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A novel radiochemical approach to 1-(2 '-deoxy-2 '-[F-18] fluoro-beta-D-arabinofuranosyl)cytosine (F-18-FAC)

Meyer, Jan-Philip, Probst, Katrin C., Trist, Iuni Margaret, McGuigan, Christopher and Westwell, Andrew David 2014. A novel radiochemical approach to 1-(2 '-deoxy-2 '-[F-18] fluoro-beta-D-arabinofuranosyl)cytosine (F-18-FAC). Journal of Labelled Compounds and Radiopharmaceuticals 57 (11) , pp. 637-644. 10.1002/jlcr.3233

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18F-FAC (1-(2'-deoxy-2'-[18F]fluoro-β-D-arabinofuranosyl)-cytosine) is an important 2'-fluoro-nucleoside-based positron emission tomography (PET) tracer that has been used for in vivo prediction of response to the widely used cancer chemotherapy drug gemcitabine. Previously reported synthetic routes to 18F-FAC have relied on early introduction of the 18F radiolabel prior to attachment to protected cytosine base. Considering the 18F radiochemical half-life (110 min) and the technical challenges of multi-step syntheses on PET radiochemistry modular systems, late-stage radiofluorination is preferred for reproducible and reliable radiosynthesis with in vivo applications. Herein, we report the first late-stage radiosynthesis of 18F-FAC. Cytidine derivatives with leaving groups at the 2'-position are particularly prone to undergo anhydro side-product formation upon heating because of their electron density at the 2-carbonyl pyrimidone oxygen. Our rationally developed fluorination precursor showed an improved reactivity-to-stability ratio at elevated temperatures. 18F-FAC was obtained in radiochemical yields of 4.3–5.5% (n = 8, decay-corrected from end of bombardment), with purities ≥98% and specific activities ≥63 GBq/µmol. The synthesis time was 168 min.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords: nucleosides; positron emission tomography; radiochemistry; radiopharmaceuticals; computational chemistry
Publisher: Wiley-Blackwell
Date of First Compliant Deposit: 30 March 2016
Date of Acceptance: 8 August 2014
Last Modified: 09 Aug 2022 15:51

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