Identification of subunit- and antagonist-specific amino acid residues in the N-methyl-D-aspartate receptor glutamate-binding pocket

Journal of Pharmacology and Experimental Therapeutics

Volumn 313, Issue 3, 2005, Pages 1066-1074

  Kinarsky, Leo ^a   Feng, Bihua ^a   Skifter, Donald A ^a   Morley, Richard M ^b   Sherman, Simon ^a   Jane, David E ^b   Monaghan, Daniel T ^a,c  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c 985800 Nebraska Medical Center ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (PHENANTHRENE 2 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 4 (3 PHOSPHONOALLYL) 2 PIPERAZINECARBOXYLIC ACID; 4 (3 PHOSPHONOPROPYL)PIPECOLIC ACID; 4 PHOSPHONOMETHYLPIPECOLIC ACID; [1 (4 BROMOPHENYL)ETHYLAMINO](2,3 DIOXO 1,2,3,4 TETRAHYDROQUINOXALIN 5 YL)METHYLPHOSPHONIC ACID; ALPHA AMINO 5 (PHOSPHONOMETHYL)[1,1' BIPHENYL] 3 PROPANOIC ACID; AMINO ACID; DECAHYDRO 6 (2H TETRAZOL 5 YLMETHYL) 3 ISOQUINOLINECARBOXYLIC ACID; GLUTAMIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 1; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2A; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2B; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PHENYLALANINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING SITE; CONTROLLED STUDY; FEMALE; ISOMER; LIGAND BINDING; NONHUMAN; POINT MUTATION; PRIORITY JOURNAL; RECEPTOR INTRINSIC ACTIVITY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; FEMALE; GLUTAMIC ACID; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; POINT MUTATION; PROTEIN SUBUNITS; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 19444366505     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.082990     Document Type: Article

References (40)

1. Andaloro VJ, Jane DJ, Tse HW, Watkins JC, and Monaghan DT (1996) Pharmacology of NMDA receptor subtypes. Soc Neurosci Abstr 22:604.
2. Anson LC, Chen PE, Wyllie DJA, Colquhoun D, and Schoepfer R (1998) Identification of amino acid residues of the NR2A subunit that control glutamate potency in recombinant NR1/NR2A NMDA receptors. J Neurosci 18:581-589.
3. Armstrong N and Gouaux E (2000) Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core. Neuron 28:165-181.
4. Armstrong N, Sun Y, Chen GQ, and Gouaux E (1998) Structure of a glutamate-receptor ligand-binding core in complex with kainate. Nature (Lond) 395:913-917.
5. Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, and Schmutz M (2002) 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. Bioorg Med Chem Lett 12:1099-1102.
6. Bear MF, Kleinschmidt A, Gu QA, and Singer W (1990) Disruption of experience-dependent synaptic modifications in striate cortex by infusion of an NMDA receptor antagonist. J Neurosci 10:909-925.
7. Beaton JA, Stemsrud K, and Monaghan DT (1992) Identification of a novel N-methyl-D-aspartate receptor population in the rat medial thalamus. J Neurochem 59:754-757.
8. Bigge CF (1993) Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists. Biochem Pharmacol 45:1547-1561.
9. Buller AL, Larson HC, Schneider BE, Beaton JA, Morrisett RA, and Monaghan DT (1994) The molecular basis of NMDA receptor subtypes: native receptor diversity is predicted by subunit composition. J Neurosci 14:5471-5484.
10. Buller AL and Monaghan DT (1997) Pharmacological heterogeneity of NMDA receptors: characterization of NR1a/NR2D heteromers expressed in Xenopus oocytes. Eur J Pharmacol 320:87-94.
11. Cheung NS, O'Callaghan D, Ryan MC, Dutton R, Wong MG, and Beart PM (1996) Structure-activity relationships of competitive NMDA receptor antagonists. Eur J Pharmacol 313:159-162.
12. Choi DW (1992) Excitotoxic cell death. J Neurobiol 23:1261-1276.
13. Christie JM, Jane DE, and Monaghan DT (2000) Native N-methyl-D-aspartate receptors containing NR2A and NR2B subunits have pharmacologically distinct competitive antagonist binding sites. J Pharmacol Exp Ther 292:1169-1174.
14. Collingridge GL and Bliss TV (1995) Memories of NMDA receptors and LTP. Trends Neurosci 18:54-56.
15. Feng B, Tse HW, Skifter DA, Morley R, Jane DE, and Monaghan DT (2004) Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid. Br J Pharmacol 141:508-516.
16. Furukawa H and Gouaux E (2003) Mechanisms of activation, inhibition and specificity: crystal structures of the NMDA receptor NR1 ligand-binding core. EMBO (Eur Mol Biol Organ) J 22:2873-2885.
17. Ikeda K, Nagasawa M, Mori H, Araki K, Sakimura K, Watanabe M, Inoue Y, and Mishina M (1992) Cloning and expression of the epsilon 4 subunit of the NMDA receptor channel. FEBS Lett 313:34-38.
18. Ishii T, Moriyoshi K, Sugihara H, Sakurada K, Kadotani H, Yokoi M, Akazawa C, Shigemoto R, Mizuno N, Masu M, et al. (1993) Molecular characterization of the family of the N-methyl-D-aspartate receptor subunits. J Biol Chem 268:2836-2843.
19. Kulagowski JJ, Baker R, Curtis NR, Leeson PD, Mawer IM, Moseley AM, Ridgill MP, Rowley M, Stansfield I, Foster AC, et al. (1994) 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 37:1402-1405.
20. Laube B, Hirai H, Sturgess M, Betz H, and Kuhse J (1997) Molecular determinants of agonist discrimination by NMDA receptor subunits: analysis of the glutamate binding site on the NR2B subunit. Neuron 18:493-503.
21. Laube B, Kuhse J, and Betz H (1998) Evidence for a tetrameric structure of recombinant NMDA receptors. J Neurosci 18:2954-2961.
22. Laune DJ and Seeburg PH (1994) Ligand affinities at recombinant N-methyl-D-aspartate receptors depend on subunit composition. Eur J Pharmacol 268:335-345.
23. Monaghan DT, Bridges RJ, and Cotman CW (1989) The excitatory amino acid receptors: their classes, pharmacology and distinct properties in the function of the central nervous system. Annu Rev Pharmacol. Toxicol 29:365-402.
24. Monaghan DT and Larson H (1997) NR1 and NR2 subunit contributions to N-methyl-D-aspartate receptor channel blocker pharmacology. J Pharmacol Exp Ther 280:614-620.
25. Monaghan DT, Olverman HJ, Nguyen L, Watkins JC, and Cotman CW (1988) Two classes of N-methyl-D-aspartate recognition sites: differential distribution and differential regulation by glycine. Proc Natl Acad Sci USA 85:9836-9840.
26. 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.
27. Monyer H, Sprengel R, Schoepfer R, Herb A, Higuchi M, Lomeli H, Burnashev N, Sakmann B, and Seeburg PH (1992) Heteromeric NMDA receptors: molecular and functional distinction of subtypes. Science (Wash DC) 256:1217-1221.
28. Nakanishi N, Shneider NA, and Axel R (1990) A family of glutamate receptor genes: evidence for the formation of heteromultimeric receptors with distinct channel properties. Neuron 5:569-581.
29. Oh BH, Pandit J, Kang CH, Nikaido K, Gokcen S, Ames GF, and Kim SH (1993) Three-dimensional structures of the periplasmic lysine/arginine/ornithine- binding protein with and without a ligand. J Biol Chem 268:11348-11355.
30. O'Hara PJ, Sheppard PO, Thogersen H, Venezia D, Haldeman BA, McGrane V, Houamed KM, Thomsen C, Gilbert TL, and Mulvihill ER (1993) The ligand-binding domain in metabotropic glutamate receptors is related to bacterial periplasmic binding proteins. Neuron 11:41-52.
31. Ortwine DF, Malone TC, Bigge CF, Drummond JT, Humblet C, Johnson G, and Pinter GW (1992) Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophore models: design and synthesis of phosphonoalkyl- substituted tetrahydroisoquinolines as novel antagonists. J Med Chem 35:1345-1370.
32. Small B, Thomas J, Kemp M, Hoo K, Ballyk B, Deverill M, Ogden AM, Rubio A, Pedregal C, and Bleakman D (1998) LY339434, a GluR5 kainate receptor agonist. Neuropharmacology 37:1261-1267.
33. Sucher NJ, Akbarian S, Chi CL, Leclerc CL, Awobuluyi M, Deitcher DL, Wu MK, Yuan JP, Jones EG, and Lipton SA (1995) Developmental and regional expression pattern of a novel NMDA receptor-like subunit (NMDAR-L) in the rodent brain. J Neurosci 15:6509-6520.
34. Sugihara H, Moriyoshi K, Ishii T, Masu M, and Nakanishi S (1992) Structures and properties of seven isoforms of the NMDA receptor generated by alternative splicing. Biochem Biophys Res Commun 185:826-832.
35. Tikhonova IG, Baskin II, Palyulin VA, and Zefirov NS (2002) Computer simulation of the three-dimensional structure of the glutamate site of the NR2B subunit of the NMDA receptor. Dokl Biochem Biophys 382:38-41.
36. Urwyler S, Campbell E, Fricker G, Jenner P, Lemaire M, McAllister KH, Neijt HC, Park CK, Perkins M, Rudin M, et al. (1996) Biphenyl-derivatives of 2-amino-7-phosphono-heptanoic acid, a novel class of potent competitive N-methyl-D-aspartate receptor antagonists: II. Pharmacological characterization in vivo. Neuropharmacology 35:655-669.
37. Watanabe M, Inoue Y, Sakimura K, and Mishina M (1993) Distinct spatio-temporal distributions of the NMDA receptor channel subunit mRNAs in the brain. Ann NY Acad Sci 707:463-466.
38. Watkins JC and Evans RH (1981) Excitatory amino acid transmitters. Annu Rev Pharmacol Toxicol 21:165-204.
39. Watkins JC, Krogsgaard Larsen P, and Honore T (1990) Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol Sci 11:25-33.
40. Whitten JP, Harrison BL, Weintraub HJ, and McDonald IA (1992) Modeling of competitive phosphono amino acid NMDA receptor antagonists. J Med Chem 35:1509-1514.