A multi-signal fluorescent probe for the discrimination of cysteine/homocysteine and glutathione and application in living cells and zebrafish†,New Journal of Chemistry

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A multi-signal fluorescent probe for the discrimination of cysteine/homocysteine and glutathione and application in living cells and zebrafish†
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1039/c8nj01793j
Gaoping Xu _{1,

2,

3,

4,

5} , Yonghe Tang _{1,

2,

3,

4,

5} , Weiying Lin _{1,

2,

3,

4,

5}

Affiliation

Biological thiols are ubiquitous, common in living organisms and play an important role in metabolism and redox homeostasis. Abnormal concentrations of biological thiols may lead to many malignant diseases. It is difficult to distinguish biological thiols by fluorescence techniques because they possess similar chemical structures and properties. Herein, we developed a new fluorescent probe CI to distinguish cysteine/homocysteine (Cys/Hcy) and glutathione (GSH) by a multi-signal fluorescence mode. When the respective biological thiols were introduced, the probe reacted with these biological thiols by a thiol–halogen S_NAr nucleophilic substitution–rearrangement mechanism and showed two different fluorescent signals with two different excitation wavelengths. After identifying Cys/Hcy and GSH, CI showed a good two-photon property because of the coumarin structure. Significantly, the probe was effectively applied for the imaging of Cys/Hcy and GSH in living cells via two-color fluorescence imaging.

中文翻译：

用于区分半胱氨酸/同型半胱氨酸和谷胱甘肽的多信号荧光探针及其在活细胞和斑马鱼中的应用†

生物硫醇无处不在，常见于活生物体中，并在新陈代谢和氧化还原稳态中发挥重要作用。生物硫醇浓度异常可能导致许多恶性疾病。通过荧光技术难以区分生物硫醇，因为它们具有相似的化学结构和性质。在这里，我们开发了一种新的荧光探针CI，以通过多信号荧光模式来区分半胱氨酸/高半胱氨酸（Cys / Hcy）和谷胱甘肽（GSH）。当引入相应的生物硫醇时，探针通过硫醇-卤素S _N与这些生物硫醇反应Ar亲核取代-重排机制，并显示出具有两个不同激发波长的两个不同荧光信号。鉴定出Cys / Hcy和GSH后，由于香豆素的结构，CI显示出良好的双光子性质。重要的是，该探针通过双色荧光成像有效地用于活细胞中Cys / Hcy和GSH的成像。

更新日期：2018-06-20

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