Novel lysosome-targeted fluorescent molecular rotors based on a cyanine-like modular system and their application in living cells.

[Display omitted] • DpIn and NaIn were synthesized involving of indolium units with aryldiol moiety. • DpIn, a lysosome-targeting probe, showed strong NIR emission in viscous solutions. • NaIn was an ideal lysosome-targeting & viscous-sensitivity probe in living cells. Two novel fluorescence molecular rotors DpIn and NaIn were designed and synthesized involving of indolium units linked with meta -diphenol or ortha -naphthalenediol moiety, respectively. They underwent intramolecular charge transfer to form a cyanine-like modular system at a physiological pH. In glycerol aqueous solutions, the probe DpIn exhibited NIR strong emission (3-fold) at ca. 700 nm, while the probe NaIn displayed a turn-on emission (8-fold) with a larger Stokes shift (⊿λ ≈ 97 nm). The HeLa cell imaging experiments indicated probe DpIn and NaIn both exhibited excellent selectivity for staining intracellular lysosomes instead of mitochondria. 1H NMR spectra revealed that more electrons were accumulated around benzene ring of indolium groups, which could be the evidence for its basic character leading to the lysosomes targeted staining. Furthermore, the probe NaIn proved to be an ideal lysosome-targeting tracer for monitor the changes of viscosity caused by stimuli in living cells. [ABSTRACT FROM AUTHOR]