一种极性依赖性双光子溶酶体荧光探针的合成及性能  

Synthesis and Properties of A Lysosomal Polarity-specific Tw-photo Fluorescent Probe

作　　者：王碧玉 刘成露 徐奥琼 冯可心 李龙春 WANG Biyu;LIU Chenglu;XU Aoqiong;FENG Kexin;LI Longchun(School of Science,Anhui Agricultural University,Hefei 230036,China)

机构地区：[1]安徽农业大学理学院,安徽合肥230036

出　　处：《合成化学》2024年第2期128-135,共8页Chinese Journal of Synthetic Chemistry

基　　金：安徽省大学生创业训练计划项目(S202110364092);安徽农业大学大学生创业训练计划项目(202110364194);2020年度安徽省自然科学基金资助项目(2008085MB41)。

摘　　要：探针Lyso-LCL是一种极性依赖双光子荧光探针,具有低毒性,可成功靶向溶酶体。以4-溴-1,8-萘二甲酸酐为原料合成了具有D-π-A结构的荧光探针Lyso-LCL,通过^(1)H NMR,^(13)C NMR和HR-MS(ESI)对目标分子结构进行了表征,并对Lyso-LCL的紫外吸收光谱、荧光发射光谱以及双光子荧光光谱进行了测试和分析。结果表明:该探针具有溶剂致变色效应,随着溶剂极性的增大,探针的荧光发射峰发生明显红移,且荧光强度下降,并且探针具有双光子性质。此外,探针Lyso-LCL具有低毒性,可成功靶向溶酶体,与溶酶体商品化染料的共定位系数高达0.93。因此,Lyso-LCL可作为一种新型的极性荧光探针,用于细胞溶酶体靶向成像。The probe Lyso-LCL is a polar-dependent two-photon fluorescence probe with low toxicity that can successfully target lysosomes.A novel donor-π-acceptor(D-π-A)type of fluorescent probe,Lyso-LCL,based on the 4-bromo-1,8-naphthalic anhydride has been developed.The structures of these compounds were assigned based on the results from^(1)H NMR,^(13)C NMR spectroscopy and HR-MS(ESI).Moreover,the optical properties of Lyso-LCL,such as UV absorption spectrum and fluorescence emission spectrum,were further investigated.The results show that it has a significant response to the polarity with a solvatochromic effect.With the increase in solvent polarity,the fluorescence emission peak of Lyso-LCL is red-shifted and the fluorescence intensity is decreased.Importantly,Lyso-LCL had the large two-photon absorption cross-section and good two-photon absorption performance.Moveover,Lyso-LCL has the low cytotoxicity and accurate lysosome-targeting ability,and the pearson correlation coefficient is 0.93.Therefore,Lyso-LCL could be used as a novel polarity-specific fluorescent probe and lysosomal tracking agent for cell imaging.

关 键 词：D-π-A 荧光探针 溶致变色 双光子 极性 溶酶体靶向 

分 类 号：O625.15[理学—有机化学]