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Radiosynthesis and bioconjugation of [18F]FPy5yne, a prosthetic group for the 18F labeling of bioactive peptides

✍ Scribed by James A. H. Inkster; Brigitte Guérin; Thomas J. Ruth; Michael J. Adam

Publisher
John Wiley and Sons
Year
2008
Tongue
French
Weight
214 KB
Volume
51
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A new ^18^F‐based prosthetic group has been prepared for the labeling of azide‐modified peptides for use in PET imaging. 2‐[^18^F]fluoro‐3‐(hex‐5‐ynyloxy)pyridine ([^18^F]FPy5yne, [^18^F]‐1) was prepared via efficient nucleophilic heteroaromatic substitution of either the corresponding 2‐nitro (2) or 2‐trimethylammonium trifluoromethanesulfonate pyridine (3). Best radiochemical yield of [^18^F]FPy5yne from 2 was 91% by radioTLC (15 min, 110°C, DMSO). From 3, best radiochemical yield by radioTLC was 93% (15 min, 110°C, MeCN). HPLC‐purified [^18^F]FPy5yne was ligated to model peptide N~3~–(CH~2~)~4~–CO–YKRI–OH by way of Cu^I^‐mediated Huisgen [3+2] cycloaddition in the presence of copper‐stabilizing ligand tris(benzyltriazolylmethyl)amine (TBTA) and N,N‐diisopropylethylamine (DIEA). Bioconjugate radiochemical yields were obtained in average yields of 89%±8.6% (n=4), as judged by radioHPLC. Best non‐decay‐corrected, collected radiochemical yield of modified peptide from end‐of‐bombardment was 5.8% (18.7% decay‐corrected), with a total preparation time of 160 min from start of synthesis. Copyright © 2008 John Wiley & Sons, Ltd.

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