Fluorous Soluble Cyanine Dyes for Visualizing Perfluorocarbons in Living Systems

J Am Chem Soc. 2020 Sep 16;142(37):16072-16081. doi: 10.1021/jacs.0c07761. Epub 2020 Sep 4.

Abstract

The bioorthogonal nature of perfluorocarbons provides a unique platform for introducing dynamic nano- and microdroplets into cells and organisms. To monitor the localization and deformation of the droplets, fluorous soluble fluorophores that are compatible with standard fluorescent protein markers and applicable to cells, tissues, and small organisms are necessary. Here, we introduce fluorous cyanine dyes that represent the most red-shifted fluorous soluble fluorophores to date. We study the effect of covalently appended fluorous tags on the cyanine scaffold and evaluate the changes in photophysical properties imparted by the fluorous phase. Ultimately, we showcase the utility of the fluorous soluble pentamethine cyanine dye for tracking the localization of perfluorocarbon nanoemulsions in macrophage cells and for measurements of mechanical forces in multicellular spheroids and zebrafish embryonic tissues. These studies demonstrate that the red-shifted cyanine dyes offer spectral flexibility in multiplexed imaging experiments and enhanced precision in force measurements.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Carbocyanines / chemical synthesis
  • Carbocyanines / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorocarbons / analysis*
  • Microscopy, Fluorescence
  • Molecular Structure
  • Optical Imaging
  • Solubility
  • Zebrafish

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Fluorocarbons