A Triple-Emission Fluorescent Probe for Discriminatory Detection of Cysteine/Homocysteine, Glutathione/Hydrogen Sulfide, and Thiophenol in Living Cells

ACS Sens. 2018 Sep 28;3(9):1863-1869. doi: 10.1021/acssensors.8b00685. Epub 2018 Sep 4.

Abstract

Thiols, such as cysteine (Cys), homocysteine (Hcy), glutathione (GSH), hydrogen sulfide (H2S), and thiophenol are metabolically correlated with each other via redox reactions. As a result of the similarity of chemical properties between Cys, Hcy, GSH, H2S, and thiophenol, it is very challenging to develop an effective methodology to differentiate them. In this work, a triple-emission fluorescent probe, NCQ, was reported for the simultaneous detection of Cys/Hcy, GSH/H2S, and thiophenol with high sensitivity and selectivity. The solution of NCQ displayed distinct fluorescent signals toward Cys/Hcy, GSH/H2S, and thiophenol: blue and green for Cys/Hcy, blue for GSH/H2S, blue and red for thiophenol. Through the blue-green-red emission color combination, Cys/Hcy, GSH/H2S, and thiophenol could be discriminatively detected in solution and in living cells.

Keywords: discriminatory; fluorescent probe; imaging; thiols; triple-emission.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Color
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / toxicity
  • Cysteine / analysis*
  • Dinitrobenzenes / chemical synthesis
  • Dinitrobenzenes / chemistry
  • Dinitrobenzenes / toxicity
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / toxicity
  • Glutathione / analysis*
  • HeLa Cells
  • Homocysteine / analysis*
  • Humans
  • Hydrogen Sulfide / analysis*
  • Microscopy, Confocal / methods
  • Microscopy, Fluorescence / methods
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Oxadiazoles / toxicity
  • Phenols / analysis*
  • Sulfhydryl Compounds / analysis*

Substances

  • Coumarins
  • Dinitrobenzenes
  • Fluorescent Dyes
  • Oxadiazoles
  • Phenols
  • Sulfhydryl Compounds
  • Homocysteine
  • thiophenol
  • Glutathione
  • Cysteine
  • Hydrogen Sulfide