A "distorted-BODIPY"-based fluorescent probe for imaging of cellular viscosity in live cells

Chemistry. 2014 Apr 14;20(16):4691-6. doi: 10.1002/chem.201304296. Epub 2014 Mar 5.

Abstract

Cellular viscosity is a critical factor in governing diffusion-mediated cellular processes and is linked to a number of diseases and pathologies. Fluorescent molecular rotors (FMRs) have recently been developed to determine viscosity in solutions or biological fluid. Herein, we report a "distorted-BODIPY"-based probe BV-1 for cellular viscosity, which is different from the conventional "pure rotors". In BV-1, the internal steric hindrance between the meso-CHO group and the 1,7-dimethyl group forced the boron-dipyrrin framework to be distorted, which mainly caused nonradiative deactivation in low-viscosity environment. BV-1 gave high sensitivity (x=0.62) together with stringent selectivity to viscosity, thus enabling viscosity mapping in live cells. Significantly, the increase of cytoplasmic viscosity during apoptosis was observed by BV-1 in real time.

Keywords: dyes; fluorescent probes; imaging agents; steric hindrance; viscosity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron / chemistry
  • Boron Compounds / chemistry*
  • Boron Compounds / metabolism
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • Humans
  • MCF-7 Cells
  • Microscopy, Confocal
  • Pyrroles / chemistry*
  • Pyrroles / metabolism
  • Viscosity

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • BV-1 compound
  • Boron Compounds
  • Fluorescent Dyes
  • Pyrroles
  • Boron