Cyclo-Ketal Xanthene Dyes: A New Class of Near-Infrared Fluorophores for Super-Resolution Imaging of Live Cells

Chemistry. 2021 Feb 19;27(11):3688-3693. doi: 10.1002/chem.202005296. Epub 2021 Jan 26.

Abstract

Newly emerging super-resolution imaging techniques provide opportunities for precise observations on cellular microstructures. However, they also impose severe demands on fluorophores. Here, we develop a new series of NIR xanthene dyes, named as KRhs, by replacing the 10-position O of rhodamines with a cyclo-ketal. KRhs display an intense NIR emission peak at 700 nm with fluorescence quantum yields up to 0.64. More importantly, they, without the aid of enhancing buffer, exhibit stochastic fluorescence off-on switches to support time-resolved localization of single fluorophore. KRhs are functionalized into KRh-MitoFix, KRh-Mem and KRh-Halo that demonstrate mitochondria, plasma membrane and fusion protein targeting ability, respectively. Consequently, these KRh probes demonstrate straightforward usage for super-resolution imaging of these targets in live cells. Therefore, KRhs merit future development for fluorescence labeling and super-resolution imaging in the NIR region.

Keywords: element replacement; near-infrared fluorophore; super-resolution imaging; xanthene dyes.

MeSH terms

  • Cell Survival
  • Fluorescence
  • Fluorescent Dyes / analysis*
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Infrared Rays*
  • Optical Imaging / methods*
  • Rhodamines / chemistry
  • Xanthenes / analysis*
  • Xanthenes / chemistry*

Substances

  • Fluorescent Dyes
  • Rhodamines
  • Xanthenes