3-Substituted phenylalanines as selective AMPA- and kainate receptor ligands
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3-Substituted phenylalanines as selective AMPA- and kainate receptor ligands. / Szymanska, Ewa; Pickering, Darryl S; Nielsen, Birgitte; Johansen, Tommy N.
In: Bioorganic & Medicinal Chemistry, Vol. 17, No. 17, 2009, p. 6390-401.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - 3-Substituted phenylalanines as selective AMPA- and kainate receptor ligands
AU - Szymanska, Ewa
AU - Pickering, Darryl S
AU - Nielsen, Birgitte
AU - Johansen, Tommy N
N1 - Keywords: Animals; Binding Sites; Computer Simulation; Ligands; Neurotransmitter Agents; Phenylalanine; Rats; Receptors, AMPA; Receptors, Kainic Acid; Recombinant Proteins
PY - 2009
Y1 - 2009
N2 - On the basis of X-ray structures of ionotropic glutamate receptor constructs in complex with amino acid-based AMPA and kainate receptor antagonists, a series of rigid as well as flexible biaromatic alanine derivatives carrying selected hydrogen bond acceptors and donors have been synthesized in order to investigate the structural determinants for receptor selectivity between AMPA and the GluR5 subtype of kainate receptors. Compounds selective for either GluR5 or AMPA receptors were identified. One particular substituent position appeared to be of special importance for control of ligand selectivity. Using molecular modeling the observed structure-activity relationships at AMPA and GluR5 receptors were deduced.
AB - On the basis of X-ray structures of ionotropic glutamate receptor constructs in complex with amino acid-based AMPA and kainate receptor antagonists, a series of rigid as well as flexible biaromatic alanine derivatives carrying selected hydrogen bond acceptors and donors have been synthesized in order to investigate the structural determinants for receptor selectivity between AMPA and the GluR5 subtype of kainate receptors. Compounds selective for either GluR5 or AMPA receptors were identified. One particular substituent position appeared to be of special importance for control of ligand selectivity. Using molecular modeling the observed structure-activity relationships at AMPA and GluR5 receptors were deduced.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1016/j.bmc.2009.07.021
DO - 10.1016/j.bmc.2009.07.021
M3 - Journal article
C2 - 19656686
VL - 17
SP - 6390
EP - 6401
JO - Bioorganic & Medicinal Chemistry
JF - Bioorganic & Medicinal Chemistry
SN - 0968-0896
IS - 17
ER -
ID: 17084258