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We report a fluorescent nanoprobe based on the co-assembly of amphiphilic BODIPY and fluorescein for selective detection of GSH. The amphiphilic BODIPY derivative, consisting of hydrophobic BODIPY unit and hydrophilic PEG chains, co-assembled with fluorescein to give non-fluorescent nanoparticles due to the aggregation caused quenching. Upon addition of GSH, the thiol group of GSH reacted with BODIPY through nucleophilic substitution to afford highly polar GSH-substituted BODIPY with high solubility in water, resulting in the disassembly of the nanoparticles. The GSH-induced disassembly of the nanoparticles released the highly fluorescent BODIPY derivative and fluorescein, enabling the dual-emissive detection of GSH. This nanoprobe was applied for the dual-channel fluorescence imaging of GSH in living cells. [ABSTRACT FROM AUTHOR]

We report a fluorescent probe for thiophenol based on a new sensing strategy via the aromatic nucleophilic substitution reaction between thiophenol and mono-chlorinated BODIPY, which enable the ratiometric detection of thiophenol. The probe showed fast response towards thiophenols over aliphatic thiols and displayed ∼650-fold fluorescence ratio variation and a remarkable detection limit of 36.9 nM. A linear calibration graph indicated that it can be potentially employed to detect thiophenol quantitatively. Its potential applications were confirmed by employing it for detection of thiophenol in water samples and fluorescence imaging of thiophenol in living cells. [ABSTRACT FROM AUTHOR]

Photothermal therapy (PTT) is one of innovative therapeutics types that have been widely applied in cancer treatment, antibiosis and insecticide. It is of significance to investigate photothermal conversion agents (PCAs) with outstanding photothermal conversion ability, photostability and biocompatibility. Here, we developed three novel phenothiazine-based aza-BODIPYs for high-efficient PTT applications. Phenothiazine, as the electron-donating moiety, was introduced into aza-BODIPY core to achieve red-shifted absorption band (∼20–40 nm) with λ max at 730–745 nm and high molar extinction efficient (105 M−1 cm−1). TEG linker was decorated for further increasing the hydrophilicity and biocompatibility of aza-BODIPYs. After self-assembly, the nanoparticles exhibited the preferable photothermal conversion efficient (53–63%) and high photostability with the appropriate hydrated sizes (60–110 nm) and homogenous morphologies. Finally, the aza-BODIPY nanoparticles can significantly decrease the HeLa cell viability under 808 nm laser irradiation, but have the negligible cytotoxicity in dark environments. The series of phenothiazine-based aza-BODIPY PCAs have much potential for the more applications of clinic photothermal therapy in future. • Phenothiazine is the electron-donating and large π-conjugated moiety to red-shift the absorption band of aza-BODIPYs. • Three amphiphilic aza-BODIPYs exhibit red-shifted absorption band and ca. 105 M−1 cm−1 molar extinction coefficient (ε). • The aza-BODIPY nanoparticles show outstanding photothermal efficiency (over 50%) and photostability. • The aza-BODIPY nanoparticles have preferable phototoxicity under 808 nm laser irradiation, but negligible toxicity in dark. [ABSTRACT FROM AUTHOR]