Interaction of tyrosine 151 in norepinephrine transporter with the 2β group of cocaine analog RTI-113

Neuropharmacology

Volumn 61, Issue 1-2, 2011, Pages 112-120

  Hill, Erik R ^a,d   Huang, Xiaoqin ^b   Zhan, Chang Guo ^b   Ivy Carroll, F ^c   Gu, Howard H ^a  

^a THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b University of Kentucky   (United States)

^c RTI INTERNATIONAL   (United States)

^d STONY BROOK UNIVERSITY   (United States)

Author keywords

Analog; Binding site; Cocaine; Computer modeling; Dopamine; Norepinephrine; Structure; Transporter

Indexed keywords

3BETA (4 CHLOROPHENYL) 2BETA TROPANECARBOXYLIC ACID PHENYL ESTER; COCAINE DERIVATIVE; NORADRENALIN TRANSPORTER; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; CRYSTAL STRUCTURE; HUMAN; HUMAN CELL; MUTAGENESIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN INTERACTION; PROTEIN LOCALIZATION;

ANIMALS; CELLS, CULTURED; COCAINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; MICE; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; RANDOM ALLOCATION; TYROSINE;

EID: 79957808687     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2011.03.014     Document Type: Article

References (48)

1. Amara, S.G., Sonders, M.S., 1998. Neurotransmitter transporters as molecular targets for addictive drugs. Drug Alcohol Depend 51, 87-96. (Pubitemid 28353758)
2. Beuming, T., Kniazeff, J., Bergmann, M.L., Shi, L., Gracia, L., Raniszewska, K., Newman, A.H., Javitch, J.A., Weinstein, H., Gether, U., Loland, C.J., 2008. The binding sites for cocaine and dopamine in the dopamine transporter overlap. Nat. Neurosci. 11, 780-789.
3. Beuming, T., Shi, L., Javitch, J.A., Weinstein, H., 2006. A comprehensive structure-based alignment of prokaryotic and eukaryotic neurotransmitter/Na+ symporters (NSS) aids in the use of the LeuT structure to probe NSS structure and function. Mol. Pharmacol. 70, 1630-1642.
4. Bisgaard, H., Larsen, M.A., Mazier, S., Beuming, T., Newman, A.H., Weinstein, H., Shi, L., Loland, C.J., Gether, U., 2010. The binding sites for benztropines and dopamine in the dopamine transporter overlap. Neuropharmacology.
5. Carroll, F.I., 2003. 2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy. J. Med. Chem. 46, 1775-1794.
6. Carroll, F.I., Kotian, P., Dehghani, A., Gray, J.L., Kuzemko, M.A., Parham, K.A., Abraham, P., Lewin, A.H., Boja, J.W., Kuhar, M.J., 1995. Cocaine and 3 beta-(4′-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter. J. Med. Chem. 38, 379-388.
7. Case, D., Darden, T., Cheatham, Simmerling, C., Wang, J., Duke, R., Luo, R., Merz, K., Pearlman, D., Crowley, M.,Walker, R., Zhang,W.,Wang, B., Hayik, S., Roitberg, A., Seabra, G., Wong, K., Paesani, F., Wu, X., Brozell, S., Tsui, V., Gohlke, H., Yang, L., Tan, C., Mongan, J., Hornak, V., Cui, G., Beroza, P., Mathews, D., Schafmeister, C., Ross,W., Kollman, P., 2006. Amber 9.
8. Chen, J.G., Sachpatzidis, A., Rudnick, G., 1997. The third transmembrane domain of the serotonin transporter contains residues associated with substrate and cocaine binding. J. Biol. Chem. 272, 28321-28327.
9. Chen, N., Ferrer, J.V., Javitch, J.A., Justice Jr., J.B., 2000. Transport-dependent accessibility of a cytoplasmic loop cysteine in the human dopamine transporter. J. Biol. Chem. 275 (3), 1608-1614.
10. Chen, N., Reith, M.E., 2002. Structure-function relationships for biogenic amine neurotransmitter transporters. In: Reith, M.E.A. (Ed.), Neurotransmitter Transporters. Structure, Function, and Regulation Humana Press, Totowa, NJ, pp. 53-109.
11. Chen, R., Han, D.D., Gu, H.H., 2005. A triple mutation in the second transmembrane domain of mouse dopamine transporter markedly decreases sensitivity to cocaine and methylphenidate. J. Neurochem. 94, 352-359. (Pubitemid 40995251)
12. Chen, R., Wei, H., Hill, E.R., Chen, L., Jiang, L., Han, D.D., Gu, H.H., 2007. Direct evidence that two cysteines in the dopamine transporter form a disulfide bond. Mol. Cell Biochem. 298, 41-48.
13. Churchill, C.D., Wetmore, S.D., 2009. Noncovalent interactions involving histidine: the effect of charge on pi-pi stacking and T-shaped interactions with the DNA nucleobases. J. Phys. Chem. B. 113, 16046-16058.
14. Dutta, A.K., Zhang, S., Kolhatkar, R., Reith, M.E., 2003. Dopamine transporter as target for drug development of cocaine dependence medications. Eur. J. Pharmacol. 479, 93-106.
15. Ferrer, J.V., Javitch, J.A., 1998. Cocaine alters the accessibility of endogenous cysteines in putative extracellular and intracellular loops of the human dopamine transporter. Proc. Natl. Acad. Sci. U S A 95, 9238-9243.
16. Field, J.R., Henry, L.K., Blakely, R.D., 2010. Transmembrane domain 6 of the human serotonin transporter contributes to an aqueously accessible binding pocket for serotonin and the psychostimulant 3,4-methylene dioxymethamphetamine. J. Biol. Chem. 285 (15), 11270-11280.
17. Forrest, L.R., Tavoulari, S., Zhang, Y.W., Rudnick, G., Honig, B., 2007. Identification of a chloride ion binding site in Na+/Cl -dependent transporters. Proc. Natl. Acad. Sci. U S A 104, 12761-12766.
18. Forrest, L.R., Zhang, Y.W., Jacobs, M.T., Gesmonde, J., Xie, L., Honig, B.H., Rudnick, G., 2008. Mechanism for alternating access in neurotransmitter transporters. Proc. Natl. Acad. Sci. U S A 105, 10338-10343.
19. Geiss, B.J., Thompson, A.A., Andrews, A.J., Sons, R.L., Gari, H.H., Keenan, S.M., Peersen, O.B., 2009. Analysis of flavivirus NS5 methyltransferase cap binding. J. Mol. Biol. 385, 1643-1654.
20. Gu, H., Wall, S.C., Rudnick, G., 1994. Stable expression of biogenic amine transporters reveals differences in inhibitor sensitivity, kinetics, and ion dependence. J. Biol. Chem. 269, 7124-7130.
21. Han, D.D., Gu, H.H., 2006. Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs. BMC Pharmacol. 6, 6.
22. Henikoff, S., Henikoff, J.G., 1992. Amino acid substitution matrices from protein blocks. Proc. Natl. Acad. Sci. U S A 89, 10915-10919.
23. Henry, L.K., Adkins, E.M., Han, Q., Blakely, R.D., 2003. Serotonin and cocaine-sensitive inactivation of human serotonin transporters by methanethiosulfonates targeted to transmembrane domain I. J. Biol. Chem. 278, 37052-37063.
24. Henry, L.K., Defelice, L.J., Blakely, R.D., 2006. Getting the message across: a recent transporter structure shows the way. Neuron 49, 791-796. (Pubitemid 43376076)
25. Hill, E.R., Tian, J., Tilley, M.R., Zhu, M.X., Gu, H.H., 2009. Potencies of cocaine methiodide on major cocaine targets in mice. PLoS One 4, e7578.
26. Hong,W.C., Amara, S.G., 2010. Membrane cholesterol modulates the outward facing conformation of the dopamine transporter and alters cocaine binding. J. Biol. Chem. 285, 32616-32626.
27. Huang, X., Gu, H.H., Zhan, C.G., 2009. Mechanism for cocaine blocking the transport of dopamine: insights from molecular modeling and dynamics simulations. J. Phys. Chem. B. 113, 15057-15066.
28. Huang, X., Zhan, C.G., 2007. How dopamine transporter interacts with dopamine: insights from molecular modeling and simulation. Biophys. J. 93, 3627-3639. (Pubitemid 350190825)
29. Huang, X., Zheng, F., Crooks, P.A., Dwoskin, L.P., Zhan, C.G., 2005. Modeling multiple species of nicotine and deschloroepibatidine interacting with alpha4beta2 nicotinic acetylcholine receptor: from microscopic binding to phenomenological binding affinity. J. Am. Chem. Soc. 127, 14401-14414.
30. Loland, C.J., Desai, R.I., Zou, M.F., Cao, J., Grundt, P., Gerstbrein, K., Sitte, H.H., Newman, A.H., Katz, J.L., Gether, U., 2008. Relationship between conformational changes in the dopamine transporter and cocaine-like subjective effects of uptake inhibitors. Mol. Pharmacol. 73, 813-823.
31. Loland, C.J., Norgaard-Nielsen, K., Gether, U., 2003. Probing dopamine transporter structure and function by Zn2+-site engineering. Eur. J. Pharmacol. 479,187-197.
32. Morris, G., Goodsell, D., Halliday, R., Huey, R., Hart, W., Belew, R., Olson, A., 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Computational Chem. 19, 1639-1662. (Pubitemid 128590223)
33. Norregaard, L., Frederiksen, D., Nielsen, E.O., Gether, U., 1998. Delineation of an endogenous zinc-bindingsite inthehumandopaminetransporter. EMBOJ.17,4266-4273.
34. Ritz, M.C., Lamb, R.J., Goldberg, S.R., Kuhar, M.J., 1987. Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 237,1219-1223. (Pubitemid 17131228)
35. Rudnick, G., 2007. What is an antidepressant binding site doing in a bacterial transporter? ACS Chem. Biol. 2, 606-609. (Pubitemid 350019777)
36. Schmitt, K.C., Zhen, J., Kharkar, P., Mishra, M., Chen, N., Dutta, A.K., Reith, M.E., 2008. Interaction of cocaine-, benztropine-, and GBR12909-like compounds with wild-type and mutant human dopamine transporters: molecular features that differentially determine antagonist-binding properties. J. Neurochem. 107, 928-940.
37. Singh, S., 2000. Chemistry, design, and structure-activity relationship of cocaine antagonists. Chem. Rev. 100, 925-1024.
38. Singh, S.K., Yamashita, A., Gouaux, E., 2007. Antidepressant binding site in a bacterial homologue of neurotransmitter transporters. Nature 448, 952-956. (Pubitemid 47312772)
39. Solis, F.J., Wets, R.J.-B., 1981. Minimization by random search techniques. Math. Operations Res. 6, 19-30.
40. Tao, Z., Zhang, Y.W., Agyiri, A., Rudnick, G., 2009. Ligand effects on cross-linking support a conformational mechanism for serotonin transport. J. Biol. Chem. 284, 33807-33814.
41. Thompson, J.D., Higgins, D.G., Gibson, T.J., 1994. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 4673-4680. (Pubitemid 24354800)
42. Torres, G.E., Gainetdinov, R.R., Caron, M.G., 2003. Plasma membrane monoamine transporters: structure, regulation and function. Nat. Rev. Neurosci. 4, 13-25.
43. Wei, H., Hill, E.R., Gu, H.H., 2009. Functional mutations in mouse norepinephrine transporter reduce sensitivity to cocaine inhibition. Neuropharmacology 56, 399-404.
44. Wu, X., Gu, H.H., 2003. Cocaine affinity decreased by mutations of aromatic residue phenylalanine 105 in the transmembrane domain 2 of dopamine transporter. Mol. Pharmacol. 63, 653-658.
45. Yamashita, A., Singh, S.K., Kawate, T., Jin, Y., Gouaux, E., 2005. Crystal structure of a bacterial homologue of Na+/Cledependent neurotransmitter transporters. Nature 437, 215-223. (Pubitemid 41294479)
46. Zhan, C.G., Zheng, F., Landry, D.W., 2003. Fundamental reaction mechanism for cocaine hydrolysis in human butyrylcholinesterase. J. Am. Chem. Soc. 125, 2462-2474.
47. Zhang, Y.W., Rudnick, G., 2006. The cytoplasmic substrate permeation pathway of serotonin transporter. J. Biol. Chem. 281, 36213-36220.
48. Zomot, E., Bendahan, A., Quick, M., Zhao, Y., Javitch, J.A., Kanner, B.I., 2007. Mechanism of chloride interaction with neurotransmitter:sodium symporters. Nature 449, 726-730. (Pubitemid 47552085)