5-Azidoepibatidine: an exceptionally potent photoaffinity ligand for neuronal alpha 4 beta 2 and alpha 7 nicotinic acetylcholine receptors.
Racemic 5-azidoepibatidine [(+/-)-1] was synthesized via 5-aminoepibatidine as a candidate photoaffinity ligand with exceptionally high affinity at the mammalian neuronal nicotinic receptors (K(i) values of 0.027 nM for alpha 4 beta 2 and 9.7 nM for alpha 7) and excellent photoreactivity.
Zhang
Nanjing
N
Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, CA 94720-3112, USA.
Tomizawa
Motohiro
M
Casida
John E
JE
D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D018678:Cholinergic Agents / Q000378:metabolism; D004330:Drosophila / Q000187:drug effects / Q000378:metabolism; D005347:Fibroblasts; D006801:Humans; D007093:Imidazoles / Q000378:metabolism; D007202:Indicators and Reagents; D008024:Ligands; D051379:Mice; D000073943:Neonicotinoids; D009474:Neurons / Q000187:drug effects / Q000378:metabolism*; D009538:Nicotine / Q000378:metabolism; D009574:Nitro Compounds; D010084:Oxidation-Reduction; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000494:pharmacology*; D010782:Photolysis; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D011978:Receptors, Nicotinic / Q000187:drug effects / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D064569:alpha7 Nicotinic Acetylcholine Receptor
C476378:5-azidoepibatidine; D001952:Bridged-Ring Compounds; D018678:Cholinergic Agents; C579167:Chrna7 protein, human; C579166:Chrna7 protein, mouse; D007093:Imidazoles; D007202:Indicators and Reagents; D008024:Ligands; D000073943:Neonicotinoids; D009574:Nitro Compounds; D019920:Photoaffinity Labels; D011725:Pyridines; D011978:Receptors, Nicotinic; D064569:alpha7 Nicotinic Acetylcholine Receptor; C403531:nicotinic receptor alpha4beta2; C082359:imidacloprid; D009538:Nicotine