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Volumn 51, Issue 7, 2008, Pages 2128-2136

First CoMFA characterization of vesamicol analogs as ligands for the vesicular acetylcholine transporter

Author keywords

[No Author keywords available]

Indexed keywords

4 TERT BUTYLVESAMICOL; BENZOVESAMICOL; DECAHYDRONAPHTHALENEVESAMICOL; LIGAND; SPIROVESAMICOL; TROPANVESAMICOL; TROZAMICOL; UNCLASSIFIED DRUG; VESAMICOL DERIVATIVE; VESICULAR ACETYLCHOLINE TRANSPORTER;

EID: 41849140819     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm700961r     Document Type: Article
Times cited : (10)

References (52)
  • 1
    • 0011162190 scopus 로고
    • Selective loss of central cholinergic neurons in Alzheimer's disease
    • Davies, P.; Maloney, A. J. Selective loss of central cholinergic neurons in Alzheimer's disease. Lancet 1976, 2, 1403.
    • (1976) Lancet , vol.2 , pp. 1403
    • Davies, P.1    Maloney, A.J.2
  • 2
    • 0020686674 scopus 로고
    • Alzheimer's disease: A disorder of cortical cholinergic innervation
    • Coyle, J. T.; Price, D. L.; DeLong, M. R. Alzheimer's disease: A disorder of cortical cholinergic innervation. Science 1983, 219, 1184-90.
    • (1983) Science , vol.219 , pp. 1184-1190
    • Coyle, J.T.1    Price, D.L.2    DeLong, M.R.3
  • 3
    • 31144450053 scopus 로고    scopus 로고
    • Current pharmacotherapy for Alzheimer's disease
    • Lleo, A.; Greenberg, S. M.; Growdon, J. H. Current pharmacotherapy for Alzheimer's disease. Annu. Rev. Med. 2006, 57, 513-33.
    • (2006) Annu. Rev. Med , vol.57 , pp. 513-533
    • Lleo, A.1    Greenberg, S.M.2    Growdon, J.H.3
  • 4
    • 0042020173 scopus 로고    scopus 로고
    • Treatment of Alzheimer's disease: Current status and new perspectives
    • Scarpini, E.; Scheltens, P.; Feldman, H. Treatment of Alzheimer's disease: Current status and new perspectives. Lancet Neurol. 2003, 2, 539-547.
    • (2003) Lancet Neurol , vol.2 , pp. 539-547
    • Scarpini, E.1    Scheltens, P.2    Feldman, H.3
  • 5
    • 10744231003 scopus 로고    scopus 로고
    • The vesicular amine transporter family (SLC18): Amine/proton antiporters required for vesicular accumulation and regulated exocytotic secretion of monoamines and acetylcholine
    • Eiden, L. E.; Schäfer, M. K.; Weihe, E.; Schütz, B. The vesicular amine transporter family (SLC18): Amine/proton antiporters required for vesicular accumulation and regulated exocytotic secretion of monoamines and acetylcholine. Pflugers Arch. 2004, 447, 636-640.
    • (2004) Pflugers Arch , vol.447 , pp. 636-640
    • Eiden, L.E.1    Schäfer, M.K.2    Weihe, E.3    Schütz, B.4
  • 8
    • 22844432580 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors: Structural revelations, target identifications, and therapeutic inspirations
    • Jensen, A. A.; Frolund, B.; Liljefors, T.; Krogsgaard-Larsen, P. Neuronal nicotinic acetylcholine receptors: Structural revelations, target identifications, and therapeutic inspirations. J. Med. Chem. 2005, 48, 4705-4745.
    • (2005) J. Med. Chem , vol.48 , pp. 4705-4745
    • Jensen, A.A.1    Frolund, B.2    Liljefors, T.3    Krogsgaard-Larsen, P.4
  • 9
    • 0035040591 scopus 로고    scopus 로고
    • Synthesis and evaluation of radiolabeled piperazine derivatives of vesamicol as SPECT agents for cholinergic neurons
    • Bando, K.; Taguchi, K.; Ginoza, Y.; Naganuma, T.; Tanaka, Y.; Koike, K.; Takatoku, K. Synthesis and evaluation of radiolabeled piperazine derivatives of vesamicol as SPECT agents for cholinergic neurons. Nucl. Med. Biol. 2001, 28, 251-260.
    • (2001) Nucl. Med. Biol , vol.28 , pp. 251-260
    • Bando, K.1    Taguchi, K.2    Ginoza, Y.3    Naganuma, T.4    Tanaka, Y.5    Koike, K.6    Takatoku, K.7
  • 10
    • 0033668691 scopus 로고    scopus 로고
    • In vivo imaging of the vesicular acetylcholine transporter and the vesicular monoamine transporter
    • Efange, S. M. N. In vivo imaging of the vesicular acetylcholine transporter and the vesicular monoamine transporter. FASEB J. 2000, 14, 2401-2413.
    • (2000) FASEB J , vol.14 , pp. 2401-2413
    • Efange, S.M.N.1
  • 12
    • 39049193949 scopus 로고    scopus 로고
    • Fluorine-18 labeling methods: Features and possibilities of basic reactions
    • Coenen, H. H. Fluorine-18 labeling methods: Features and possibilities of basic reactions. Ernst Schering Res. Found. Workshop 2007, 62, 15-50.
    • (2007) Ernst Schering Res. Found. Workshop , vol.62 , pp. 15-50
    • Coenen, H.H.1
  • 14
    • 0020561444 scopus 로고
    • Pharmacological characterization of the acetylcholine transport system in purified Torpedo electric organ synaptic vesicles
    • Anderson, D. C.; King, S. C.; Parsons, S. M. Pharmacological characterization of the acetylcholine transport system in purified Torpedo electric organ synaptic vesicles. Mol. Pharmacol. 1983, 24, 48-54.
    • (1983) Mol. Pharmacol , vol.24 , pp. 48-54
    • Anderson, D.C.1    King, S.C.2    Parsons, S.M.3
  • 16
    • 0023820380 scopus 로고
    • 3H]Vesamicol binding in brain: Autoradiographic distribution, pharmacology, and effects of cholinergic lesions
    • Altar, C. A.; Marien, M. R. [3H]Vesamicol binding in brain: Autoradiographic distribution, pharmacology, and effects of cholinergic lesions. Synapse 1988, 2, 486-493.
    • (1988) Synapse , vol.2 , pp. 486-493
    • Altar, C.A.1    Marien, M.R.2
  • 17
    • 0346331816 scopus 로고    scopus 로고
    • Loading and recycling of synaptic vesicles in the Torpedo electric organ and the vertebrate neuromuscular junction
    • Van der Kloot, W. Loading and recycling of synaptic vesicles in the Torpedo electric organ and the vertebrate neuromuscular junction. Prog. Neurobiol. 2003, 71, 269-303.
    • (2003) Prog. Neurobiol , vol.71 , pp. 269-303
    • Van der Kloot, W.1
  • 20
    • 33644785824 scopus 로고    scopus 로고
    • Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor
    • Shiba, K.; Ogawa, K.; Ishiwata, K.; Yajima, K.; Mori, H. Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor. Bioorg. Med. Chem. 2006, 14, 2620-2626.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 2620-2626
    • Shiba, K.1    Ogawa, K.2    Ishiwata, K.3    Yajima, K.4    Mori, H.5
  • 21
    • 0027323936 scopus 로고
    • Kinetic and equilibrium characterization of vesamicol receptor-ligand complexes with picomolar dissociation constants
    • Rogers, G. A.; Kornreich, W. D.; Hand, K.; Parsons, S. M. Kinetic and equilibrium characterization of vesamicol receptor-ligand complexes with picomolar dissociation constants. Mol. Pharmacol. 1993, 44, 633-641.
    • (1993) Mol. Pharmacol , vol.44 , pp. 633-641
    • Rogers, G.A.1    Kornreich, W.D.2    Hand, K.3    Parsons, S.M.4
  • 26
  • 30
    • 0035216288 scopus 로고    scopus 로고
    • Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography
    • Voytko, M. L.; Mach, R. H.; Gage, H. D.; Ehrenkaufer, R. L.; Efange, S. M.; Tobin, J. R. Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography. Synapse 2001, 39, 95-100.
    • (2001) Synapse , vol.39 , pp. 95-100
    • Voytko, M.L.1    Mach, R.H.2    Gage, H.D.3    Ehrenkaufer, R.L.4    Efange, S.M.5    Tobin, J.R.6
  • 37
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 38
    • 0344564976 scopus 로고
    • 3D-QSAR in Drug Design
    • Kubinyi, H, Ed, ESCOM: Leiden, The Netherlands
    • Kubinyi, H., Ed. 3D-QSAR in Drug Design. Theory, Methods and Applications; ESCOM: Leiden, The Netherlands, 1993.
    • (1993) Theory, Methods and Applications
  • 39
    • 0034528043 scopus 로고    scopus 로고
    • Efange, S. M.; von Hohenberg, K.; Khare, A. B.; Tu, Z.; Mach, R. H.; Parsons, S. M. Synthesis and biological characterization of stable and radioiodinated (±)-trans-2-hydroxy-3-P[4-(3-iodophenyl)piperidyl]- 1,2,3,4-tetrahydronaphthalene (3′-IBVM). Nucl. Med. Biol. 2000, 27, 749-755.
    • Efange, S. M.; von Hohenberg, K.; Khare, A. B.; Tu, Z.; Mach, R. H.; Parsons, S. M. Synthesis and biological characterization of stable and radioiodinated (±)-trans-2-hydroxy-3-P[4-(3-iodophenyl)piperidyl]- 1,2,3,4-tetrahydronaphthalene (3′-IBVM). Nucl. Med. Biol. 2000, 27, 749-755.
  • 41
    • 0032830612 scopus 로고    scopus 로고
    • N-(3-Iodophenyl)trozamicol (IPHT) and related inhibitors of vesicular acetylcholine transport: Synthesis and preliminary biological characterization
    • Khare, A. B.; Langason, R. B.; Parsons, S. M.; Mach, R. H.; Efange, S. M. N-(3-Iodophenyl)trozamicol (IPHT) and related inhibitors of vesicular acetylcholine transport: Synthesis and preliminary biological characterization. Nucl. Med. Biol. 1999, 26, 609-617.
    • (1999) Nucl. Med. Biol , vol.26 , pp. 609-617
    • Khare, A.B.1    Langason, R.B.2    Parsons, S.M.3    Mach, R.H.4    Efange, S.M.5
  • 42
    • 0033614921 scopus 로고    scopus 로고
    • Hydroxylated decahydroquinolines as ligands for the vesicular acetylcholine transporter: Synthesis and biological evaluation
    • Efange, S. M.; Khare, A. B.; Mach, R. H.; Parsons, S. M. Hydroxylated decahydroquinolines as ligands for the vesicular acetylcholine transporter: Synthesis and biological evaluation. J. Med. Chem. 1999, 42, 2862-2869.
    • (1999) J. Med. Chem , vol.42 , pp. 2862-2869
    • Efange, S.M.1    Khare, A.B.2    Mach, R.H.3    Parsons, S.M.4
  • 43
    • 0027935474 scopus 로고    scopus 로고
    • Efange, S. M.; Khare, A. B.; Foulon, C.; Akella, S. K.; Parsons, S. M. Spirovesamicols: Conformationally restricted analogs of 2-(4-phenylpiperidino) cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function. J. Med. Chem. 1994, 37, 2574-2582.
    • Efange, S. M.; Khare, A. B.; Foulon, C.; Akella, S. K.; Parsons, S. M. Spirovesamicols: Conformationally restricted analogs of 2-(4-phenylpiperidino) cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function. J. Med. Chem. 1994, 37, 2574-2582.
  • 44
    • 0030778645 scopus 로고    scopus 로고
    • N-Hydroxyalkyl derivatives of 3-beta-phenyltropane and 1-methylspiro[1H-indoline-3,4′-piperidine]: Vesamicol analogues with affinity for monoamine transporters
    • Efange, S. M.; Kamath, A. P.; Khare, A. B.; Kung, M. P.; Mach, R. H.; Parsons, S. M. N-Hydroxyalkyl derivatives of 3-beta-phenyltropane and 1-methylspiro[1H-indoline-3,4′-piperidine]: Vesamicol analogues with affinity for monoamine transporters. J. Med. Chem. 1997, 40, 3905-3914.
    • (1997) J. Med. Chem , vol.40 , pp. 3905-3914
    • Efange, S.M.1    Kamath, A.P.2    Khare, A.B.3    Kung, M.P.4    Mach, R.H.5    Parsons, S.M.6
  • 45
    • 0001681052 scopus 로고
    • The collinearity problem in linear regression. The partial least-squares (PLS) approach to generalized inverses
    • Wold, S.; Ruhe, A.; Wold, H.; Dunn, W. J. The collinearity problem in linear regression. The partial least-squares (PLS) approach to generalized inverses. Siam J. Sci. Stat. Comp. 1984, 5, 735-743.
    • (1984) Siam J. Sci. Stat. Comp , vol.5 , pp. 735-743
    • Wold, S.1    Ruhe, A.2    Wold, H.3    Dunn, W.J.4
  • 46
    • 84987100711 scopus 로고
    • Cross-validation, bootstrapping, and partial least-squares compared with multiple-regression in conventional QSAR studies
    • Cramer, R. D.; Bunce, J. D.; Patterson, D. E.; Frank, I. E. Cross-validation, bootstrapping, and partial least-squares compared with multiple-regression in conventional QSAR studies. Quant. Struct.-Act. Rel. 1988, 7, 18-25.
    • (1988) Quant. Struct.-Act. Rel , vol.7 , pp. 18-25
    • Cramer, R.D.1    Bunce, J.D.2    Patterson, D.E.3    Frank, I.E.4
  • 47
    • 22744458773 scopus 로고    scopus 로고
    • Tripos Inc, St. Louis, MO
    • SYBYL 7.0; Tripos Inc.: St. Louis, MO, 2004.
    • (2004) SYBYL 7.0
  • 48
    • 0027310371 scopus 로고
    • Generating optimal linear PLS estimations (GOLPE): An advanced chemometric tool for handling 3D QSAR problems
    • Baroni, M.; Costantino, G.; Crucian, G.; Riganelli, D.; Valigi, R.; Clementi, S. Generating optimal linear PLS estimations (GOLPE): An advanced chemometric tool for handling 3D QSAR problems. Quant. Struct.-Act. Relat. 1993, 12, 9-20.
    • (1993) Quant. Struct.-Act. Relat , vol.12 , pp. 9-20
    • Baroni, M.1    Costantino, G.2    Crucian, G.3    Riganelli, D.4    Valigi, R.5    Clementi, S.6
  • 49
    • 21144474350 scopus 로고
    • Linear model selection by cross-validation
    • Shao, J. Linear model selection by cross-validation. J. Am. Stat. Assoc. 1993, 88, 486-494.
    • (1993) J. Am. Stat. Assoc , vol.88 , pp. 486-494
    • Shao, J.1
  • 50
    • 0036277133 scopus 로고    scopus 로고
    • Impact of orthogonal signal correction (OSC) on the predictive ability of CoMFA models for the ciliate toxicity of nitrobenzenes
    • Boháč, M.; Loeprecht, B.; Damborský, J.; Schüürmann, G. Impact of orthogonal signal correction (OSC) on the predictive ability of CoMFA models for the ciliate toxicity of nitrobenzenes. Quant. Struct.-Act. Relat. 2002, 21, 3-11.
    • (2002) Quant. Struct.-Act. Relat , vol.21 , pp. 3-11
    • Boháč, M.1    Loeprecht, B.2    Damborský, J.3    Schüürmann, G.4
  • 52
    • 0000490166 scopus 로고
    • From atoms and bonds to three-dimensional atomic coordinates: Automatic model builders
    • Sadowski, J.; Gasteiger, J. From atoms and bonds to three-dimensional atomic coordinates: Automatic model builders. Chem. Rev. 1993, 93, 2567-2581.
    • (1993) Chem. Rev , vol.93 , pp. 2567-2581
    • Sadowski, J.1    Gasteiger, J.2


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