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Flubatine
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Flubatine ([18F]-norchloro-fluoro-homoepibatidine) is a fluorine-18 (18F) labeled radiotracer and radioligand for positron emission tomography (PET) imaging, developed as a high-affinity ligand for brain nicotinic acetylcholine receptors (nAChRs) of the α4β2 subtype.[2][3] It is used to image cholinergic deficits in disorders such as Alzheimer’s disease and Parkinson’s disease.[4] Both (+)- and (−)- enantiomer bind specifically to α4β2 nAChRs.[5]
Synthesis
[edit]Flubatine is prepared by radiolabeling a precursor molecule with fluorine-18 under no-carrier-added conditions. The synthetic route involves two main steps:
- Precursor synthesis: Optically pure precursor compounds (one for each enantiomer) are synthesized by organic chemical methods starting from epibatidine-like intermediates.[2]
- Radiolabeling: The [18F]fluoride ion is introduced by nucleophilic aromatic substitution of the precursor under controlled conditions (often using cryptand-assisted [18F]fluoride and heat).[5] Using a trimethylammonium leaving group on the pyridine ring allows for efficient fluorination.
References
[edit]- ^ a b "(-)-(18F)Flubatine". PubChem. U.S. National Library of Medicine. Retrieved May 12, 2025.
- ^ a b Fischer S, Hiller A, Deuther-Conrad W, Wenzel B, Patt M, Cumming P, et al. (2014-01-15). "Synthesis and biological evaluation of both enantiomers of [(18)F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors". Bioorganic & Medicinal Chemistry. 22 (2): 804–812. doi:10.1016/j.bmc.2013.12.011. ISSN 1464-3391. PMID 24369841.
- ^ Tiepolt S, Becker GA, Wilke S, Cecchin D, Rullmann M, Meyer PM, et al. (2020). "(+)-[18F]Flubatine as a novel α4β2 nicotinic acetylcholine receptor PET ligand—results of the first-in-human brain imaging application in patients with β-amyloid PET-confirmed Alzheimer's disease and healthy controls". Eur. J. Nucl. Med. Mol. Imaging. 48 (3): 731–746. doi:10.1007/s00259-020-05029-w. PMC 8036219. PMID 32935187.
- ^ Esterlis I, Gallezot JD, Bois F, Zheng MQ, Nabulsi N, Lin SF, et al. (2016-11-01). "Imaging of cerebral α4β2* nicotinic acetylcholine receptors with (-)-[(18)F]Flubatine PET: Implementation of bolus plus constant infusion and sensitivity to acetylcholine in human brain". NeuroImage. 141: 71–80. doi:10.1016/j.neuroimage.2016.07.026. ISSN 1095-9572. PMC 5026941. PMID 27426839.
- ^ a b Steffen F, René S, Winnie DC, Alexander H, Solveig T, Marianne P, et al. (February 2018). "Exploring the Metabolism of (+)-[18F]Flubatine In Vitro and In Vivo: LC-MS/MS Aided Identification of Radiometabolites in a Clinical PET Study †". Molecules. 23 (2). doi:10.3390/molecule (inactive 1 July 2025). ISSN 1420-3049. Archived from the original on 2025-05-09. Retrieved 2025-05-12.
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