4.4 Article

Fluorogenic probes based on polycyclic sydnone scaffolds

Journal

TETRAHEDRON
Volume 76, Issue 51, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131250

Keywords

Sydnones; Mesoionics; Click chemistry; Fluorescent probes; Cycloadditions

Funding

  1. French Research National Agency [ANR-17-CE07-0035-01]
  2. CEA

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We report the synthesis, photophysical characterization and kinetics of a series of polycyclic sydnone derivatives as a potential new class of fluorogenic clickable reagents. After strain-promoted cycloaddition with cyclooctyne BCN, the fluorescence generated by pyrazole products displayed up-to 115-fold fluo-rescence enhancement compared to reactants. These preliminary results are of interest for possible future applications in bioorthogonal chemistry. (C) 2020 Elsevier Ltd. All rights reserved.

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