基于2-(2'-羟基苯基)苯并噻唑衍生物的过氧化氢荧光探针及其合成方法与应用  

Fluorescent Probe Derived from 2-(2'-Hydroxyphenyl)-Benzothiazole for Hydrogen Peroxide Sensing:Synthesis,Characterization and Application

作　　者：石磊 黄玲 黄泽键 李东华 龚盛昭 SHI Lei;HUANG Ling;HUANG Zejian;LI Donghua;GONG Shengzhao(College of Light Chemical Engineering,Guangdong Polytechnic Normal University,Guangzhou 510300,China;Anan Cosmetics and Healthcare Products Co.,Ltd.,Foshan 528099,China)

机构地区：[1]广东轻工职业技术大学轻化工技术学院,广东广州510300 [2]佛山市安安美容保健品有限公司,广东佛山528099

出　　处：《发光学报》2024年第10期1741-1746,共6页Chinese Journal of Luminescence

基　　金：广东省普通高校特色创新类项目(2022KTSCX228);广东省科技创新战略专项资金项目(pdjh2023a0799)。

摘　　要：过氧化氢(H_(2)O_(2))作为小分子活性氧(ROS)的一员,在正常生理活动和许多疾病的发生中起着至关重要的作用。本工作以2-(2'-羟基苯基)苯并噻唑(HBT)为荧光团,以对硝基苯乙酸酯部分为识别位点,合成了一种新型荧光探针1。该探针对H2O2表现出高灵敏度(检测限为1.26μmol/L),并且对H2O2显示出良好的特异性识别能力。通过高效液相色谱(HPLC)分析表明,该探针的识别机制是通过α-酮酯基团的氧化和酯基的水解以释放荧光团HBT。此外,探针1具有较低的细胞毒性和良好的细胞渗透性,并成功应用于HeLa细胞内H_(2)O_(2)的生物成像分析,证实了其在细胞水平上检测H_(2)O_(2)的可行性和实用性。Hydrogen peroxide(H2O2),a member of small-molecule reactive oxygen species(ROS),plays vital roles in normal physiological activities and the occurrence of many diseases.In this work,a novel fluorescent probe was synthesized with the 2⁃(2′⁃hydroxyaryl)benzothiazoles(HBT)as the fluorophores and 4-nitrophenyl acetate moiety as the reaction sites.The probe 1 exhibited a high sensitivity for H2O2 with the detection limit of 1.26μmol/L,and displayed a good selectivity for H2O2 over other reactants such as ROS,amino acids,and vari⁃ous ions and anions.Through high-performance liquid chromatography(HPLC)analysis,the probe’s recognition mechanism was based on the oxidation of theα-keto ester group and the hydrolysis of the ester moiety to release the fluorophore HBT.Moreover,probe 1 has low cytotoxicity and cell permeability,and was successfully applied to bioimaging analysis of H_(2)O_(2)within HeLa cells,confirming its feasibility and practicality for H_(2)O_(2)detection at the cellular level.

关 键 词：荧光探针 过氧化氢 生物成像分析 2-(2′-羟基苯基)苯并噻唑 

分 类 号：O657.3[理学—分析化学]