A fluorescent probe emitting in near-infrared region for sensitive and selective detection of biothiols in both solution and living cells
A fluorescent probe emitting in near-infrared region for sensitive and selective detection of biothiols in both solution and living cells
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DOI：
10.1016/j.tetlet.2015.11.040
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发表时间：
2015-12-30
影响因子：
1.8
通讯作者：
Song, Xiangzhi
中科院分区：
文献类型：
--
作者：
Chen, Wenqiang;Luo, Hongchen;Song, Xiangzhi
研制了一种近红外荧光探针1，4-diethyl-7-(3-pyridin-2-yl-acroyloyl)-1，2，3，4-tetrahydro-5-oxa-1，4-diazaanthracen-6-one(Probe 1)，用于生物硫醇的灵敏和选择性检测。探针1基本上是非荧光的，因为从给电子的四氢喹恶啉部分到拉电子的吡啶基团有很强的分子内电荷转移(ICT)。经生物硫醇处理后，通过生物硫醇与α，β-不饱和酮的Michael加成反应破坏了偶联体系，抑制了ICT过程，导致了显著的荧光增强，其最大发射波长为660 nm。此外，探针1被成功地应用于活体细胞内硫醇的成像。(C)2015爱思唯尔有限公司。保留所有权利。
A fluorescent probe, 1,4-diethyl-7-(3-pyridin-2-yl-acroyloyl)-1,2,3,4-tetrahydro-5-oxa-1,4-diazaanthracen-6-one (probe 1), with an emission in near-infrared region was developed for sensitive and selective detection of biothiols. Probe 1 is essentially non-fluorescent due to the strong intramolecular charge transfer (ICT) from the electron-donating tetrahydroquinoxaline moiety to the electron-withdrawing pyridine group. Upon the treatment with biothiols, the conjugation system was broken via Michael addition reaction between biothiols and alpha,beta-unsaturated ketone, which inhibited the ICT process and resulted in a remarkable fluorescence enhancement with an emission maximum at 660 nm. Moreover, probe 1 was successfully applied to image intracellular thiols in living cells. (C) 2015 Elsevier Ltd. All rights reserved.