A turn on ESIPT probe for rapid and ratiometric fluorogenic detection of homocysteine and cysteine in water with live cell-imaging
A turn on ESIPT probe for rapid and ratiometric fluorogenic detection of homocysteine and cysteine in water with live cell-imaging
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DOI：
10.1016/j.tetlet.2013.11.055
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发表时间：
2014-01-08
影响因子：
1.8
通讯作者：
Saha, Partha
中科院分区：
文献类型：
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作者：
Goswami, Shyamaprosad;Manna, Abhishek;Saha, Partha
5-（苯并噻唑-2-基）-4-羟基苯甲醛（BHI）是一种在混合介质中含有强ESIPT的分子，在无水介质中由于共振辅助氢键（RAHB）而失去其性质。由于共振辅助氢键，邻醛比另一个更具反应性。在此溶液中加入半胱氨酸/高半胱氨酸后，邻醛基分别转化为噻唑烷/噻嗪环，酚质子自由转移到激发态苯并噻唑环的氮上，即BHI的ESIPT被打开，因此我们可以检测水和活细胞中的半胱氨酸/高半胱氨酸。(C)2013爱思唯尔有限公司保留所有权利。
5(Benzothiazol-2-yl)-4-hydroxyisophthalaldehyde (BHI), an intense ESIPT containing molecule in mixed media loses its properties due to resonance-assisted H-bond (RAHB) in absolute water. Due to resonance-assisted H-bond the o-aldehyde is more reactive than the other one. With addition of cysteine/homocysteine into this solution the o-aldehyde group gets transformed into thiazolidine/thiazine ring, respectively, and the phenolic proton becomes free enough for transfer to nitrogen of the benzothiazole ring in excited state, that is, the ESIPT of BHI is turned on. Thus we can detect cysteine/homocysteine in water as well as in live cells. (C) 2013 Elsevier Ltd. All rights reserved.