New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Chemistry. 2019 Jun 18;25(34):7998-8002. doi: 10.1002/chem.201900412. Epub 2019 May 17.

Abstract

In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near-infrared-light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.

Keywords: cyanines; fluorescence; life cell imaging; near-infrared light; polyfluorinated molecules.

MeSH terms

  • A549 Cells
  • Carbocyanines / chemical synthesis
  • Carbocyanines / chemistry*
  • Cell Line
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Halogenation
  • HeLa Cells
  • Hep G2 Cells
  • Human Umbilical Vein Endothelial Cells
  • Humans
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / chemistry*
  • Infrared Rays
  • Microscopy, Confocal / methods
  • Microscopy, Fluorescence / methods*
  • Mitochondria / ultrastructure*
  • Optical Imaging / methods*

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Hydrocarbons, Fluorinated