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.
MeSH terms
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2-Amino-5-phosphonovalerate / analogs & derivatives
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2-Amino-5-phosphonovalerate / metabolism
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Affinity Labels*
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Animals
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Azides / chemical synthesis*
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Azides / metabolism
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Binding Sites
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Brain / metabolism
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Glutamates / metabolism*
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Glutamic Acid
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Iodine Radioisotopes
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Isotope Labeling
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Organophosphorus Compounds / chemical synthesis*
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Organophosphorus Compounds / metabolism
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Photochemistry
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Rats
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Receptors, N-Methyl-D-Aspartate / metabolism*
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Spectrometry, Mass, Fast Atom Bombardment
Substances
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Affinity Labels
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Azides
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Glutamates
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Iodine Radioisotopes
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Organophosphorus Compounds
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Receptors, N-Methyl-D-Aspartate
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CGP 39653
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CGP 55802A
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Glutamic Acid
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2-Amino-5-phosphonovalerate