SYNTHESIS AND BINDING-PROPERTIES OF 2-AMINO-5-PHOSPHONO-3-PENTENOIC ACID PHOTOAFFINITY LIGANDS AS PROBES FOR THE GLUTAMATE RECOGNITION SITEOF THE NMDA RECEPTOR

Authors
HECKENDORN R ALLGEIER H BAUD J GUNZENHAUSER W ANGST C
Citation
R. Heckendorn et al., SYNTHESIS AND BINDING-PROPERTIES OF 2-AMINO-5-PHOSPHONO-3-PENTENOIC ACID PHOTOAFFINITY LIGANDS AS PROBES FOR THE GLUTAMATE RECOGNITION SITEOF THE NMDA RECEPTOR, Journal of medicinal chemistry, 36(23), 1993, pp. 3721-3726
Citations number
27
Categorie Soggetti
Chemistry Medicinal
Journal title
Journal of medicinal chemistry → ACNP
ISSN journal
00222623
Volume
36
Issue
23
Year of publication
1993
Pages
3721 - 3726
Database
ISI
SICI code
0022-2623(1993)36:23<3721:SABO2A>2.0.ZU;2-P
Abstract
Four omega-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding affinity to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) r eceptor. The omega-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 va lue of 34 nM in the in vitro [H-3]CGP 39653 binding assay. This compou nd and its radioactive I-125-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.