A colorimetric fluorescent probe for reversible detection of HSO3-/H2O2 and effective discrimination of HSO3-/ClO- and its application in food and bioimaging.

Yuexing Gao, Yan Peng, Lei Shi, Siyun Zhang, Ruiyang Bai, Yunhe Lang, Yonggui He, Buyue Zhang, Ziyi Zhang, Xiufeng Zhang
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Abstract

In view of the significant role of reactive sulfur species (RSS) and reactive oxygen species (ROS) in maintaining the redox homeostasis of organisms, we proposed a colorimetric fluorescent probe (HTN) for reversible detection of HSO3-/H2O2 and effective discrimination of HSO3-/ClO-. C = C is the active site for the Michael addition of HSO3- and the oxidation of ClO-. When HTN interacts with HSO3- and ClO-, it exhibits fluorescence quenching. The addition of oxidizing H2O2 to the system can restore the conjugate structure of the addition product of HSO3- (HTN-HSO3-) and the fluorescence recovery, but it cannot restore the structure of the oxidation product of ClO- (HTN-ClO-). By studying the change of the reversibility/non-reversibility of the probe structure with the addition of H2O2, the purpose of reversible detection of HSO3-/H2O2 and distinguishing HSO3-/ClO- is achieved. In addition, HTN can not only be used as a fluorescent ink to detect HSO3- on the test paper, but also has excellent detection effect on HSO3- and ClO- in real food samples and water samples. Meantime, HTN has good biocompatibility and can target mitochondria to achieve reversible detection of HSO3-/H2O2 and effective discrimination of HSO3-/ClO- in living cells. Therefore, HTN has great potential as a molecular tool for studying redox homeostasis in the interaction network of complex living systems.

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用于可逆检测 HSO3-/H2O2 和有效区分 HSO3-/ClO- 的比色荧光探针及其在食品和生物成像中的应用。
鉴于活性硫物种(RSS)和活性氧物种(ROS)在维持生物体氧化还原平衡中的重要作用,我们提出了一种比色荧光探针(HTN),用于可逆检测 HSO3-/H2O2,并有效区分 HSO3-/ClO-。C = C 是 HSO3- 迈克尔加成和 ClO- 氧化的活性位点。当 HTN 与 HSO3- 和 ClO- 作用时,会出现荧光淬灭。向体系中加入氧化性 H2O2 可以恢复 HSO3- 的加成产物(HTN-HSO3-)的共轭结构和荧光恢复,但不能恢复 ClO- 的氧化产物(HTN-ClO-)的结构。通过研究加入 H2O2 后探针结构的可逆/不可逆变化,达到了可逆检测 HSO3-/H2O2、区分 HSO3-/ClO-的目的。此外,HTN 不仅可以作为荧光墨水检测试纸上的 HSO3-,而且对实际食品样品和水样中的 HSO3- 和 ClO- 也有很好的检测效果。同时,HTN 具有良好的生物相容性,可靶向线粒体实现对 HSO3-/H2O2 的可逆检测,并能有效区分活细胞中的 HSO3-/ClO-。因此,HTN 作为一种分子工具,在研究复杂生命系统相互作用网络中的氧化还原稳态方面具有巨大潜力。
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