γ-Resorcyclic Acid-Based AIEgens for Illuminating Endoplasmic Reticulum

Chemistry. 2022 May 25;28(30):e202200203. doi: 10.1002/chem.202200203. Epub 2022 Apr 20.

Abstract

Endoplasmic reticulum (ER) has emerged as one of the interesting sub-cellular organelles due to its role in myriads of biological phenomena. Subsequently, visualization of the structure-function and dynamics of ER remained a major challenge to understand its involvement in different diseased states including cancer. To illuminate the ER, herein we have designed and synthesized γ-resorcyclic acid-based small molecules, which showed remarkable aggregation-induced emission (AIE) property in water. This AIE property was originated from the dual intramolecular H-bonding leading to the self-assembled 2D aggregation confirmed by pH- and temperature-dependent fluorescence quenching studies as well as scanning electron microscopy. These small molecules illuminated the sub-cellular ER in HeLa cervical cancer cells as well as non-cancerous RPE-1 human retinal epithelial cells within 1 h. These novel small molecules have the potential to light up ER chemical biology in diseased states.

Keywords: aggregation-induced emission; endoplasmic reticulum; hydrazide-hydrazones; intramolecular dual H-bonding.

MeSH terms

  • Endoplasmic Reticulum*
  • Fluorescence
  • HeLa Cells
  • Humans