以喹啉酮为核心高选择快速检测谷胱甘肽的荧光探针  

A Quinolinone-Based Fluorescent Probe for Rapid andHighly Selective Detection of Glutathione

作　　者：张成路[1] 孙越冬 丁言伟[1] 王静[1] 刘兴兵 王楠 宋府璐 ZHANG Chenglu;SUN Yuedong;DING Yanwei;WANG Jing;LIU Xingbing;WANG Nan;SONG Fulu(College of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China)

机构地区：[1]辽宁师范大学化学化工学院,辽宁大连116029

出　　处：《应用化学》2020年第7期847-854,共8页Chinese Journal of Applied Chemistry

基　　金：辽宁省教育厅科学技术项目资助(2009A426)。

摘　　要：为了选择性检测小分子生物硫醇,以具有优良荧光性能的喹啉酮为荧光团,依据依布硒啉中Se—N键易与硫醇分子反应的性质,将喹啉酮组块(E)-3-(5-巯基-1,3,4-恶二唑-2-基)-N-(4-甲基-2-氧代-1,2-二氢喹啉-7-基)丙烯酰胺(MQ5)与依布硒啉2-(4-溴苯基)苯并[d][1,2]硒唑-3(2 H)-酮(SQ6)对接,设计合成了一种新型荧光探针(E)-N-(4-甲基-2-氧代-1,2-二氢喹啉-7-基)-3-(5-((4-(3-氧代苯并[d][1,2]硒烯唑-2(3 H)-基)苯基)硫基)-1,3,4-噁二唑-2-基)丙烯酰胺(MNQ)。通过傅里叶变换红外光谱(FT-IR)、核磁共振波谱仪(NMR)和高分辨质谱(HRMS)和荧光光谱等测试手段对其进行了结构表征,探究了其荧光性能。结果表明,MNQ对谷胱甘肽(GSH)有明显的荧光猝灭,在其他氨基酸等干扰时,探针具有良好的抗干扰能力,可作为识别检测GSH的荧光猝灭型探针。检测限为2.99×10-8 mol/L,响应时间在35 s可完成,有望作为检测谷胱甘肽的荧光探针。In order to recognize small-molecule biothiols selectively,quinolinone was used as a fluorophore.Since thiol molecules can easily break the Se—N bond,a new fluorescent probe(E)-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)-3-(5-((4-(3-oxobenzo[d][1,2]selenazol-2(3 H)-yl)phenyl)thio)-1,3,4-oxadiazol-2-yl)acrylamide(MNQ)was designed and synthesized by splicing quinolinone(E)-3-(5-mercapto-1,3,4-oxadiazol-2-yl)-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)acrylamide(MQ5)with ebselen 2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2 H)-one(SQ6).The structure was characterized by infrared spectroscopy(IR),nuclear magnetic resonance spectroscopy(NMR)and high-resolution mass spectrometry(HRMS),and its fluorescence properties were explored by fluorescence spectroscopy.The result shows that MNQ has obvious fluorescence quenching ability for glutathione(GSH).When other amino acids exist,the probe has good anti-interference ability,and can be used as a fluorescence quenching probe for identifying and detecting GSH.The detection limit is 2.99×10^-7 mol/L,and the response time can be as low as 35 s.It has potential application as a fluorescent probe for detecting GSH.

关 键 词：喹啉酮 荧光识别 谷胱甘肽 依布硒啉 

分 类 号：O657.3[理学—分析化学]