ArticleJournal of medicinal chemistry2010
Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter.
Article in Journal of medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Radiation dosimetry and fasting-dependent hepatobiliary clearance of the VAChT-specific PET radioligandEJNMMI research · 2025Article
- Imaging the Vesicular Acetylcholine Transporter in Schizophrenia: A Positron Emission Tomography Study Using [Biological psychiatry · 2024Article
- The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review.Molecules (Basel, Switzerland) · 2024Review
- In vitro evaluation of PET radiotracers for imaging synaptic density, the acetylcholine transporter, AMPA-tarp-γ8 and muscarinic M4 receptors in Alzheimer's disease.American journal of nuclear medicine and molecular imaging · 2024Article
- In vitro characterization of [European journal of pharmacology · 2021Article
- Radiosynthesis and evaluation of a fluorine-18 labeled radioligand targeting vesicular acetylcholine transporter.Bioorganic & medicinal chemistry letters · 2018Article
- Kinetic modeling of [Journal of neurochemistry · 2018Article
- In Vivo and In Vitro Characteristics of Radiolabeled Vesamicol Analogs as the Vesicular Acetylcholine Transporter Imaging Agents.Contrast media & molecular imaging · 2018Review
- Synthesis, resolution, and in vitro evaluation of three vesicular acetylcholine transporter ligands and evaluation of the lead fluorine-18 radioligand in a nonhuman primate.Organic & biomolecular chemistry · 2017Article
- Synthesis and biological characterization of a promising F-18 PET tracer for vesicular acetylcholine transporter.Bioorganic & medicinal chemistry · 2015Article
- In vitro and ex vivo characterization of (-)-TZ659 as a ligand for imaging the vesicular acetylcholine transporter.European journal of pharmacology · 2015Article
- Syntheses and radiosyntheses of two carbon-11 labeled potent and selective radioligands for imaging vesicular acetylcholine transporter.Molecular imaging and biology · 2014Article
- In vitro and in vivo characterization of two C-11-labeled pet tracers for vesicular acetylcholine transporter.Molecular imaging and biology · 2014Article
- Radiosynthesis andMedChemComm · 2014Article
- Heteroaromatic and aniline derivatives of piperidines as potent ligands for vesicular acetylcholine transporter.Journal of medicinal chemistry · 2013Article
- Synthesis and evaluation of in vitro bioactivity for vesicular acetylcholine transporter inhibitors containing two carbonyl groups.Bioorganic & medicinal chemistry · 2012Article
- Synthesis and in vitro biological evaluation of carbonyl group-containing analogues for σ1 receptors.Journal of medicinal chemistry · 2011Article
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6 authors.
Funding
Abstract
To identify selective high-affinity inhibitors of the vesicular acetylcholine transporter (VAChT), we have interposed a carbonyl group between the phenyl and piperidyl groups of the prototypical VAChT ligand vesamicol and its more potent analogues benzovesamicol and 5-aminobenzovesamicol. Of 33 compounds synthesized and tested, 6 display very high affinity for VAChT (K(i), 0.25-0.66 nM) and greater than 500-fold selectivity for VAChT over sigma(1) and sigma(2) receptors. Twelve compounds have high affinity (K(i), 1.0-10 nM) and good selectivity for VAChT. Furthermore, 3 halogenated compounds, namely, trans-3-[4-(4-fluorobenzoyl)piperidinyl]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (28b) (K(i) = 2.7 nM, VAChT/sigma selectivity index = 70), trans-3-[4-(5-iodothienylcarbonyl)piperidinyl]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (28h) (K(i) = 0.66 nM, VAChT/sigma selectivity index = 294), and 5-amino-3-[4-(p-fluorobenzoyl)piperidinyl]-2-hydroxy-1,2,3,4,-tetrahydronaphthalene (30b) (K(i) = 2.40 nM, VAChT/sigma selectivity index = 410) display moderate to high selectivity for VAChT. These three compounds can be synthesized with the corresponding radioisotopes so as to serve as PET/SPECT probes for imaging the VAChT in vivo.
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