Reactive Affinity Probes for the Mapping of the Glycine-Binding Site of the NMDA Receptor NR1 Subunit

References

• Daw N. W., Stein P. S. G., Fox K. The Role of NMDA Receptors in Information Processing. Annu. Rev. Neurosci. 1993; 16: 207–222
   PubMed Web of Science ®Google Scholar
• McBain C. J., Mayer M. L. N-methyl-D-aspartic acid receptor structure and function. Physiol. Rev. 1994; 74: 723–760
   PubMed Web of Science ®Google Scholar
• Scatton B. The NMDA receptor complex. Fundam. Clin. Pharmacol. 1993; 7: 389–400
   PubMed Web of Science ®Google Scholar
• Lodge D., Collingridge G. The pharmacology of excitatory amino acids: a TIPS special report. Trends Pharmacol. Sci. (special issue) 1991; 1–89
   Google Scholar
• Small D. L., Buchan A. L. NMDA antagonists: their role in neuroprotection. Int. Rev. Neurobiol. 1997; 40: 137–171
   PubMed Web of Science ®Google Scholar
• Lodge D., Jones M., Fletcher E. The NMDA receptor, G. L. Collingridge, J. C. Watkins. Oxford University Press, Oxford 1994; 105–131
   Google Scholar
• Jane D. E., Olverman H. J., Watkins J. C. The NMDA receptor, G. L. Collingridge, J. C. Watkins. Oxford University Press, Oxford 1994; 31–104
   Google Scholar
• Kroemer R. T., Koutsilieri E., Hecht P., Liedl K. R., Riederer P., Kornhuber J. Quantitative analysis of the structural requirements for blockade of the N-methyl-D-aspartate receptor at the phencyclidine binding site. J. Med. Chem. 1998; 41: 393–400
   PubMed Web of Science ®Google Scholar
• Leeson P. D., Baker R., Carling R. W., Curtis N. R., Moore K. W., Williams B. J., Foster A. C., Donald A. E., Kemp J. A., Marshall G. R. Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor. J. Med. Chem. 1991; 34: 1343–1352
   Web of Science ®Google Scholar
• Leeson P. D., Iversen L. L. The glycine site on the NMDA receptor: Structure activity relationships and therapeutic potentials. J. Med. Chem. 1994; 37: 4053–4067
   PubMed Web of Science ®Google Scholar
• Ferrer-Montiel A. V., Sun W., Montal M. Molecular design of the N-methyl-D-aspartate receptor binding site for phencyclidine and dizolcipine. Proc. Natl. Acad. Sci. USA 1995; 92: 8021–8025
   PubMed Web of Science ®Google Scholar
• Kuryatov A., Laube B., Betz H., Kuhse J. Mutational analysis of the glycine-binding site of the NMDA receptor: Structural similarity with bacterial amino acid-binding proteins. Neuron 1994; 12: 1291–1300
   PubMed Web of Science ®Google Scholar
• Wafford K. A., Kathoria M., Bain C. J., Marshall G., Lebourdelles B., Kemp J. A., Whiting P. J. Identification of amino acids in the N-methyl-D-aspartate receptor NR1 subunit that contribute to the glycine-binding site. Mol. Pharmacol. 1995; 47: 374–380
   PubMed Web of Science ®Google Scholar
• Williams K., Chao J., Kashiwagi K., Masuko T., Igarashi K. Activation of N-methyl-D-aspartate receptors by glycine: Role of an aspartate residue in the M3-M4 loop of the NR1 subunit. Mol. Pharmacol. 1996; 50: 701–708
   PubMed Web of Science ®Google Scholar
• Wood M. W., VanDongen H. M. A., VanDongen A. M. J. An alanine residue in the M3-M4 linker lines the glycine binding pocket of the N-methyl-D-aspartate receptor. J. Biol. Chem. 1997; 272: 3532–3537
   PubMed Web of Science ®Google Scholar
• Uchino S., NakajimaLijima S., Okuda K., Mishina M., Kawamoto S. Analysis of the glycine binding domain of the NMDA receptor channel zeta 1 subunit. Neuroreport 1997; 8: 445–449
   PubMed Web of Science ®Google Scholar
• Hirai H., Kirsch J., Laube B., Betz H., Kuhse J. The glycine binding site of the N-methyl-D-aspartate receptor subunit NR1: Identification of novel determinants of co-agonist potentiation in the extracellular M3-M4 loop region. Proc. Natl. Acad. Sci. USA 1996; 93: 6031–6036
   PubMed Web of Science ®Google Scholar
• Laube B., Hirai H., Sturgess M., Betz H., Kuhse J. Molecular determinants of agonist discrimination by NMDA receptor subunits: Analysis of the glutamate binding site on the NR2B subunit. Neuron 1997; 18: 493–503
   PubMed Web of Science ®Google Scholar
• Rowley M., Leeson P., Grimwood S., Marshall G., Saywell K. 5,6,7,8-tetrahydroquinolones as antagonists at the glycine site of the NMDA receptor. Bioorg. Medicinal Chem. Lett. 1995; 5: 2089–2092
   Web of Science ®Google Scholar
• Seidel H., Bittner J. C. Über Derivate der Nitrophtalsäuren. Monatshefte Chem. 1902; 23: 415–425
   Google Scholar
• Campagna F., Carotti A., Casini G. A convenient synthesis of nitriles from primary amides under mild conditions. Tetrahedron Lett. 1997; 21: 1813–1816
   Google Scholar
• Ho T.-L., Wong C. M. Reduction of aromatic nitro compounds by titanium(III) chloride. J. Org. Chem. 1974; 39: 45
   Google Scholar
• Danysz W., Fadda E., Wroblewski J. T., Costa E. Different modes of action of 3-amino-1-hydroxy-2-pyrrolidone (HA-966) and 7-chlorokynurenic acid in the modulation of N-methyl-D-aspartate-sensitive glutamate receptor. Mol. Pharmacol. 1989; 36: 912–916
   PubMed Web of Science ®Google Scholar
• Jimonet P., Audiau F., Aloup J. C., Barreau M., Blanchard J. C., Bohme A., Boireau A., Cheve M., Damour D., Doble A., Lavayre J., Dutrucrosset G., Randle J. C. R., Rataud J., Stutzmann J. M., Mignani S. Synthesis and SAR of 2H-1,2,4-benzothiadiazine-1,1-dioxide-3-carboxylic acid derivatives as novel potent glycine antagonists of the NMDA receptor-channel complex. Bioorg. Medicinal Chem. Lett. 1994; 4: 2735–2740
   Web of Science ®Google Scholar
• Bowen W. P., Jerman J. C. Nonlinear regression using spreadsheets. Trends Pharmacol. Sci. 1995; 16: 413–417
   PubMed Web of Science ®Google Scholar
• Kulagowski J. J., Baker R., Curtis R. R., Leeson P. D., Mawer I. M., Moseley A. M., Ridgill M. P., Rowley M., Stansfield I., Foster A. C., Grimwood S., Hill R. G., Kempf J. A., Marshall G. R., Saywell K. L., Tricklebank M. D. 3'-(arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor. J. Med. Chem. 1994; 37: 1402–1405
   PubMed Web of Science ®Google Scholar
• Carling R. W., Leeson P. D., Moore K. W., Moyes C. R., Duncton M., Hudson M. L., Baker R., Foster A. C., Grimwood S., Kemp J. A., Marshall G. R., Tricklebank M. D., Saywell K. L. 4-substituted-3-phenylquinolin-2(1H)-ones: Acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity. J. Med. Chem. 1997; 40: 754–765
   PubMed Web of Science ®Google Scholar
• Cai S. X., Zhou Z. L., Huang J. C., Whittemore E. R., Egbuwoku Z. O., Lu Y. X., Hawkinson J. E., Woodward R. M., Weber E., Keana J. F. W. Synthesis and structure-activity relationships of 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes: Novel and highly potent antagonists for NMDA receptor glycine site. J. Med. Chem. 1996; 39: 3248–3255
   PubMed Web of Science ®Google Scholar
• Durand G. M., Gregor P., Zheng X., Bennett M. V. L., Uhl G. R., Zukin R. S. Cloning of an apparent splice variant of the rat N-methyl-D-aspartate receptor NMDAR1 with altered sensitivity to polyamines and activators of protein kinase-C. Proc. Natl. Acad. Sci. USA 1992; 89: 9359–9363
   PubMed Web of Science ®Google Scholar
• Laurie D. J., Seeburg P. H. Ligand affinities at recombinant N-methyl-D-aspartate receptors depend on subunit composition. Eur. J. Pharmacol.-Molec. Pharm. 1994; 268: 335–345
   PubMed Web of Science ®Google Scholar
• Foucaud B., Gombos G. Multiple sigma and PCP receptor ligands: mechanism for neuromodulation and neuroprotection?, J. M. Kamenka, E. F. Domino. NPP books, Ann Arbor 1992; 211–220
   Google Scholar
• Parsons C. G., Danysz W., Quack G., Hartmann S., Lorenz B., Wollenburg C., Baran L., Przegalinski E., Kostowski W., Krzascik P., Chizh B., Headley P. M. Novel systemically active antagonists of the glycine site of the N-methyl-D-aspartate receptor: Electrophysiological, biochemical and behavioral characterization. J. Pharmacol. Exp. Ther. 1997; 283: 1264–1275
   PubMed Web of Science ®Google Scholar