p-Aminostyryl thiazole orange derivatives for monitoring mitochondrial viscosity in live cells

Viscosity of cell microenvironment plays a significant role in maintaining the normal life activities of cells. Particularly, the abnormal viscosity in mitochondria is closely associated with lots of diseases and cellular dysfunctions. Herein, we developed a group of p-aminostyryl thiazole orange derivatives with different amino side chains. These probes showed good fluorescence response to viscosity with twisted intramolecular charge transfer mechanism, among them, the probes with diethylamino (TOB), dibutylamino (TOC) and pyrrolidin (TOE) side chains showed better response to the viscosity with 78-fold, 55-fold, and 88-fold fluorescence enhancement in 95% glycerol solution respectively. TOB, TOC, and TOE could enter live cells and mainly located in mitochondria. Treatment HeLa cells with nystatin, lipopolysaccharide or oleic acid caused significant fluorescence enhancement of these probes, suggesting the good potential for monitoring the variation of mitochondrial viscosity, as well as for investigating the related physiological process of inflammation and lipid metabolism.