Synthesis and binding properties of 2-amino-5-phosphono-3-pentenoic acid photoaffinity ligands as probes for the glutamate recognition site of the NMDA receptor

  • J Med Chem. 1993 Nov 12;36(23):3721-6. doi: 10.1021/jm00075a029.
R Heckendorn  1 ,  H Allgeier ,  J Baud ,  W Gunzenhauser ,  C Angst
Affiliations
  • 1. Research Department, Ciba-Geigy Ltd., Basel, Switzerland.
PMID: 7902441 DOI: 10.1021/jm00075a029
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) receptor. The omega-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro [3H]CGP 39653 binding assay. This compound and its radioactive 125I-form are the first photoaffinity ligands for the NMDA Receptor with high affinity to the glutamate recognition site.

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