Development of a small molecule probe capable of discriminating cysteine, homocysteine, and glutathione with three distinct turn-on fluorescent outputs.
Development of a small molecule probe capable of discriminating cysteine, homocysteine, and glutathione with three distinct turn-on fluorescent outputs.
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DOI：
10.1002/chem.201403450
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发表时间：
2014-09
期刊：
影响因子：
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通讯作者：
Feiyi Wang;Zhiqian Guo;Xia Li;Xiuai Li;Chunchang Zhao
中科院分区：
文献类型：
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作者：
Feiyi Wang;Zhiqian Guo;Xia Li;Xiuai Li;Chunchang Zhao
通过单个探针同时区分 Cys、Hcy 和 GSH 仍然是一个尚未解决的挑战。提出了小分子探针 MeO-BODIPY-Cl（BODIPY=二吡咯亚甲基硼）的设计和合成，该探针可以根据三种不同的荧光开启响应同时区分 Cys、Hcy 和 GSH。探针与这些硫醇反应形成硫基取代的 BODIPY，然后进行分子内置换，产生氨基取代的 BODIPY。分子内置换反应的动力学速率决定了观察到的不同传感行为。因此，探针响应Cys、Hcy和GSH，荧光开启颜色分别为黄色、黄红和红色。凭借这一有前景的功能，该探针成功用于活细胞中 Cys、Hcy 和 GSH 的成像。
The simultaneous discrimination of Cys, Hcy, and GSH by a single probe is still an unmet challenge. The design and synthesis of a small molecule probe MeO-BODIPY-Cl (BODIPY=boron dipyrromethene) is presented, which can allow Cys, Hcy, and GSH to be simultaneously discriminated on the basis of three distinct fluorescence turn-on responses. The probe reacts with these thiols to form sulfenyl-substituted BODIPY, which is followed by intramolecular displacement to yield amino-substituted BODIPY. The kinetic rate of the intramolecular displacement reaction determines the observed different sensing behavior. Therefore, the probe responds to Cys, Hcy, and GSH with fluorescence turn-on colors of yellow, yellow and red, and red, respectively. With this promising feature in hand, the probe was successfully used in imaging of Cys, Hcy and GSH in living cells.