三唑基团功能化的三苯胺类Cu^(2+)荧光探针的合成及在检测和HeLa细胞中的应用  

Synthesis of Triazole Functionalized Triphenylamine Cu^(2+)Fluorescent Probe and Its Application in Detection and HeLa Cells

作　　者：文乙评 解正峰 史天柱 褚义成 周荣贵 陶奕杉 梁焕敏 邱海燕 赵云辉[4] Wen Yiping;Xie Zhengfeng;Shi Tianzhua;Chu Yicheng;Zhou Ronggui;Tao Yishan;Liang Huanmin;Qiu Haiyan;Zhao Yunhui(Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province,College of Chemistry and Chemical Engineering,Southwest Petroleum University,Chengdu 610500;Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization,Southwest Petroleum University,Chengdu 610500;Department of Brewing Engineering,Moutai Institute,Renhuai,Guizhou 564500;School of Chemistry and Chemical Engineering,Hunan University of Science and Technology,Xiangtan,Hunan 411201)

机构地区：[1]西南石油大学化学化工学院油气田应用化学四川省重点实验室,成都610500 [2]西南石油大学工业危废处置与资源化利用研究院,成都610500 [3]茅台学院酿酒工程系,贵州仁怀564500 [4]湖南科技大学化学化工学院,湖南湘潭411201

出　　处：《有机化学》2022年第5期1463-1473,共11页Chinese Journal of Organic Chemistry

基　　金：四川省青年科技创新研究团队(No.2020JDTD0018);贵州省遵义市科学技术局及茅台学院市校联合科技合作资金(遵市科合HZ字[2021]333号)资助项目。

摘　　要：以2-(4-溴苯基)-2H-1,2,3-三唑-4-甲醛、(4-(二苯基氨基)苯基)硼酸和氨基硫脲为原料,设计合成了一种新型的可高选择性快速识别Cu^(2+)的荧光探针分子N'-((2-(4'-(二苯胺基)-[1,1'-联苯]-4-基)-2H-1,2,3-三唑-4-基)亚甲基)肼-1-硫代酰胺(DBTMC).DBTMC展示出优异的溶剂效应和聚集态效应,对Cu^(2+)展现出高选择、高灵敏和快速响应性,检测限为4.48×10^(-8) mol/L.通过job’s曲线、1H NMR滴定、HRMS及密度泛函理论(DFT)计算对其可能的响应机理进行了探究.用探针DBTMC制备的测试条,可用于快速检测Cu^(2+).将DBTMC应用于检测HeLa细胞中的Cu^(2+),也取得了良好的效果,具有潜在的应用价值.A novel fluorescence probe N'-((2-(4'-(diphenyl)-[1,1'-biphenyl]-4-yl)-2H-1,2,3-triazole-4-yl)methylene)hydrazine-1-thioamide(DBTMC)was designed and synthesized from(4-(diphenylamino)-phenyl)boronic acid,(4-bromophenyl)-2H-[1,2,3]-triazole-4-carbaldehyde and thiosemicarbazide.DBTMC possessed excellent solvent effect and aggregation effect,and exhibited high selectivity,high sensitivity and rapid response to Cu^(2+) with detection limit of 4.48×10^(-8) mol/L.The possible response mechanism was explored through job’s curve,1H NMR titration,HRMS and density functional theory(DFT)calculations.The test strip prepared with the probe DBTMC solution could be used for quick recognition of Cu^(2+).DBTMC was applied to HeLa cells to detect Cu^(2+) and excellent results were achieved,possessing potential application.

关 键 词：荧光探针 铜离子 溶剂效应 聚集态效应 HELA细胞 

分 类 号：R318[医药卫生—生物医学工程] O657.3[医药卫生—基础医学]