Facile mitochondria localized fluorescent probe for viscosity detection in living cells

Fluorescent probes act as a powerful tool to understand the function of intracellular viscosity, which are closely associated with many functional disorders and diseases. Herein we report a boron-dipyrromethene (4,4-difluoro-4-borata-3a,4a-diaza-s-indacene, BODIPY) group based new fluorescent probe (BV-1), which was synthesized facilely by a one-step Knoevenagel-type condensation reaction, to detect viscosity in living cells with high selectivity and sensitivity. DFT calculation demonstrated that the unsaturated moiety at the meso-position of BODIPY suppressed the fluorescence via twisted intramolecular charge transfer (TICT) mechanism in low viscosity media. By restricting the rotation of the molecular rotor, the fluorescence would be enhanced significantly with redshift in emission wavelength in high viscosity conditions. The fluorescence intensity ratio (log (I/I0)) at 570 nm showed a good linearity (R2 = 0.991) with the viscosity (log η) in the range of 2–868 cP. And the limit of detection (LOD) and limit of quantification (LOQ) for viscosity were calculated to be 0.16 cP and 0.54 cP, respectively. BV-1 was demonstrated to be mitochondria localized with low cytotoxicity. Utilizing the new probe BV-1, the changes in mitochondrial viscosity caused by monensin or nystatin have been monitored successfully in real time. This work will provide new efficient ways for the development of viscosity probes, which are expected to be used for the study of intracellular viscosity properties and functions.