带功能手柄的二苯并呫吨类染料(EC5)用于生物成像  

Dibenzoxanthene dyes with functional handles(EC5)for bioimaging

作　　者：李紧 张晓东 邱杨挺 姚成 鲁锡存 魏茹薇 罗潇 钱旭红[1,2] 杨有军 LI Jin;ZHANG Xiaodong;QIU Yangting;YAO Cheng;LU Xicun;WEI Ruwei;LUO Xiao;QIAN Xuhong;YANG Youjun(School of Pharmacy,East China University of Science and Technology,Shanghai 200237,China;School of Chemistry and Molecular Engineering,East China Normal University,Shanghai 200241,China)

机构地区：[1]华东理工大学药学院,上海200237 [2]华东师范大学化学与分子工程学院,上海200241

出　　处：《化工学报》2024年第4期1687-1696,共10页CIESC Journal

基　　金：国家自然科学基金项目(22078098,22278138);上海市优秀学术/技术带头人计划项目(22XD1421000)。

摘　　要：短波红外光谱区(大于800 nm)的荧光团目前广泛用于生物医学领域,理想的染料应明亮、光化学稳定性高、生物相容性好并且易于衍生以便引入功能性基团。开发了一种具有双可修饰位点的二苯并呫吨类近红外荧光染料EC5,可用于荧光成像。以7-溴-2-萘酚为起始原料,通过高效的5步级联反应得到EC5,并由核磁共振氢谱、碳谱、高分辨质谱及X射线衍射鉴定。EC5在二氯甲烷中最大吸收和发射波长分别为871 nm和923 nm,荧光亮度高达38715,荧光寿命为0.70 ns。同时测试了EC5在极性溶剂中的聚集性、光化学稳定性,结果表明:EC5即使高达100μmol/L也不会出现聚集现象,高功率880 nm激光持续照射仍能保持吸光度几乎不变,同时高浓度生物活性物质亦不会使EC5染料降解,说明其具有优异的抗聚集性、抗光漂白能力及化学稳定性。最后使用EC5对BALB/c小鼠进行了高时空分辨的荧光成像以及防伪书写,说明EC5在近红外荧光活体成像领域具有广泛的应用前景。Fluorophores in the shortwave infrared spectral region(greater than 800 nm)are currently widely used in the biomedical field.The ideal dye should be bright,highly photochemically stable,biocompatible and easy to derivatize to introduce functional groups.In this work,an NIR fluorescent dye EC5 with dual modifiable sites was developed through an efficient 5-step synthesis route using 7-bromo-2-naphthol as a raw material.The resulted compound was characterized by nuclear magnetic resonance(NMR)hydrogen spectroscopy,carbon spectroscopy,high-resolution mass spectrometry(HRMS)and X-ray diffraction(XRD).The maximum absorption and emission wavelengths of EC5 were 871 nm and 923 nm,respectively,with a high fluorescence brightness of 38715 and a fluorescence lifetime of 0.70 ns in dichloromethane.EC5 was also exhibited an excellent anti-aggregate ability with the concentration up to 100μmol/L and a high photostability with a high-density power of 880 nm laser beam.Finally,EC5 was used for high temporal and spatial resolution fluorescence imaging of BALB/c mice as well as anti-counterfeiting writing,which demonstrated that EC5 has a wide range of application prospects in the field of nearinfrared fluorescence in vivo imaging.

关 键 词：近红外 分子合成 有机化合物 染料 成像 

分 类 号：O613[理学—无机化学]