SwissKnife-Inspired Multifunctional Fluorescence Probes for Cellular Organelle Targeting Based on Simple AIEgens

Anal Chem. 2019 Feb 5;91(3):2169-2176. doi: 10.1021/acs.analchem.8b04736. Epub 2019 Jan 9.

Abstract

Facile, efficient, and mass production of aggregation-induced emission (AIE) luminogens (AIEgens) with excited-state intramolecular proton transfer (ESIPT) characteristics was achieved by a one-step condensation reaction of 2-(hydrazonomethyl)phenol with benzaldehydes. The function of as-prepared AIEgens could be tuned easily by varying the functional group being carried on the phenyl ring of benzaldehyde just like a Swiss knife handle. The suitable distance and angle of the intramolecular hydrogen bond in these AIEgens endowed them with ESIPT properties, intense solid-state luminescence, and large Stokes shifts (155-169 nm). These AIEgens could not only serve as biological probes showing specific targeting to lipid droplets, endoplasmic reticulum, and lysosomes, respectively, but also generate reactive oxygen species upon visible light irradiation to make them promise for photodynamic therapy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / chemistry*
  • Cell Survival
  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Light
  • Molecular Structure
  • Optical Imaging*
  • Organelles / chemistry*
  • Phenols / chemistry*
  • Protons
  • Reactive Oxygen Species / analysis
  • Structure-Activity Relationship

Substances

  • Benzaldehydes
  • Fluorescent Dyes
  • Phenols
  • Protons
  • Reactive Oxygen Species