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

作　　者：Hongjuan Tong Yajun Zhang ShengnanMa Minghao Zhang Na Wang Rui Wang Kaiyan Lou Wei Wang 

机构地区：[1]Shanghai Key Laboratory of New Drug Design, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, State Key Laboratory of Bioengineering Reactor, East China University of Science & Technology, Shanghai 200237, China [2]Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA

出　　处：《Chinese Chemical Letters》2018年第1期139-142,共4页中国化学快报（英文版）

基　　金：supported by the China 111 Project(No. B07023, W. Wang);East China University of Science and Technology(startup 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)

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 I derived from an Aft binding fluorophore NIAD-4 for fast and selective detection of HOC1/C10 over other ROS. Upon exposure to HOCI/CIO-, the pinacol boronate caging group of the probe 1 was quickly converted to electron-donating hydroxyl group, which increased intramolecular charge transfer OCT） 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 HOCl over peroxynitrite. Moreover, the utility of the probe in imaging HOCllClO- was demonstrated in in vitro phantom imaging studies using mouse brain homogenate as biological relevant media.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 I derived from an Aft binding fluorophore NIAD-4 for fast and selective detection of HOC1/C10 over other ROS. Upon exposure to HOCI/CIO-, the pinacol boronate caging group of the probe 1 was quickly converted to electron-donating hydroxyl group, which increased intramolecular charge transfer OCT） 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 HOCl over peroxynitrite. Moreover, the utility of the probe in imaging HOCllClO- was demonstrated in in vitro phantom imaging studies using mouse brain homogenate as biological relevant media.

关 键 词：Fluorescent probeHypochlorous acidBoronateReactive oxygen species （ROS）Near-infrared （NIR） imaging 

分 类 号：O6[理学—化学]