| Title | Synthesis and pharmacological studies of novel kainic acid based selective ligands suitable for photoaffinity labelling of non-NMDA excitatory aminoacid receptors in chick brain | |
| Authors | Emmanuel Sivvas1, Georgia Voukelatou1, Elias Kouvelas1, Alexios Aletras2 and Dionissios Papaioannou2
1. Laboratory of Physiology, Faculty of Medicine, School of Health Sciences 2. Department of Chemistry, School of Natural Sciences, University of Patras, 261 10 Patras, Greece |
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| Citation | Sivvas, E., Voukelatou, G., Kouvelas, E., Aletras, A., Papaioannou, D.: Synthesis and pharmacological studies of novel kainic acid based selective ligands suitable for photoaffinity labelling of non-NMDA excitatory aminoacid receptors in chick brain, Epitheorese Klin. Farmakol. Farmakokinet. 9(2-3): 117-120 (1995) | |
| Publication Date | 1995 | |
| Full Text Language | English | |
| Order – Buy | Ηλεκτρονική Μορφή: pdf (10 €) – Digital Type: pdf (10 €)
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| Keywords | Kainic acid, synthesis, analogues, pharmacological studies. | |
| Other Terms | review article | |
| Summary | The multistep syntheses of four analogues of kainic acid (KA) incorporating, photoactivatibte moieties attached either on the γ-carboxy function (KABED and KAGAN) or the isopropenyl side-chain (ABCPA and A TCP A) are described. The synthesis of KABED and KAGAN involves coupling of KA derivative ABCPA with 2-(4-azidobenzoyl) aminoethyiamine and the methoxy-2-nitroanilide of glycine respectively, followed by trifiuoroacetic acid mediated complete deprotection. ABCPA and ATCPA were synthesized by palladium mediated allylic amination, with 4,4′-dimethoxybenzhydryiamine (DMBA), of KA derivative MFCPA, followed by splitting the DMB- group with formic acid, coupling with N-hydroxy-succinimidyl 4-azidobenzoate and 4-azidophenyl isothiocyanate respectively and finally complete deprotection by saponification. Pharmacological studies showed that ABCPA and ATCPA are stronger inhibitors of [³H]KA binding on chick cerebellar membranes than KABED and KAGAN and that the former have specificity only for the cerebellar as opposed to telencephalon, type of non-NMDA binding sites. A tritiated analogue (T-ABCPA) of ABCPA, readily obtained by the same synthetic protocol and using commercially available tritiated 4-aminobenzoic acid, was successfully applied to label the cerebellar type of binding sites. Electrophoretic analysis showed the presence of two radioactive polypeptides with apparent Mr 45.0±1.5 and 33.5±1.7 kD. | |
| References | 1. Monaghan D.T., Bridges R.J., Cotman C.W.: Ann. Rev. Pharmacol. Toxicol 29: 365 (1989)
2. Henley J.M., Barnard E.A.: J. Neurochem. 56: 702 (1991) 3. Krogsgaard-Larsen P., Honoré T., Hansen J.J., Curtis D.R., Lodge D.: Nature (London) 284: 64 (1980) 4. See for example: Voukelatou G., Aletras A.J., Kouvelas E.D.: Eur. J. Pharmacol. 162: 179 (1989) 5. Goldberg O., Teichberg V.U.: J. Med. Chem. 28: 1957 (1985) 6. Trost B.M.: Acc. Chem. Res. 13: 385 (1980) 7. Mitsunobu O.: Synthesis: 1 (1981) 8. Galardy R.E., Craig L.C., Jamieson J.D., Printz M.-P.: J. Biol. Chem. 249: 3510 (1974) |
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Online ISSN 1011-6575
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| ΕΤΗΣΙΑ ΣΥΝΔΡΟΜΗ 1995 – ANNUAL SUBSCRIPTION 1995 | |
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