新型近红外氧杂蒽荧光染料用于线粒体荧光成像  

A Novel Near-infrared Xanthene Fluorescent Dye for Mitochondrial Fluorescence Imaging

作　　者：曾红[1] 郭小美 朱玉莲 练萍 范小林[1] 吴勇权[1] ZENG Hong;GUO Xiao-mei;ZHU Yu-lian;LIAN Ping;FAN Xiao-lin;WU Yong-quan(Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province,School of Chemistry and Chemical Engineering,Gannan Normal University,Ganzhou 341000,China)

机构地区：[1]赣南师范大学化学化工学院江西省有机药物化学重点实验室,江西赣州341000

出　　处：《化学试剂》2022年第4期531-537,共7页Chemical Reagents

基　　金：国家自然科学基金资助项目(21967001);江西省“双千计划”培养类科技创新高端人才(青年)项目(jxsq201920109);赣州市科技创新领军人才计划项目(赣市科发2020-60)。

摘　　要：荧光成像具有操作简单、灵敏度高和实时等优点,而近红外荧光成像能够有效避免生物组织自发荧光干扰。通过设计和合成3个新型近红外氧杂蒽荧光染料NXD-1~NXD-3用于细胞荧光成像。首先,3个氧杂蒽荧光染料分子结构得到核磁共振谱和高分辨质谱的确认。其次,详细研究了这些荧光染料的吸收光谱和荧光光谱,实验数据表明3个荧光染料的发射光谱能够达到近红外区域,其中NXD-3的光谱更为红移,它的最大吸收波长和发射波长分别为611 nm和759 nm。另外,密度泛函理论(DFT)计算结果与实际测试光谱数据相匹配。最后,将制备的氧杂蒽荧光染料用于细胞荧光染色成像,实验结果表明荧光染料NXD-3具有良好的细胞线粒体靶向荧光标记效果。Fluorescence imaging has the advantages of simple operation,high sensitivity and real-time,while near-infrared fluorescence imaging can effectively avoid the interference of spontaneous fluorescence of biological tissues.In this work,three novel near-infrared xanthene fluorescent dyes NXD-1~NXD-3 were designed and synthesized for cell fluorescence imaging.Firstly,the molecular structures of the xanthene fluorescent dyes were confirmed by ^(1)HNMR and HR-MS.Secondly,the absorption and fluorescence spectra of these fluorescent dyes are studied in detail.The experimental data showed that the emission spectra of the three fluorescent dyes can reach the near-infrared region,in which the spectrum of NXD-3 was more red-shifted,and its maximum absorption and emission wavelengths were 611 nm and 759 nm,respectively.In addition,the theoretical results obtained from density functional theory(DFT) calculations can match the measured spectral data for the three dyes.Finally,the prepared xanthene fluorescent dyes were used for cell fluorescence imaging.The experimental results showed that the dye NXD-3 had a good effect of cell mitochondrial-targeted fluorescence labeling.

关 键 词：氧杂蒽 近红外 线粒体 荧光染料 荧光成像 

分 类 号：O625.15[理学—有机化学]