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Chem Commun (Camb). 2018 Sep 20;54(76):10758-10761. doi: 10.1039/c8cc06070c.

Sydnone-coumarins as clickable turn-on fluorescent sensors for molecular imaging.

Chemical communications (Cambridge, England)

Elodie Decuypère, Margaux Riomet, Antoine Sallustrau, Sarah Bregant, Robert Thai, Grégory Pieters, Gilles Clavier, Davide Audisio, Frédéric Taran

Affiliations

  1. Service de Chimie Bio-organique et Marquage DRF-JOLIOT-SCBM, CEA, Université Paris-Saclay, 91191 Gif-sur-Yvette, France. [email protected].

PMID: 30198046 DOI: 10.1039/c8cc06070c

Abstract

Copper-catalyzed and copper-free sydnone-alkyne cycloaddition reactions have emerged as complementary click tools for chemical biology but their use in bioorthogonal labeling is still in its infancy. Herein, combinations of alkynes and coumarin-sydnones were screened for their ability to generate pyrazole products displaying strong fluoroscence enhancement compared to reactants. One sydnone was identified as a particularly suitable new turn-on probe for protein labeling.

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