Late stage benzylic C-H fluorination with [18F]fluoride for PET imaging

Xiongyi Huang, Wei Liu, Hong Ren, Ramesh Neelamegam, Jacob M. Hooker, John T. Groves

Research output: Contribution to journalArticle

133 Scopus citations

Abstract

We describe the first late-stage 18F labeling chemistry for aliphatic C-H bonds with no-carrier-added [18F]fluoride. The method uses Mn(salen)OTs as an F-transfer catalyst and enables the facile labeling of a variety of bioactive molecules and building blocks with radiochemical yields (RCY) ranging from 20% to 72% within 10 min without the need for preactivation of the labeling precursor. Notably, the catalyst itself can directly elute [18F]fluoride from an ion exchange cartridge with over 90% efficiency. Using this feature, the conventional and laborious dry-down step prior to reaction is circumvented, greatly simplifying the mechanics of this protocol and shortening the time for automated synthesis. Eight drug molecules, including COX, ACE, MAO, and PDE inhibitors, have been successfully [ 18F]-labeled in this way.

Original languageEnglish (US)
Pages (from-to)6842-6845
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number19
DOIs
StatePublished - May 14 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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