ArticleJournal of medicinal chemistry2014
Imaging evaluation of 5HT2C agonists, [(11)C]WAY-163909 and [(11)C]vabicaserin, formed by Pictet-Spengler cyclization.
Article in Journal of medicinal chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
16 citing papers in PubMed.
- Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[Molecules (Basel, Switzerland) · 2024Article
- Rapid 'on-column' preparation of hydrogen [Chemical science · 2022Article
- Synthesis and Evaluation of [Frontiers in neuroscience · 2021Article
- The Pictet-Spengler Reaction Updates Its Habits.Molecules (Basel, Switzerland) · 2020Review
- Synthesis and Biological Evaluation of Disubstituted Pyrimidines as Selective 5-HTMolecules (Basel, Switzerland) · 2019Article
- Studies on the antifungal and serotonin receptor agonist activities of the secondary metabolites from piezotolerant deep-sea fungusMycology · 2019Article
- Chemistry for Positron Emission Tomography: Recent Advances inAngewandte Chemie (International ed. in English) · 2019Review
- Recent metal-catalysed approaches for the synthesis of cyclopenta[RSC advances · 2018Review
- Synthesis and Evaluation of Pyridyloxypyridyl Indole Carboxamides as Potential PET Imaging Agents for 5-HTACS medicinal chemistry letters · 2018Article
- Effects of the serotonin 2C receptor agonist WAY163909 on the abuse-related effects and mesolimbic dopamine neurochemistry induced by abused stimulants in rhesus monkeys.Psychopharmacology · 2017Article
- Identification of Optically Active Pyrimidine Derivatives as Selective 5-HTMolecules (Basel, Switzerland) · 2017Article
- Synthesis and Structure-Activity Relationships of Tool Compounds Based on WAY163909, a 5-HTACS chemical neuroscience · 2017Article
- New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals.Clinical and translational imaging · 2017Review
- Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.Journal of the American Chemical Society · 2015Article
- A philosophy for CNS radiotracer design.Accounts of chemical research · 2014Review
- PET tracers for serotonin receptors and their applications.Central nervous system agents in medicinal chemistry · 2014Review
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The serotonin subtype 2C (5HT2C) receptor is an emerging and promising drug target to treat several disorders of the human central nervous system. In this current report, two potent and selective 5HT2C full agonists, WAY-163909 (2) and vabicaserin (3), were radiolabeled with carbon-11 via Pictet-Spengler cyclization with [(11)C]formaldehyde and used in positron emission tomography (PET) imaging. Reaction conditions were optimized to exclude the major source of isotope dilution caused by the previously unknown breakdown of N,N-dimethylformamide (DMF) to formaldehyde at high temperature under mildly acid conditions. In vivo PET imaging was utilized to evaluate the pharmacokinetics and distribution of the carbon-11 labeled 5HT2C agonists. Both radiolabeled molecules exhibit high blood-brain barrier (BBB) penetration and nonspecific binding, which was unaltered by preadministration of the unlabeled agonist. Our work demonstrates that Pictet-Spengler cyclization can be used to label drugs with carbon-11 to study their pharmacokinetics and for evaluation as PET radiotracers.
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Registered trials
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