Sugar-bearing tetraphenylethylene: novel fluorescent probe for studies of carbohydrate-protein interaction based on aggregation-induced emission

Neutral sugar-bearing tetraphenylethenes (TPE) are designed and prepared as turn-on luminescent sensors for lectins and glycosidases based on aggregation-induced emission. Through aggregation derived from carbohydrate-lectin binding, multivalent mannosyl-bearing TPE shows a good selectivity and sensitivity to Con A by switching on the fluorescence of water-soluble tetraphenylethylene-based glyco-conjugates in aqueous solution. Meanwhile, cellobiosyl-bearing TPE can be used to investigate enzymatic hydrolysis based on emission enhancing by glycosidase-induced aggregation.