Fiche publication
Date publication
décembre 2022
Journal
Bioconjugate chemistry
Auteurs
Membres identifiés du Cancéropôle Est :
Dr VILLA Pascal
,
Dr BONNET Dominique
Tous les auteurs :
Maujean T, Wagner P, Valencia C, Riché S, Iturrioz X, Villa P, Girard N, Karpenko J, Gulea M, Bonnet D
Lien Pubmed
Résumé
Herein, we describe a catalyst-free thia-Diels-Alder cycloaddition for the chemoselective labeling of fully deprotected phosphonodithioester-peptides in solution with fluorophores functionalized with an exocyclic diene. The reaction was optimized on the model tripeptide containing a lysine residue, which enabled its rapid and straightforward labeling with three different fluorophores (fluorescein, lissamine rhodamine B, and squaraine) in very mild conditions (HO/PrOH, 37 °C, 1 h). The reaction was then successfully applied to the chemoselective labeling of fully deprotected apelin-13 with squaraine dye. The resulting fluorescent ligand exhibited a high affinity (0.17 ± 0.03 nM) for apelinR. It enabled the development of time-resolved FRET-based competition assays for high-throughput screening and drug discovery. Thanks to its fluorogenic properties, ligand was also successfully involved in the live-cell optical imaging of apelinR in no-wash conditions.
Référence
Bioconjug Chem. 2022 12 19;:
