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Capturing aqueous [F-18]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [F-18]-labeled aryltrifluoroborate

TitleCapturing aqueous [F-18]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [F-18]-labeled aryltrifluoroborate
Publication TypeJournal Article
Year of Publication2008
AuthorsTing, R, Lo, J, Adam, MJ, Ruth, TJ, Perrin, DM
JournalJournal of Fluorine Chemistry
Volume129
Pagination349-358
Date PublishedMay
Type of ArticleArticle
ISBN Number0022-1139
KeywordsACIDS, aryltrifluoroborate, CROSS-COUPLING REACTIONS, KINETICS, PET, SYNTHESIS, [F-18]-labeling
Abstract

The aqueous stability of aryltrifluoroborates is of importance to their use in transition metal mediated coupling reactions as well as their potential use in [F-18]-labeled aryltrifluoroborate PET imaging agents. Nevertheless, few studies have fully characterized the solvolysis of fluoride from an aryltrifluoroborate in water. Using [F-19] NMR, fluorescence and [F-18]-labeling techniques, we disclose the composition of an aryltrifluoroborate of exceptional kinetic stability with respect to solvolytic defluoridation. This work not only highlights the potential of using [F-18]-labeled aryltrifluoroborates for PET tracers, but provides a chemical platform and a general approach for evaluating the stability of other aryltrifluoroborates. (c) 2008 Elsevier B.V. All rights reserved.

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