Molecular analysis and structure-activity relationship modeling of the substrate/inhibitor interaction site of plasma membrane monoamine transporter

Journal of Pharmacology and Experimental Therapeutics

Volumn 339, Issue 2, 2011, Pages 376-385

  Ho, Horace T B ^a   Pan, Yongmei ^b   Cui, Zhiyi ^a   Duan, Haichuan ^a   Swaan, Peter W ^b   Wang, Joanne ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; BETA CARBOLINE DERIVATIVE; CARRIER PROTEINS AND BINDING PROTEINS; CATION; N TETRAALKYLAMMONIUM; PHENYLALKYLAMINE; PLASMA MEMBRANE MONOAMINE TRANSPORTER; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL ANALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY TEST; ENZYME SUBSTRATE COMPLEX; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; IC 50; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN INTERACTION; PROTEIN LOCALIZATION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANILINE COMPOUNDS; ANIMALS; BENZENE DERIVATIVES; CARBOLINES; CELL LINE; CLONING, MOLECULAR; DOGS; DRUG EVALUATION, PRECLINICAL; EQUILIBRATIVE NUCLEOSIDE TRANSPORT PROTEINS; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054791045     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.111.184036     Document Type: Article

References (33)

1. Bednarczyk D, Ekins S, Wikel JH, and Wright SH (2003) Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol 63:489-498. (Pubitemid 36297318)
2. Chang C, Bahadduri PM, Polli JE, Swaan PW, and Ekins S (2006a) Rapid identification of P-glycoprotein substrates and inhibitors. Drug Metab Dispos 34:1976-1984. (Pubitemid 44837758)
3. Chang C, Ekins S, Bahadduri P, and Swaan PW (2006b) Pharmacophore-based discovery of ligands for drug transporters. Adv Drug Deliv Rev 58:1431-1450. (Pubitemid 44794430)
4. + as environmental neurotoxins, in Neurotoxic Factors in Parkinson's Disease and Related Disorders (Storch A and Collins MA eds) pp 115-130, Kluwer Academic Publishing/Plenum, New York.
5. Dahlin A, Royall J, Hohmann JG, and Wang J (2009) Expression profiling of the solute carrier gene family in the mouse brain. J Pharmacol Exp Ther 329:558-570.
6. Dahlin A, Xia L, Kong W, Hevner R, and Wang J (2007) Expression and immunolocalization of the plasma membrane monoamine transporter in the brain. Neuroscience 146:1193-1211. (Pubitemid 46694120)
7. Douglas KT, Sharma RK, Walmsley JF, and Hider RC (1983) Ionization processes of some harmala alkaloids. Mol Pharmacol 23:614-618. (Pubitemid 13089778)
8. Dresser MJ, Xiao G, Leabman MK, Gray AT, and Giacomini KM (2002) Interactions of n-tetraalkylammonium compounds and biguanides with a human renal organic cation transporter (hOCT2). Pharm Res 19:1244-1247. (Pubitemid 34985011)
9. Duan H and Wang J (2010) Selective transport of monoamine neurotransmitters by human plasma membrane monoamine transporter and organic cation transporter 3. J Pharmacol Exp Ther 335:743-753.
10. Engel K and Wang J (2005) Interaction of organic cations with a newly identified plasma membrane monoamine transporter. Mol Pharmacol 68:1397-1407. (Pubitemid 41539995)
11. Engel K, Zhou M, and Wang J (2004) Identification and characterization of a novel monoamine transporter in the human brain. J Biol Chem 279:50042-50049. (Pubitemid 39577815)
12. Fujita T, Urban TJ, Leabman MK, Fujita K, and Giacomini KM (2006) Transport of drugs in the kidney by the human organic cation transporter, OCT2 and its genetic variants. J Pharm Sci 95:25-36.
13. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, and Koepsell H (1997) Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol 16:871-881. (Pubitemid 27332696)
14. Ho HT and Wang J (2010) Tyrosine 112 is essential for organic cation transport by the plasma membrane monoamine transporter. Biochemistry 49:7839-7846.
15. Kabsch W (1978) A discussion of the solution for the best rotation to relate two sets of vectors. Acta Cryst A 34:827-828.
16. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, and Ganapathy V (1998) Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem 273:15971-15979. (Pubitemid 28311362)
17. Koepsell H and Endou H (2004) The SLC22 drug transporter family. Pflugers Arch 447:666-676. (Pubitemid 38241452)
18. Larger T and Hoffmann RD (2006) Pharmacophore and Pharmacophore Searches, vol 32, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
19. Nagatsu T (1997) Isoquinoline neurotoxins in the brain and Parkinson's disease. Neurosci Res 29:99-111.
20. Otsuka M, Matsumoto T, Morimoto R, Arioka S, Omote H, and Moriyama Y (2005) A human transporter protein that mediates the final excretion step for toxic organic cations. Proc Natl Acad Sci USA 102:17923-17928. (Pubitemid 41798478)
21. Storch A, Hwang YI, Gearhart DA, Beach JW, Neafsey EJ, Collins MA, and Schwarz J (2004) Dopamine transporter-mediated cytotoxicity of β-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. J Neurochem 89:685-694. (Pubitemid 38534154)
22. Suhre WM, Ekins S, Chang C, Swaan PW, and Wright SH (2005) Molecular determinants of substrate/inhibitor binding to the human and rabbit renal organic cation transporters hOCT2 and rbOCT2. Mol Pharmacol 67:1067-1077. (Pubitemid 40410407)
23. +-dependent purine nucleoside transporter from human kidney: cloning and functional characterization. Am J Physiol 273:F1058-F1065.
24. Wright SH and Dantzler WH (2004) Molecular and cellular physiology of renal organic cation and anion transport. Physiol Rev 84:987-1049. (Pubitemid 38823772)
25. Xia L, Engel K, Zhou M, and Wang J (2007) Membrane localization and pH-dependent transport of a newly cloned organic cation transporter (PMAT) in kidney cells. Am J Physiol Renal Physiol 292:F682-F690. (Pubitemid 46220537)
26. Xia L, Zhou M, Kalhorn TF, Ho HT, and Wang J (2009) Podocyte-specific expression of organic cation transporter PMAT: implication in puromycin aminonucleoside nephrotoxicity. Am J Physiol Renal Physiol 296:F1307-F1313.
27. Zhang L, Gorset W, Dresser MJ, and Giacomini KM (1999) The interaction of n-tetraalkylammonium compounds with a human organic cation transporter, hOCT1. J Pharmacol Exp Ther 288:1192-1198. (Pubitemid 29254158)
28. Zheng X, Ekins S, Raufman JP, and Polli JE (2009) Computational models for drug inhibition of the human apical sodium-dependent bile acid transporter. Mol Pharm 6:1591-1603.
29. Zhou M, Duan H, Engel K, Xia L, and Wang J (2010) Adenosine transport by plasma membrane monoamine transporter: reinvestigation and comparison with organic cations. Drug Metab Dispos 38:1798-1805.
30. Zhou M, Engel K, and Wang J (2007a) Evidence for significant contribution of a newly identified monoamine transporter (PMAT) to serotonin uptake in the human brain. Biochem Pharmacol 73:147-154. (Pubitemid 44853932)
31. Zhou M, Xia L, Engel K, and Wang J (2007b) Molecular determinants of substrate selectivity of a novel organic cation transporter (PMAT) in the SLC29 family. J Biol Chem 282:3188-3195. (Pubitemid 47084340)
32. Zhou M, Xia L, and Wang J (2007c) Metformin transport by a newly cloned proton-stimulated organic cation transporter (plasma membrane monoamine transporter) expressed in human intestine. Drug Metab Dispos 35:1956-1962. (Pubitemid 47481592)
33. Zolk O, Solbach TF, König J, and Fromm MF (2009) Structural determinants of inhibitor interaction with the human organic cation transporter OCT2 (SLC22A2). Naunyn Schmiedebergs Arch Pharmacol 379:337-348.