Efficient Synthesis of ω-[18F]Fluoroaliphatic Carboxylic Esters and Acids for Positron Emission Tomography

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Abstract

[18F]Fluoroaliphatic carboxylic acids are important PET tracers that have demonstrated a considerable potential to address the fatty acid oxidation-dependent processes in clinical patients. Herein, we report an efficient radiosynthetic approach to ω-[18F]fluoroaliphatic carboxylic esters and acids by nucleophilic radiofluorination of the readily available iodocarboxylic esters. Methyl 6-[18F]fluorohexanoate was further applied as a starting material for the preparation of the succinimide ester (NHS ester)-containing bifunctional radiofluorinated prosthetic group in two simple steps, 10 min each. The synthesized NHS ester of 6-[18F]fluorohexanoic acid can serve as an important reagent for a quick and efficient conjugation with peptides or proteins via amino groups of lysines.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2020

Keywords

  • Fluorinated compounds
  • Isotopes
  • PET radiotracers
  • Radiofluorination
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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