Utilizing a Pyrazine-Containing Aggregation-Induced Emission Luminogen as an Efficient Photosensitizer for Imaging-Guided Two-Photon Photodynamic Therapy

Chemistry. 2018 Nov 7;24(62):16603-16608. doi: 10.1002/chem.201803580. Epub 2018 Oct 17.

Abstract

The development of novel photosensitizers with aggregation-induced emission (AIE) characteristics has aroused tremendous interest, because it could combine efficient bioimaging with precise photodynamic therapy, which would thus dramatically promote applications in biomedical treatment. Among various AIE luminogens (AIEgens), heterocycle-containing molecules are highly promising for this usage because of their high photostability and tunable electronic properties. In this work, a pyrazine-containing AIEgen with a dicyanopyrazine moiety as an electron acceptor and a triphenylamine unit as an electron donor was chosen for study. The V-shaped donor-π-acceptor-π-donor structure of the AIEgen endowed its nanoparticles with excellent nonlinear optical properties for two-photon cell imaging under near-infrared laser excitation. Also, under the same excitation, the nanoparticles could produce reactive oxygen species and further kill the cells efficiently and accurately. The present work thus presents a pyrazine-containing AIEgen as a new photosensitizer for imaging-guided two-photon photodynamic therapy and gives more opportunities for deep-tissue treatment of cancer in future research.

Keywords: aggregation-induced emission; nonlinear optics; photodynamic therapy; photosensitizers; two-photon imaging.

MeSH terms

  • Cell Survival / drug effects
  • Cell Survival / radiation effects
  • Dynamic Light Scattering
  • Fluorescent Dyes / chemistry
  • HeLa Cells
  • Humans
  • Infrared Rays
  • Microscopy, Electron, Transmission
  • Microscopy, Fluorescence, Multiphoton
  • Nanoparticles / chemistry
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Photochemotherapy
  • Photons
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology
  • Photosensitizing Agents / therapeutic use
  • Pyrazines / chemistry*
  • Pyrazines / pharmacology
  • Pyrazines / therapeutic use
  • Reactive Oxygen Species / metabolism
  • Silicon Dioxide / chemistry

Substances

  • Fluorescent Dyes
  • Photosensitizing Agents
  • Pyrazines
  • Reactive Oxygen Species
  • Silicon Dioxide