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Fluorescent Agonists of the α 7 Nicotinic Acetylcholine Receptor Derived from 3‐Amino‐Quinuclidine
Author(s) -
Bürgi Justus J.,
Bertrand Sonia,
Marger Fabrice,
Bertrand Daniel,
Reymond JeanLouis
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201600120
Subject(s) - chemistry , fluorescence , nicotinic agonist , nicotinic acetylcholine receptor , pharmacophore , cytisine , acetylcholine receptor , quinuclidine , xenopus , receptor , amino acid , stereochemistry , agonist , acetylcholine , torpedo , ligand (biochemistry) , biophysics , biochemistry , pharmacology , medicine , physics , quantum mechanics , biology , gene
Here, we investigated whether fluorescence labeled small molecule agonists of the α 7 nicotinic acetylcholine receptor ( nAChR ) might be identified to enhance receptor studies. Enantiomerically pure 3‐amino‐quinuclidines appended with fluorophores at the 3‐amino group were synthesized and tested by electrophysiology on human α 7 nAChR in Xenopus oocytes, uncovering ( R )‐ 4 and ( R )‐ 9 as the first examples of fluorescent α 7 nAChR agonists. These molecules elegantly incorporate the fluorescent reporter group as part of the pharmacophore itself and provide a new class of tool compounds for the study of these ligand‐gated ion channels.