Towards perylenequinonoid: Effective application to reversible fluorescent probe for monitoring hydrogen persulfide in solvents and living cells

Talanta. 2017 Mar 1:164:529-533. doi: 10.1016/j.talanta.2016.12.020. Epub 2016 Dec 10.

Abstract

Hydrogen persulfide (H2S2), as a direct redox form of H2S, may have its own physiological processes in maintaining intracellular redox homeostasis. The research on hydrogen persulfide was rapidly growing. As it is the actual signalling molecules derived from hydrogen sulfide, reversible detection of hydrogen persulfide changes in cells is of great significance. To address this critical need, we present a reversible fluorescent switch-on H2S2 probe, the tautomeric of 6, 7-dihydroxyperylene-1, 12-quinone (DHPQ), capable of tracking H2S2 in solvents and living cells. The probe can be applied to quantified H2S2 expressions ranging linearly from 2.0×10-6 to 2.0×10-5 M. The limit of detection was found to be 1.82×10-8M. In addition, the fluorescent alterations are remarkably specific for H2S2 in the presence of other reactive sulfur species. These features are favorable for imaging application. Taking advantage of favorable cycle stability and admirable selectivity, the DHPQ dye can be used as a reversible fluorescent platform to construct novel H2S2 probes. Since such reversible H2S2 probes are rare, this work provide a potential approach for reversible probing fluctuation of hydrogen persulfide in biological systems.

Keywords: Bioimaging; Excited-state intramolecular hydrogen atom transfer; Hydrogen persulfide detection; Perylenequinonoid dye; Reversible fluorescent probe.

MeSH terms

  • Cell Survival
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / analysis*
  • Hydrogen Sulfide / chemistry*
  • Optical Imaging
  • Perylene / analogs & derivatives*
  • Perylene / chemistry*
  • Quinones / chemistry*
  • Solvents / chemistry*

Substances

  • Fluorescent Dyes
  • Quinones
  • Solvents
  • Perylene
  • Hydrogen Sulfide