Fluorogenic iminosydnones: bioorthogonal tools for double turn-on click-and-release reactions

Chem Commun (Camb). 2020 Jul 4;56(52):7183-7186. doi: 10.1039/d0cc03067h. Epub 2020 May 28.

Abstract

In this article, we report the synthesis and use of iminosydnone-based profluorophores as bioorthogonal cleavable linkers for imaging applications. These linkers react with cycloalkynes via subsequent [3+2] cycloaddition and retro Diels-Alder reactions, allowing simultaneous release of two dyes in biological media.

MeSH terms

  • Animals
  • CHO Cells
  • Catalysis
  • Click Chemistry
  • Cricetulus
  • Cycloaddition Reaction
  • Cyclooctanes / chemistry
  • Fluorescence Resonance Energy Transfer
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / metabolism
  • Optical Imaging
  • Palladium / chemistry
  • Pyrazoles / chemistry
  • Solvents / chemistry
  • Structure-Activity Relationship
  • Sydnones / chemical synthesis*
  • Sydnones / metabolism

Substances

  • Cyclooctanes
  • Fluorescent Dyes
  • Pyrazoles
  • Solvents
  • Sydnones
  • Palladium