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5-substituted derivatives of 6-halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with low picomolar affinity for alpha4beta2 nicotinic acetylcholine receptor and wide range of lipophilicity: potential probes for imaging with positron emission tomography.
Yi Zhang; Olga A Pavlova; Svetlana I Chefer; Andrew W Hall; Varughese Kurian; LaVerne L Brown; Alane S Kimes; Alexey G Mukhin; Andrew G Horti (Profiled Author: Andrew Horti)
Neuroimaging Research Branch, Intramural Research Program, National Institute on Drug Abuse, NIH, DHHS, 5500 Nathan Shock Drive, Baltimore, Maryland 21224, USA.
Journal of medicinal chemistry 2004;47(10):2453-65.
Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[(18)F]fluoro-5-(pyridin-3-yl)-A-85380 ([(18)F]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[(18)F]fluoropyridin-5-yl)pyridine) ([(18)F]35), were radiolabeled with (18)F. Comparison of PET data for [(18)F]31 and 2-[(18)F]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [(18)F]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[(18)F]FA. Therefore, [(18)F]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.
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Svetlana I Chefer; Olga A Pavlova; Yi Zhang; D Bruce Vaupel; Alane S Kimes; Andrew G Horti; Elliot Stein; Alexey G MukhinJournal of neurochemistry 2008;104(2):306-15.
LaVerne L Brown; Santosh Kulkarni; Olga A Pavlova; Andrei O Koren; Alexey G Mukhin; Amy H Newman; Andrew G Horti
Synthesis and evaluation of a novel series of 2-chloro-5-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-3-(2-(4-pyridinyl)vinyl)pyridine analogues as potential positron emission tomography imaging agents for nicotinic acetylcholine receptors.Journal of medicinal chemistry 2002;45(13):2841-9.
Jianhua Liu; J Brek Eaton; Barbara Caldarone; Ronald J Lukas; Alan P Kozikowski
Chemistry and pharmacological characterization of novel nitrogen analogues of AMOP-H-OH (Sazetidine-A, 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol) as α4β2-nicotinic acetylcholine receptor-selective partial agonists.Journal of medicinal chemistry 2010;53(19):6973-85.
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