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Volumn 35, Issue 6, 1996, Pages 643-654

Biphenyl-derivatives of 2-amino-7-phosphonoheptanoic acid, a novel class of potent competitive N-Methyl-D-aspartate receptor antagonists - I. Pharmacological characterization in vitro

Author keywords

Antagonists; Biphenyl AP7 derivatives; In vitro profile; NMDA receptor; Receptor affinities; Structure activity relationships

Indexed keywords

2 AMINO 4 PHOSPHONOMETHYL 3 HEPTENOIC ACID; 2 AMINO 7 PHOSPHONOHEPTANOIC ACID; DIZOCILPINE; GLUTAMIC ACID; GLYCINE; HEPTANOIC ACID DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; STRYCHNINE;

EID: 0030175267     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0028-3908(96)00049-4     Document Type: Article
Times cited : (22)

References (50)
  • 1
    • 0024349541 scopus 로고
    • Synthesis and NMDA antagonistic properties of the enantiomers of 4-(3-phosphono-propyl)piperazine-2-carboxylic acid (CPP) and of the unsaturated analogue (E)-4-(3-phosphono-prop-2-enyl)piperazine-2-carboxylic acid (CPPene)
    • Aebischer B., Frey P., Härter H. -P., Herrling P. L., Müller W., Olverman H. J. and Watkins J. C. (1989) Synthesis and NMDA antagonistic properties of the enantiomers of 4-(3-phosphono-propyl)piperazine-2-carboxylic acid (CPP) and of the unsaturated analogue (E)-4-(3-phosphono-prop-2-enyl)piperazine-2-carboxylic acid (CPPene). Helv. Chim. Acta 72: 1043-1051.
    • (1989) Helv. Chim. Acta , vol.72 , pp. 1043-1051
    • Aebischer, B.1    Frey, P.2    Härter, H.-P.3    Herrling, P.L.4    Müller, W.5    Olverman, H.J.6    Watkins, J.C.7
  • 2
    • 0026527118 scopus 로고
    • Excitatory amino acid binding sites in the basal ganglia of the rat: A quantitative autoradiographic study
    • Albin R. L., Makowiec R. L., Hollingsworth Z. R., Dure L. S., Penney J. B. and Young A. B. (1992) Excitatory amino acid binding sites in the basal ganglia of the rat: a quantitative autoradiographic study. Neuroscience 46: 35-48.
    • (1992) Neuroscience , vol.46 , pp. 35-48
    • Albin, R.L.1    Makowiec, R.L.2    Hollingsworth, Z.R.3    Dure, L.S.4    Penney, J.B.5    Young, A.B.6
  • 4
    • 0018139770 scopus 로고
    • Muscimol binding in rat brain: Association with synaptic GABA receptors
    • Beaumont K., Chilton W. S., Yamamura H. I. and Enna S. J. (1978) Muscimol binding in rat brain: Association with synaptic GABA receptors. Brain Res. 148: 153-162.
    • (1978) Brain Res. , vol.148 , pp. 153-162
    • Beaumont, K.1    Chilton, W.S.2    Yamamura, H.I.3    Enna, S.J.4
  • 5
    • 0027241403 scopus 로고
    • Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists
    • Bigge C. F. (1993) Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists. Biochem. Pharmacol. 45: 1547-1561.
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 1547-1561
    • Bigge, C.F.1
  • 7
    • 0024453755 scopus 로고
    • Glycine regulation of the N-methyl-D-aspartate receptor-gated ion channel in hippocampal membranes
    • Bonhaus D. W., Yen G. C., Skaryak L. and McNamara J. O. (1989) Glycine regulation of the N-methyl-D-aspartate receptor-gated ion channel in hippocampal membranes. Molec. Pharmacol. 36: 273-279.
    • (1989) Molec. Pharmacol. , vol.36 , pp. 273-279
    • Bonhaus, D.W.1    Yen, G.C.2    Skaryak, L.3    McNamara, J.O.4
  • 8
    • 0024390049 scopus 로고
    • Characterization and partial purification of a chloride- and calcium-dependent glutamate-binding protein from rat brain
    • Brose N., Halpain S., Suchanek C. and Jahn R. (1989) Characterization and partial purification of a chloride-and calcium-dependent glutamate-binding protein from rat brain. J. biol. Chem. 264: 9619-9625.
    • (1989) J. Biol. Chem. , vol.264 , pp. 9619-9625
    • Brose, N.1    Halpain, S.2    Suchanek, C.3    Jahn, R.4
  • 9
    • 0025314266 scopus 로고
    • A chloride- and calcium-dependent glutamate-binding protein from rat brain. Identification as a ubiquitous constituent of the inner mitochondrial membrane
    • Brose N., Thomas A., Weber M. G. and Jahn R. (1990) A chloride-and calcium-dependent glutamate-binding protein from rat brain. Identification as a ubiquitous constituent of the inner mitochondrial membrane. J. biol. Chem. 265: 10604-10610.
    • (1990) J. Biol. Chem. , vol.265 , pp. 10604-10610
    • Brose, N.1    Thomas, A.2    Weber, M.G.3    Jahn, R.4
  • 11
    • 0028236134 scopus 로고
    • Synthesis of a pyrimidine isostere of the N-methyl-D-aspartate antagonist SDZ EAB 515
    • Chengzhi C., Buechler D., Lowe D., Urwyler S. and Shapiro G. (1994) Synthesis of a pyrimidine isostere of the N-methyl-D-aspartate antagonist SDZ EAB 515. Tetrahedron 50: 5735-5740.
    • (1994) Tetrahedron , vol.50 , pp. 5735-5740
    • Chengzhi, C.1    Buechler, D.2    Lowe, D.3    Urwyler, S.4    Shapiro, G.5
  • 12
  • 13
    • 0017723178 scopus 로고
    • Influences of ions, enzymes, and detergents on γ-aminobutyric acid-receptor binding in synaptic membranes of rat brain
    • Enna S. J. and Snyder S. H. (1977) Influences of ions, enzymes, and detergents on γ-aminobutyric acid-receptor binding in synaptic membranes of rat brain. Molec. Pharmacol. 13: 442-453.
    • (1977) Molec. Pharmacol. , vol.13 , pp. 442-453
    • Enna, S.J.1    Snyder, S.H.2
  • 16
    • 0022005967 scopus 로고
    • Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex
    • Harrison N. L. and Simmonds M. A. (1985) Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex. Br. J. Pharmacol. 84: 381-391.
    • (1985) Br. J. Pharmacol. , vol.84 , pp. 381-391
    • Harrison, N.L.1    Simmonds, M.A.2
  • 19
    • 0025369549 scopus 로고
    • Characterization of the adenosine receptor in porcine coronary arteries
    • King A. D., Milavec-Krizman M. and Müller-Schweinitzer E. (1990) Characterization of the adenosine receptor in porcine coronary arteries. Br. J. Pharmacol. 100: 483-486.
    • (1990) Br. J. Pharmacol. , vol.100 , pp. 483-486
    • King, A.D.1    Milavec-Krizman, M.2    Müller-Schweinitzer, E.3
  • 20
    • 0023818953 scopus 로고
    • 3H]dibenzocycloalkeneimine (MK-801) to the N-methyl-D-aspartate (NMDA) receptor and its therapeutic implication
    • 3H]dibenzocycloalkeneimine (MK-801) to the N-methyl-D-aspartate (NMDA) receptor and its therapeutic implication. FEBS Lett. 230: 167-170.
    • (1988) FEBS Lett. , vol.230 , pp. 167-170
    • Kloog, Y.1    Nadler, V.2    Sokolovsky, M.3
  • 21
    • 0028169661 scopus 로고
    • Ligand affinities at recombinant N-methyl-D-aspartate receptors depend on subunit composition
    • Laurie D. J. and Seeburg P. H. (1994) Ligand affinities at recombinant N-methyl-D-aspartate receptors depend on subunit composition. Eur. J. Pharmac. molec. Pharmacol. 268: 335-345.
    • (1994) Eur. J. Pharmac. Molec. Pharmacol. , vol.268 , pp. 335-345
    • Laurie, D.J.1    Seeburg, P.H.2
  • 23
    • 0029001397 scopus 로고
    • Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells
    • Li J.-H., Bigge C. F., Williamson R. M., Borosky S. A., Vartanian M. G. and Ortwine D. F. (1995) Potent, orally active, competitive N-methyl-D-aspartate (NMDA) receptor antagonists are substrates for a neutral amino acid uptake system in Chinese hamster ovary cells. J. Med. Chem. 38: 1955-1965.
    • (1995) J. Med. Chem. , vol.38 , pp. 1955-1965
    • Li, J.-H.1    Bigge, C.F.2    Williamson, R.M.3    Borosky, S.A.4    Vartanian, M.G.5    Ortwine, D.F.6
  • 25
    • 0025292168 scopus 로고
    • D-CPPene (SDZ EAA 494), a potent and competitive N-methyl-D-aspartate (NMDA) antagonist: Effects on spontaneous activity and NMDA-induced depolarizations in a rat neocortical slice preparation, compared with other CPP derivatives and MK-801
    • Lowe D. A., Neijt H. C. and Aebischer B. (1990) D-CPPene (SDZ EAA 494), a potent and competitive N-methyl-D-aspartate (NMDA) antagonist: effects on spontaneous activity and NMDA-induced depolarizations in a rat neocortical slice preparation, compared with other CPP derivatives and MK-801. Neurosci. Lett. 113: 315-321.
    • (1990) Neurosci. Lett. , vol.113 , pp. 315-321
    • Lowe, D.A.1    Neijt, H.C.2    Aebischer, B.3
  • 26
    • 0026752755 scopus 로고
    • Pharmacologically distinct NMDA receptor populations of the cerebellum, medial thalamic nuclei and forebrain
    • Monaghan D. T. and Beaton J. A. (1992) Pharmacologically distinct NMDA receptor populations of the cerebellum, medial thalamic nuclei and forebrain. Molec. Neuropharmacol. 2: 71-75.
    • (1992) Molec. Neuropharmacol. , vol.2 , pp. 71-75
    • Monaghan, D.T.1    Beaton, J.A.2
  • 27
    • 0010548403 scopus 로고
    • Two classes of N-methyl-D-aspartate recognition sites: Differential distribution and differential regulation by glycine
    • Monaghan D. T., Olverman H. J., Nguyen L., Watkins J. C. and Cotman C. W. (1988) Two classes of N-methyl-D-aspartate recognition sites: Differential distribution and differential regulation by glycine. Proc. natn. Acad. Sci. U.S.A. 85: 9836-9840.
    • (1988) Proc. Natn. Acad. Sci. U.S.A. , vol.85 , pp. 9836-9840
    • Monaghan, D.T.1    Olverman, H.J.2    Nguyen, L.3    Watkins, J.C.4    Cotman, C.W.5
  • 30
    • 0028879389 scopus 로고
    • Syntheses of biphenyl analogues of AP7, a new class of competitive N-methyl-D-aspartate (NMDA) receptor antagonists
    • Müller W., Kipfer P., Lowe D. A. and Urwyler S. (1995) Syntheses of biphenyl analogues of AP7, a new class of competitive N-methyl-D-aspartate (NMDA) receptor antagonists. Helv. Chim. Acta 78: 2026-2035.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 2026-2035
    • Müller, W.1    Kipfer, P.2    Lowe, D.A.3    Urwyler, S.4
  • 31
    • 0026581612 scopus 로고
    • 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
    • Müller W., Lowe D. A., Neijt H., Urwyler S., Herrling P. L., Blaser D. and Seebach D. (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: 855-864.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 855-864
    • Müller, W.1    Lowe, D.A.2    Neijt, H.3    Urwyler, S.4    Herrling, P.L.5    Blaser, D.6    Seebach, D.7
  • 32
    • 0023220868 scopus 로고
    • 3H]α-amino-3-hydroxy-5-methyl-isoxazole-4-propionic acid (AMPA) and a filtration assay
    • 3H]α-amino-3-hydroxy-5-methyl-isoxazole-4-propionic acid (AMPA) and a filtration assay. Neurochem. Res. 12: 775-782.
    • (1987) Neurochem. Res. , vol.12 , pp. 775-782
    • Murphy, D.E.1    Snowhill, E.W.2    Williams, M.3
  • 34
    • 0015918260 scopus 로고
    • Opiate receptor: Demonstration in nervous tissue
    • Pert C. B. and Snyder S. H. (1973) Opiate receptor: demonstration in nervous tissue. Science 179: 1011-1014.
    • (1973) Science , vol.179 , pp. 1011-1014
    • Pert, C.B.1    Snyder, S.H.2
  • 35
    • 0023116796 scopus 로고
    • Chloride transport blockers inhibit the chloride-dependent glutamate binding to rat brain membranes
    • Récasens M., Pin J. P. and Bockaert J. (1987) Chloride transport blockers inhibit the chloride-dependent glutamate binding to rat brain membranes. Neurosci. Lett. 74: 211-216.
    • (1987) Neurosci. Lett. , vol.74 , pp. 211-216
    • Récasens, M.1    Pin, J.P.2    Bockaert, J.3
  • 36
    • 0027487896 scopus 로고
    • The NMDA receptor complex
    • Scatton B. (1993) The NMDA receptor complex. Fund. clin. Pharmacol. 7: 389-400.
    • (1993) Fund. Clin. Pharmacol. , vol.7 , pp. 389-400
    • Scatton, B.1
  • 37
    • 0026589406 scopus 로고
    • 3H]glycine to its strychnine-insensitive recognition site associated with the N-methyl-D-aspartate receptor complex
    • 3H]glycine to its strychnine-insensitive recognition site associated with the N-methyl-D-aspartate receptor complex. Biochem. Pharmacol. 43: 1693-1699.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 1693-1699
    • Schneider, C.I.1    Urwyler, S.2
  • 38
    • 0026757535 scopus 로고
    • 3H]glutamate receptor binding in membranes
    • 3H]glutamate receptor binding in membranes. Neurosci. Lett. 145: 100-104.
    • (1992) Neurosci. Lett. , vol.145 , pp. 100-104
    • Schoepp, D.D.1    True, R.A.2
  • 40
    • 0018855192 scopus 로고
    • Interaction of SQ 20009 and GABA-like drugs as modulators of benzodiazepine receptor binding
    • Supavilai P. and Karobath M. (1980) Interaction of SQ 20009 and GABA-like drugs as modulators of benzodiazepine receptor binding. Eur. J. Pharmacol. 62: 229-233.
    • (1980) Eur. J. Pharmacol. , vol.62 , pp. 229-233
    • Supavilai, P.1    Karobath, M.2
  • 41
    • 0017750409 scopus 로고
    • Binding characteristics of a radiolabeled agonist and antagonist at central nervous system alpha noradrenergic receptors
    • U'Prichard D. C., Greenberg D. A. and Snyder S. H. (1977) Binding characteristics of a radiolabeled agonist and antagonist at central nervous system alpha noradrenergic receptors. Molec. Pharmacol. 13: 454-476.
    • (1977) Molec. Pharmacol. , vol.13 , pp. 454-476
    • U'Prichard, D.C.1    Greenberg, D.A.2    Snyder, S.H.3
  • 43
    • 0023161038 scopus 로고
    • 3H-sulpiride to dopamine D2 receptors in rat striatal membranes: Methodological considerations and demonstration of the identical nature of the binding sites for the two ligands
    • 3H-sulpiride to dopamine D2 receptors in rat striatal membranes: methodological considerations and demonstration of the identical nature of the binding sites for the two ligands. Naunyn-Schmiedeberg's Arch. Pharmacol. 335: 115-122.
    • (1987) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.335 , pp. 115-122
    • Urwyler, S.1    Coward, D.2
  • 44
    • 4243552198 scopus 로고
    • Biphenyl-AP7-derivatives, a new class of competitive N-methyl-d-aspartate receptor antagonists: In vitro pharmacology
    • Urwyler S., Lowe D., Meier C. and Müller W. (1995) Biphenyl-AP7-derivatives, a new class of competitive N-methyl-D-aspartate receptor antagonists: in vitro pharmacology. J. Neurochem. (Suppl.) 65: S12C.
    • (1995) J. Neurochem. (Suppl.) , vol.65
    • Urwyler, S.1    Lowe, D.2    Meier, C.3    Müller, W.4
  • 45
    • 0025191432 scopus 로고
    • Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists
    • Watkins J. C., 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.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 25-33
    • Watkins, J.C.1    Krogsgaard-Larsen, P.2    Honore, T.3
  • 48
    • 0027323942 scopus 로고
    • Mammalian ionotropic glutamate receptors
    • Wisden W. and Seeburg P. H. (1993) Mammalian ionotropic glutamate receptors. Curr. Opin. Neurobiol. 3: 291-298.
    • (1993) Curr. Opin. Neurobiol. , vol.3 , pp. 291-298
    • Wisden, W.1    Seeburg, P.H.2
  • 50
    • 0023091127 scopus 로고
    • Characteristics of chloride-dependent incorporation of glutamate into brain membranes argue against a receptor binding site
    • Zaczek R., Arlis S., Marki A., Murphy T., Drucker H. and Coyle J. T. (1987) Characteristics of chloride-dependent incorporation of glutamate into brain membranes argue against a receptor binding site. Neuropharmacology 26: 281-287
    • (1987) Neuropharmacology , vol.26 , pp. 281-287
    • Zaczek, R.1    Arlis, S.2    Marki, A.3    Murphy, T.4    Drucker, H.5    Coyle, J.T.6


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