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一系列具有双光子特性的水溶性A-π-A'型吲哚鎓衍生物,用于在活细胞中快速检测HSO₃⁻/SO₃²⁻ 。

A series of water-soluble A-π-A' typological indolium derivatives with two-photon properties for rapidly detecting HSO /SO in living cells.

作者信息

Zhu Yingzhong, Du Wei, Zhang Mingzhu, Xu Ying, Song Leilei, Zhang Qiong, Tian Xiaohe, Zhou Hongping, Wu Jieying, Tian Yupeng

机构信息

Department of Chemistry, Key Laboratory of Functional Inorganic Material Chemistry of Anhui Province, Anhui University, Hefei 230039, P. R. China.

出版信息

J Mater Chem B. 2017 Jun 7;5(21):3862-3869. doi: 10.1039/c7tb00726d. Epub 2017 May 8.

Abstract

It is believed that HSO and SO play important roles in several physiological processes. However, probes with two-photon absorption to detect HSO or SO in living cells are still limited. Herein, a series of novel indolium derivatives (L1-L4) with an A-π-A' structure was designed and synthesized as ratiometric probes to detect HSO /SO in vitro. L3 and L4 display a colorimetric and ratiometric fluorescence dual response to HSO /SO with a very fast (∼15 s) and high specificity, as well as low detection limits (∼22 nM). Furthermore, their detection is also carried out by using a two-photon excited fluorescence method. A nucleophilic addition reaction is proposed for the sensing mechanism, which is supported by MS, H NMR, and density functional theory (DFT) investigations. Importantly, L3 was successfully used for detecting intrinsically generated intracellular HSO /SO in cancerous cells under one- and two-photon excited fluorescence imaging.

摘要

据信,HSO和SO在多个生理过程中发挥着重要作用。然而,用于在活细胞中检测HSO或SO的双光子吸收探针仍然有限。在此,设计并合成了一系列具有A-π-A'结构的新型吲哚衍生物(L1-L4)作为比率探针,用于体外检测HSO/SO。L3和L4对HSO/SO呈现比色和比率荧光双重响应,响应速度非常快(约15秒)且具有高特异性,以及低检测限(约22 nM)。此外,还通过双光子激发荧光法进行了它们的检测。提出了一种亲核加成反应作为传感机制,质谱、氢核磁共振和密度泛函理论(DFT)研究支持了这一机制。重要的是,L3在单光子和双光子激发荧光成像下成功用于检测癌细胞内源性产生的HSO/SO。

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