Carbofluoresceins and carborhodamines as scaffolds for high-contrast fluorogenic probes

ACS Chem Biol. 2013;8(6):1303-10. doi: 10.1021/cb4000822. Epub 2013 Apr 24.

Abstract

Fluorogenic molecules are important tools for advanced biochemical and biological experiments. The extant collection of fluorogenic probes is incomplete, however, leaving regions of the electromagnetic spectrum unutilized. Here, we synthesize green-excited fluorescent and fluorogenic analogues of the classic fluorescein and rhodamine 110 fluorophores by replacement of the xanthene oxygen with a quaternary carbon. These anthracenyl "carbofluorescein" and "carborhodamine 110" fluorophores exhibit excellent fluorescent properties and can be masked with enzyme- and photolabile groups to prepare high-contrast fluorogenic molecules useful for live cell imaging experiments and super-resolution microscopy. Our divergent approach to these red-shifted dye scaffolds will enable the preparation of numerous novel fluorogenic probes with high biological utility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Cell Survival
  • Fluorescein / analysis
  • Fluorescein / chemical synthesis
  • Fluorescein / chemistry*
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Microscopy, Confocal
  • Rhodamines / analysis
  • Rhodamines / chemical synthesis
  • Rhodamines / chemistry*
  • Xanthenes / chemistry

Substances

  • Fluorescent Dyes
  • Rhodamines
  • Xanthenes
  • rhodamine 110
  • Carbon
  • Fluorescein