A 7-Hydroxybenzoxazinone-Containing Fluorescence Turn-On Probe for Biothiols and Its Bioimaging Applications

Molecules. 2019 Aug 27;24(17):3102. doi: 10.3390/molecules24173102.

Abstract

In this work, a novel 7-hydroxybenzoxazinone-based fluorescent probe (PBD) for the selective sensing of biothiols is reported. Upon treatment with biothiols, PBD shows a strong fluorescence enhancement (up to 70-fold) and a large Stokes shift (155 nm). Meanwhile, this probe exhibits high resistance to interference from other amino acids and competing species. PBD features good linearity ranges with a low detection limit of 14.5 nM for glutathione (GSH), 17.5 nM for cysteine (Cys), and 80.0 nM for homocysteine (Hcy), respectively. Finally, the potential utility of this probe for biothiol sensing in living HeLa cells is demonstrated.

Keywords: 2,4-dinitrobenzenesulfonate; 7-hydroxy-3-phenyl-benzoxazinone; biothiols; fluorescence probe; large Stokes shift.

MeSH terms

  • Benzoxazines / chemistry*
  • Biosensing Techniques / methods*
  • Cysteine / analysis
  • Fluorescent Dyes / chemistry*
  • Glutathione / analysis
  • HeLa Cells
  • Homocysteine / analysis
  • Humans
  • Limit of Detection
  • Optical Imaging

Substances

  • Benzoxazines
  • Fluorescent Dyes
  • Homocysteine
  • Glutathione
  • Cysteine