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

doi:10.6023/cjoc201509045

有机化学 ›› 2016, Vol. 36 ›› Issue (3): 555-561.DOI: 10.6023/cjoc201509045 上一篇下一篇

研究论文

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

牛艳芳, 钱鹰, 胡秀东

东南大学化学化工学院南京 211189

收稿日期:2015-09-30 修回日期:2015-11-06 发布日期:2015-11-26
通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
基金资助:
国家自然科学基金(No. 61178057)资助项目.

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

Niu Yanfang, Qian Ying, Hu Xiudong

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2015-09-30 Revised:2015-11-06 Published:2015-11-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 61178057).

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1. 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.PDF(333KB)

摘要/Abstract

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/SiO₂, 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.

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

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, ¹³C 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 H₂O/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.

Key words: pyridine naphthalimide-PAMAM dendrimer, water-soluble fluorescent molecule, aggregation-induced emission, nanoparticles, cells imaging

引用此文

牛艳芳, 钱鹰, 胡秀东. 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[J]. 有机化学, 2016, 36(3): 555-561.

Niu Yanfang, Qian Ying, Hu Xiudong. Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer[J]. Chin. J. Org. Chem., 2016, 36(3): 555-561.

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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

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