Abstract
Bisulfite (HSO3-) has been widely used as an important food additive in daily life. Furthermore, a normal amount of HSO3- plays a significant role in biological systems. However, excessive intake of HSO3- will lead to a variety of diseases. Therefore, it is of great significance to develop an efficient fluorescent probe that can be used for detection of HSO3- in biological systems and food samples. In this work, a near-infrared (NIR) emitted fluorescent probe (SZY) based on hemicyanine dye was successfully synthesized and applied to detect HSO3- in several food samples and live animals. The proposed nucleophilic addition sensing mechanism of SZY towards HSO3- has been confirmed by 1H NMR titration, high resolution mass spectrometry (HR-MS) and density functional theory (DFT) theoretical computation. The HSO3--induced nucleophilic reaction with α,β-unsaturated CC binding of SZY results in the dramatic decline of the UV-vis absorption and remarkable quenching of the fluorescence emission. SZY features the advantages of near infrared emission (centered at 720nm), high water solubility (in 98% aqueous solution), fast response time (50s), large Stokes shift (244nm) and low cytotoxicity. The probe SZY was successfully applied to image of HSO3- in live nude mouse and adult zebrafish. Semi-quantitatively analyzing the HSO3- level by "naked eye" in several food samples including canned fruit, white wine, white sugar and jasmine tea drinks has been realized by the colorimetric method.
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