文献类型：期刊文献

英文题名：Rational Design of an Ultrasensitive and Highly Selective Chemodosimeter by a Dual Quenching Mechanism for Cysteine Based on a Facile Michael-Transcyclization Cascade Reaction

作者：Li, Xiangmin[1,2,3];Zheng, Yongjun[1,2];Tong, Hongjuan[1,2];Qian, Rui[1,2];Zhou, Lin[3];Liu, Guixia[1,2];Tang, Yun[1,2];Li, Hao[1,2];Lou, Kaiyan[1,2];Wang, Wei[1,2,3]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Shanghai Key Lab New Drug Design, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ New Mexico, Dept Chem & Chem Biol, MSC03 2060, Albuquerque, NM 87131 USA

年份：2016

卷号：22

期号：27

起止页码：9247

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20162402489549);WOS:【SCI-EXPANDED(收录号:WOS:000380271100032)】；

基金：The work was supported by East China University of Science and Technology, the Fundamental Research Funds for the Central Universities (K.L., WY1213013), the Pujiang Talent Project (K.L., 14J1402200), the National Science Foundation of China (No. 21577037), and the China 111 Project (W.W., Grant B07023).

语种：英文

外文关键词：cascade reactions; chemodosimeter; click chemistry; cysteine; fluorescent probes

摘要：Differentiation of biologically important thiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) is still a challenging task. Herein, we present a novel fluorescent chemodosimeter capable of selectively detecting Cys over other biothiols including Hcy and GSH and other amino acids by a facile thiol-Michael addition/transcyclization rearrangement cascade click process. The unique trans-cyclization step is critical for the selectivity as a result of the kinetically favorable formation of a six-membered ring with the Cys Michael adduct. Moreover, the probe adopts a dis-tinctive dual quenching mechanism-photoinduced electron transfer (PET) and photoinduced intramolecular charge transfer (ICT) to deliver a drastic turn-on fluorescence response only at the Cys-selective transcylization step. The judicious selection of strong electron-withdrawing naphthalimide fluorophore with maleimide group enhances the electrophilicity and thus reactivity for the cascade process leading to fast detection and ultrasensitivity with a detection limit of 2.0 nm (S/N=3). The probe has demonstrated its practical utility potential in Cys imaging in live cells.