Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors
A series of homoazanicotine derivatives 3 was found to bind at α4β2 nACh receptors in a manner that appears to parallel that of their corresponding racemic nicotine counterparts.
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Acknowledgements
This work was supported in part by DA 05274 and by funding from MURST Cofinanziamento (Rome).
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2005, Bioorganic and Medicinal Chemistry LettersMedicinal Chemistry of α4β2 Nicotinic Cholinergic Receptor Ligands
2004, Progress in Medicinal ChemistryCitation Excerpt :For example, the affinities of anabasine (7) (R=H; Ki=210 nM) [33], N-methylanabasine (7) (R=Me; Ki=180 nM) [33], cotinine (8) (Ki>100,000 nM) [37], N1,N1′-dimethylnicotinium (Ki>10,000 nM) [26], and myosmine (30) (Ki=3,300 nM) [66] were well below that of nicotine. However, trans-metanicotine (31b) (Ki=26 nM; Table 2.2), also known as RJR-2403, TC-2403, or simply as ‘metanicotine’, binds with higher affinity [67]. The structural requirements for the binding of (31b) at nACh receptors were rather strict and modifications diminished its affinity (Table 2.2).
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