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

Mariia S. Larkina, Anastasia V. Ozerskaya, Ekaterina V. Podrezova, Mikhail V. Belousov, Vladimir Tolmachev, Viktor V. Zhdankin, Mekhman S. Yusubov

Research output: Contribution to journalArticlepeer-review

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 (US)
Pages (from-to)6375-6381
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number40
DOIs
StatePublished - Oct 31 2020
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF‐16‐13‐10081‐P) and the Ministry of Science and Higher Education of the Russian Federation (grant 075‐15‐2019‐1925). The research was carried out using the core facilities of TPU's “Physical and chemical methods of analysis”.

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Keywords

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

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