4-4-difluoro-4-bora-3a-4a-diaza-s-indacene and thiophenol

A highly selective and sensitive turn-on red fluorescent 1-amino BODIPY-based probe (where BODIPY denotes indole-based boron-dipyrromethene) with high off-to-on contrast ratio has been developed. The probe displayed selective response to thiophenols over aliphatic thiols. Probe 1 is promising for the quantitative detection of thiophenol with a linear response from 6 × 10(-6) M to 1 × 10(-4) M, and the detection limit for thiophenol (PhSH) reaches 4 × 10(-6) M measured in acetonitrile/PBS buffer. The detection limit could be improved to 37 nM (detection limit to 4 ppb) in water when 1% Tween 20 was used to assist the dissolvation of probe 1 in water. Probe 1 is also a useful fluorescent probe for detecting thiophenols in living cells in red emission, which may greatly improve the detectable sensitivity.

Topics: Boron Compounds; Carcinoma, Hepatocellular; Contrast Media; Crystallography, X-Ray; Fluorescent Dyes; Humans; Hydrogen-Ion Concentration; Image Processing, Computer-Assisted; Limit of Detection; Liver Neoplasms; Microscopy, Fluorescence; Phenols; Sensitivity and Specificity; Sulfhydryl Compounds; Tumor Cells, Cultured

A BODIPY-based selective thiophenol probe capable of discriminating aliphatic thiols is reported. The fluorescence off-on effect upon reaction with thiol is elucidated with theoretical calculations. The sensing of thiophenol is associated with a color change from red to yellow and 63-fold enhancement in green fluorescence. Application of the probe for selective thiophenol detection is demonstrated by live cell imaging.

Topics: Boron Compounds; Colorimetry; Fluorescent Dyes; HeLa Cells; Humans; Hydrogen-Ion Concentration; Models, Theoretical; Phenols; Quantum Theory; Sulfhydryl Compounds