Ratiometric Fluorescent Probe for Vicinal Dithiol-Containing Proteins in Living Cells Designed via Modulating the Intramolecular Charge Transfer–Twisted Intramolecular Charge Transfer Conversion Process,Analytical Chemistry

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Ratiometric Fluorescent Probe for Vicinal Dithiol-Containing Proteins in Living Cells Designed via Modulating the Intramolecular Charge Transfer–Twisted Intramolecular Charge Transfer Conversion Process
Analytical Chemistry ( IF 6.7 ) Pub Date : 2016-09-29 00:00:00 , DOI: 10.1021/acs.analchem.6b02923
Yuanyuan Wang ₁ , Yaogang Zhong ₂ , Qin Wang ₁ , Xiao-Feng Yang ₁ , Zheng Li ₂ , Hua Li _{1,

3}

Affiliation

Vicinal dithiol-containing proteins (VDPs) play a significant role in maintaining the cellular redox homeostasis and are implicated in many diseases. To provide new chemical tools for VDPs imaging, we report here a ratiometric fluorescent probe CAsH2 for VDPs using 7-diethylaminiocoumarin as the fluorescent reporter and cyclic 1,3,2-dithiarsenolane as the specific ligand. CAsH2 shows peculiar dual fluorescence emission from the excited intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT) states in aqueous media. However, upon selective binding of protein vicinal dithiols to the trivalent arsenical of CAsH2, the probe was brought from the polar water media into the hydrophobic protein domain, causing the excited state ICT to TICT conversion to be restricted; as a result, an increase from the ICT emission band and a decrease from the TICT emission band were observed simultaneously. The designed probe shows high selectivity toward VDPs over other proteins and biological thiols. Preliminary experiments show that CAsH2 can be used for the ratiometric imaging of endogenous VDPs in living cells. So far as we know, this is a rare example of the ratiometric fluorescent probe designed via modulating the ICT–TICT conversion process, which provides a new way to construct various protein-specific ratiometric fluorescent probes.

中文翻译：

通过调节分子内电荷转移-扭曲的分子内电荷转移转化过程设计的活细胞中含邻二硫醇蛋白质的比例荧光探针

含邻二硫醇的蛋白质（VDP）在维持细胞氧化还原稳态中起着重要作用，并与许多疾病有关。为了为VDP成像提供新的化学工具，我们在这里报告了一种比例荧光探针CAsH2，用于VDP，使用7-二乙基氨基香豆素作为荧光报告分子，并以环状1,3,2-二硫杂戊烯烷作为特定配体。CAsH2在水介质中显示出来自激发的分子内电荷转移（ICT）和扭曲的分子内电荷转移（TICT）状态的特殊双重荧光发射。但是，在蛋白质邻域二硫醇与CAsH2的三价砷选择性结合后，将探针从极性水介质中带入疏水蛋白结构域，从而限制了激发态ICT到TICT的转换；结果，同时观察到来自ICT发射带的增加和来自TICT发射带的减小。设计的探针对VDP的选择性高于其他蛋白质和生物硫醇。初步实验表明，CAsH2可用于活细胞中内源性VDP的比例成像。据我们所知，这是通过调节ICT–TICT转换过程设计的比例荧光探针的罕见示例，它为构建各种蛋白质特异性比例荧光探针提供了一种新方法。

更新日期：2016-09-29

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