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Volumn 89, Issue 5, 2016, Pages 541-551

A novel binding mode reveals two distinct classes of NMDA receptor GluN2B-selective antagonists s

Author keywords

[No Author keywords available]

Indexed keywords

DIZOCILPINE; EVT 101; IFENPRODIL; IONOTROPIC RECEPTOR ANTAGONIST; MK 22; PHENYLETHANOLAMINE; UNCLASSIFIED DRUG; AGENTS AFFECTING WATER, MOLECULE OR ION TRANSPORT; ALPHA ADRENERGIC RECEPTOR BLOCKING AGENT; EVT-101; HYBRID PROTEIN; IMIDAZOLE DERIVATIVE; LIGAND; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N-(3-(3-(4-METHYLBENZYL)-1,2,4-OXADIAZOL-5-YL)CYCLOPENTYL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-4-AMINE; NEW DRUG; NR2B NMDA RECEPTOR; OXADIAZOLE DERIVATIVE; PIPERIDINE DERIVATIVE; PROTEIN SUBUNIT; PYRIDAZINE DERIVATIVE; PYRIMIDINE DERIVATIVE; XENOPUS PROTEIN;

EID: 84963807733     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.115.103036     Document Type: Article
Times cited : (86)

References (63)
  • 3
    • 17044446594 scopus 로고    scopus 로고
    • Antagonist properties of the stereoisomers of ifenprodil at NR1A/NR2A and NR1A/NR2B subtypes of the NMDA receptor expressed in Xenopus oocytes
    • Avenet P, Léonardon J, Besnard F, Graham D, Frost J, Depoortere H, Langer SZ, and Scatton B (1996) Antagonist properties of the stereoisomers of ifenprodil at NR1A/NR2A and NR1A/NR2B subtypes of the NMDA receptor expressed in Xenopus oocytes. Eur J Pharmacol 296:209-213.
    • (1996) Eur J Pharmacol , vol.296 , pp. 209-213
    • Avenet, P.1    Léonardon, J.2    Besnard, F.3    Graham, D.4    Frost, J.5    Depoortere, H.6    Langer, S.Z.7    Scatton, B.8
  • 4
    • 33646537447 scopus 로고    scopus 로고
    • NR2B selective NMDA antagonists: The evolution of the ifenprodil-type pharmacophore
    • Borza I and Domány G (2006) NR2B selective NMDA antagonists: the evolution of the ifenprodil-type pharmacophore. Curr Top Med Chem 6:687-695.
    • (2006) Curr Top Med Chem , vol.6 , pp. 687-695
    • Borza, I.1    Domány, G.2
  • 8
    • 0015186976 scopus 로고
    • Synthesis and pharmacological properties of a series of 2-piperidino alkanol derivatives
    • Carron C, Jullien A, and Bucher B (1971) Synthesis and pharmacological properties of a series of 2-piperidino alkanol derivatives. Arzneimittelforschung 21:1992-1998.
    • (1971) Arzneimittelforschung , vol.21 , pp. 1992-1998
    • Carron, C.1    Jullien, A.2    Bucher, B.3
  • 10
    • 0032914455 scopus 로고    scopus 로고
    • Antagonists selective for NMDA receptors containing the NR2B subunit
    • Chenard BL and Menniti FS (1999) Antagonists selective for NMDA receptors containing the NR2B subunit. Curr Pharm Des 5:381-404.
    • (1999) Curr Pharm Des , vol.5 , pp. 381-404
    • Chenard, B.L.1    Menniti, F.S.2
  • 12
    • 0035577313 scopus 로고    scopus 로고
    • NMDA receptor antagonists as analgesics: Focus on the NR2B subtype
    • Chizh BA, Headley PM, and Tzschentke TM (2001) NMDA receptor antagonists as analgesics: focus on the NR2B subtype. Trends Pharmacol Sci 22:636-642.
    • (2001) Trends Pharmacol Sci , vol.22 , pp. 636-642
    • Chizh, B.A.1    Headley, P.M.2    Tzschentke, T.M.3
  • 14
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project, Number 4 (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr D Biol Crystallogr 50:760-763.
    • (1994) Acta Crystallogr D Biol Crystallogr , vol.50 , pp. 760-763
  • 17
    • 0031443289 scopus 로고    scopus 로고
    • Ro 25-6981, a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit. Characterization in vitro
    • Fischer G, Mutel V, Trube G, Malherbe P, Kew JN, Mohacsi E, Heitz MP, and Kemp JA (1997) Ro 25-6981, a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit. Characterization in vitro. J Pharmacol Exp Ther 283:1285-1292.
    • (1997) J Pharmacol Exp Ther , vol.283 , pp. 1285-1292
    • Fischer, G.1    Mutel, V.2    Trube, G.3    Malherbe, P.4    Kew, J.N.5    Mohacsi, E.6    Heitz, M.P.7    Kemp, J.A.8
  • 20
    • 0029871365 scopus 로고    scopus 로고
    • Interactions between ifenprodil and the NR2B subunit of the N-methyl-D-aspartate receptor
    • Gallagher MJ, Huang H, Pritchett DB, and Lynch DR (1996) Interactions between ifenprodil and the NR2B subunit of the N-methyl-D-aspartate receptor. J Biol Chem 271:9603-9611.
    • (1996) J Biol Chem , vol.271 , pp. 9603-9611
    • Gallagher, M.J.1    Huang, H.2    Pritchett, D.B.3    Lynch, D.R.4
  • 21
    • 84871027024 scopus 로고    scopus 로고
    • Synthesis and biological characterization of 3-substituted 1H-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors. Part 2
    • Gitto R, De Luca L, Ferro S, Buemi MR, Russo E, De Sarro G, Chisari M, Ciranna L, and Chimirri A (2012) Synthesis and biological characterization of 3-substituted 1H-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors. Part 2. J Med Chem 55:10532-10539.
    • (2012) J Med Chem , vol.55 , pp. 10532-10539
    • Gitto, R.1    De Luca, L.2    Ferro, S.3    Buemi, M.R.4    Russo, E.5    De Sarro, G.6    Chisari, M.7    Ciranna, L.8    Chimirri, A.9
  • 22
    • 0031473847 scopus 로고    scopus 로고
    • SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modeling
    • Guex N and Peitsch MC (1997) SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling. Electrophoresis 18:2714-2723.
    • (1997) Electrophoresis , vol.18 , pp. 2714-2723
    • Guex, N.1    Peitsch, M.C.2
  • 23
    • 84863719297 scopus 로고    scopus 로고
    • A Randomized, placebo-controlled, crossover pilot trial of the oral selective NR2B antagonist MK-0657 in patients with treatment-resistant major depressive disorder
    • Ibrahim L, Diaz Granados N, Jolkovsky L, Brutsche N, Luckenbaugh DA, Herring WJ, Potter WZ, and Zarate CA, Jr (2012) A Randomized, placebo-controlled, crossover pilot trial of the oral selective NR2B antagonist MK-0657 in patients with treatment-resistant major depressive disorder. J Clin Psychopharmacol 32:551-557.
    • (2012) J Clin Psychopharmacol , vol.32 , pp. 551-557
    • Ibrahim, L.1    Diaz Granados, N.2    Jolkovsky, L.3    Brutsche, N.4    Luckenbaugh, D.A.5    Herring, W.J.6    Potter, W.Z.7    Zarate, C.A.8
  • 24
    • 46849097142 scopus 로고    scopus 로고
    • NMDA receptors in clinical neurology: Excitatory times ahead
    • Kalia LV, Kalia SK, and Salter MW (2008) NMDA receptors in clinical neurology: excitatory times ahead. Lancet Neurol 7:742-755.
    • (2008) Lancet Neurol , vol.7 , pp. 742-755
    • Kalia, L.V.1    Kalia, S.K.2    Salter, M.W.3
  • 25
    • 84901640125 scopus 로고    scopus 로고
    • Crystal structure of a heterotetrameric NMDA receptor ion channel
    • Karakas E and Furukawa H (2014) Crystal structure of a heterotetrameric NMDA receptor ion channel. Science 344:992-997.
    • (2014) Science , vol.344 , pp. 992-997
    • Karakas, E.1    Furukawa, H.2
  • 26
    • 72449151659 scopus 로고    scopus 로고
    • Structure of the zinc-bound amino-terminal domain of the NMDA receptor NR2B subunit
    • Karakas E, Simorowski N, and Furukawa H (2009) Structure of the zinc-bound amino-terminal domain of the NMDA receptor NR2B subunit. EMBO J 28:3910-3920.
    • (2009) EMBO J , vol.28 , pp. 3910-3920
    • Karakas, E.1    Simorowski, N.2    Furukawa, H.3
  • 27
    • 79960417429 scopus 로고    scopus 로고
    • Subunit arrangement and phenylethanolamine binding in GluN1/GluN2B NMDA receptors
    • Karakas E, Simorowski N, and Furukawa H (2011) Subunit arrangement and phenylethanolamine binding in GluN1/GluN2B NMDA receptors. Nature 475:249-253.
    • (2011) Nature , vol.475 , pp. 249-253
    • Karakas, E.1    Simorowski, N.2    Furukawa, H.3
  • 29
    • 0030450983 scopus 로고    scopus 로고
    • A novel mechanism of activity-dependent NMDA receptor antagonism describes the effect of ifenprodil in rat cultured cortical neurones
    • Kew JN, Trube G, and Kemp JA (1996) A novel mechanism of activity-dependent NMDA receptor antagonism describes the effect of ifenprodil in rat cultured cortical neurones. J Physiol 497:761-772.
    • (1996) J Physiol , vol.497 , pp. 761-772
    • Kew, J.N.1    Trube, G.2    Kemp, J.A.3
  • 31
    • 33646594995 scopus 로고    scopus 로고
    • Recent advances in the development of NR2B subtype-selective NMDA receptor antagonists
    • Layton ME, Kelly MJ, 3rd, and Rodzinak KJ (2006) Recent advances in the development of NR2B subtype-selective NMDA receptor antagonists. Curr Top Med Chem 6:697-709.
    • (2006) Curr Top Med Chem , vol.6 , pp. 697-709
    • Layton, M.E.1    Kelly, M.J.2    Rodzinak, K.J.3
  • 33
    • 84904199124 scopus 로고    scopus 로고
    • NMDA receptor structures reveal subunit arrangement and pore architecture
    • Lee CH, Lü W, Michel JC, Goehring A, Du J, Song X, and Gouaux E (2014) NMDA receptor structures reveal subunit arrangement and pore architecture. Nature 511:191-197.
    • (2014) Nature , vol.511 , pp. 191-197
    • Lee, C.H.1    Lü, W.2    Michel, J.C.3    Goehring, A.4    Du, J.5    Song, X.6    Gouaux, E.7
  • 35
    • 0344304828 scopus 로고    scopus 로고
    • Identification of critical residues in the amino terminal domain of the human NR2B subunit involved in the RO 25-6981 binding pocket
    • Malherbe P, Mutel V, Broger C, Perin-Dureau F, Kemp JA, Neyton J, Paoletti P, and Kew JN (2003) Identification of critical residues in the amino terminal domain of the human NR2B subunit involved in the RO 25-6981 binding pocket. J Pharmacol Exp Ther 307:897-905.
    • (2003) J Pharmacol Exp Ther , vol.307 , pp. 897-905
    • Malherbe, P.1    Mutel, V.2    Broger, C.3    Perin-Dureau, F.4    Kemp, J.A.5    Neyton, J.6    Paoletti, P.7    Kew, J.N.8
  • 37
    • 0033051714 scopus 로고    scopus 로고
    • A regulatory domain (R1-R2) in the amino terminus of the N-methyl-D-aspartate receptor: Effects of spermine, protons, and ifenprodil, and structural similarity to bacterial leucine/isoleucine/valine binding protein
    • Masuko T, Kashiwagi K, Kuno T, Nguyen ND, Pahk AJ, Fukuchi J, Igarashi K, and Williams K (1999) A regulatory domain (R1-R2) in the amino terminus of the N-methyl-D-aspartate receptor: effects of spermine, protons, and ifenprodil, and structural similarity to bacterial leucine/isoleucine/valine binding protein. Mol Pharmacol 55:957-969.
    • (1999) Mol Pharmacol , vol.55 , pp. 957-969
    • Masuko, T.1    Kashiwagi, K.2    Kuno, T.3    Nguyen, N.D.4    Pahk, A.J.5    Fukuchi, J.6    Igarashi, K.7    Williams, K.8
  • 39
    • 37249023309 scopus 로고    scopus 로고
    • New and original pKa prediction method using grid molecular interaction fields
    • Milletti F, Storchi L, Sforna G, and Cruciani G (2007) New and original pKa prediction method using grid molecular interaction fields. J Chem Inf Model 47:2172-2181.
    • (2007) J Chem Inf Model , vol.47 , pp. 2172-2181
    • Milletti, F.1    Storchi, L.2    Sforna, G.3    Cruciani, G.4
  • 40
    • 70350324907 scopus 로고    scopus 로고
    • Allosteric modulators of NR2B-containing NMDA receptors: Molecular mechanisms and therapeutic potential
    • Mony L, Kew JN, Gunthorpe MJ, and Paoletti P (2009a) Allosteric modulators of NR2B-containing NMDA receptors: molecular mechanisms and therapeutic potential. Br J Pharmacol 157:1301-1317.
    • (2009) Br J Pharmacol , vol.157 , pp. 1301-1317
    • Mony, L.1    Kew, J.N.2    Gunthorpe, M.J.3    Paoletti, P.4
  • 42
    • 79961020657 scopus 로고    scopus 로고
    • Molecular basis of positive allosteric modulation of GluN2B NMDA receptors by polyamines
    • Mony L, Zhu S, Carvalho S, and Paoletti P (2011) Molecular basis of positive allosteric modulation of GluN2B NMDA receptors by polyamines. EMBO J 30:3134-3146.
    • (2011) EMBO J , vol.30 , pp. 3134-3146
    • Mony, L.1    Zhu, S.2    Carvalho, S.3    Paoletti, P.4
  • 43
    • 0028343648 scopus 로고
    • Developmental and regional expression in the rat brain and functional properties of four NMDA receptors
    • Monyer H, Burnashev N, Laurie DJ, Sakmann B, and Seeburg PH (1994) Developmental and regional expression in the rat brain and functional properties of four NMDA receptors. Neuron 12:529-540.
    • (1994) Neuron , vol.12 , pp. 529-540
    • Monyer, H.1    Burnashev, N.2    Laurie, D.J.3    Sakmann, B.4    Seeburg, P.H.5
  • 45
    • 0036250086 scopus 로고    scopus 로고
    • NR2B selective NMDA receptor antagonists
    • Nikam SS and Meltzer LT (2002) NR2B selective NMDA receptor antagonists. Curr Pharm Des 8:845-855.
    • (2002) Curr Pharm Des , vol.8 , pp. 845-855
    • Nikam, S.S.1    Meltzer, L.T.2
  • 46
    • 79954630544 scopus 로고    scopus 로고
    • Molecular basis of NMDA receptor functional diversity
    • Paoletti P (2011) Molecular basis of NMDA receptor functional diversity. Eur J Neurosci 33:1351-1365.
    • (2011) Eur J Neurosci , vol.33 , pp. 1351-1365
    • Paoletti, P.1
  • 47
    • 0030746608 scopus 로고    scopus 로고
    • High-affinity zinc inhibition of NMDA NR1-NR2A receptors
    • Paoletti P, Ascher P, and Neyton J (1997) High-affinity zinc inhibition of NMDA NR1-NR2A receptors. J Neurosci 17:5711-5725.
    • (1997) J Neurosci , vol.17 , pp. 5711-5725
    • Paoletti, P.1    Ascher, P.2    Neyton, J.3
  • 48
    • 84878254691 scopus 로고    scopus 로고
    • NMDA receptor subunit diversity: Impact on receptor properties, synaptic plasticity and disease
    • Paoletti P, Bellone C, and Zhou Q (2013) NMDA receptor subunit diversity: impact on receptor properties, synaptic plasticity and disease. Nat Rev Neurosci 14:383-400.
    • (2013) Nat Rev Neurosci , vol.14 , pp. 383-400
    • Paoletti, P.1    Bellone, C.2    Zhou, Q.3
  • 49
    • 0037101607 scopus 로고    scopus 로고
    • Mapping the binding site of the neuroprotectant ifenprodil on NMDA receptors
    • Perin-Dureau F, Rachline J, Neyton J, and Paoletti P (2002) Mapping the binding site of the neuroprotectant ifenprodil on NMDA receptors. J Neurosci 22:5955-5965.
    • (2002) J Neurosci , vol.22 , pp. 5955-5965
    • Perin-Dureau, F.1    Rachline, J.2    Neyton, J.3    Paoletti, P.4
  • 50
    • 59049098262 scopus 로고    scopus 로고
    • An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N-methyl-D-aspartate antagonist, CP-101, 606, in patients with treatment-refractory major depressive disorder
    • Preskorn SH, Baker B, Kolluri S, Menniti FS, Krams M, and Landen JW (2008) An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N-methyl-D-aspartate antagonist, CP-101, 606, in patients with treatment-refractory major depressive disorder. J Clin Psychopharmacol 28:631-637.
    • (2008) J Clin Psychopharmacol , vol.28 , pp. 631-637
    • Preskorn, S.H.1    Baker, B.2    Kolluri, S.3    Menniti, F.S.4    Krams, M.5    Landen, J.W.6
  • 51
    • 0028466540 scopus 로고
    • Comparison of Automatic Three-Dimensional Model Builders Using 639 X-Ray Structures
    • Sadowski J, Gasteiger J, and Klebe G (1994) Comparison of Automatic Three-Dimensional Model Builders Using 639 X-Ray Structures. J Chem Inf Comput Sci 34:1000-1008.
    • (1994) J Chem Inf Comput Sci , vol.34 , pp. 1000-1008
    • Sadowski, J.1    Gasteiger, J.2    Klebe, G.3
  • 52
    • 84880529288 scopus 로고    scopus 로고
    • Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments
    • Sastry GM, Adzhigirey M, Day T, Annabhimoju R, and Sherman W (2013) Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des 27:221-234.
    • (2013) J Comput Aided Mol Des , vol.27 , pp. 221-234
    • Sastry, G.M.1    Adzhigirey, M.2    Day, T.3    Annabhimoju, R.4    Sherman, W.5
  • 53
    • 52449106452 scopus 로고    scopus 로고
    • Measurement of dissociation constants (pKa values) of organic compounds by multiplexed capillary electrophoresis using aqueous and cosolvent buffers
    • Shalaeva M, Kenseth J, Lombardo F, and Bastin A (2008) Measurement of dissociation constants (pKa values) of organic compounds by multiplexed capillary electrophoresis using aqueous and cosolvent buffers. J Pharm Sci 97:2581-2606.
    • (2008) J Pharm Sci , vol.97 , pp. 2581-2606
    • Shalaeva, M.1    Kenseth, J.2    Lombardo, F.3    Bastin, A.4
  • 54
    • 0028219211 scopus 로고
    • Changing subunit composition of heteromeric NMDA receptors during development of rat cortex
    • Sheng M, Cummings J, Roldan LA, Jan YN, and Jan LY (1994) Changing subunit composition of heteromeric NMDA receptors during development of rat cortex. Nature 368:144-147.
    • (1994) Nature , vol.368 , pp. 144-147
    • Sheng, M.1    Cummings, J.2    Roldan, L.A.3    Jan, Y.N.4    Jan, L.Y.5
  • 56
    • 84939203840 scopus 로고    scopus 로고
    • Enantiomerically pure 2-methyltetrahydro-3-benzazepin-1-ols selectively blocking GluN2B subunit containing N-methyl-D-aspartate receptors
    • Tewes B, Frehland B, Schepmann D, Robaa D, Uengwetwanit T, Gaube F, Winckler T, Sippl W, and Wünsch B (2015) Enantiomerically pure 2-methyltetrahydro-3-benzazepin-1-ols selectively blocking GluN2B subunit containing N-methyl-D-aspartate receptors. J Med Chem 58:6293-6305.
    • (2015) J Med Chem , vol.58 , pp. 6293-6305
    • Tewes, B.1    Frehland, B.2    Schepmann, D.3    Robaa, D.4    Uengwetwanit, T.5    Gaube, F.6    Winckler, T.7    Sippl, W.8    Wünsch, B.9
  • 59
    • 0027525324 scopus 로고
    • Ifenprodil discriminates subtypes of the N-methyl-D-aspartate receptor: Selectivity and mechanisms at recombinant heteromeric receptors
    • Williams K (1993) Ifenprodil discriminates subtypes of the N-methyl-D-aspartate receptor: selectivity and mechanisms at recombinant heteromeric receptors. Mol Pharmacol 44:851-859.
    • (1993) Mol Pharmacol , vol.44 , pp. 851-859
    • Williams, K.1
  • 61
    • 84909947167 scopus 로고    scopus 로고
    • Allosteric modulators of NMDA receptors: Multiple sites and mechanisms
    • Zhu S and Paoletti P (2015) Allosteric modulators of NMDA receptors: multiple sites and mechanisms. Curr Opin Pharmacol 20:14-23.
    • (2015) Curr Opin Pharmacol , vol.20 , pp. 14-23
    • Zhu, S.1    Paoletti, P.2
  • 63
    • 84876183319 scopus 로고    scopus 로고
    • Allosteric signaling and dynamics of the clamshell-like NMDA receptor GluN1 N-terminal domain
    • Zhu S, Stroebel D, Yao CA, Taly A, and Paoletti P (2013) Allosteric signaling and dynamics of the clamshell-like NMDA receptor GluN1 N-terminal domain. Nat Struct Mol Biol 20:477-485.
    • (2013) Nat Struct Mol Biol , vol.20 , pp. 477-485
    • Zhu, S.1    Stroebel, D.2    Yao, C.A.3    Taly, A.4    Paoletti, P.5


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