Tetraphenylethylene conjugated p-hydroxyphenacyl: fluorescent organic nanoparticles for the release of hydrogen sulfide under visible light with real-time cellular imaging

Org Biomol Chem. 2018 Oct 31;16(42):7903-7909. doi: 10.1039/c8ob01629a.

Abstract

Hydrogen sulfide (H2S) behaves like a two-edged sword, at low concentrations it has beneficial and cytoprotective effects, while at higher concentrations it exhibits toxicity. Hence there is a keen interest in developing light responsive H2S donors with a spatio-temporal controlled release. Herein, we report visible light activatable tetraphenylethylene conjugated p-hydroxyphenacyl (TPE-pHP-H2S) nanoparticles for the release of hydrogen sulfide (H2S) with a real time monitoring ability. Our newly designed photoresponsive single component organic nanoparticle based H2S donor is built by integrating the tetraphenylethylene (TPE) moiety and p-hydroxyphenacyl (pHP) group so that it can display both aggregation-induced emission (AIE) and excited state intramolecular proton transfer (ESIPT) properties. Aggregation-induced emission enhancement was exhibited by our TPE-pHP-H2S NP donor, which was then explored for the cellular imaging application. The ESIPT by the pHP moiety provided unique advantages to our TPE-pHP-H2S NP donor which include (i) the excitation wavelength extended to >410 nm (ii) a large Stokes shift (iii) a low inner filter effect and (iv) real-time monitoring of H2S release by a simple fluorescent colour change. In vitro studies showed that the TPE-pHP-H2S NP donor presents excellent properties like real-time monitoring, photoregulated H2S release and biocompatibility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Liberation*
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / chemistry*
  • Light*
  • Microscopy, Confocal
  • Models, Molecular
  • Molecular Conformation
  • Molecular Imaging / methods*
  • Nanoparticles / chemistry*
  • Stilbenes / chemistry*
  • Time Factors

Substances

  • Fluorescent Dyes
  • Stilbenes
  • tetraphenylethylene
  • Hydrogen Sulfide