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

doi:10.1002/ejoc.202000934

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	6375-6381
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	40
DOIs	https://doi.org/10.1002/ejoc.202000934
State	Published - Oct 31 2020

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

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.",

keywords = "Fluorinated compounds, Isotopes, PET radiotracers, Radiofluorination, Synthetic methods",

author = "Larkina, {Mariia S.} and Ozerskaya, {Anastasia V.} and Podrezova, {Ekaterina V.} and Belousov, {Mikhail V.} and Vladimir Tolmachev and Zhdankin, {Viktor V.} and Yusubov, {Mekhman S.}",

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: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2020",

month = oct,

day = "31",

doi = "10.1002/ejoc.202000934",

language = "English (US)",

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AU - Larkina, Mariia S.

AU - Ozerskaya, Anastasia V.

AU - Podrezova, Ekaterina V.

AU - Belousov, Mikhail V.

AU - Tolmachev, Vladimir

AU - Zhdankin, Viktor V.

AU - Yusubov, Mekhman S.

N1 - 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

PY - 2020/10/31

Y1 - 2020/10/31

N2 - [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.

AB - [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.

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