메뉴 건너뛰기




Volumn 38, Issue 4, 1998, Pages 742-760

Predictive study by molecular modeling to promote specific probes of glutamate receptors, using methylated cyclic glutamic acid derivatives (trans- and cis-ACPD). Comparison with specific agonists

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 1,3 CYCLOPENTANEDICARBOXYLIC ACID; 1-AMINO-1,3-DICARBOXYCYCLOPENTANE; AMINO ACID RECEPTOR STIMULATING AGENT; CYCLOLEUCINE; DRUG DERIVATIVE; GLUTAMATE RECEPTOR; METABOTROPIC RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR;

EID: 0032112831     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci9802023     Document Type: Article
Times cited : (3)

References (40)
  • 2
    • 0020401599 scopus 로고
    • Conformational aspects of the actions of some piperidine dicarboxylic acids at excitatory amino acid receptors in the mammalian and amphibian spinal cord
    • Davies, J.; Evans, R. H.; Francis, A. A.; Jones, A. W.; Smith, D. A. S.; Watkins, J. C. Conformational aspects of the actions of some piperidine dicarboxylic acids at excitatory amino acid receptors in the mammalian and amphibian spinal cord. Neurochem. Res. 1982, 7, 1119-1133.
    • (1982) Neurochem. Res. , vol.7 , pp. 1119-1133
    • Davies, J.1    Evans, R.H.2    Francis, A.A.3    Jones, A.W.4    Smith, D.A.S.5    Watkins, J.C.6
  • 3
    • 0027476024 scopus 로고
    • A synaptic model of memory: Long term potentiation in the hyppocampus
    • Bliss, T. V. P.; Collingridge, G. L. A synaptic model of memory: Long term potentiation in the hyppocampus. Nature 1993, 361, 31-39.
    • (1993) Nature , vol.361 , pp. 31-39
    • Bliss, T.V.P.1    Collingridge, G.L.2
  • 4
    • 0024093449 scopus 로고
    • Glutamate Neurotoxicity and Diseases of the Nervous System
    • Choi, D. W. Glutamate Neurotoxicity and Diseases of the Nervous System. Neuron 1988, 1, 623-643.
    • (1988) Neuron , vol.1 , pp. 623-643
    • Choi, D.W.1
  • 5
    • 0028912822 scopus 로고
    • The Metabotropic Glutamate Receptors: Structure and Functions
    • Pin, J. P.; Duvoisin, R. The Metabotropic Glutamate Receptors: Structure and Functions. Neuropharmacology 1995, 34, 1-26.
    • (1995) Neuropharmacology , vol.34 , pp. 1-26
    • Pin, J.P.1    Duvoisin, R.2
  • 6
    • 0027395275 scopus 로고
    • Metabotropic glutamate receptors in brain function and pathology
    • Schoepp, D. D.; Conn, P. J. Metabotropic glutamate receptors in brain function and pathology. Trends Pharmacol. Sci. 1993, 14, 13-20.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 13-20
    • Schoepp, D.D.1    Conn, P.J.2
  • 7
    • 0026437728 scopus 로고
    • Molecular diversity of glutamate receptors and implications for brain function
    • Nakanishi, S. Molecular diversity of glutamate receptors and implications for brain function. Science 1992, 258, 597-603.
    • (1992) Science , vol.258 , pp. 597-603
    • Nakanishi, S.1
  • 12
    • 0027410488 scopus 로고
    • Signal transduction, pharmacological properties and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4
    • Tanabe, Y.; Nomura, A.; Masu, M.; Shigemoto, R.; Mizuno, N.; Nakanishi, S. Signal transduction, pharmacological properties and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4. J. Neurosci. 1993, 13, 1372-1378.
    • (1993) J. Neurosci. , vol.13 , pp. 1372-1378
    • Tanabe, Y.1    Nomura, A.2    Masu, M.3    Shigemoto, R.4    Mizuno, N.5    Nakanishi, S.6
  • 13
    • 0027435172 scopus 로고
    • A new metabotropic glutamate receptor agonist: Developmental change of its sensitivity to receptors in the newborn rat spinal cord
    • Ishida, M.; Saitoh, T.; Shinozaki, H. A new metabotropic glutamate receptor agonist: Developmental change of its sensitivity to receptors in the newborn rat spinal cord. Neurosci. Lett. 1993, 160, 156-158.
    • (1993) Neurosci. Lett. , vol.160 , pp. 156-158
    • Ishida, M.1    Saitoh, T.2    Shinozaki, H.3
  • 15
    • 0027955170 scopus 로고
    • Molecular characterization of a new metabotropic glutamate receptor mGluR7 coupled to inhibitory cyclic AMP signal transduction
    • Okamoto, N.; Hori, S.; Akazawa, C.; Hayashi, Y.; Shigemoto, R.; Mizuno, N.; Nakanishi, S. Molecular characterization of a new metabotropic glutamate receptor mGluR7 coupled to inhibitory cyclic AMP signal transduction. J. Biol. Chem. 1994, 269, 1231-1236.
    • (1994) J. Biol. Chem. , vol.269 , pp. 1231-1236
    • Okamoto, N.1    Hori, S.2    Akazawa, C.3    Hayashi, Y.4    Shigemoto, R.5    Mizuno, N.6    Nakanishi, S.7
  • 18
    • 37049073320 scopus 로고
    • Conformational Analysis by NMR Spectroscopy, Molecular Dynamics Simulation in Water and X-Ray Crystallography of Glutamic Acid Analogues: Isomers of 1-Amino-1,3 Cyclopentane Dicarboxylic Acid (ACPD)
    • Larue, V.; Gharbi-Benarous, J.; Acher, F.; Valle, G.; Crisma, M.; Toniolo, C.; Azerad, R.; Girault, J. P. Conformational Analysis by NMR Spectroscopy, Molecular Dynamics Simulation in Water and X-Ray Crystallography of Glutamic Acid Analogues: Isomers of 1-Amino-1,3 Cyclopentane Dicarboxylic Acid (ACPD). J. Chem. Soc., Perkin Trans. 2 1995, 1111-1126.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1111-1126
    • Larue, V.1    Gharbi-Benarous, J.2    Acher, F.3    Valle, G.4    Crisma, M.5    Toniolo, C.6    Azerad, R.7    Girault, J.P.8
  • 19
    • 0345063054 scopus 로고    scopus 로고
    • Conformational analysis by NMR spectroscopy and molecular simulation in water of methylated glutamic acids, agonists at glutamate receptors
    • Todeschi, N.; Gharbi-Benarous, J.; Acher, F.; Azerad, R.; Girault, J. P. Conformational analysis by NMR spectroscopy and molecular simulation in water of methylated glutamic acids, agonists at glutamate receptors. J. Chem. Soc.) Perkin Trans. 2. 1996, 1337-1351.
    • (1996) J. Chem. Soc. Perkin Trans. 2. , pp. 1337-1351
    • Todeschi, N.1    Gharbi-Benarous, J.2    Acher, F.3    Azerad, R.4    Girault, J.P.5
  • 20
    • 0031081518 scopus 로고    scopus 로고
    • Conformational Analysis of Glutamic Acid Analogues as Probes of Glutamate Receptors using Molecular Modeling and NMR methods. Comparison with Specific Agonists
    • Todeschi, N.; Gharbi-Benarous, J.; Acher, F.; Larue, V.; Pin, J. P.; Bockaert, J.; Azerad, R.; Girault, J. P. Conformational Analysis of Glutamic Acid Analogues as Probes of Glutamate Receptors using Molecular Modeling and NMR methods. Comparison with Specific Agonists. Bioorg. Med. Chem. 1997, 5, 335-352.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 335-352
    • Todeschi, N.1    Gharbi-Benarous, J.2    Acher, F.3    Larue, V.4    Pin, J.P.5    Bockaert, J.6    Azerad, R.7    Girault, J.P.8
  • 21
    • 0031094509 scopus 로고    scopus 로고
    • Conformational Study in Water by NMR and Molecular Modeling of α-Methyl α-Amino Acid: Differential Conformational Properties of α-Cyclic and α-Methylglutamic Acid
    • in press
    • Todeschi, N.; Gharbi-Benarous, J.; Arulmozhi, V.; Acher, F.; Azerad, R.; Girault, J. P. Conformational Study in Water by NMR and Molecular Modeling of α-Methyl α-Amino Acid: Differential Conformational Properties of α-Cyclic and α-Methylglutamic Acid. J. Chem. Inf. Comput. Sci., in press.
    • J. Chem. Inf. Comput. Sci.
    • Todeschi, N.1    Gharbi-Benarous, J.2    Arulmozhi, V.3    Acher, F.4    Azerad, R.5    Girault, J.P.6
  • 22
    • 0030775262 scopus 로고    scopus 로고
    • Structure of Kainic Acid Totally Elucidated by NMR and Molecular Modeling
    • Todeschi, N.; Gharbi-Benarous, J.; Girault, J. P. Structure of Kainic Acid Totally Elucidated by NMR and Molecular Modeling. Bioorg. Med. Chem. 1997, 5, 1943-1957.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 1943-1957
    • Todeschi, N.1    Gharbi-Benarous, J.2    Girault, J.P.3
  • 23
    • 0344783439 scopus 로고    scopus 로고
    • Conformational Analysis of 2-(Carboxy-Cyclopropyl) Glycines Agonists of Glutamate Receptors in Aqueous Solution using a combination of NMR and Molecular Modelling Experiments and charges calculations
    • Evrard-Todeschi, N.; Gharbi-Benarous, J.; Cosse-Barbi, A.; Thirot, G.; Girault, J.-P. Conformational Analysis of 2-(Carboxy-Cyclopropyl) Glycines Agonists of Glutamate Receptors in Aqueous Solution using a combination of NMR and Molecular Modelling Experiments and charges calculations. J. Chem. Soc., Perkins Trans 2 1997, 2677-2689.
    • (1997) J. Chem. Soc., Perkins Trans 2 , pp. 2677-2689
    • Evrard-Todeschi, N.1    Gharbi-Benarous, J.2    Cosse-Barbi, A.3    Thirot, G.4    Girault, J.-P.5
  • 25
    • 0015913888 scopus 로고
    • Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. Improved Methods for the Interpretation of Proton Magnetic Resonance Coupling Constants
    • Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. Improved Methods for the Interpretation of Proton Magnetic Resonance Coupling Constants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2333-2344
    • Altona, C.1    Sundaralingam, M.2
  • 26
    • 20444483055 scopus 로고
    • The relation between proton-proton NMR coupling constants and substituent electronegativities. I. An empirical generalization of the Karplus equation
    • Haasnoot, C. A. G.; De Leeuw, F. A. A. M.; Altona, C. The relation between proton-proton NMR coupling constants and substituent electronegativities. I. An empirical generalization of the Karplus equation. Tetrahedron 1980, 36, 2783-2792.
    • (1980) Tetrahedron , vol.36 , pp. 2783-2792
    • Haasnoot, C.A.G.1    De Leeuw, F.A.A.M.2    Altona, C.3
  • 27
    • 0000816491 scopus 로고
    • An attempt to derive a new Karplus-type equation of vicinal proton-carbon coupling constants for C-O-C-H segments of bonded atoms
    • Tvaroska, I.; Hricovini, M.; Petrakova, E. An attempt to derive a new Karplus-type equation of vicinal proton-carbon coupling constants for C-O-C-H segments of bonded atoms. Carbohydr. Res. 1989, 189, 359-362.
    • (1989) Carbohydr. Res. , vol.189 , pp. 359-362
    • Tvaroska, I.1    Hricovini, M.2    Petrakova, E.3
  • 30
    • 0010993424 scopus 로고
    • Perun, T. J., Propst, C. L., Eds.; Marcel Dekker and Basel: New York
    • Burt, S. K.; Mackay, D.; Nagler, A. T. In Computer-Aided Drug Design; Perun, T. J., Propst, C. L., Eds.; Marcel Dekker and Basel: New York, 1989; p 66.
    • (1989) Computer-Aided Drug Design , pp. 66
    • Burt, S.K.1    Mackay, D.2    Nagler, A.T.3
  • 31
    • 37049090044 scopus 로고
    • Conformational analysis of cyclohexane-derived analogues of glutamic acid by X-ray cristallography, NMR spectroscopy in solution and molecular dynamics
    • Morelle, N.; Gharbi-Benarous, J.; Acher, F.; Valle, G.; Crisma, M.; Toniolo, C.; Azerad, R.; Girault, J. P. Conformational analysis of cyclohexane-derived analogues of glutamic acid by X-ray cristallography, NMR spectroscopy in solution and molecular dynamics. J. Chem. Soc., Perkin Trans. 2 1993, 525-533.
    • (1993) J. Chem. Soc., Perkin Trans. 2 , pp. 525-533
    • Morelle, N.1    Gharbi-Benarous, J.2    Acher, F.3    Valle, G.4    Crisma, M.5    Toniolo, C.6    Azerad, R.7    Girault, J.P.8
  • 32
    • 2142813682 scopus 로고
    • Computer Simulation of Molecular Dynamics: Methodology. Applications, and Perspectives in Chemistry
    • van Gunsteren, W. F.; Berendsen, H. J. C. Computer Simulation of Molecular Dynamics: Methodology. Applications, and Perspectives in Chemistry. Angew. Chem., Int. Ed. Engl. 1990, 29, 992-1023.
    • (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 992-1023
    • Van Gunsteren, W.F.1    Berendsen, H.J.C.2
  • 34
    • 0029092698 scopus 로고
    • Fluctuation and cross-correlation analysis of protein motions observed in nano-second molecular dynamics simulations
    • Hünenberger, P. H.; Mark, A. E.; van Gunsteren, W. F. Fluctuation and cross-correlation analysis of protein motions observed in nano-second molecular dynamics simulations. J. Mol. Biol. 1995, 252, 492-503.
    • (1995) J. Mol. Biol. , vol.252 , pp. 492-503
    • Hünenberger, P.H.1    Mark, A.E.2    Van Gunsteren, W.F.3
  • 35
    • 84908806186 scopus 로고
    • Efficient Synthesis of 4-Methylene-L-glutamic Acid and its Analogues
    • Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Efficient Synthesis of 4-Methylene-L-glutamic Acid and its Analogues. Synlett 1993, 409-410.
    • (1993) Synlett , pp. 409-410
    • Ouerfelli, O.1    Ishida, M.2    Shinozaki, H.3    Nakanishi, K.4    Ohfune, Y.5
  • 36
    • 0029045977 scopus 로고
    • Synthesis. Resolution and Biological Evaluation of the Four Stereoisomers of 4-Methylglutamic Acid: Selective Probes of Kainate Receptors
    • Gu, Z. Q.; Hessen, D.; Pelletier, J. C.; Meccecchini, M. L. Synthesis. Resolution and Biological Evaluation of the Four Stereoisomers of 4-Methylglutamic Acid: Selective Probes of Kainate Receptors. J. Med. Chem. 1995, 38, 2518-2520.
    • (1995) J. Med. Chem. , vol.38 , pp. 2518-2520
    • Gu, Z.Q.1    Hessen, D.2    Pelletier, J.C.3    Meccecchini, M.L.4
  • 37
    • 0026476478 scopus 로고
    • Alternative splicing generates metabotropic glutamate receptors inducing different patterns of calcium release in Xenopus oocytes
    • Pin, J. P.; Waeber, C.; Prézeau, L.; Bockaert, J.; Heinemann, S. F. Alternative splicing generates metabotropic glutamate receptors inducing different patterns of calcium release in Xenopus oocytes. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10331-10335.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 10331-10335
    • Pin, J.P.1    Waeber, C.2    Prézeau, L.3    Bockaert, J.4    Heinemann, S.F.5
  • 38
    • 0023921081 scopus 로고
    • Synthesis. Resolution, and Absolute Configuration of the Isomers of the Neuronal Excitant 1-Amino-1,3-cyclopentanedicarboxylic Acid
    • Curry, K.; Peet, M. J.; Magnuson, D. S. K.; McLennan, H. Synthesis. Resolution, and Absolute Configuration of the Isomers of the Neuronal Excitant 1-Amino-1,3-cyclopentanedicarboxylic Acid. J. Med. Chem. 1988, 31, 864-867.
    • (1988) J. Med. Chem. , vol.31 , pp. 864-867
    • Curry, K.1    Peet, M.J.2    Magnuson, D.S.K.3    McLennan, H.4
  • 39
    • 0026094232 scopus 로고
    • Rigid analogues as probes of excitatory amino acid receptors
    • Curry, K. Rigid analogues as probes of excitatory amino acid receptors. Can. J. Physiol. Pharmacol. 1991, 69, 1076-1083.
    • (1991) Can. J. Physiol. Pharmacol. , vol.69 , pp. 1076-1083
    • Curry, K.1
  • 40
    • 0344620689 scopus 로고
    • Gradient-enhancement proton-detected heteronuclear multiple-quantum coherence spectroscopy
    • Hurd, R. E.; John, B. K. Gradient-enhancement proton-detected heteronuclear multiple-quantum coherence spectroscopy. J. Magic Reson. 1991, 91, 648-653.
    • (1991) J. Magic Reson. , vol.91 , pp. 648-653
    • Hurd, R.E.1    John, B.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.