水溶性吡啶萘酰亚胺-聚酰胺-胺荧光树形分子的合成、聚集诱导荧光增强及细胞成像  

Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer

作　　者：牛艳芳[1] 钱鹰[1] 胡秀东[1] 

机构地区：[1]东南大学化学化工学院,南京211189

出　　处：《有机化学》2016年第3期555-561,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.61178057)资助项目~~

摘　　要：将具有聚集诱导荧光的4-(2-吡啶乙烯基)-1,8-萘酰亚胺单元通过酰胺化反应连接到聚酰胺-胺(PAMAM)树形分子上,制备了一种水溶性吡啶萘酰亚胺-聚酰胺-胺荧光树形分子PN-PAMAM.结构经核磁共振氢谱、核磁共振碳谱、红外及高分辨质谱表征.吡啶萘酰亚胺-聚酰胺-胺树形分子PN-PAMAM具有明显的聚集诱导荧光增强(AIEE)特性.在固体态时的最大荧光发射波长为532 nm,紫外灯下发出黄绿色荧光.在纯水中的最大荧光发射波长为494 nm,荧光量子产率为4.42%.在水含量为60%的水/四氢呋喃混合溶液中,其荧光强度达到最大,荧光发射波长为485 nm,荧光量子产率增大到17.54%.制备了一种负载聚集诱导荧光染料PN-PAMAM的二氧化硅纳米粒子PN-PAMAM/Si O_2,测得该纳米粒子的荧光发射波长为473 nm,粒径约为40 nm.测定了水溶液中树形分子PN-PAMAM与乳腺癌细胞MCF-7共同孵化后的共聚焦荧光成像,得到清晰的蓝场荧光照片.研究表明,吡啶萘酰亚胺-聚酰胺-胺树形分子PN-PAMAM是一种水溶性荧光分子,具有明显的聚集诱导荧光增强特性,可广泛应用于肿瘤定位、生物追踪及纳米材料等重要领域.A water-soluble pyridine naphthalimide-polyamidoamine dendrimer（PN-PAMAM） was synthesized by the amidation reaction of 4-（2-vinylpyridine）-1,8-naphthalimide unit and the polyamidoamine（PAMAM）. The structure was characterized by ~1H NMR, ^（13） C NMR, IR and HRMS techniques. PN-PAMAM displayed obvious aggregation-induced emission enhancement（AIEE） behavior. The experimental results demonstrated that dendrimer PN-PAMAM in solid state emitted a yellow-green fluorescence and the maximum emission wavelength was 532 nm. In aqueous solution the maximum emission wavelength was 494 nm and the fluorescence quantum yield was 4.42%. The fluorescence intensity reached the maximum at 60% water volume fraction in H_2O/THF mixed solution. The fluorescence emission wavelength was 485 nm and the fluorescence quantum yield was increased to 17.54%. The photophysical properties of the silica nanoparticles loaded AIEE dye PN-PAMAM were examined. The fluorescence emission wavelength was 473 nm and the particle diameter was about 40 nm.In addition, dendrimer PN-PAMAM were applied for breast cancer MCF-7 cells imaging, getting clear blue-field photograph.In summary, the pyridine naphthalimide-PAMAM dendrimer is a water-soluble fluorescent dye and displays AIEE behavior.PN-PAMAM can be widely used in areas of tumor localization, bio-tracking and nano-materials.

关 键 词：吡啶萘酰亚胺-聚酰胺-胺树形分子 水溶性荧光分子 聚集诱导荧光增强 纳米粒子 细胞成像 

分 类 号：O657[理学—分析化学] O631.1[理学—化学]