Structure-activity relationships of competitive NMDA receptor antagonists

European Journal of Pharmacology

Volumn 313, Issue 1-2, 1996, Pages 159-162

  Cheung, Nam S ^a   O'Callaghan, Daniel ^b   Ryan, Mary C ^b   Dutton, Renée ^a   Wong, Margaret G ^c   Beart, Philip M ^a  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c SWINBURNE UNIVERSITY OF TECHNOLOGY   (Australia)

Author keywords

Competitive antagonist; Molecular modelling; Neuroprotection; NMDA receptor; Radioligand binding

Indexed keywords

2 AMINO 4,5 (1,2 CYCLOHEXYL) 7 PHOSPHONOHEPTANOIC ACID; 4 PHOSPHONOMETHYLPIPECOLIC ACID; ALPHA AMINO 5 (PHOSPHONOMETHYL)[1,1' BIPHENYL] 3 PROPANOIC ACID; DECAHYDRO 6 PHOSPHONOMETHYL 3 ISOQUINOLINECARBOXYLIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CELL CULTURE; COMPUTER SIMULATION; CONTROLLED STUDY; DRUG STRUCTURE; IN VITRO STUDY; MOLECULAR MODEL; MOUSE; NERVE CELL; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0030579092     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/0014-2999(96)00608-5     Document Type: Article

References (16)

1. Beart, P.M., M.C. Ryan, L.D. Mercer, B. Jarrott and M.G. Wong, 1994, Heterocyclic aminoalcohols related to ifenprodil as σ receptor ligands: binding and conformational analyses, Eur. J. Pharmacol. 269, 193.
2. Bigge, C.F., 1993, Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists, Biochem. Pharmacol. 45, 1547.
3. Buller, A.L., R.A. Morrisett and D.T. Monaghan, 1993, The NR2 subunit contributes to the pharmacological diversity of native NMDA receptors, Soc. Neurosci. Abstr. 19, 1356.
4. Ferkany, J.W., G.S. Hamilton, R.J. Patch, Z. Huang, S.A. Borosky, D.L. Bednar, B.E. Jones, J. Willetts and E.W. Karbon, 1993, Pharmacological profile of NPC 17742 [2R,4R,5S-(2-amino-4,5-(1,2-cyclohexyl))-7-phosphonoheptanoic acid], a potent, selective and competitive N-methyl-D-aspartate receptor antagonist, J. Pharmacol. Exp. Ther. 264, 1993.
5. Hutchinson. A.J., M. Williams, C. Angst, R. De Jesus, L. Blanchard, R.H. Jackson, E.J. Wilusz, D.E. Murphy, P.S. Bernard, J. Schneider, T. Campbell, W. Guida and M.A. Sills, 1989, 4-(Phosphonoaklyl)-and 4-(phosphonoalkenyl)-2-piperidinecarboxylic acids: synthesis, activity at N-methyl-D-aspartic acid receptors, and anticonvulsant activity, J. Med. Chem. 32, 2171.
6. Jane, D.E., H.J. Olverman and J.C. Watkins, 1994, Agonists and competitive antagonists: structure-activity and molecular modelling studies, in: The NMDA Receptor, 2nd edn., eds. G.L. Collingridge and J.C. Watkins, p. 31.
7. Manev, H., M. Bertolino and G. De Erausquin, 1990, Amiloride blocks glutamate-operated cationic channels and protects neurones in culture from glutamate-induced death, Neuropharmacology 29, 1103.
8. 125I-labeled CGP 55802A, Proc. Natl. Acad. Sci. USA 90, 8434.
9. McBain, C.J. and M.L. Mayer, 1994, N-Methyl-D-aspartic acid receptor structure and function, Physiol. Rev. 74, 723.
10. Meldrum, B. and J. Garthwaite, 1990, Excitatory amino acid neurotoxicity and neurodegenerative disease, Trends Pharmacol. Sci. 11, 379.
11. Müller, W., D.A. Lowe, H. Neijt, S. Urwyler, P. Herrling, D. Blaser and D. Seebach, 1992, Synthesis and N-methyl-D-aspartate (NMDA) antagonist properties of the enantiomers of α-amino-5(phosphonomethyl)[1,1′-biphenyl]-3-propanoic acid. Use of a new chiral glycine derivative, Helv. Chim. Acta 75, 855.
12. O'Callaghan, D., M.G. Wong and P.M. Beart, 1992, Molecular modelling of N-methyl-D-aspartate receptor agonists, Mol. Neuropharmacol. 2, 89.
13. Ornstein, P.L., M.B. Arnold, N.K. Augenstein, J.B. Deeter, J.D. Leander, D. Lodge, D.O. Calligaro and D. Schoepp, 1993, Tetrazole amino acids as competitive NMDA antagonists, Biorg. Med. Chem. Lett. 3, 2067.
14. Ortwine, D.F., T.C. Malone, C.F. Bigge, J.T. Drummond, C. Humblet, G. Johnson and G.W. Pinter, 1992, Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophone models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists, J. Med. Chem. 35, 1345.
15. Ryan, M.C., P.M. Beart and D.J. De Vries, 1993, Extracts of marine biota with bioactivity at glutamate receptor subtypes, Pharmacol. Commun. 3, 225.
16. 3H]arginine in cultured neurons: characteristics and inhibition by nitric oxide synthase inhibitors, J. Neurochem. 61, 364.