摘要
有机小分子荧光探针可以通过与特定分子结合来靶向定位生物体内的各种细胞器,也可以对生物微环境的变化进行检测。以1,8-萘亚酰胺为荧光发色团,通过酰胺化、Sonogashira偶联反应设计合成了一种分子内电荷转移(ICT)双光子荧光探针(Lyso-XAQ)。引入的吗啉结构在靶向溶酶体的同时还可以提高水溶性以及对生物的兼容性,为后续在生物体内进行测试提供了可能。通过核磁、高分辨质谱和荧光光谱对Lyso-XAQ的结构与性能进行表征与分析。研究结果表明:探针最大发射波长和荧光强度与极性参数存在良好的线性关系,相关系数(R2)达到了0.91和0.99。探针对pH和黏度没有响应,同时对常见离子具备较强的抗干扰能力。Lyso-XAQ具有低毒性,可成功靶向于溶酶体,与溶酶体商品化染料的共定位系数高达0.92。因此,Lyso-XAQ可作为新型的极性荧光探针,用于细胞溶酶体靶向成像。
Organic small molecule fluorescent probes can be used to target various organelles in organisms by binding to specific molecules,and can also detect changes in the biological microenvironment.In this paper,An intramolecular charge transfer(ICT)two-photon fluorescent probe(Lyso-XAQ)was designed and synthesized by amidation and Sonogashira coupling reactions using 1,8 naphthylene amide as the fluorescent chromophore.The introduced morpholine structure targets the lysosome while also improving water solubility as well as biocompatibility,offering the possibility of subsequent testing in organisms.The structure and properties of the Lyso-XAQ were characterized and analyzed by nuclear magnetic resonance spectroscopy,high-resolution mass spectroscopy,and fluorescence spectroscopy.These results showed that the maximum emission wavelength and fluorescence intensity of the probe had good linearity with polarity parameters,and the correlation coefficient(r)values reached 0.91 and 0.99.Lyso-XAQ did not respond to pH and viscosity.Moreover,it also had strong anti-interference ability to common ions.Owing to the low cytotoxicity and accurate lysosome-targeting ability(Pearson correlation coefficient is 0.92),lysosomal tracking agent for cell imaging.Therefore,Lyso-XAQ could be used as a lysosomal tracking agent for cell imaging.
作者
徐奥琼
冯可心
张婕
徐文骏
桂斌
姜玉楠
李龙春
XU Aoqiong;FENG Kexin;ZHANG Jie;XU Wenjun;GUI Bin;JIANG Yunan;LI Longchun(School of Materials and Chemistry,Anhui Agricultural University,Hefei 230036,China)
出处
《合成化学》
2025年第8期537-545,共9页
Chinese Journal of Synthetic Chemistry
基金
国家级大学生创训练计划项目(S02310364038)
安徽省大学生创业训练计划项目(S202210364100,S202310364088)
2020年度安徽省自然科学基金资助项目(2008085MB41)。
关键词
萘酰亚胺
双光子
荧光探针
极性
溶酶体
naphthalimide
two-photon
fluorescent probe
polarity
lysosome
