Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far-Red Ligand for Apelin Receptor Imaging.
Fiche publication
Date publication
janvier 2016
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Pr HIBERT Marcel, Dr BONNET Dominique, Mr HUMBERT Nicolas
Tous les auteurs :
Margathe JF, Iturrioz X, Regenass P, Karpenko IA, Humbert N, de Rocquigny H, Hibert M, Llorens-Cortes C, Bonnet D
Lien Pubmed
Résumé
Herein, we develop a convenient method to facilitate the solution-phase fluorescent labelling of peptides based on the chemoselective acylation of α-hydrazinopeptides. This approach combines the advantages of using commercially available amine-reactive dyes and very mild conditions, which are fully compatible with the chemical sensitivity of the dyes. The usefulness of this approach was demonstrated by the labelling of apelin-13 peptide. Various fluorescent probes were readily synthesized, enabling the rapid optimization of their affinities for the apelin receptor. Thus, the first far-red fluorescent ligand with sub-nanomolar affinity for the apelin receptor was characterized and shown to track the receptor efficiently in living cells by fluorescence confocal microscopy.
Mots clés
Acylation, Fluorescent Dyes, chemistry, Hydrazines, chemical synthesis, Intercellular Signaling Peptides and Proteins, chemistry, Ligands, Peptides, chemical synthesis, Receptors, G-Protein-Coupled, chemistry
Référence
Chemistry. 2016 Jan;22(4):1399-405