A highly sensitive ratiometric fluorescence probe for sensing and imaging sulfite in food samples and living cells.

In this work, a ratiometric and chromogenic fluorescent probe 1 was synthesized for the detection of SO32-. The probe 1 at PBS (10 mM, pH = 7.4) presented a marked emission band at 661 nm. Upon addition of SO32- ions, a highly emissive adduct with a marked fluorescence at 471 nm were obtained through a Michael addition. The probe 1 displayed a noticeable fluorescence ratiometric response with a large shift (190 nm) in emission wavelength. The probe can quantitatively detect SO32- with high specificity, fast response (within 130 s) as well as low detection limit (13 nM), and a large Stokes shift (139 nm). Fluorescence imaging of HeLa cells indicated that 1 could be used for monitoring the intrinsically generated intracellular SO32- in living cells by ratiometric fluorescence imaging. Furthermore, 1 could be application in real water and sugar samples with high sensitivity and good recoveries.

Mitochondria-targeted fluorescent probe for visualization of exogenous and endogenous methylglyoxal in living cells.

An activatable mitochondria-targeted fluorescent probe Hcy-OPD was synthesized for the detection of methylglyoxal (MGO). For the introduction of a preorganized isopropylamino group on the aromatic o-diamine framework to regulate the hindrance effect, Hcy-OPD showed high selectivity and sensitivity (0.22 µM) for monitoring MGO. The probe can be applied successfully in the imaging of exogenous and endogenous MGO in living cells.

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