메뉴 건너뛰기




Volumn 53, Issue 23, 2010, Pages 8354-8361

Biostructural and pharmacological studies of bicyclic analogues of the 3-isoxazolol glutamate receptor agonist ibotenic acid

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4,5,6,7 TETRAHYDROISOXAZOLO[5,4 C]PYRIDINE 7 CARBOXYLIC ACID; 4,5,6,7 TETRAHYDRO 3 HYDROXYISOXAZOLO[5,4 C]PYRIDINE 5 CARBOXYLIC ACID; AMPA RECEPTOR; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR AGONIST; IBOTENIC ACID; UNCLASSIFIED DRUG;

EID: 78649880923     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101218a     Document Type: Article
Times cited : (18)

References (55)
  • 4
    • 8744278883 scopus 로고    scopus 로고
    • Glutamate as a therapeutic target in psychiatric disorders
    • Javitt, D. C. Glutamate as a therapeutic target in psychiatric disorders Mol. Psychiatry 2004, 9, 984-997
    • (2004) Mol. Psychiatry , vol.9 , pp. 984-997
    • Javitt, D.C.1
  • 5
    • 0032467053 scopus 로고    scopus 로고
    • Glutamate in CNS disorders as a target for drug development: An update
    • Parsons, C. G.; Danysz, W.; Quack, G. Glutamate in CNS disorders as a target for drug development: an update Drug News Perspect. 1998, 11, 523-569
    • (1998) Drug News Perspect. , vol.11 , pp. 523-569
    • Parsons, C.G.1    Danysz, W.2    Quack, G.3
  • 6
    • 17744387125 scopus 로고    scopus 로고
    • Ionotropic and metabotropic glutamate receptor structure and pharmacology
    • Kew, J. N. C.; Kemp, J. A. Ionotropic and metabotropic glutamate receptor structure and pharmacology Psychopharmacology 2005, 179, 4-29
    • (2005) Psychopharmacology , vol.179 , pp. 4-29
    • Kew, J.N.C.1    Kemp, J.A.2
  • 8
    • 20444429431 scopus 로고    scopus 로고
    • Glutamate receptor ion channels
    • Mayer, M. L. Glutamate receptor ion channels Curr. Opin. Neurobiol. 2005, 15, 282-288
    • (2005) Curr. Opin. Neurobiol. , vol.15 , pp. 282-288
    • Mayer, M.L.1
  • 9
    • 0035819074 scopus 로고    scopus 로고
    • Heteromeric AMPA receptors assemble with a preferred subunit stoichiometry and spatial arrangement
    • Mansour, M.; Nagarajan, N.; Nehring, R. B.; Clements, J. D.; Rosenmund, C. Heteromeric AMPA receptors assemble with a preferred subunit stoichiometry and spatial arrangement Neuron 2001, 32, 841-853
    • (2001) Neuron , vol.32 , pp. 841-853
    • Mansour, M.1    Nagarajan, N.2    Nehring, R.B.3    Clements, J.D.4    Rosenmund, C.5
  • 10
    • 0032578635 scopus 로고    scopus 로고
    • Structure of a glutamate-receptor ligand-binding core in complex with kainate
    • Armstrong, N.; Sun, Y.; Chen, G. Q.; Gouaux, E. Structure of a glutamate-receptor ligand-binding core in complex with kainate Nature 1998, 395, 913-917
    • (1998) Nature , vol.395 , pp. 913-917
    • Armstrong, N.1    Sun, Y.2    Chen, G.Q.3    Gouaux, E.4
  • 11
    • 0033636314 scopus 로고    scopus 로고
    • Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: Crystal structures of the GluR2 ligand binding core
    • Armstrong, N.; Gouaux, E. Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core Neuron 2000, 28, 165-181
    • (2000) Neuron , vol.28 , pp. 165-181
    • Armstrong, N.1    Gouaux, E.2
  • 12
    • 0036968894 scopus 로고    scopus 로고
    • Structural basis for AMPA receptor activation and ligand selectivity: Crystal structures of five agonist complexes with the GluR2 ligand-binding core
    • Hogner, A.; Kastrup, J.; Jin, R.; Liljefors, T.; Mayer, M.; Egebjerg, J.; Larsen, I.; Gouaux, E. Structural basis for AMPA receptor activation and ligand selectivity: crystal structures of five agonist complexes with the GluR2 ligand-binding core J. Mol. Biol. 2002, 322, 93-109
    • (2002) J. Mol. Biol. , vol.322 , pp. 93-109
    • Hogner, A.1    Kastrup, J.2    Jin, R.3    Liljefors, T.4    Mayer, M.5    Egebjerg, J.6    Larsen, I.7    Gouaux, E.8
  • 13
    • 56649107905 scopus 로고    scopus 로고
    • Molecular mechanism of agonist recognition by the ligand-binding core of the ionotropic glutamate receptor 4
    • Kasper, C.; Frydenvang, K.; Naur, P.; Gajhede, M.; Pickering, D. S.; Kastrup, J. S. Molecular mechanism of agonist recognition by the ligand-binding core of the ionotropic glutamate receptor 4 FEBS Lett. 2008, 582, 4089-4094
    • (2008) FEBS Lett. , vol.582 , pp. 4089-4094
    • Kasper, C.1    Frydenvang, K.2    Naur, P.3    Gajhede, M.4    Pickering, D.S.5    Kastrup, J.S.6
  • 14
    • 0038037859 scopus 로고    scopus 로고
    • Mechanisms of activation, inhibition and specificity: Crystal structures of the NMDA receptor NR1 ligand-binding core
    • Furukawa, H.; Gouaux, E. Mechanisms of activation, inhibition and specificity: crystal structures of the NMDA receptor NR1 ligand-binding core EMBO J. 2003, 22, 2873-2885
    • (2003) EMBO J. , vol.22 , pp. 2873-2885
    • Furukawa, H.1    Gouaux, E.2
  • 15
    • 27744500994 scopus 로고    scopus 로고
    • Subunit arrangement and function in NMDA receptors
    • Furukawa, H.; Singh, S. K.; Mancusso, R.; Gouaux, E. Subunit arrangement and function in NMDA receptors Nature 2005, 438, 185-192
    • (2005) Nature , vol.438 , pp. 185-192
    • Furukawa, H.1    Singh, S.K.2    Mancusso, R.3    Gouaux, E.4
  • 16
    • 13844266202 scopus 로고    scopus 로고
    • Crystal structures of the GluR5 and GluR6 ligand binding cores: Molecular mechanisms underlying kainate receptor selectivity
    • Mayer, M. L. Crystal structures of the GluR5 and GluR6 ligand binding cores: molecular mechanisms underlying kainate receptor selectivity Neuron 2005, 45, 539-552
    • (2005) Neuron , vol.45 , pp. 539-552
    • Mayer, M.L.1
  • 17
    • 13444281913 scopus 로고    scopus 로고
    • Structure of the kainate receptor subunit GluR6 agonist-binding domain complexed with domoic acid
    • Nanao, M. H.; Green, T.; Stern-Bach, Y.; Heinemann, S. F.; Choe, S. Structure of the kainate receptor subunit GluR6 agonist-binding domain complexed with domoic acid Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 1708-1713
    • (2005) Proc. Natl. Acad. Sci. U.S.A. , vol.102 , pp. 1708-1713
    • Nanao, M.H.1    Green, T.2    Stern-Bach, Y.3    Heinemann, S.F.4    Choe, S.5
  • 18
    • 13844272397 scopus 로고    scopus 로고
    • Crystal structure of the kainate receptor GluR5 ligand-binding core in complex with (S)-glutamate
    • Naur, P.; Vestergaard, B.; Skov, L. K.; Egebjerg, J.; Gajhede, M.; Kastrup, J. S. Crystal structure of the kainate receptor GluR5 ligand-binding core in complex with (S)-glutamate FEBS Lett. 2005, 579, 1154-1160
    • (2005) FEBS Lett. , vol.579 , pp. 1154-1160
    • Naur, P.1    Vestergaard, B.2    Skov, L.K.3    Egebjerg, J.4    Gajhede, M.5    Kastrup, J.S.6
  • 21
    • 49149095000 scopus 로고    scopus 로고
    • Molecular mechanism of ligand recognition by NR3 subtype glutamate receptors
    • Yao, Y.; Harrison, C. B.; Freddolino, P. L.; Schulten, K.; Mayer, M. L. Molecular mechanism of ligand recognition by NR3 subtype glutamate receptors EMBO J. 2008, 27, 2158-2170
    • (2008) EMBO J. , vol.27 , pp. 2158-2170
    • Yao, Y.1    Harrison, C.B.2    Freddolino, P.L.3    Schulten, K.4    Mayer, M.L.5
  • 22
    • 0043033172 scopus 로고    scopus 로고
    • Structural basis for partial agonist action at ionotropic glutamate receptors
    • Jin, R.; Banke, T. G.; Mayer, M. L.; Traynelis, S. F.; Gouaux, E. Structural basis for partial agonist action at ionotropic glutamate receptors Nat. Neurosci. 2003, 6, 803-810
    • (2003) Nat. Neurosci. , vol.6 , pp. 803-810
    • Jin, R.1    Banke, T.G.2    Mayer, M.L.3    Traynelis, S.F.4    Gouaux, E.5
  • 24
    • 72049124287 scopus 로고    scopus 로고
    • X-ray structure, symmetry and mechanism of an AMPA-subtype glutamate receptor
    • Sobolevsky, A. I.; Rosconi, M. P.; Gouaux, E. X-ray structure, symmetry and mechanism of an AMPA-subtype glutamate receptor Nature 2009, 462, 745-756
    • (2009) Nature , vol.462 , pp. 745-756
    • Sobolevsky, A.I.1    Rosconi, M.P.2    Gouaux, E.3
  • 26
    • 0021953106 scopus 로고
    • Synthesis and structure-activity studies on excitatory amino acids structurally related to ibotenic acid
    • DOI 10.1021/jm50001a023
    • Krogsgaard-Larsen, P.; Brehm, L.; Johansen, J. S.; Vinzents, P.; Lauridsen, J.; Curtis, D. R. Synthesis and structure-activity studies on excitatory amino acids structurally related to ibotenic acid J. Med. Chem. 1985, 28, 673-679 (Pubitemid 15098175)
    • (1985) Journal of Medicinal Chemistry , vol.28 , Issue.5 , pp. 673-679
    • Krogsgaard-Larsen, P.1    Brehm, L.2    Johansen, J.S.3
  • 27
    • 0942290249 scopus 로고    scopus 로고
    • A stereochemical anomaly: The cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4- c ]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors
    • Vogensen, S. B.; Greenwood, J. R.; Varming, A. R.; Brehm, L.; Pickering, D. S.; Nielsen, B.; Liljefors, T.; Clausen, R. P.; Johansen, T. N.; Krogsgaard-Larsen, P. A stereochemical anomaly: the cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4- c ]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors Org. Biomol. Chem. 2004, 2, 206-213
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 206-213
    • Vogensen, S.B.1    Greenwood, J.R.2    Varming, A.R.3    Brehm, L.4    Pickering, D.S.5    Nielsen, B.6    Liljefors, T.7    Clausen, R.P.8    Johansen, T.N.9    Krogsgaard-Larsen, P.10
  • 28
    • 40949163431 scopus 로고    scopus 로고
    • Role of the active site solvent in the thermodynamics of factor Xa-ligand binding
    • Abel, R.; Young, T.; Farid, R.; Berne, B. J.; Friesner, R. A. Role of the active site solvent in the thermodynamics of factor Xa-ligand binding J. Am. Chem. Soc. 2008, 130, 2817-2831
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2817-2831
    • Abel, R.1    Young, T.2    Farid, R.3    Berne, B.J.4    Friesner, R.A.5
  • 30
    • 78649839869 scopus 로고    scopus 로고
    • Desmond, WaterMap, OPLS2005. Schrödinger Suite 2010; Schrodinger Inc. (101 SW Main Street, Suite 1300, Portland, OR 97204)
    • Desmond, WaterMap, OPLS2005. Schrödinger Suite 2010; Schrodinger Inc. (101 SW Main Street, Suite 1300, Portland, OR 97204), 2010.
    • (2010)
  • 31
    • 33745209653 scopus 로고    scopus 로고
    • 3-Hydroxypyridazine 1-oxides as carboxylate bioisosteres: A new series of subtype-selective AMPA receptor agonists
    • Greenwood, J. R.; Mewett, K. N.; Allan, R. D.; Martin, B. O.; Pickering, D. S. 3-Hydroxypyridazine 1-oxides as carboxylate bioisosteres: a new series of subtype-selective AMPA receptor agonists Neuropharmacology 2006, 51, 52-59
    • (2006) Neuropharmacology , vol.51 , pp. 52-59
    • Greenwood, J.R.1    Mewett, K.N.2    Allan, R.D.3    Martin, B.O.4    Pickering, D.S.5
  • 33
    • 0021991131 scopus 로고
    • Complex structure of quisqualate-sensitive glutamate receptors in rat cortex
    • Honore, T.; Nielsen, M. Complex structure of quisqualate-sensitive glutamate receptors in rat cortex Neurosci. Lett. 1985, 54, 27-32
    • (1985) Neurosci. Lett. , vol.54 , pp. 27-32
    • Honore, T.1    Nielsen, M.2
  • 34
    • 0023162156 scopus 로고
    • 3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel
    • 3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel Neuropharmacology 1987, 26, 1247-1251
    • (1987) Neuropharmacology , vol.26 , pp. 1247-1251
    • Braitman, D.J.1    Coyle, J.T.2
  • 37
    • 0023820777 scopus 로고
    • 3H]MK-801 binding to the N -methyl- d -aspartate receptor ion channel complex by l -glutamate, glycine, and polyamines
    • 3H]MK-801 binding to the N -methyl- d -aspartate receptor ion channel complex by l -glutamate, glycine, and polyamines J. Neurochem. 1988, 51, 830-836
    • (1988) J. Neurochem. , vol.51 , pp. 830-836
    • Ransom, R.W.1    Stec, N.L.2
  • 39
    • 47749151054 scopus 로고    scopus 로고
    • Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: New insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7
    • Sagot, E.; Pickering, D. S.; Pu, X.; Umberti, M.; Stensbol, T. B.; Nielsen, B.; Chapelet, M.; Bolte, J.; Gefflaut, T.; Bunch, L. Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7 J. Med. Chem. 2008, 51, 4093-4103
    • (2008) J. Med. Chem. , vol.51 , pp. 4093-4103
    • Sagot, E.1    Pickering, D.S.2    Pu, X.3    Umberti, M.4    Stensbol, T.B.5    Nielsen, B.6    Chapelet, M.7    Bolte, J.8    Gefflaut, T.9    Bunch, L.10
  • 40
    • 0031471216 scopus 로고    scopus 로고
    • Overexpression of a glutamate receptor (GluR2) ligand binding domain in Escherichia coli: Application of a novel protein folding screen
    • Chen, G. Q.; Gouaux, E. Overexpression of a glutamate receptor (GluR2) ligand binding domain in Escherichia coli: application of a novel protein folding screen Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 13431-13436
    • (1997) Proc. Natl. Acad. Sci. U.S.A. , vol.94 , pp. 13431-13436
    • Chen, G.Q.1    Gouaux, E.2
  • 41
    • 0031677656 scopus 로고    scopus 로고
    • Probing the ligand binding domain of the GluR2 receptor by proteolysis and deletion mutagenesis defines domain boundaries and yields a crystallizable construct
    • Chen, G. Q.; Sun, Y.; Jin, R. S.; Gouaux, E. Probing the ligand binding domain of the GluR2 receptor by proteolysis and deletion mutagenesis defines domain boundaries and yields a crystallizable construct Protein Sci. 1998, 7, 2623-2630
    • (1998) Protein Sci. , vol.7 , pp. 2623-2630
    • Chen, G.Q.1    Sun, Y.2    Jin, R.S.3    Gouaux, E.4
  • 42
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray Diffraction Data Collected in Oscillation Mode
    • Eds.; Methods in Enzymology, Vol.; Academic Press:; Part A
    • Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. Macromolecular Crystallography; Carter, C. W., Jr.; Sweet, R. M., Eds.; Methods in Enzymology, Vol. 276; Academic Press: 1997; Part A, pp 307 - 326.
    • (1997) Macromolecular Crystallography , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2    Carter, Jr.C.W.3    Sweet, R.M.4
  • 45
    • 0037468424 scopus 로고    scopus 로고
    • Three-dimensional structure of the ligand-binding core of GluR2 in complex with the agonist (S)-ATPA: Implications for receptor subunit selectivity
    • Lunn, M. L.; Hogner, A.; Stensbøl, T. B.; Gouaux, E.; Egebjerg, J.; Kastrup, J. S. Three-dimensional structure of the ligand-binding core of GluR2 in complex with the agonist (S)-ATPA: implications for receptor subunit selectivity J. Med. Chem. 2003, 46, 872-875
    • (2003) J. Med. Chem. , vol.46 , pp. 872-875
    • Lunn, M.L.1    Hogner, A.2    Stensbøl, T.B.3    Gouaux, E.4    Egebjerg, J.5    Kastrup, J.S.6
  • 46
    • 0032964481 scopus 로고    scopus 로고
    • Automated protein model building combined with iterative structure refinement
    • Perrakis, A.; Morris, R.; Lamzin, V. S. Automated protein model building combined with iterative structure refinement Nat. Struct. Biol. 1999, 6, 458-463
    • (1999) Nat. Struct. Biol. , vol.6 , pp. 458-463
    • Perrakis, A.1    Morris, R.2    Lamzin, V.S.3
  • 47
    • 84889120137 scopus 로고
    • Improved methods for building protein models in electron-density maps and the location of errors in these models
    • Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron-density maps and the location of errors in these models Acta Crystallogr., Sect. A: Found. Crystallogr. 1991, 47, 110-119
    • (1991) Acta Crystallogr., Sect. A: Found. Crystallogr. , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, M.4
  • 52
    • 0036888353 scopus 로고    scopus 로고
    • Improvements in the analysis of domain motions in proteins from conformational change: DynDom version 1.50
    • Hayward, S.; Lee, R. A. Improvements in the analysis of domain motions in proteins from conformational change: DynDom version 1.50 J. Mol. Graphics Modell. 2002, 21, 181-183
    • (2002) J. Mol. Graphics Modell. , vol.21 , pp. 181-183
    • Hayward, S.1    Lee, R.A.2
  • 55
    • 0030589514 scopus 로고    scopus 로고
    • Phi/psi-chology: Ramachandran revisited
    • Kleywegt, G. J.; Jones, T. A. Phi/psi-chology: ramachandran revisited Structure 1996, 4, 1395-1400
    • (1996) Structure , vol.4 , pp. 1395-1400
    • Kleywegt, G.J.1    Jones, T.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.