L-trans-2,3-Pyrrolidine dicarboxylate: Characterization of a novel excitotoxin

Neuropharmacology

Volumn 35, Issue 5, 1996, Pages 531-539

  Willis, C L ^a   Humphrey, J M ^b   Koch, H P ^a   Hart, J A ^b   Blakely, T ^a   Ralston, L ^a   Baker, C A ^a   Shim, S ^a   Kadri, M ^a   Chamberlin, A R ^b   Bridges, R J ^a  

^a UNIVERSITY OF MONTANA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Glutamate transporter; Hippocampus; Neurotoxicity; NMDA agonist; Pyrrolidine dicarboxylate

Indexed keywords

2,3 PYRROLIDINEDICARBOXYLIC ACID; 6 NITRO 7 SULFAMOYLBENZO[F]QUINOXALINE 2,3 DIONE; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; ASPARTIC ACID; DIZOCILPINE; EXCITOTOXIN; GLUTAMIC ACID; GLUTAMIC ACID DERIVATIVE; KAINIC ACID; KAINIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; QUISQUALIC ACID; RADIOISOTOPE; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN; BRAIN CORTEX; BRAIN SYNAPTOSOME; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG CONFORMATION; DRUG MECHANISM; FETUS; HIPPOCAMPUS; INTRACEREBRAL DRUG ADMINISTRATION; INTRAPERITONEAL DRUG ADMINISTRATION; LIGAND BINDING; MALE; MICROINJECTION; NERVE CELL CULTURE; NERVE CELL LESION; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 0013420816     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/0028-3908(96)84623-5     Document Type: Article

References (28)

1. Arriza J.L., Fairman W.A., Wadiche J.I., Murdoch G.H., Kavanaugh M.P., Amara S.G. Functional comparisons of three glutamate transporter subtypes cloned from human motor cortex. J. Neurosci. 14:1994;5559-5569.
2. Booth R.F.G., Clark J.B. A rapid method for the preparation of relatively pure metabolically competent synaptosomes from rat brain. Biochem. J. 176:1978;365-370.
3. Bridges R.J., Hatalski C., Shim S.N., Nunn P.B. Gliotoxic properties of the Lathyrus excitotoxin β-N-oxalyl-L-α,β-diaminopropionic acid (β-L-ODAP). Brain Res. 561:1991;262-268.
4. Bridges R.J., Lovering F.E., Humphrey J.M., Stanley M.S., Blakely T.N., Cristofaro M.F., Chamberlin A.R. Conformationally restricted inhibitors of the high affinity L-glutamate transporter. Bioorg. Med. Chem. Lett. 3:1993;115-121.
5. Bridges R.J., Stanley M.S., Anderson M.W., Cotman C.W., Chamberlin A.R. Conformationally defined neurotransmitter analogues. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer. J. Med. Chem. 34:1991;717-725.
6. Bridges R.J., Stevens D.R., Kahle J.S., Nunn P.B., Kadri M., Cotman C.W. Structure-function studies on N-oxalyl-diaminodicarboxylic acids and excitatory amino acid receptors: evidence that β-L-ODAP is a selective non-NMDA agonist. J. Neurosci. 9:1989;2073-2079.
7. Chamberlin A.R. and Bridges R.J. (1993) Conformationally constrained acid amino acids as probes of glutamate receptors and transporters. In: Drug Design for Neuroscience (A. P. Kozikowski, Ed.), pp. 231-259. Raven Press, New York.
8. Choi D.W. The role of glutamate neurotoxicity in hypoxic-ischemic neuronal death. A. Rev. Neurosci. 13:1990;171-182.
9. Choi D.W. Glutamate receptors and the induction of excitotoxic neuronal death. Prog. Brain Res. 100:1994;47-51.
10. Collingridge G.L., Bliss T.V.P. Memories of NMDA receptors and LTP. TINS. 18:1995;54-56.
11. Cotman C.W., Kahle J.S., Miller S.E., Ulas J. and Bridges R.J. (1995) Excitatory amino acid neurotransmission. In: Psychopharmacology: The Fourth Generation of Progress (F.E. Bloom and D.J. Kupfer, Eds), pp. 75-85. Raven Press, New York.
12. Daw N.W., Stein P.S., Fox K. The role of NMDA receptors in information processing. A. Rev. Neurosci. 16:1993;207-222.
13. 3H-AMPA, a structural analogue of glutamic acid, to rat brain membranes. J. Neurochem. 38:1982;173-178.
14. Humphrey J.M., Bridges R.J., Chamberlin A.R. 2,3-Pyrrolidine dicarboxylates as neurotransmitter conformer mimics: enantioselective synthesis via chelation-controlled enolate alkylation. J. Org. Chem. 59:1994;2467-2472.
15. Ishida M., Ohfune Y., Shimada Y., Shimamoto K., Shinozaki H. Changes in a preference for receptor subtypes of configurational variants of a glutamate analog: conversion from the NMDA-type to the non-NMDA type. Brain Res. 550:1991;152-156.
16. 2+ increase. Eur. J. Pharmacol. 211:1992;195-202.
17. Koh J., Choi D.W. Quantitative determination of glutamate mediated cortical neuronal injury in cell culture by lactate dehydrogenase efflux assay. J. Neurosci. Meth. 20:1987;83-90.
18. Kuhar M.J., Zarbin M. Synaptosomal transport: a chloride dependence for choline, GABA, glycine and several other compounds. J. Neurochem. 31:1978;251-256.
19. 3H-kainic acid receptor site in rat brain. Molec. Pharmacol. 15:1979;492-505.
20. Meldrum B.S. Excitotoxicity and selective neuronal loss in epilepsy. Brain Pathol. 3:1993;405-412.
21. Monaghan D.T., Cotman C.W. Identification and properties of NMDA receptors in rat brain synaptic plasma membranes. Proc. Natn. Acad. Sci. USA. 83:1986;7532-7536.
22. Ortwine D.F., Malone T.C., Bigge C.F., Drummond J.T., Humblet C., Johnson G., Pinter G.W. 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. 35:1992;1345-1370.
23. Rothman S.M., Olney J.W. Excitotoxicity and the NMDA receptor-still lethal after eight years. TINS. 18:1995;57-58.
24. 3H-kainic acid, an analogue of L-glutamate, to rat brain membranes. J. Neurochem. 26:1976;141-147.
25. Smith P.K., Krohn R.I., Hermanson G.T., Mallia A.K., Gartner F.H., Provenzano M.D.et al. Measurement of protein using bicinchoninic acid. Analyt. Biochem. 150:1985;76-85.
26. Watkins J.C., Krogsgaard-Larsen P., Honore T. Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. TIPS. 11:1990;25-33.
27. Willis C.L., Meldrum B.S., Nunn P.B., Anderton B.H., Leigh P.N. Neuronal damage induced by β-Noxalylamino-L-alanine, in the rat hippocampus, can be prevented by a non-NMDA antagonist, 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo(f)quinoxaline. Brain Res. 627:1993;55-62.
28. Willis C.L., Humphrey J.M., Chamberlin A.R., Bridges R.J. Identification of a novel NMDA agonist. Soc. Neurosci. Abstr. 21:1995;1028.