有机化学 ›› 2018, Vol. 38 ›› Issue (10): 2700-2705.DOI: 10.6023/cjoc201803029 上一篇    下一篇

所属专题: 荧光探针-生物传感合辑 有机超分子化学合辑

研究论文

基于四苯基乙烯的荧光纳米探针的合成及细胞成像研究

夏琦a, 陈子康a, 张志德b, 刘瑞源a,b   

  1. a 南方医科大学药学院 广州 510515;
    b 南方医科大学生物医学工程学院 广州 510515
  • 收稿日期:2018-03-19 修回日期:2018-05-18 发布日期:2018-06-06
  • 通讯作者: 刘瑞源,E-mail:ruiyliu@smu.edu.cn E-mail:ruiyliu@smu.edu.cn
  • 基金资助:

    国家自然科学基金(No.81671749)资助项目.

Synthesis and Live Cell Imaging of Tetraphenylethene-Based Fluorescent Nanoprobes

Xia Qia, Chen Zikanga, Zhang Zhideb, Liu Ruiyuana,b   

  1. a School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515;
    b School of Biomedical Engineering, Southern Medical University, Guangzhou 510515
  • Received:2018-03-19 Revised:2018-05-18 Published:2018-06-06
  • Contact: 10.6023/cjoc201803029 E-mail:ruiyliu@smu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 81671749).

近年来,设计合成具有生物相容性好、光学性质稳定、细胞毒性低的荧光纳米探针是生物医学领域的研究热点.通过1,1,2-三苯基-2-(4-甲醛基苯)乙烯与2-(4-氧代-3-苯基-1,3-噻唑-2-亚基)丙二腈反应合成新型四苯基乙烯类荧光探针(TPE-Rho),考察其聚集诱导发光(AIE)特性;使用共沉淀法将TPE-Rho包裹于两亲性表面活性剂Pluronic F-127中得到粒径分布均匀的荧光纳米探针(TPE-Rho dots).TPE-Rho dots显示黄色荧光发射、良好的稳定性、长斯托克斯位移(约200 nm)等光学性能,并且对细胞生长活性基本无影响,随后以人肝癌细胞SK-Hep1和人结肠癌细胞LoVo作为模型细胞进行细胞成像,观察染色部位和荧光强度.结果表明,TPE-Rho dots能够对活细胞进行染色,选择性作用于细胞质.由此可以确定TPE-Rho dots的生物相容性良好、细胞毒性小、细胞膜通透性高、光稳定性好,可作为一种活细胞染色剂.

关键词: 四苯基乙烯, 聚集诱导发光, 纳米探针, 细胞成像

In recent years, designing and synthesizing fluorescent nanoprobes with good biocompatibility, stable optical properties and low cytotoxicity are research hotspots in the biomedical field. The novel tetraphenylethene-based fluorescent probe (TPE-Rho) was synthesized by reaction of 1,1,2-triphenyl-2-(4-formylphenyl)ethene with 2-(4-oxo-3-phenyl-1,3-thia-zol-2-ylidene)malononitrile. After the aggregation-induced emission (AIE) characteristics of TPE-Rho were investigated, TPE-Rho dots with uniform particle size distribution were obtained through a modified nanoprecipitation method by using Pluronic F-127 (amphiphilic surfactant) as the encapsulation. TPE-Rho dots have excellent optical property such as strong yellow fluorescence, good stability and long Stokes shift (ca. 200 nm), and have little effect on cell growth activity. Then, TPE-Rho dots were utilized to stain live SK-Hep1 cells and LoVo cells, the staining region and fluorescent intensity were analyzed. The experimental results show that TPE-Rho dots have no significant effect on cell viability, and can stain live cells and selectively act on the cytoplasm. Thus, it can be confirmed that TPE-Rho dots has good biocompatibility, low cytotoxicity, high cell membrane permeability, and good stability, therefore it can be used as a viable cell staining agent.

Key words: tetraphenylethene, aggregation-induced emission, nanoprobes, cell imaging