Issue 20, 2010

Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

Abstract

A novel synthesis of 4-[18F]fluorobenzylamine ([18F]FBA) by means of transition metal-assisted sodium borohydride reduction of 4-[18F]fluorobenzonitrile ([18F]FBN) is described. This approach could successfully be extended to borohydride exchange resin (BER) enabling a viable option for use in automated syntheses. [18F]FBA was used for the synthesis of 4-[18F]fluorobenzylamine-based thiol group-reactive prosthetic groups 4-[18F]fluorobenzyl-2-bromoacetamide ([18F]FBBA) and 4-[18F]fluorobenzylamidopropionyl maleimide ([18F]FBAPM). [18F]FBBA and [18F]FBAPM were obtained in radiochemical yields of 75% and 55%, respectively. Feasibility of using [18F]FBAPM as novel prosthetic group for peptide and protein labelling was demonstrated with cysteine-containing tripeptide glutathione (GSH). [18F]FBBA was used for labelling of a fully phosphorothioated 20mer oligodesoxynucleotide (ODN).

Graphical abstract: Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

Supplementary files

Article information

Article type
Paper
Submitted
14 Jun 2010
Accepted
16 Jul 2010
First published
25 Aug 2010

Org. Biomol. Chem., 2010,8, 4730-4735

Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

I. Koslowsky, J. Mercer and F. Wuest, Org. Biomol. Chem., 2010, 8, 4730 DOI: 10.1039/C0OB00255K

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