R.A. Castro Effect of genetic variation in the organic cation transporter 1 (OCT1) on metformin action J Clin Invest 117 2007 1422 1431 (Pubitemid 46718430)
23. N. Kimura, S. Masuda, Y. Tanihara, H. Ueo, M. Okuda, and T. Katsura Metformin is a superior substrate for renal organic cation transporter OCT2 rather than hepatic OCT1 Drug Metab Pharmacokinet 20 2005 379 386
24. M. Tsuda, T. Terada, T. Mizuno, T. Katsura, J. Shimakura, and K. Inui Targeted disruption of the multidrug and toxin extrusion 1 (mate1) gene in mice reduces renal secretion of metformin Mol Pharmacol 75 2009 1280 1286
25. N. Kimura, S. Masuda, T. Katsura, and K. Inui Transport of guanidine compounds by human organic cation transporters, hOCT1 and hOCT2 Biochem Pharmacol 77 2009 1429 1436
26. V. Gorboulev, J.C. Ulzheimer, A. Akhoundova, I. Ulzheimer-Teuber, U. Karbach, and S. Quester Cloning and characterization of two human polyspecific organic cation transporters DNA Cell Biol 16 1997 871 881 (Pubitemid 27332696)
27. L. Zhang, M.J. Dresser, A.T. Gray, S.C. Yost, S. Terashita, and K.M. Giacomini Cloning and functional expression of a human liver organic cation transporter Mol Pharmacol 51 1997 913 921 (Pubitemid 27249124)
28. M.V. Tzvetkov, A.R. Saadatmand, K. Bokelmann, I. Meineke, R. Kaiser, and J. Brockmoller Effects of OCT1 polymorphisms on the cellular uptake, plasma concentrations and efficacy of the 5-HT(3) antagonists tropisetron and ondansetron Pharmacogenomics J 12 2012 22 29
29. M.V. Tzvetkov, A.R. Saadatmand, J. Lotsch, I. Tegeder, J.C. Stingl, and J. Brockmoller Genetically polymorphic OCT1: another piece in the puzzle of the variable pharmacokinetics and pharmacodynamics of the opioidergic drug tramadol Clin Pharmacol Ther 90 2011 143 150
30. S. Wilde, E. Schlatter, H. Koepsell, B. Edemir, S. Reuter, and H. Pavenstadt Calmodulin-associated post-translational regulation of rat organic cation transporter 2 in the kidney is gender dependent Cell Mol Life Sci 66 2009 1729 1740
31. Y. Shu, M.K. Leabman, B. Feng, L.M. Mangravite, C.C. Huang, and D. Stryke Evolutionary conservation predicts function of variants of the human organic cation transporter, OCT1 Proc Natl Acad Sci USA 100 2003 5902 5907 (Pubitemid 36576905)
32. P.K. Smith, R.I. Krohn, G.T. Hermanson, A.K. Mallia, F.H. Gartner, and M.D. Provenzano Measurement of protein using bicinchoninic acid Anal Biochem 150 1985 76 85 (Pubitemid 16258399)
33. V.A. Pereira, J.O. Auler Jr., M.J. Carmona, F.H. Mateus, V.L. Lanchote, and D.D. Breimer A micromethod for quantitation of debrisoquine and 4-hydroxydebrisoquine in urine by liquid chromatography Braz J Med Biol Res 33 2000 509 514 (Pubitemid 30341418)
34. M.V. Tzvetkov, S.V. Vormfelde, D. Balen, I. Meineke, T. Schmidt, and D. Sehrt The effects of genetic polymorphisms in the organic cation transporters OCT1, OCT2, and OCT3 on the renal clearance of metformin Clin Pharmacol Ther 86 2009 299 306
35. M.L. Dahl, I. Johansson, L. Bertilsson, M. Ingelman-Sundberg, and F. Sjoqvist Ultrarapid hydroxylation of debrisoquine in a Swedish population. Analysis of the molecular genetic basis J Pharmacol Exp Ther 274 1995 516 520
36. 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 Psychiatr Scand 87 1993 23 28 (Pubitemid 23024862)
37. A. Llerena, P. Dorado, and E.M. Penas-Lledo Pharmacogenetics of debrisoquine and its use as a marker for CYP2D6 hydroxylation capacity Pharmacogenomics 10 2009 17 28
38. A. Llerena, J. Cobaleda, C. Martinez, and J. Benitez Interethnic differences in drug metabolism: influence of genetic and environmental factors on debrisoquine hydroxylation phenotype Eur J Drug Metab Pharmacokinet 21 1996 129 138 (Pubitemid 26246156)
39. J.M. Guidice, D. Marez, N. Sabbagh, M. Legrand-Andreoletti, C. Spire, and E. Alcaide Evidence for CYP2D6 expression in human lung Biochem Biophys Res Commun 241 1997 79 85 (Pubitemid 28033542)
40. K.T. Kivisto, E.U. Griese, T. Stuven, P. Fritz, G. Friedel, and H.K. Kroemer Analysis of CYP2D6 expression in human lung: implications for the association between CYP2D6 activity and susceptibility to lung cancer Pharmacogenetics 7 1997 295 302 (Pubitemid 27356929)
41. H. Raunio, J. Hakkola, J. Hukkanen, O. Pelkonen, R. Edwards, and A. Boobis Expression of xenobiotic-metabolizing cytochrome P450s in human pulmonary tissues Arch Toxicol Suppl 20 1998 465 469
42. K.S. Lips, C. Volk, B.M. Schmitt, U. Pfeil, P. Arndt, and D. Miska Polyspecific cation transporters mediate luminal release of acetylcholine from bronchial epithelium Am J Respir Cell Mol Biol 33 2005 79 88 (Pubitemid 40961017)
43. S.P. Markey, J.N. Johannessen, C.C. Chiueh, R.S. Burns, and M.A. Herkenham Intraneuronal generation of a pyridinium metabolite may cause drug-induced parkinsonism Nature 311 1984 464 467
44. J.H. Silas, M.S. Lennard, G.T. Tucker, A.J. Smith, S.L. Malcolm, and T.R. Marten The disposition of debrisoquine in hypertensive patients Br J Clin Pharmacol 5 1978 27 34 (Pubitemid 8249365)
45. H. Motohashi, Y. Sakurai, H. Saito, S. Masuda, Y. Urakami, and M. Goto Gene expression levels and immunolocalization of organic ion transporters in the human kidney J Am Soc Nephrol 13 2002 866 874 (Pubitemid 34274082)
46. D. Grundemann, V. Gorboulev, S. Gambaryan, M. Veyhl, and H. Koepsell Drug excretion mediated by a new prototype of polyspecific transporter Nature 372 1994 549 552 (Pubitemid 24368536)
47. D. Bednarczyk, S. Ekins, J.H. Wikel, and S.H. Wright Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1 Mol Pharmacol 63 2003 489 498 (Pubitemid 36297318)
48. R. Moaddel, S. Patel, K. Jozwiak, R. Yamaguchi, P.C. Ho, and I.W. Wainer Enantioselective binding to the human organic cation transporter-1 (hOCT1) determined using an immobilized hOCT1 liquid chromatographic stationary phase Chirality 17 2005 501 506 (Pubitemid 41395674)
49. R. Moaddel, S. Ravichandran, F. Bighi, R. Yamaguchi, and I.W. Wainer Pharmacophore modelling of stereoselective binding to the human organic cation transporter (hOCT1) Br J Pharmacol 151 2007 1305 1314 (Pubitemid 47255908)
50. A.T. Nies, U. Hofmann, C. Resch, E. Schaeffeler, M. Rius, and M. Schwab Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs) PLoS One 6 2011 e22163
51. G. Ahlin, J. Karlsson, J.M. Pedersen, L. Gustavsson, R. Larsson, and P. Matsson Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1 J Med Chem 51 2008 5932 5942