设计、合成了一种基于巴比妥酸衍生物的具有D-π-A结构的光学探针3。该探针能够作为一种高度灵敏和选择性的次氯酸指示剂，快速实现对次氯酸的比色和荧光信号(开-关)的双响应(约15 s)。推测的响应机制是ClO-与C=C之间发生了亲电加成和氧化裂解反应，导致探针的D-π-A结构遭到破坏，从而阻断了其分子内电荷转移(intramolecular charge transfer，ICT)进程。探针只需一步即可合成，同时具有红光发射(628 nm)和较大的斯托克斯位移(158 nm)，检测限(limit of detection，LOD)低至14nmol·L-1。此外，探针还表现出低细胞毒性，并成功应用于活细胞成像。
A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid
An optical probe(3)with a donor-π-acceptor(D-π-A)structure for the detection of hypochlorous acid(HClO)was synthesized by a one-step reaction.It employed a barbituric acid derivative as the electron acceptor and 4-(dimethylamino)cinnamaldehyde as the electron donor.The probe exhibited high sensitivity and selectivity for the detection of HClO,rapidly responding with distinct colorimetric and fluorescent"on-off"signals(about 15 s).The probe displayed a linear relationship between fluorescence intensity and HClO concentration,with a low detection limit(LOD)of 14 nmol·L-1,which made it suitable for quantitative HClO detection.Moreover,the probe exhibited red light emission(628 nm)with a significant Stokes shift(158 nm)and good photostability,which provided advan-tages for its application in cell imaging.The proposed reaction mechanism,which was deduced from high-resolution mass spectrometry data,involved electrophilic addition and oxidative cleavage of the C=C bond by ClO-,which led to the disruption of the probe's D-π-A structure.Consequently,this effectively halted the intramolecular charge transfer(ICT)process of the probe.MTT cytotoxicity assays demonstrated minimal toxicity of the probe following 12,24,and 48 h of incubation with HepG2 cells.The probe was successfully applied to living cell imaging and enabled the detection of HClO via fluorescence quenching within the living cellular milieu.
large Stokes shifthypochlorite detectioncolorimetric and fluorescent dual-responsered-emittingcell imaging
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维普
