基于3-羟基黄酮的pH荧光探针合成及线粒体靶向荧光成像  

Synthesis and application of a 3-hydroxyflavone fluorescent pH probe for intracellular mitochondria targeted imaging

作　　者：王超 杨方舟 吉鹏博 王婷婷[1] 马养民[1] WANG Chao;YANG Fang-zhou;JI Peng-bo;WANG Ting-ting;MA Yang-min(College of Chemistry and Chemical Engineering,Shaanxi University of Science&Technology,Xi′an 710021,China)

机构地区：[1]陕西科技大学化学与化工学院

出　　处：《陕西科技大学学报》2020年第1期88-92,共5页Journal of Shaanxi University of Science & Technology

基　　金：国家自然科学基金项目(21708023);陕西省科技厅自然科学基础研究计划项目(2019JQ-061);中国博士后科学基金面上项目(2019M653851XB);陕西科技大学博士科研启动基金项目(2017GBJ-04)

摘　　要：线粒体是真核细胞能量代谢的重要场所,对于细胞生理功能具有重要意义.将荧光分子定位于线粒体可以实现可视化的荧光成像,为线粒体形态及功能研究提供了有力工具.设计以3-羟基黄酮为荧光母核,以三苯基膦为靶向基团,合成一例用于活细胞线粒体特异性成像的荧光探针HF-Mito.3-羟基黄酮部分的激发态分子内质子转移(ESIPT)机理赋予了它优异的荧光性能,同时由于质子性溶剂对其ESIPT过程和荧光性能的影响,该探针可以用于pH的检测.而三苯基膦部分具有亲脂性且带正电荷,可以特异性的嵌入线粒体内膜并与膜电位差形成的负电荷稳定结合.荧光光谱测试与细胞荧光成像实验均表明该探针适用于细胞内线粒体的靶向标记与荧光成像.Mitochondria are the primary sites for energy metabolism in eukaryotic cells.They are of great significance in cell physiology.Visual imaging of mitochondria based on the targeted fluorescent molecules is a powerful tool for the researches on mitochondrial morphology and functions.In this paper,a novel fluorescent probe HF-Mito for intracellular mitochondria targeted imaging was synthesized with the 3-hydroxyflavone fluorophore and a mitochondria-targeting group triphenylphosphine.The excited-state intramolecular proton transfer(ESIPT)effect of the 3-hydroxyflavone moiety endowed it with excellent spectral properties.At the same time,the probe can be used to detect pH due to the influence of proton solvent on its ESIPT process and fluorescence performance.The triphenylphosphine moiety is lipophilic and positively charged,which can specifically bind to the mitochondrial inner membrane with the negative charge established by the mitochondrial membrane potential.The fluorescent spectra and the fluorescent imaging experiments indicate that the probe is suitable for targeted labeling and fluorescent imaging of intracellular mitochondria.

关 键 词：线粒体 荧光探针 三苯基膦 3-羟基黄酮 ESIPT效应 

分 类 号：O657.3[理学—分析化学]