메뉴 건너뛰기




Volumn 48, Issue 16, 2005, Pages 5123-5130

Ligand selectivity for the acetylcholine binding site of the rat α4β2 and α3β4 nicotinic subtypes investigated by molecular docking

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 AZETIDINYLMETHOXY)PYRIDINE; 3 METHYL 5 (1 METHYL 2 PYRROLIDINYL)ISOXAZOLE; A 84543; A 98795; ACETYLCHOLINE; AMINE; AMPHIBIAN VENOM; EPIBATIDINE; LIGAND; LYSINE; N METHYL DECHLOROEPIBATIDINE; NICOTINE; NICOTINE DERIVATIVE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR ALPHA3BETA4; NICOTINIC RECEPTOR ALPHA4BETA2; RECEPTOR SUBTYPE; TRYPTOPHAN; UNCLASSIFIED DRUG;

EID: 23444452103     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040881a     Document Type: Article
Times cited : (24)

References (37)
  • 1
    • 0028031541 scopus 로고
    • Neurotransmitter-gated ion channels as unconventional allosteric proteins
    • Galzi, J.-L.; Changeux, J. P. Neurotransmitter-gated ion channels as unconventional allosteric proteins. Curr. Opin. Struct. Biol. 1994, 4, 554-565.
    • (1994) Curr. Opin. Struct. Biol. , vol.4 , pp. 554-565
    • Galzi, J.-L.1    Changeux, J.P.2
  • 2
    • 0028922693 scopus 로고
    • Molecular evolution of the nicotinic acetylcholine receptor: An example of multigene family in excitable cells
    • Le Novère, N.; Changeux, J. P. Molecular evolution of the nicotinic acetylcholine receptor: an example of multigene family in excitable cells. J. Mol. Evol. 1995, 40, 155-172.
    • (1995) J. Mol. Evol. , vol.40 , pp. 155-172
    • Le Novère, N.1    Changeux, J.P.2
  • 3
    • 0027213356 scopus 로고
    • Evidence for "preterminal" nicotinic receptors on GABAergic axons in the rat interpeduncular nucleus
    • Léna, C.; Changeux, J. P.; Mulle, C. Evidence for "preterminal" nicotinic receptors on GABAergic axons in the rat interpeduncular nucleus. J. Neurosci. 1993, 13, 2680-2688.
    • (1993) J. Neurosci. , vol.13 , pp. 2680-2688
    • Léna, C.1    Changeux, J.P.2    Mulle, C.3
  • 4
    • 0032215090 scopus 로고    scopus 로고
    • Allosteric receptors after 30 years
    • Changeux, J. P.; Edelstein, S. J. Allosteric receptors after 30 years. Neuron 1998, 21, 959-980.
    • (1998) Neuron , vol.21 , pp. 959-980
    • Changeux, J.P.1    Edelstein, S.J.2
  • 5
    • 0031450275 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as targets for drug discovery
    • Holladay, M. W.; Dart, M. J.; Lynch, J. K. Neuronal nicotinic acetylcholine receptors as targets for drug discovery. J. Med. Chem. 1997, 40, 4169-4194.
    • (1997) J. Med. Chem. , vol.40 , pp. 4169-4194
    • Holladay, M.W.1    Dart, M.J.2    Lynch, J.K.3
  • 6
    • 0028230727 scopus 로고
    • Epibatidine, a potent analgetic and nicotinic agonist
    • Badio, B.; Daly, J. W. Epibatidine, a potent analgetic and nicotinic agonist. Mol. Pharmacol. 1994, 45, 563-569.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 563-569
    • Badio, B.1    Daly, J.W.2
  • 7
    • 13344282051 scopus 로고    scopus 로고
    • Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors
    • Abreo, M. A.; Lin, N.-H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A.-M.; et al. Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J. Med. Chem. 1996, 39, 817-825.
    • (1996) J. Med. Chem. , vol.39 , pp. 817-825
    • Abreo, M.A.1    Lin, N.-H.2    Garvey, D.S.3    Gunn, D.E.4    Hettinger, A.-M.5
  • 8
    • 14444277023 scopus 로고    scopus 로고
    • Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine(ABT-594), a potent, orally active, nonopiate analgesic agent acting via neuronal nicotinic acetylcholine receptors
    • Holladay, M. W.; Wasicak, J. T.; Lin, N. H.; He, Y.; Ryther, K. B.; et al. Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine(ABT-594), a potent, orally active, nonopiate analgesic agent acting via neuronal nicotinic acetylcholine receptors. J. Med. Chem. 1998, 41, 407-412.
    • (1998) J. Med. Chem. , vol.41 , pp. 407-412
    • Holladay, M.W.1    Wasicak, J.T.2    Lin, N.H.3    He, Y.4    Ryther, K.B.5
  • 9
    • 0033960085 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as novel drug targets
    • Lloyd, G. K.; Williams, M. Neuronal nicotinic acetylcholine receptors as novel drug targets. J. Pharmacol. Exp. Ther. 2000, 292, 461-467.
    • (2000) J. Pharmacol. Exp. Ther. , vol.292 , pp. 461-467
    • Lloyd, G.K.1    Williams, M.2
  • 10
    • 0028838303 scopus 로고
    • Comparative pharmacology of epibatidine: A potent agonist for neuronal nicotinic acetylcholine receptors
    • Gerzanich, V.; Peng, X.; Wang, F.; Wells, G.; Anand, R.; et al. Comparative pharmacology of epibatidine: a potent agonist for neuronal nicotinic acetylcholine receptors. Mol. Pharmacol. 1995, 48, 774-782.
    • (1995) Mol. Pharmacol. , vol.48 , pp. 774-782
    • Gerzanich, V.1    Peng, X.2    Wang, F.3    Wells, G.4    Anand, R.5
  • 11
    • 0033009745 scopus 로고    scopus 로고
    • Epibatidine: High potency and broad spectrum activity on neuronal and neuromuscular nicotinic acetylcholine receptors
    • Lembeck, F. Epibatidine: high potency and broad spectrum activity on neuronal and neuromuscular nicotinic acetylcholine receptors. Naunyn-Schmiedebergs Arch. Pharmacol. 1999, 359, 378-385.
    • (1999) Naunyn-Schmiedebergs Arch. Pharmacol. , vol.359 , pp. 378-385
    • Lembeck, F.1
  • 12
    • 0035902009 scopus 로고    scopus 로고
    • Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors
    • Brejc, K.; Van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van der Oost, J.; et al. Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors. Nature 2001, 411, 269-276.
    • (2001) Nature , vol.411 , pp. 269-276
    • Brejc, K.1    Van Dijk, W.J.2    Klaassen, R.V.3    Schuurmans, M.4    Van Der Oost, J.5
  • 13
    • 0035902187 scopus 로고    scopus 로고
    • A glia-derived acetylcholine-binding protein that modulates synaptic transmission
    • Smit, A. B.; Syed, N. I.; Schaap, D.; Van Minnen, J.; Klumpermann, J.; et al. A glia-derived acetylcholine-binding protein that modulates synaptic transmission. Nature 2001, 411, 261-268.
    • (2001) Nature , vol.411 , pp. 261-268
    • Smit, A.B.1    Syed, N.I.2    Schaap, D.3    Van Minnen, J.4    Klumpermann, J.5
  • 14
    • 0029011701 scopus 로고
    • A second-generation force field for the simulation of proteins, nucleic acids, and organic molecules
    • Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; et al. A second-generation force field for the simulation of proteins, nucleic acids, and organic molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5179-5197
    • Cornell, W.D.1    Cieplak, P.2    Bayly, C.I.3    Gould, I.R.4    Merz, K.M.5
  • 15
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystall. 1993, 26, 283-291.
    • (1993) J. Appl. Crystall. , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 16
    • 0034026472 scopus 로고    scopus 로고
    • Structural aspects of high affinity ligands for the alpha 4 beta 2 neuronal nicotinic receptor
    • Dart, M. J.; Wasicak, J. T.; Ryther, K. B.; Schrimpf, M. R.; Kim, K. H.; et al. Structural aspects of high affinity ligands for the alpha 4 beta 2 neuronal nicotinic receptor. Pharm. Acta Helv. 2000, 74, 115-123.
    • (2000) Pharm. Acta Helv. , vol.74 , pp. 115-123
    • Dart, M.J.1    Wasicak, J.T.2    Ryther, K.B.3    Schrimpf, M.R.4    Kim, K.H.5
  • 17
    • 0033588905 scopus 로고    scopus 로고
    • Structure-activity studies on a novel series of cholinergic channel activators based on a heteroaryl ether framework
    • Lin, N. H.; Abreo, M. A.; Gunn, D. E.; Lebold, S. A.; Lee, E. L.; et al. Structure-activity studies on a novel series of cholinergic channel activators based on a heteroaryl ether framework. Bioorg. Med. Chem. Lett. 1999, 9, 2747-2752.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2747-2752
    • Lin, N.H.1    Abreo, M.A.2    Gunn, D.E.3    Lebold, S.A.4    Lee, E.L.5
  • 18
    • 0031181870 scopus 로고    scopus 로고
    • Multiple automatic base selection: Protein-ligand docking based on incremental construction without manual intervention
    • Rarey, M.; Kramer, B.; Lengauer, T. Multiple automatic base selection: protein-ligand docking based on incremental construction without manual intervention. J. Comput.-Aided Mol. Des. 1997, 11, 369-384.
    • (1997) J. Comput.-Aided Mol. Des. , vol.11 , pp. 369-384
    • Rarey, M.1    Kramer, B.2    Lengauer, T.3
  • 19
    • 0032738842 scopus 로고    scopus 로고
    • Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking
    • Kramer, B. R., M.; Lengauer, T. Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking. Proteins: Struct., Funct., Genet. 1999, 37, 228-241.
    • (1999) Proteins: Struct., Funct., Genet. , vol.37 , pp. 228-241
    • Kramer, B.R.M.1    Lengauer, T.2
  • 20
    • 33644564231 scopus 로고    scopus 로고
    • Tripos Home Page
    • Tripos Home Page. http://www.tripos.com/sciTech/inSilicoDisc/ virtualScreening/cscore.html (accessed May 2005).
  • 21
    • 0034649618 scopus 로고    scopus 로고
    • Protein-based virtual screening of chemical databases. 1. Evaluation of different docking/scoring combinations
    • Bissantz, C.; Folkers, G.; Rognan, D. Protein-based virtual screening of chemical databases. 1. Evaluation of different docking/scoring combinations. J. Med. Chem. 2000, 43, 4759-4767.
    • (2000) J. Med. Chem. , vol.43 , pp. 4759-4767
    • Bissantz, C.1    Folkers, G.2    Rognan, D.3
  • 23
    • 0344441288 scopus 로고    scopus 로고
    • A structural model of agonist binding to the α3β4 neuronal nicotinic receptor
    • Costa, V.; Nistri, A.; Cavalli, A.; Carloni, P. A structural model of agonist binding to the α3β4 neuronal nicotinic receptor. Br. J. Pharmacol. 2003, 140, 921-931.
    • (2003) Br. J. Pharmacol. , vol.140 , pp. 921-931
    • Costa, V.1    Nistri, A.2    Cavalli, A.3    Carloni, P.4
  • 24
    • 1842475289 scopus 로고    scopus 로고
    • Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures
    • Celie, P. H. N.; van Rossum-Fikkert, S. E.; van Dijk, W. J.; Brejc, K.; Smit, A. B.; Sixma, T. K. Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures. Neuron 2004, 41, 907-914.
    • (2004) Neuron , vol.41 , pp. 907-914
    • Celie, P.H.N.1    Van Rossum-Fikkert, S.E.2    Van Dijk, W.J.3    Brejc, K.4    Smit, A.B.5    Sixma, T.K.6
  • 25
    • 0037072311 scopus 로고    scopus 로고
    • Cation-pi interactions in ligand recognition by serotonergic (5-HT3A) and nicotinic acetylcholine receptors: The anomalous binding properties of nicotine
    • Beene, D. L.; Brandt, G. S.; Zhong, W.; Zacharias, N. M.; Lester, H. A.; et al. Cation-pi interactions in ligand recognition by serotonergic (5-HT3A) and nicotinic acetylcholine receptors: the anomalous binding properties of nicotine. Biochemistry 2002, 41, 10262-10269.
    • (2002) Biochemistry , vol.41 , pp. 10262-10269
    • Beene, D.L.1    Brandt, G.S.2    Zhong, W.3    Zacharias, N.M.4    Lester, H.A.5
  • 26
    • 0033925760 scopus 로고    scopus 로고
    • Chemical modification of epibatidine causes a switch from agonist to antagonist and modifies its selectivity for neuronal nicotinic acetylcholine receptors
    • Spang, J. E.; Bertrand, S.; Westera, G.; Patt, J. T.; Schubiger, P. A.; et al. Chemical modification of epibatidine causes a switch from agonist to antagonist and modifies its selectivity for neuronal nicotinic acetylcholine receptors. Chem. Biol. 2000, 7, 545-555.
    • (2000) Chem. Biol. , vol.7 , pp. 545-555
    • Spang, J.E.1    Bertrand, S.2    Westera, G.3    Patt, J.T.4    Schubiger, P.A.5
  • 27
    • 0032514762 scopus 로고    scopus 로고
    • From ab initio quantum mechanics to molecular neurobiology: A cation-pi binding site in the nicotinic receptor
    • Zhong, W.; Gallivan, J. P.; Zhang, Y.; Li, L.; Lester, H. A.; et al. From ab initio quantum mechanics to molecular neurobiology: a cation-pi binding site in the nicotinic receptor. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12088-12093.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 12088-12093
    • Zhong, W.1    Gallivan, J.P.2    Zhang, Y.3    Li, L.4    Lester, H.A.5
  • 28
    • 0000826617 scopus 로고    scopus 로고
    • Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles
    • Nobeli, I.; Price, S. L.; Lommerse, J. P. M.; Taylor, R. Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles. J. Comput. Chem. 1997, 18, 2060-2074.
    • (1997) J. Comput. Chem. , vol.18 , pp. 2060-2074
    • Nobeli, I.1    Price, S.L.2    Lommerse, J.P.M.3    Taylor, R.4
  • 29
    • 0034213308 scopus 로고    scopus 로고
    • Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D-QSAR analysis
    • Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis. J. Med. Chem. 2000, 43, 2217-2226.
    • (2000) J. Med. Chem. , vol.43 , pp. 2217-2226
    • Nielsen, S.F.1    Nielsen, E.O.2    Olsen, G.M.3    Liljefors, T.4    Peters, D.5
  • 30
    • 0033837670 scopus 로고    scopus 로고
    • Development of ligands for in vivo imaging of cerebral nicotinic receptor
    • Sihver, W.; Nordberg, A.; Långström, B.; Mukhin, A. G.; Koren, A. O.; et al. Development of ligands for in vivo imaging of cerebral nicotinic receptor. Behav. Brain Res. 2000, 113, 143-157.
    • (2000) Behav. Brain Res. , vol.113 , pp. 143-157
    • Sihver, W.1    Nordberg, A.2    Långström, B.3    Mukhin, A.G.4    Koren, A.O.5
  • 31
    • 0028172276 scopus 로고
    • (±)-epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors
    • Sullivan, J. P.; Decker, M. W.; Brioni, J. D.; Donnelly Roberts, D.; Anderson, D. J.; et al. (±)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors. J. Pharmacol. Exp. Ther. 1994, 271, 624-631.
    • (1994) J. Pharmacol. Exp. Ther. , vol.271 , pp. 624-631
    • Sullivan, J.P.1    Decker, M.W.2    Brioni, J.D.3    Donnelly Roberts, D.4    Anderson, D.J.5
  • 32
    • 33644563762 scopus 로고    scopus 로고
    • Biotrend Home Page
    • Sharpies, C. G. V.; Wonnacott, S. Biotrend Home Page, http://www.biotrend.com/pdf/nicotinicrev.pdf (accessed Aug 2004).
    • Sharpies, C.G.V.1    Wonnacott, S.2
  • 33
    • 0031595642 scopus 로고    scopus 로고
    • Rat α3β4 subtype of neuronal nicotinic acetylcholine receptor stably expressed in a transfected cell line: Pharmacology of ligand binding and function
    • Xiao, Y.; Meyer, E. L.; Thompson, J. M.; Surin, A.; Wroblewski, J.; Kellar, K. J. Rat α3β4 subtype of neuronal nicotinic acetylcholine receptor stably expressed in a transfected cell line: pharmacology of ligand binding and function. Mol. Pharmacol. 1998, 54, 322-333.
    • (1998) Mol. Pharmacol. , vol.54 , pp. 322-333
    • Xiao, Y.1    Meyer, E.L.2    Thompson, J.M.3    Surin, A.4    Wroblewski, J.5    Kellar, K.J.6
  • 34
    • 0034576476 scopus 로고    scopus 로고
    • Ligands for in vivo imaging of nicotinic receptor subtypes in Alzheimer brain
    • Sihver, W.; Langstrom, B.; Nordberg, A. Ligands for in vivo imaging of nicotinic receptor subtypes in Alzheimer brain. Acta Neurol. Scand. 2000, 176, 27-33.
    • (2000) Acta Neurol. Scand. , vol.176 , pp. 27-33
    • Sihver, W.1    Langstrom, B.2    Nordberg, A.3
  • 35
    • 0019993686 scopus 로고
    • Nicotinic cholinergic receptors labeled by [3H]acetylcholine in rat brain
    • Schwartz, R. D.; McGee, R., Jr.; Kellar, K. J. Nicotinic cholinergic receptors labeled by [3H]acetylcholine in rat brain. Mol. Pharmacol. 1982, 22, 56-62.
    • (1982) Mol. Pharmacol. , vol.22 , pp. 56-62
    • Schwartz, R.D.1    McGee Jr., R.2    Kellar, K.J.3
  • 36
    • 33644573687 scopus 로고    scopus 로고
    • J. T. Baker Home Page
    • J. T. Baker Home Page. http://www.jtbaker.com/msds/englishhtml/ a0830.htm (accessed Aug 2004).
  • 37
    • 0028243316 scopus 로고
    • (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)-isoxazole (ABT 418): A novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. In vivo characterization
    • Decker, M. W.; Brioni, J. D.; Sullivan, J. P.; Buckley, M. J.; Radek, R. J.; et al. (S)-3-Methyl-5-(1-methyl-2-pyrrolidinyl)-isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. in vivo characterization. J. Pharmacol. Exp. Ther. 1994, 270, 319-328.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 319-328
    • Decker, M.W.1    Brioni, J.D.2    Sullivan, J.P.3    Buckley, M.J.4    Radek, R.J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.