Rotor-Tuning Boron Dipyrromethenes for Dual-Functional Imaging of Aß Oligomers and Viscosity.

ABSTRACT

Alzheimer's disease (AD), known as a common incurable and elderly neurodegenerative disease, has been widely explored for accurate detection of its biomarker (Aß oligomers) for early diagnosis. Although great efforts have been made, it is still of great importance to develop fluorescence probes for Aß oligomers with good selectivity and low background. Herein, starting from BODIPY493/503 (a commercial dye for neutral lipid droplets), which exhibited a small Stokes shift and no response toward Aß peptides, two fluorescence probes 5MB-SZ and B-SZ with a benzothiazole rotor at the 2-position of the BODIPY core and a methyl or benzyl group at the meso position have been designed and synthesized, which exhibited excellent optical properties/stability and could successfully image ß-amyloid fibrils and viscosity. Upon exposure to Aß oligomers, the fluorescence intensity of 5MB-SZ was enhanced by 43.64-fold with the corresponding fluorescence quantum yields changing from 0.85% to 27.43%. Meanwhile, probe 5MB-SZ showed a highly sensitive viscosity response in both solutions and living cells. In vitro and in vivo experiments confirmed that probe 5MB-SZ exhibited an excellent capacity for imaging ß-amyloid fibrils. Therefore, 5MB-SZ, as a rotor-tuning BODIPY analogue, could possibly serve as a highly potential and powerful fluorescence probe for early diagnosis of AD.