Design of fluorescent probes with optimized responsiveness and selectivity to GSH
Design of fluorescent probes with optimized responsiveness and selectivity to GSH
复制标题
设计对 GSH 具有优化响应性和选择性的荧光探针
DOI：
10.1016/j.tetlet.2019.03.051
复制
发表时间：
2019-05-02
影响因子：
1.8
通讯作者：
Gu, Xian-Feng
中科院分区：
文献类型：
--
作者：
Chen, Ji-An;Zhang, Zhen-Yu;Gu, Xian-Feng
我们设计并合成了一系列基于BODIPY的探针，其具有快速和独特的比率响应性，用于区分检测GSH与Cys和Hcy。区别性检测是基于通过探针和含巯基氨基酸之间的SNAr获得的不同产物。通过与Cys或Hcy反应而不是与GSH反应得到的硫醚的氨基将通过五元或六元环状过渡态引发分子内亲核取代，最终得到氨基取代的衍生物。为了实现高分辨检测和快速响应，通过延长π-共轭和引入吸电子基团进行了一系列结构修饰和改进，最终提供具有优化响应性和选择性的探针BOD-DBNPF。重要的是，BOD-DBNPF被成功地用于从Cys中选择性检测GSH，在活的HeLa细胞中具有不同的荧光比率响应。(C)2019爱思唯尔有限公司版权所有。
We designed and synthesized a series of BODIPY based probes with fast and distinct ratiometric responsiveness for discriminative detection of GSH from Cys and Hcy. The discriminative detection is based on the different products obtained by the SNAr between probes and thiol-containing amino acids. The amino group of the obtained thioether from the reaction with Cys or Hcy but not GSH would trigger an intramolecular nucleophilic substitution through five- or six-membered cyclic transition state, finally yielding an amino substituted derivative. To achieve highly discriminative detection and fast response, a series of structure modifications and improvements have been made by elongating the pi-conjugation and introducing electron withdrawing groups, finally affording probe BOD-DBNPF with optimized responsiveness and selectivity. Importantly, BOD-DBNPF was successfully used for the selective detection of GSH from Cys with distinct fluorescent ratiometric responses in living HeLa cells. (C) 2019 Elsevier Ltd. All rights reserved.