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丙二腈作为钝化-活化调节两种分子内电荷转移的“双刃剑”,用于生物体系中次氯酸的高灵敏和准确的比率荧光检测。

Malononitrile as the 'double-edged sword' of passivation-activation regulating two ICT to highly sensitive and accurate ratiometric fluorescent detection for hypochlorous acid in biological system.

作者信息

Shi Yan, Huo Fangjun, Yin Caixia

机构信息

Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China.

College of Food Sciences, Shanxi Normal University, Linfen, Shanxi, 041004, China.

出版信息

Sens Actuators B Chem. 2020 Dec 15;325:128793. doi: 10.1016/j.snb.2020.128793. Epub 2020 Aug 25.

Abstract

Hypochlorous acid (HOCl) as one of the most important reactive oxygen species in the organism, its role is more and more recognized. In fact, in recent years, various HOCl fluorescent probes have been developed unprecedentively based on various mechanisms. However, because most of the mechanisms are based on the oxidation characteristics of HOCl, the excellent detection performance of probes depends on the activation ability of some functional groups to reaction sites. The C[bond, double bond]C bond in the probe is often oxidized by HOCl to realize HOCl detection. However, due to the break of conjugated structure, the probe often present as a quenchable or turning on fluorescence emission. In this work, malononitrile was introduced as the "double-edged sword" of passivation-activation when in HOCl fluorescent probe was designed. Passivation-activation regulated two ICT (Intermolecular Charge Transfer, ICT) processes to ratiometric fluorescent detection for HOCl. Highly sensitive and accurate detection realized efficient application in biological imaging.

摘要

次氯酸(HOCl)作为生物体中最重要的活性氧之一,其作用越来越受到认可。事实上,近年来,基于各种机制,各种HOCl荧光探针得到了前所未有的发展。然而,由于大多数机制基于HOCl的氧化特性,探针的优异检测性能取决于一些官能团对反应位点的活化能力。探针中的C=C键常被HOCl氧化以实现HOCl检测。然而,由于共轭结构的破坏,探针通常呈现为可猝灭或开启荧光发射。在这项工作中,在设计HOCl荧光探针时引入丙二腈作为钝化-活化的“双刃剑”。钝化-活化调节两个分子间电荷转移(ICT)过程以实现对HOCl的比率荧光检测。高灵敏度和准确的检测实现了在生物成像中的高效应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3516/7446621/e904ae6d2490/ga1_lrg.jpg

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