Convenient Access to Fluorescent Probes by Chemoselective Acylation of Hydrazinopeptides: Application to the Synthesis of the First Far‐Red Ligand for Apelin Receptor Imaging |
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| Authors: | Dr Jean‐François Margathe Dr Xavier Iturrioz Pierre Regenass Iuliia A Karpenko Dr Nicolas Humbert Dr Hugues de?Rocquigny Prof Marcel Hibert Dr Catherine Llorens‐Cortes Dr Dominique Bonnet |
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| Institution: | 1. Laboratoire d'Innovation Thérapeutique, UMR7200 CNRS/Université de Strasbourg, Labex MEDALIS, Faculté de Pharmacie, Illkirch, France;2. Neuropeptides Centraux et Régulations Hydrique et Cardiovasculaire, UMR 7241/Inserm U1050, Centre Interdisciplinaire de Recherche en Biologie, Collège de France, Paris, France;3. Laboratoire de Biophotonique et Pharmacologie, UMR-CNRS 7213, Faculté de Pharmacie, Illkirch, France |
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| Abstract: | 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. |
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| Keywords: | chemical ligation fluorescent probes G-protein-coupled receptors hydrazinopeptides receptors |
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