Target-Triggered NIR Emission with a Large Stokes Shift for the Detection and Imaging of Cysteine in Living Cells

Target-Triggered NIR Emission with a Large Stokes Shift for the Detection and Imaging of Cysteine in Living Cells
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具有大斯托克斯位移的目标触发近红外发射用于活细胞中半胱氨酸的检测和成像

DOI:
10.1002/asia.201402043
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发表时间:
2014
影响因子:
4.1
通讯作者:
Feiyi Wang
Feiyi Wang
中科院分区:
化学3区
文献类型:
--
作者:
Chunchang Zhao;Xiuai Li;Feiyi Wang

文献摘要

被引文献

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来自生物系统的背景自发荧光通常会降低荧光探针对生物目标成像的灵敏度。解决这一挑战需要开发在近红外区域产生发射的荧光探针。在此,我们报告了一种荧光探针的设计和合成,该探针在对 Cys 而非 Hcy 和 GSH 的选择性响应时产生具有大斯托克斯位移的近红外发射。该探针设计由两个 Cys 传感位点组成,即彼此相邻安装的丙烯酸酯和醛。探针与半胱氨酸的反应在光激发时触发激发态分子内质子转移过程,从而产生具有大斯托克斯位移的近红外发射。因此,该探针对于生物系统中半胱氨酸的选择性检测具有广阔的前景。我们进一步证明了该探针在活细胞中进行半胱氨酸成像的能力。
Background autofluorescence from biological systems generally reduces the sensitivity of a fluorescent probe for imaging biological targets. Addressing this challenge requires the development of fluorescent probes that produce emission in the near‐infrared region. Herein, we report the design and synthesis of a fluorescent probe that generates an NIR emission with a large Stokes shift upon the selective response to Cys over Hcy and GSH. The probe is designed to consist of two Cys‐sensing sites, an acrylate ester and an aldehyde installedorthoto each other. The reaction of the probe with Cys triggers an excited state intramolecular proton transfer process upon photo‐excitation, thereby producing an NIR emission with a large Stokes shift. Accordingly, this probe hold great promise for the selective detection of Cys in biological systems. We further demonstrate the capacity of this probe for Cys imaging in living cells.