以喹啉酮为核心高选择快速检测谷胱甘肽的荧光探针

doi:10.11944/j.issn.1000-0518.2020.07.200025

摘要/Abstract

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(2H)-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 (3H)-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。

关键词: 喹啉酮, 荧光识别, 谷胱甘肽, 依布硒啉

Abstract: 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(3H)-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(2H)-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.

Key words: quinolinone, fluorescence recognition, glutathione, ebselen

张成路, 孙越冬, 丁言伟, 王静, 刘兴兵, 王楠, 宋府璐. 以喹啉酮为核心高选择快速检测谷胱甘肽的荧光探针[J]. 应用化学, 2020, 37(7): 847-854.

ZHANG Chenglu, SUN Yuedong, DING Yanwei, WANG Jing, LIU Xingbing, WANG Nan, SONG Fulu. A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione[J]. Chinese Journal of Applied Chemistry, 2020, 37(7): 847-854.

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