Extended glutamate activates metabotropic receptor types 1, 2 and 4: Selective features at mGluR4 binding site

Neuropharmacology

Volumn 38, Issue 10, 1999, Pages 1543-1551

  Bessis, Anne Sophie ^a   Jullian, Nathalie ^b   Coudert, Elisabeth ^a   Pin, Jean Philippe ^c   Acher, Francine ^a  

^a CNRS   (France)

^b Molecular Simulations Inc   (France)

^c INSERM   (France)

Author keywords

L AP4; Metabotropic glutamate receptors; Pharmacophore model; Selectivity

Indexed keywords

GLUTAMIC ACID; METABOTROPIC RECEPTOR; RECEPTOR SUBTYPE;

ARTICLE; BINDING SITE; BRAIN DISEASE; HYDROPHILICITY; MENTAL DISEASE; PHARMACOPHORE; PRIORITY JOURNAL;

ANIMALS; BINDING SITES; EXCITATORY AMINO ACID AGONISTS; GLUTAMIC ACID; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN CONFORMATION; RECEPTORS, METABOTROPIC GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032867636     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0028-3908(99)00096-9     Document Type: Article

References (27)

1. Acher F., Azerad R. Resolution and regioselective protection of glutamic acid analogues. I. Resolution of diastereomeric α-boroxazolidone derivatives. Tetrahedron Asymmetry. 5:1994;731-744.
2. Acher F., Tellier F., Brabet I., Fagni L., Azerad R., Pin J.-P. Synthesis and pharmacological characterization of aminocyclopentane tricarboxylic acids (ACPT): new tools to discriminate between metabotropic glutamate receptor subtypes. J. Med. Chem. 40:1997;3119-3129.
3. Batchelor A.M., Madge D.J., Garthwaite J. Synaptic activation of metabotropic glutamate receptors in the parallel fibre-Purkinje cell pathway in rat cerebral slices. Neuropharmacology. 32:1994;11-20.
4. Brabet I., Parmentier M.-L., De Colle C., Bockaert J., Acher F., Pin J.-P. Comparative effect of L-CCG-I DCG-IV and γ-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes. Neuropharmacology. 37:1998;1043-1051.
5. Bruno V., Copani A., Knopfel T., Kuhn R., Casabona G., Dellalbani P., Condorelli D.F., Nicoletti F. Activation of metabotropic glutamate receptors coupled to inositol phospholipid hydrolysis amplifies NMDA-induced neuronal degeneration in cultured cortical cells. Neuropharmacology. 34:1995;1089-1098.
6. Choi D.W. Glutamate neurotoxicity and diseases of the nervous system. Neuron. 1:1988;623-634.
7. Conn P.J., Pin J.-P. Pharmacology and functions of metabotropic glutamate receptors. Ann. Rev. Pharmacol. Toxicol. 37:1997;205-237.
8. Coudert, E., Acher, F., Azerad, R., 1997. Convenient and efficient synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid. Synthesis 863-865.
9. Gereau R.W., Conn P.J. Multiple presynaptic metabotropic glutamate receptors modulate excitatory and inhibitory synaptic transmission in hippocampal area CA1. J. Neurosci. 15:1995;6879-6889.
10. Gomeza J., Mary S., Brabet I., Parmentier M.-L., Restituito S., Bockaert J., Pin J.-P. Coupling of mGluR2 and mGluR4 to Gα15 Gα16 and chimeric Gαq/i proteins: characterization of new antagonists. Mol. Pharmacol. 50:1996;923-930.
11. Johansen P.A., Chase L.A., Sinor A.D., Koerner J.F., Johnson R.L., Robinson M.B. Type 4a metabotropic glutamate receptor: identification of new potent agonists and differenciation from the L-(+)-2-amino-4-phosphonobutanoic acid-sensitive receptor in the lateral perforant pathway in rats. Mol. Pharmacol. 46:1995;140-149.
12. Jullian N., Brabet I., Pin J.-P., Acher F. Agonist selectivity of mGluR1 and mGluR2 metabotropic receptors: a different environment but similar recognition of an extended glutamate conformation. J. Med. Chem. 42:1999;1546-1555.
13. Kozikowski A.P., Steensma D., Araldi G.L., Tückmantel W., Wang S., Pshenichkin S., Surina E., Wroblewski J. Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I a potent mGluR agonist. J. Med. Chem. 41:1998;1641-1650.
14. 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.
15. Lipton S.A., Rosenberg P.A. Excitatory amino acids as a final common pathway for neurologic disorders. New Engl. J. Med. 330:1994;613-622.
16. Manzoni O., Bockaert J. Metabotropic glutamate receptors inhibiting excitatory synapses in the CA1 area of the rat hippocampus. Eur. J. Neurosci. 7:1995;2518-2523.
17. McDonald J.W., Schoepp D.D. The metabotropic excitatory amino acid receptor agonist 1S 3R-ACPD selectively potentiates N-methyl-D-aspartate-induced brain injury. Eur. J. Pharmacol. 215:1992;353-354.
18. Monn J.A., Valli M.J., Massey S.M., Wright R.A., Salhoff C.R., Johnson B.G., Howe T., Alt C.A., Rhodes G.A., Robey R.L., Griffey K.R., Tizzano J.P., Kallman M.J., Helton D.R., Schoepp D.D. Design, synthesis, and pharmacological characterization of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740): a potent, selective and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties. J. Med. Chem. 40:1997;528-537.
19. Nicoletti F., Bruno V., Copani A., Casabona G., Knopfel T. Metabotropic glutamate receptors: a new target for the therapy of neurodegenerative disorders? Trends Neurosci. 19:1996;267-271.
20. O'Hara P.J., Sheppard P.O., Thogersen H., Venezia D., Haldeman B.A., Mc Grane V., Houamed K.H., Thomsen C., Gilbert T.L., Mulvihill E.R. The ligand-binding domain in metabotropic glutamate receptors is related to bacterial periplasmic binding proteins. Neuron. 11:1993;41-52.
21. Pellicciari R., Marinozzi M., Natalini B., Costantino G., Luneia R., Giorgi G., Moroni F., Thomsen C. Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2′-carboxy-3′-phenylcyclopropyl)glycine. Focus on (2S,1′S,2′S,3′R)-2-(2′-carboxy-3-phenylcyclopropyl) glycine a novel and selective group II metabotropic glutamate receptors antagonist. J. Med. Chem. 39:1996;2259-2269.
22. Pin, J.P., DeColle, C., Bessis, A.S., Acher, F., 1999. New perspective in the development of selective metabotropic glutamate receptor ligands. Eur. J. Pharmacol. 375, 277-294.
23. Rodriguez-Moreno A., Sistiaga A., Lerma J., Sanchez-Prieto J. Switch from facilitation to inhibition of excitatory synaptic transmission by group I mGluR desensitization. Neuron. 21:1998;1477-1486.
24. Schoepp D.D., Johnson B.G., Wright R.A., Salhoff C.R., Mayne N.G., Wu S., Cockerham S.L., Burnett J.P., Belegaje R., Bleakman D., Monn J.A. LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors. Neuropharmacology. 36:1997;1-11.
25. Schoepp D.D., Salhoff C.R., Wright R.A., Johnson B.G., Burnett J.P., Mayne N.G., Belagaje R., Wu S., Monn J.A. The novel metabotropic glutamate receptor agonist 2R,4R-APDC potentiates stimulation of phosphoinositide hydrolysis in the rat hippocampus by 3 5-dihydroxyphenylglycine: evidence for a synergic interaction between group1 and group 2 receptors. Neuropharmacology. 35:1996;1661-1672.
26. Shimamoto K., Ohfune Y. Synthesis and conformational analyses of glutamate analogs: 2-(2-carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors. J. Med. Chem. 39:1996;407-423.
27. Tellier F., Acher F., Brabet I., Pin J.-P., Azerad R. Aminobicyclo[2.2.1]heptane dicarboxylic acids (ABHD) rigid analogs of ACPD and glutamic acid: synthesis and pharmacological activity on metabotropic receptors mGluR1 and mGluR2. Bioorg. Med. Chem. 6:1998;195-208.