文献类型：期刊文献

中文题名：基于萘酸酐的水溶性荧光探针:合成以及在细胞成像中的应用

英文题名：Naphthalic Anhydride-Based Water-Soluble Fluorescent Probe:Synthesis and Application in Cell Imaging

作者：黄存存[1];晏琦帆[1]

机构：[1]华东理工大学化学与分子工程学院,上海200237

年份：2021

卷号：47

期号：5

起止页码：569

中文期刊名：华东理工大学学报（自然科学版）

外文期刊名：Journal of East China University of Science and Technology

收录：CSTPCD;;Scopus;北大核心:【北大核心2020】；CSCD:【CSCD_E2021_2022】；

基金：国家自然科学基金(21602061);北京分子科学国家研究中心开放课题基金(BNLMS201839)。

语种：中文

中文关键词：荧光探针;细胞成像;螺二芴;酸酐;萘酰亚胺

外文关键词：fluorescent probe;cell imaging;spiro-bifluorene;anhydride;naphthalimide

摘要：设计并合成了以螺芴刚性结构为骨架、基于萘酸酐基团的探针分子(3、6和9)。将萘酰亚胺荧光团转化为萘酸酐荧光团,利用酸酐基团在碱性条件下的水解反应,将萘酸酐基团转化为带电荷的羧酸根进而提高探针分子的水溶性,同时酸酐基团在有机溶剂中的溶解性也有利于探针分子的分离纯化过程。随着水溶液pH值的增大,探针分子的吸收光谱起峰蓝移,探针溶解性增加,表明探针的萘酸酐基团已经向羧酸根转变。探针分子3、6、9在细胞成像中皆成功染色,有效消除了背景信号干扰问题,说明通过将萘酰亚胺转化为萘酸酐提高了现有荧光团的水溶性。
The development of water-soluble fluorescent probes has become a topical research area for environmental and biological applications.Water solubility is desired for fluorescent probes to function in aqueous media.The introduction of water-soluble groups to conventional organic fluorophores is challenging in terms of preparation and purification.In this paper,fluorescent probes 3,6 and 9 based on spirobilfuorene skeleton were designed and synthesized,featuring naphthalene anhydride functionality.These compounds were prepared by hydrolysis of corresponding molecules bearing naphthalenedimide,which is a common electron acceptor often used in fluorophores.The anhydride group not only allows these compounds to be separated and purified in common organic solvents,such as chloroform and tetrahydrofuran,but also imparts enough water solubility.The anhydride group undergoes hydrolysis upon exposing to alkaline conditions in aqueous media,evidenced by a hypochromic-shift in UVvis absorption spectra with increasing pH.For example,the ratio of absorption at 365 nm to 472 nm of compound 3 in water,elevated from 2.5 at pH=2.0 continuously to 3.4 at pH=11.0.The conversion from charge neutral anhydride form to negatively charged carboxylate form switches the solubility of such probes to more polar media.These probes displayed fluorescence emission in the visible range,at 519,440,and 504 nm,respectively.After incubation Hela cells with these probes at 10μmol/L for 30 min,confocal microscopy displays clear cell contours with minimal noise,demonstrating efficiency of our strategy.