Molecular pharmacology of homologues of ibotenic acid at cloned metabotropic glutamic acid receptors

European Journal of Pharmacology

Volumn 350, Issue 2-3, 1998, Pages 311-316

  Bräuner Osborne, Hans ^a   Nielsen, Birgitte ^a   Krogsgaard Larsen, Povl ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Homoibotenic acid; Homoibotenic acid analogue; Ibotenic acid; Metabotropic glutamate receptor; mGlu(1a) receptor antagonist; mGlu(5a) receptor antagonist

Indexed keywords

4 CARBOXYPHENYLGLYCINE; DRUG ANALOG; IBOTENIC ACID; METABOTROPIC RECEPTOR; PHENYLGLYCINE;

ANIMAL CELL; ARTICLE; CHO CELL; CLONING; ENANTIOMER; ION EXCHANGE CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CHO CELLS; CRICETINAE; EXCITATORY AMINO ACID AGONISTS; IBOTENIC ACID; LIGANDS; RECEPTORS, METABOTROPIC GLUTAMATE; SECOND MESSENGER SYSTEMS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0042683081     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(98)00246-5     Document Type: Article

References (26)

1. 2+ signal transduction. J. Biol. Chem. 267:1992;13361-13368.
2. 6 subtype of metabotropic glutamic acid receptors. J. Med. Chem. 40:1997;3700-3705.
3. Aramori I., Nakanishi S. Signal transduction and pharmacological characteristics of a metabotropic glutamate receptor, mGluR1, in transfected CHO cells. Neuron. 8:1992;757-765.
4. Bischoff F., Johansen T.N., Ebert B., Krogsgaard-Larsen P., Madsen U. Excitatory amino acid receptor ligands: Asymmetric synthesis, absolute stereochemistry and pharmacology of (R)- and (S)-homoibotenic acid. Bioorg. Med. Chem. 3:1995;553-558.
5. Brabet I., Mary S., Bockaert J., Pin J.-P. Phenylglycine derivatives discriminate between mGlu1- and mGlu5-mediated responses. Neuropharmacology. 34:1995;895-903.
6. Bräuner-Osborne H., Krogsgaard-Larsen P. Pharmacology of (S)-homoquisqualic acid and (S)-2-amino-5-phosphonopentanoic acid [(S)-AP5] at cloned metabotropic glutamate receptors. Br. J. Pharmacol. 123:1998;269-274.
7. Bräuner-Osborne H., Sløk F.A., Skjærbæk N., Ebert B., Sekiyama N., Nakanishi S., Krogsgaard-Larsen P. A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid. J. Med. Chem. 39:1996;3188-3194.
8. Bräuner-Osborne H., Madsen U., Mikiciuk-Olasik E., Curry K. New analogues of ACPD with selective activity for group II metabotropic glutamate receptors. Eur. J. Pharmacol. 332:1997;327-331.
9. Chung D.S., Traynelis S.F., Murphy T.J., Conn P.J. 4-Methylhomoibotenic acid activates a novel metabotropic glutamate receptor coupled to phosphoinositide hydrolysis. J. Pharmacol. Exp. Ther. 283:1997;742-749.
10. Craig D.A. The Cheng-Prusoff relationship: something lost in the translation. Trends Pharmacol. Sci. 14:1993;89-91.
11. Hansen J.J., Nielsen B., Krogsgaard-Larsen P., Brehm L., Nielsen E.Ø., Curtis D.R. Excitatory amino acid agonists. Enzymatic resolution, X-ray structure, and enantioselective activities of (R)- and (S)-bromohomoibotenic acid. J. Med. Chem. 32:1989;2254-2260.
12. Hansen, J.J., Jørgensen, F.S., Lund, T.M., Nielsen, B., Reinhardt, A., Breum, I., Brehm, L., Krogsgaard-Larsen, P., 1992. AMPA receptor agonists: structural, conformational and stereochemical aspects. In: Krogsgaard-Larsen, P., Hansen, J.J. (Eds.), Excitatory Amino Acid Receptors, Ellis Horwood, London, pp. 216-247.
13. Hayashi Y., Tanabe Y., Aramori I., Masu M., Shimamoto K., Ohfune Y., Nakanishi S. Agonist analysis of 2-(carboxycyclopropyl)glycine isomers for cloned metabotropic glutamate receptor subtypes expressed in Chinese hamster ovary cells. Br. J. Pharmacol. 107:1992;539-543.
14. Hayashi Y., Momiyama A., Takahashi T., Ohishi H., Ogawa-Meguro R., Shigemoto R., Mizuno N., Nakanishi S. Role of a metabotropic glutamate receptor in synaptic modulation in the accessory olfactory bulb. Nature. 366:1993;687-690.
15. Hayashi Y., Sekiyama N., Nakanishi S., Jane D.E., Sunter D.C., Birse E.F., Udvarhelyi P.M., Watkins J.C. Analysis of agonist and antagonist activities of phenylglycine derivatives for different cloned metabotropic glutamate receptor subtypes. J. Neurosci. 14:1994;3370-3377.
16. Johansen T.N., Ebert B., Bräuner-Osborne H., Christensen I.T., Johansen J.S., Søby K., Krogsgaard-Larsen P., Brehm L. Resolution, absolute stereochemistry and pharmacology of the (R)-(-)- and (S)-(+)-isomers of the AMPA receptor agonist (RS)-2-amino-3-(4-butyl-3-hydroxyisoxazol-5-yl)propionic acid [(RS)-Bu-HIBO]. J. Med. Chem. 41:1998;930-939.
17. Kingston A.E., Burnett J.P., Mayne N.G., Lodge D. Pharmacological analysis of 4-carboxyphenylglycine derivatives: Comparison of effects on mGlu1α and mGluR5a subtypes. Neuropharmacology. 34:1995;887-894.
18. Knöpfel T., Kuhn R., Allgeier H. Metabotropic glutamate receptors: Novel targets for drug development. J. Med. Chem. 38:1995;1417-1426.
19. Krogsgaard-Larsen P., Ebert B., Lund T.M., Bräuner-Osborne H., Sløk F.A., Johansen T.N., Brehm L., Madsen U. Design of excitatory amino acid receptor agonists, partial agonists and antagonists: Ibotenic acid as a key lead structure. Eur. J. Med. Chem. 31:1996;515-537.
20. Moroni F., Lombardi G., Thomsen C., Leonardi P., Attucci S., Peruginelli F., Torregrossa S.A., Pellegrini-Giampietro D.E., Luneia R., Pellicciari R. Pharmacological characterization of 1-aminoindan-1,5-dicarboxylic acid, a potent mGluR1 antagonist. J. Pharmacol. Exp. Ther. 281:1997;721-729.
21. Nakanishi S., Masu M. Molecular diversity and functions of glutamate receptors. Annu. Rev. Biophys. Biomol. Struct. 23:1994;319-348.
22. 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.
23. Sløk F.A., Ebert B., Lang Y., Krogsgaard-Larsen P., Lenz S.M., Madsen U. Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid. Eur. J. Med. Chem. 32:1997;329-338.
24. Tanabe Y., Masu M., Ishii T., Shigemoto R., Nakanishi S. A family of metabotropic glutamate receptors. Neuron. 8:1992;169-179.
25. Tanabe Y., Nomura A., Masu M., Shigemoto R., Mizuno N., Nakanishi S. Signal transduction, pharmacological properties, and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4. J. Neurosci. 13:1993;1372-1378.
26. Thomsen C., Bau A., Faarup P., Foged C., Kanstrup A., Suzdak P.D. Effects of bromohomoibotenate on metabotropic glutamate receptors. Neuroreport. 5:1994;2417-2420.