Fiche publication
Date publication
juillet 2024
Journal
Molecules (Basel, Switzerland)
Auteurs
Membres identifiés du Cancéropôle Est :
Pr MULLER Sylviane
,
Dr BONNET Dominique
Tous les auteurs :
Maujean T, Ramanoudjame SM, Riché S, Le Guen C, Boisson F, Muller S, Bonnet D, Gulea M, Marchand P
Lien Pubmed
Résumé
Radiolabeled peptides are valuable tools for diagnosis or therapies; they are often radiofluorinated using an indirect approach based on an F-18 prosthetic group. Herein, we are reporting our results on the F-18 radiolabeling of three peptides using two different methods based on click reactions. The first one used the well-known CuAAC reaction, and the second one is based on our recently reported hetero-Diels-Alder (HDA) using a dithioesters (thia-Diels-Alder) reaction. Both methods have been automated, and the F-peptides were obtained in similar yields and synthesis time (37-39% decay corrected yields by both methods in 120-140 min). However, to obtain similar yields, the CuAAC needs a large amount of copper along with many additives, while the HDA is a catalyst and metal-free reaction necessitating only an appropriate ratio of water/ethanol. The HDA can therefore be considered as a minimalist method offering easy access to fluorine-18 labeled peptides and making it a valuable additional tool for the indirect and site-specific labeling of peptides or biomolecules.
Mots clés
CuAAC, automated synthesis, cycloaddition, fluorine-18, hetero-Diels–Alder, labeling, peptide, radiochemistry
Référence
Molecules. 2024 07 5;29(13):
