Synthesis of a non-peptidic PET tracer designed for α 5β1 integrin receptor

Alessandra Monaco, Olivier Michelin, John Prior, Curzio Rüegg, Leonardo Scapozza, Yann Seimbille*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)
6 Downloads (Pure)

Abstract

Arginine-glycine-aspartic acid (RGD)-containing peptides have been traditionally used as PET probes to noninvasively image angiogenesis, but recently, small selective molecules for α5β1 integrin receptor have been developed with promising results. Sixty-one antagonists were screened, and tert-butyl (S)-3-(2-((3R,5S)-1-(3-(1-(2- fluoroethyl)-1H-1,2,3-triazol-4-yl)propanoyl)-5-((pyridin-2-ylamino)methyl) pyrrolidin-3-yloxy)acetamido)-2-(2,4,6-trimethylbenzamido)propanoate (FPMt) was selected for the development of a PET tracer to image the expression of α5β1 integrin receptors. An alkynyl precursor (PMt) was initially synthesized in six steps, and its radiolabeling was performed according to the azide-alkyne copper(II)-catalyzed Huisgen's cycloaddition by using 1-azido-2-[18F]fluoroethane ([ 18F]12). Different reaction conditions between PMt and [ 18F]12 were investigated, but all of them afforded [ 18F]FPMt in 15 min with similar radiochemical yields (80-83%, decay corrected). Overall, the final radiopharmaceutical ([18F]FPMt) was obtained after a synthesis time of 60-70 min in 42-44% decay-corrected radiochemical yield.

Original languageEnglish
Pages (from-to)365-370
Number of pages6
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume57
Issue number5
DOIs
Publication statusPublished - 15 May 2014
Externally publishedYes

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