文献类型：期刊文献

英文题名：A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein

作者：Wang, Feiyi[1,2];Zhou, Li[3];Zhao, Chunchang[1,2];Wang, Rui[3];Fei, Qiang[1,2];Luo, Sihang[1,2];Guo, Zhiqian[1,2];Tian, He[1,2];Zhu, Wei-Hong[1,2]

机构：[1]E China Univ Sci & Technol, Collaborat Innovat Ctr Coal Based Energy I CCE, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Collaborat Innovat Ctr Coal Based Energy I CCE, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2015

卷号：6

期号：4

起止页码：2584

外文期刊名：CHEMICAL SCIENCE

收录：;EI(收录号：20151200660040);WOS:【SCI-EXPANDED(收录号:WOS:000351412800055)】；

基金：This work was supported by National 973 Program (2013CB733700), NSFC for Creative Research Groups (21421004) and Distinguished Young Scholars (21325625), NSFC/China, the Oriental Scholarship, Shanghai Pujiang Program (13PJD010), the Fok Ying Tong Education Foundation (142014), and the Fundamental Research Funds for the Central Universities (WJ1416005, 222201313010).

语种：英文

外文关键词：Cyclization - Probes - Covalent bonds - Fluorescence imaging - Peptides - Sulfur compounds

摘要：In situ monitoring of intracellular thiol activity in cell growth and function is highly desirable. However, the discriminative detection of glutathione (GSH) from cysteine (Cys) and homocystein (Hcy) and from common amino acids still remains a challenge due to the similar reactivity of the thiol groups in these amino acids. Here we report a novel strategy for selectively sensing GSH by a dual-response mechanism. Integrating two independent reaction sites with a disulfide linker and a thioether function into a fluorescent BODIPY-based chemsensor can guarantee the synergetic dual-response in an elegant fashion to address the discrimination of GSH. In the first synergetic reaction process, the thiol group in GSH, Cys and Hcy induces disulfide cleavage and subsequent intramolecular cyclization to release the unmasked phenol-based BODIPY (discriminating thiol amino acids from other amino acids). In the second synergetic process, upon the substitution of the thioether with the nucleophilic thiolate to form a sulfenyl-BODIPY, only the amino groups of Cys and Hcy, but not that of GSH, undergo a further intramolecular displacement to yield an amino-substituted BODIPY. In this way, we make full use of the kinetically favorable cyclic transition state in the intramolecular rearrangement, and enable photophysical distinction between sulfenyl-and amino-substituted BODIPY for allowing the discriminative detection of GSH over Cys and Hcy and thiol-lacking amino acids under physiological conditions. Moreover, this probe exhibits a distinguishable ratiometric fluorescence pattern generated from the orange imaging channel to the red channel, which proves the differentiation of GSH from Cys and Hcy in living cells.