Automated preparation of [18F]AFP and [18F]BFP: Two novel bifunctional 18F-labeling building blocks for Huisgen-click

Publikation: Beitrag in FachzeitschriftForschungsartikelBeigetragenBegutachtung

Beitragende

Abstract

A bioorthogonal labeling approach based on the Huisgen-click reaction including the one-step radiosynthesis of two novel versatile and bifunctional labeling building blocks ([18F]AFP) [18F]12 and ([ 18F]BFP) [18F]6 with the PET radionuclide fluorine-18 is described. Optimized reaction conditions for the fully automated synthesis procedure using the TRACERlab FxFN module gave both piperazine derivatives [18F]6 and [18F]12 with radiochemical yields of 31 ± 9% (S.D., n = 8, d.c.) and 29 ± 5% (S.D., n = 19, d.c.), respectively, within 40 min synthesis time and high specific activities after convenient purification using silica gel cartdridges. First biological studies of both building blocks revealed a remarkable in vitro stability in rat blood as well as rat plasma over more than 60 min. Sample ligation reactions of [ 18F]6 and [18F]12 with azide and alkyne functionalized amino acid derivatives yielded the corresponding labeled triazoles in good to high RCYs. Moreover, the azide functionalized peptide 17, which is highly affine to the EphB2 receptor due to its SNEW sequence, was synthesized and successfully radiolabeled with [18F]BFP [18F]6 under relatively mild conditions yielding the corresponding triazolyl-peptide [ 18F]18.

Details

OriginalspracheEnglisch
Seiten (von - bis)25-35
Seitenumfang11
FachzeitschriftJournal of Fluorine Chemistry
Jahrgang150
PublikationsstatusVeröffentlicht - Juni 2013
Peer-Review-StatusJa

Externe IDs

ORCID /0000-0002-6432-5694/work/151982353

Schlagworte

Schlagwörter

  • Automated synthesis, Bioorthogonal, Building block, Click chemistry, Eph receptor