Document Detail

Synthesis of a new kainic acid based selective ligand as a potential photoaffinity label of non-NMDA excitatory amino acid receptors in chicken brain.
MedLine Citation:
PMID:  8130015     Owner:  NLM     Status:  MEDLINE    
The synthesis of two analogues of kainic acid (KA) incorporating photo-activatible moieties attached either on the gamma-carboxy function (gamma-amide 1) or the isopropenyl side-chain (amide 2) is described. The synthesis of the former amide involves coupling of N-(tert-butoxycarbonyl)-protected alpha-diphenylmethyl kainate with 2-(4-azidobenzamido)ethylamine (5) followed by trifluoroacetic acid mediated complete deprotection. Amide 2 was synthesized by palladium-mediated allylic amination, with 4,4'-dimethoxybenzhydrylamine (DMBA), of N-(9-fluorenylmethoxycarbonyl)-protected dimethyl kainate, followed by splitting the DMB-group with formic acid, coupling with N-hydroxysuccinimidoyl 4-azidobenzoate and finally complete deprotection by saponification. Preliminary pharmacological studies in chicken brain membranes showed that amide 2 is a stronger inhibitor of [3H]KA binding on chicken cerebellar membranes than is amide 1 and that amide 2 has specificity only for the cerebellar, as opposed to the telencephalon, type of non-NMDA binding sites.
E Sivvas; G Voukelatou; E D Kouvelas; G W Francis; D W Aksnes; D Papaioannou
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Acta chemica Scandinavica (Copenhagen, Denmark : 1989)     Volume:  48     ISSN:  0904-213X     ISO Abbreviation:  Acta Chem. Scand.     Publication Date:  1994 Jan 
Date Detail:
Created Date:  1994-04-15     Completed Date:  1994-04-15     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9012772     Medline TA:  Acta Chem Scand     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  76-9     Citation Subset:  IM    
Department of Physiology, Medical School, University of Patras, Greece.
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MeSH Terms
Affinity Labels*
Azides / chemical synthesis*,  metabolism
Brain / metabolism*
Cell Membrane / metabolism
Cerebellum / metabolism
Kainic Acid / analogs & derivatives*,  chemical synthesis,  metabolism
Molecular Structure
Receptors, Amino Acid / metabolism*
Telencephalon / metabolism
Reg. No./Substance:
0/4-(1-(4-azidobenzamidomethyl)ethenyl)-2-carboxypyrrolidin-3-ylacetic acid; 0/Affinity Labels; 0/Azides; 0/Receptors, Amino Acid; 487-79-6/Kainic Acid

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