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第 36 卷第 2 期 精 细 化 工 Vol.36, No.2
201 9 年 2 月 FINE CHEMICALS Feb. 2019
功能材料
三苯胺类荧光探针的合成与细胞成像
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尹 培 ,马拉毛草 ,马恒昌
(1. 西北师范大学 化学化工学院 甘肃省高分子材料重点实验室 生态环境相关高分子材料教育部重点实
验室,甘肃 兰州 730070;2. 西北师范大学 逸夫图书馆,甘肃 兰州 730070)
摘要:以三苯胺为原料,通过 Vilsmeier-Haack 和 McMurry 反应合成了一个碳碳双键连接两个三苯胺的荧光分子
1,2-二(三苯胺基)乙烯(TPAS)。采用紫外-可见光谱和荧光光谱对 TPAS 的光学性质进行了考察。结果表明:TPAS
有很强的荧光发射性能,荧光发射为蓝光,荧光强度与浓度的线性关系较好,且溶剂化效应不强,光稳定性良
好。采用扫描电镜测试了 TPAS 的聚集态行为。结果显示:当水的体积分数增大后,TPAS 分子聚集,形貌改变。
采用 MTT 法对 TPAS 进行了细胞毒性测试。结果表明,不同 TPAS 浓度下,细胞的存活度都在 80%以上,说明
TPAS 对细胞的毒性很低,生物相容性好。并实现了 TPAS 对 A549 的活细胞成像。
关键词:三苯胺;荧光探针;光学性质;生物相容性;细胞成像;功能材料
中图分类号:O621.2 文献标识码:A 文章编号:1003-5214 (2019) 02-0212-06
Synthesis and Cell Imaging of Triphenylamine-based Fluorescent Probe
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YIN Pei , MALA Mao-cao , MA Heng-chang
(1. Key Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education, Key Laboratory of
Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University,
Lanzhou 730070, Gansu, China; 2. Shaw Library, Northwest Normal University, Lanzhou 730070, Gansu, China)
Abstract: 4,4'-(Ethene-1,2-diyl)bis(N,N-diphenylaniline) (TPAS), a compound was characteristic of
carbon-carbon double bond connecting triphenylamines was synthesized via Vilsmeier-Haack reaction and
McMurry reaction using triphenylamine as a raw material. The optical properties of TPAS were studied by
UV-vis absorption spectrum and fluorescence spectrum. The results showed that TPAS had strong
fluorescence emission, and the fluorescence emission was blue light. The fluorescence intensity had a good
linear relationship with the TPAS concentration. The solvation effect was not strong, and the optical
stability was good. The aggregation of TPAS was characterized by scanning electron microscope (SEM).
The results revealed that when the volume fraction of water increased, the TPAS molecules accumulated
and the morphology changed. The cytotoxicity of TPAS was tested by MTT assays, the cell viability was
above 80% at different concentrations of TPAS, indicating that TPAS had low toxicity to cells and good
biocompatibility. In addition, the imaging was successfully achieved in living human lung cancer A549 cells.
Key words: triphenylamine; fluorescent probe; optical property; biocompatibility; cell imaging; functional
materials
Foundation item: National Natural Science Foundation of China (21764012)
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荧光探针由于灵敏度高、选择性好、响应时间 从而实现检测 。与其他生物成像方式相比,荧光
短、可视化等优点,在分子、离子检测和细胞成像 成像成本低廉、易于操作,能够在细胞层面上提供
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领域获得广泛应用 。一般地,当待测体系中的物 高分辨率、高灵敏度的图像信息,是一种广泛应用
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质与识别基团发生作用时,会导致探针共轭程度和 于生物科学和临床医学的生物成像方法 。目前,
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电荷分布发生变化,使荧光强度发生敏化或猝灭, 用于标记的荧光探针染料主要有荧光素类 、罗丹
收稿日期:2018-04-11; 定用日期:2018-08-07; DOI: 10.13550/j.jxhg.20180259
基金项目:国家自然科学基金(21764012)
作者简介:尹 培(1995—),女,硕士生。联系人:马恒昌(1978—),男,副教授,电话:0931-7975257,E-mail:mahczju@hotmail.com。