Chelator-Accelerated One-Pot ‘Click’ Labeling of Small Molecule Tracers with 2-[18F]Fluoroethyl Azide

Article


Galante, E., Schoultz, Bent, Koepp, Matthias and Årstad, Erik 2013. Chelator-Accelerated One-Pot ‘Click’ Labeling of Small Molecule Tracers with 2-[18F]Fluoroethyl Azide. Molecules. 18 (5), pp. 5335-5347.
AuthorsGalante, E., Schoultz, Bent, Koepp, Matthias and Årstad, Erik
Abstract

2-[18F]Fluoroethyl azide ([18F]FEA) can readily be obtained by nucleophilic substitution of 2-azidoethyl-4-toluenesulfonate with [18F]fluoride (half-life 110 min), and has become widely used as a reagent for ‘click’ labeling of PET tracers. However, distillation of [18F]FEA is typically required, which is time-consuming and unpractical for routine applications. In addition, copper(I)-catalyzed cycloaddition of [18F]FEA with non-activated alkynes, and with substrates containing labile functional groups, can be challenging. Herein, we report a highly efficient and practical ligand-accelerated one-pot/two-step method for ‘click’ labeling of small molecule tracers with [18F]FEA. The method exploits the ability of the copper(I) ligand bathophenanthrolinedisulfonate to accelerate the rate of the cycloaddition reaction. As a result, alkynes can be added directly to the crude reaction mixture containing [18F]FEA, and as cyclisation occurs almost immediately at room temperature, the reaction is tolerant to labile functional groups. The method was demonstrated by reacting [18F]FEA with a series of alkyne-functionalized 6-halopurines to give the corresponding triazoles in 55–76% analytical radiochemical yield

JournalMolecules
Journal citation18 (5), pp. 5335-5347
ISSN1420-3049
Year2013
PublisherMDPI AG
Publisher's version
License
CC BY
Digital Object Identifier (DOI)doi:10.3390/molecules18055335
Web address (URL)https://doi.org/10.3390/molecules18055335
Publication dates
Online10 May 2013
Publication process dates
Deposited18 Aug 2017
Accepted03 May 2013
FunderSeventh Framework Programme
Seventh Framework Programme
Copyright information© The Authors 2013
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