A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid
白佳坤 1徐婷 1张璐 1彭江 1李宇强 2贾俊辉1
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作者信息
1. 山西师范大学化学与材料科学学院,教育部磁性分子与磁信息材料重点实验室,太原 030032
2. 中北大学化学与化工学院,太原 030051
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摘要
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.
Abstract
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.
关键词
大斯托克斯位移/次氯酸检测/比色荧光双响应/红光发射/细胞成像
Key words
large Stokes shift/hypochlorite detection/colorimetric and fluorescent dual-response/red-emitting/cell imaging
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