Supramolecular Assembly of TPE‐Based Glycoclusters with Dicyanomethylene‐4H‐pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Abstract

Twor ed-emitting dicyanomethylene-4H-pyran (DM) based fluorescent probesw ere designeda nd used for peroxynitrite (ONOO À)d etection. Nevertheless, the aggregation-caused quenching effect diminished the fluorescence and restricted their further applications. To overcomet his problem, tetraphenylethylene (TPE) based glycoclusters were used to self-assemblewith these DM probes to obtain supramolecular water-soluble glyco-dots. This self-assemblys trat-egy enhanced the fluorescencei ntensity,l eading to an enhanced selectivity and activity of the resulting glyco-dot comparing to DM probes alone in PBS buffer.T he glyco-dots also exhibitedb etter results during fluorescences ensing of intracellular ONOO À than the probes alone, thereby offering scope for the development of others imilars upramolecular glyco-systemsf or chemical biologicals tudies.

A general strategy to the intracellular sensing of glycosidases using AIE-based glycoclusters

“…We have previously developed a D-A-type AIE fluorogen (AIEgen) based on a tetraphenylethylene (TPE) core conjugated with a dicyano-methylene-4H-pyran (DCM) derivative (TPE-DCM or TD) with a reddish fluorescence emission ( = 625 nm). 33,34 TPE and DCM were conjugated 𝜆 𝑒𝑚 𝑚𝑎𝑥 to each other through an ethylene bridge to increase the delocalization of electrons in the system. Unlike previous reports that directly glycosylate phenol groups of conjugated dyes, we introduced a pair of dendritic arms on both phenol moieties of TPE (Fig.…”

Synthetic approaches of carbohydrate based self-assembling systems

“…Dong et al have synthesized a series of tetraphenylethylene (TPE)-based glycoclusters and studied the self-assembling properties and fluorescence properties. 96,97 As shown in Fig. 14…”

Progress of Dicyanomethylene-4H-Pyran Derivatives in Biological Sensing Based on ICT Effect

“…Thus, the probe lights up afresh. Based on this principle, a series of “off–on” DCM derivatives have been successfully constructed for the detection of ions, reactive oxygen species (ROS), and biological macromolecules in cells ( Li et al, 2014 ; Wang et al, 2019 ; Yang et al, 2019 ; Dong et al, 2020 ; Ling et al, 2021 ). Although much attention has been paid on this kind of probes in recent years, a systematic overview is rarely reported.…”