文献类型：期刊文献

英文题名：A pinacol boronate caged NIAD-4 derivative as a near-infrared fluorescent probe for fast and selective detection of hypochlorous acid

作者：Tong, Hongjuan[1,2];Zhang, Yajun[1,2];Ma, Shengnan[1,2];Zhang, Minghao[1,2];Wang, Na[1,2];Wang, Rui[1,2];Lou, Kaiyan[1,2];Wang, Wei[1,2,3]

机构：[1]Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Shanghai 200237, Peoples R China;[3]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2018

卷号：29

期号：1

起止页码：139

外文期刊名：CHINESE CHEMICAL LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000423005300029)】；

基金：The work was supported by the China 111 Project (No. B07023, W. Wang), East China University of Science and Technology (start-up funds, W. Wang), the National Natural Science Foundation of China (No. 21577037, K. Lou), the Fundamental Research Funds for the Central Universities (No. ECUST-WY1213013, K. Lou).

语种：英文

外文关键词：Fluorescent probe; Hypochlorous acid; Boronate; Reactive oxygen species (ROS); Near-infrared (NIR) imaging

摘要：Hypochlorous acid (HOCI) is one of highly reactive oxygen species (ROS). It is involved in both immune defense against invading microbes and the progression of many diseases including cardiovascular disease and neurodegeneration disorders. It is generated from hydrogen peroxide (H2O2) and chloride ions in the presence of myeloperoxidase in activated neutrophils. To illustrate HOCI's biological functions, fluorescent probes, particularly those fluorescence emissions are in the near-infrared range, are highly needed for in vivo applications. Herein, we reported the design of a pinacol boronate caged near-infrared (NIR) fluorescent probe 1 derived from an A beta binding fluorophore NIAD-4 for fast and selective detection of HOCl/ClO- over other ROS. Upon exposure to HOCl/ClO-, the pinacol boronate caging group of the probe 1 was quickly converted to electron-donating hydroxyl group, which increased intramolecular charge transfer (ICT) in the excited state and resulted in the red-shift and intensity enhancement of fluorescence emission. The probe bears several unique features: (1) It could be used as either a ratiomatic or turn-on fluorescent probe; (2) Reaction of the caging group boronate with HOCI is very fast and finishes within seconds, which provides the selectivity over H2O2; (3) The NIAD-4 fluorophore provides additional selectivity for detection of HOCI over peroxynitrite. Moreover, the utility of the probe in imaging HOCl/CIO- was demonstrated in in vitro phantom imaging studies using mouse brain homogenate as biological relevant media. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.