Fluorogenic probes based on polycyclic sydnone scaffolds

TETRAHEDRON

卷:76

Article

Plougastel, Lucie¹  Lamaa, Diana¹  Yen-Pon, Expedite¹  Audisio, Davide¹  Taran, Frederic¹ 

[1] Univ Paris Saclay, Serv Chim Bioorgan & Marquage SCBM, CEA DRF JOLIOT, F-91191 Gif Sur Yvette, France

关键词: Sydnones;    Mesoionics;    Click chemistry;    Fluorescent probes;    Cycloadditions;   

DOI  :  10.1016/j.tet.2020.131250

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free