水溶性聚噻吩衍生物的合成、表征及细胞成像

doi:10.7503/cjcu20180204

高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (11): 2594.doi: 10.7503/cjcu20180204

水溶性聚噻吩衍生物的合成、表征及细胞成像

王凤燕(), 晏妮, 魏俊基, 夏慧芸, 宋莉芳, 宋家乐, 高莉宁, 颜录科

长安大学材料科学与工程学院, 西安 710064

收稿日期:2018-03-14 出版日期:2018-11-10 发布日期:2018-10-09
作者简介:联系人简介: 王凤燕, 女, 博士, 讲师, 主要从事共轭聚合物的设计、合成及生物医药应用研究. E-mail: wfy0914@chd.edu.cn
基金资助:
国家自然科学基金(批准号: 21704005, 51502021)、陕西省自然科学基础研究计划项目(批准号: 2017JQ2003, 2017JQ2023, 2017JQ2025)和中国博士后科学基金(批准号: 2016M602745)资助.

Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative^†

WANG Fengyan^*(), YAN Ni, WEI Junji, XIA Huiyun, SONG Lifang, SONG Jiale, GAO Lining, YAN Luke

School of Materials Science & Engineering, Chang’an University, Xi’an 710064, China

Received:2018-03-14 Online:2018-11-10 Published:2018-10-09
Contact: WANG Fengyan E-mail:wfy0914@chd.edu.cn
Supported by:
† Supported by the National Natural Science Foundation of China(Nos.21704005, 51502021), the Natural Science Basic Research Plan in Shaanxi Province of China(Nos.2017JQ2003, 2017JQ2023, 2017JQ2025) and the China Postdoctoral Science Foundation(No.2016M602745).

摘要/Abstract

摘要：

采用FeCl₃氧化聚合制备了一种新型的水溶性聚噻吩衍生物: N,N,N-三甲基-2-(2-{2-[2-(3-噻吩)乙氧基]乙氧基}乙氧基)乙铵溴化物与(4-{[2-(2-{2-[2-(3-噻吩)乙氧基]乙氧基}乙氧基)乙基]氨基甲酰基}苯基)硼酸的无规共聚物(简称PT-2). 在水溶液中对其紫外/可见吸收光谱以及荧光发射光谱进行了表征, 其最大吸收波长为419 nm, 最大发射波长为579 nm, 摩尔吸光系数为4.6×10³ L/(mol·cm), 荧光量子产率为12%. 动态光散射实验表明其在水溶液中所形成的聚集体平均粒径为234 nm. PT-2在100 W汞灯照射下表现出较好的光稳定性. 3-(4,5-二甲基噻唑-2)-2,5-二苯基四氮唑溴盐(MTT)实验证明, 其对人肺癌A549细胞的毒性较低, 细胞成像及共定位分析结果表明PT-2能够富集在溶酶体中, 因此, 在溶酶体特异性的细胞成像方面具有潜在的应用价值.

关键词: 水溶性聚噻吩衍生物, 溶酶体特异性, 细胞成像

Abstract:

A new polythiophene derivative, random copolymer of N,N,N-trimethyl-2-(2-{2-[2-(thiophen-3-yl)ethoxy]ethoxy}ethoxy)ethanaminium bromide and(4-{[2-(2-{2-[2-(thiophen-3-yl)ethoxy]ethoxy}ethoxy)ethyl]carbamoyl}phenyl)boronic acid, abbreviated as PT-2, was synthesized through FeCl₃oxidative polymerization reaction. Its optical properties and applications in cellular imaging were investigated. The UV-Vis absorption and fluorescence emission spectra were measured in water solution, the absorption maximum is 419 nm, emission maximum is 579 nm, molar absorption coefficient is 4.6×10³ L/(mol·cm), fluorescence quantum yield is 12%. Dynamic light scattering test showed that the average particle size of its aggregates formed in water was about 234 nm. Under the irradiation of mercury lamp(100 W), PT-2 exhibits a satisfactory photostability. Moreover, after co-culture with human lung cancer(A549) cells for 24 h, PT-2 shows low cytotoxicity and could be enriched in the cytoplasm. It’s fluorescence image could superposed well with lysosome-specific dye(Lyso Tracker Blue DND-22). Thus, PT-2 has potential application value in lysosomal-specific cell imaging.

Key words: Water soluble polythiophene derivative, Lysosomal-specific, Cell imaging

中图分类号:

O633.3

TrendMD:

王凤燕, 晏妮, 魏俊基, 夏慧芸, 宋莉芳, 宋家乐, 高莉宁, 颜录科. 水溶性聚噻吩衍生物的合成、表征及细胞成像. 高等学校化学学报, 2018, 39(11): 2594.

WANG Fengyan, YAN Ni, WEI Junji, XIA Huiyun, SONG Lifang, SONG Jiale, GAO Lining, YAN Luke. Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative^†. Chem. J. Chinese Universities, 2018, 39(11): 2594.

图/表 8

Scheme 1 Synthetic routes of PT-2

Fig.1 Hydrodynamic diameter distribution of 100 μmol/L PT-2 in aqueous solution

Fig.2 Normalized UV-Vis absorption(a) and fluorescent(b) emission spectra of 40 μmol/L PT-2 in aqueous solution excited at 460 nm

Fig.3 Photostability of 500 μmol/L PT-2 in aqueous solution at 100 W mercury lamp irradiation(450 nm/70 nm excitation filter)

Fig.4 Cell viability data of A549 cells at different concentrations of PT-2

Fig.5 Cellular location of PT-2 after 24 h incubation with A549 cells(A—D) Experimental group A549 cells were stained with PT-2 and nuclear dye Hoechst 33342; (A'—D') control group A549 cells were stained with Hoechst 33342; (A, A') phase contrast; (B, B') Hoechst channel; (C, C') PT-2 channel; (D, D') merged. PT-2(20 μmol/L in repeated units; excitation: 488 nm; collection: 530—630 nm; false color: orange), Hoechst 33342(nuclei stain; 10 μg/mL; excitation: 405 nm; collection: 425—475 nm; false color: blue).

Fig.6 Co-location of PT-2 and Lyso Tracker Blue DND-22 in A549 cells(A) Phase contrast; (B) DND-22; (C) PT-2; (D) overlapped image of (B) and (C). PT-2(20 μmol/L in repeated units; excitation: 488 nm; collection: 530—630 nm; false color: orange).

Fig.7 Colocalization image(A) and line series analysis of PT-2(a) and Lyso Tracker Blue DND-22(b)(B)

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水溶性聚噻吩衍生物的合成、表征及细胞成像

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水溶性聚噻吩衍生物的合成、表征及细胞成像

Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative†

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Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative^†