DNA-树状聚脂肪醚杂化体的合成及组装性能研究

doi:10.6023/A13010087

化学学报 ›› 2013, Vol. 71 ›› Issue (04): 549-554.DOI: 10.6023/A13010087 上一篇下一篇

研究论文

DNA-树状聚脂肪醚杂化体的合成及组装性能研究

赵智勇^a,c, 吴芬^a, 杨忠强^b, 刘冬生^b, 范青华^a

a 中国科学院化学研究所分子识别与功能重点实验室北京分子科学国家实验室北京 100190;
b 清华大学化学系有机光电子与分子工程教育部重点实验室北京 100084;
c 中国科学院大学北京 100049

投稿日期:2013-01-17 发布日期:2013-03-01
通讯作者: 杨忠强, 范青华 E-mail:fanqh@iccas.ac.cn; zyang@tsinghua.edu.cn
基金资助:
项目受国家自然科学基金(Nos. 21232008, 21174077, 91027046)和973项目(No. 2013CB932800)资助.

Synthesis and Self-Assembly of DNA-Aliphatic Polyether Dendron Hybrids

Zhao Zhiyong^a,c, Wu Fen^a, Yang Zhongqiang^b, Liu Dongsheng^b, Fan Qing-Hua^a

a Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, China;
b Key Laboratory of Organic Optoelectronics & Molecular Engineering of the Ministry of Education,Department of Chemistry, Tsinghua University, Beijing 100084, China;
c University of Chinese Academy of Sciences, Beijing 100049, China

Received:2013-01-17 Published:2013-03-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21232008, 21174077, 91027046) and 973 Program (No. 2013CB932800).

文章分享

摘要/Abstract

通过半固相合成方法得到一类新型的具柔性骨架的树状聚脂肪醚(PMDC)与DNA的嵌段共聚物, 也称为DNA-树状聚脂肪醚杂化体, 其结构通过了MALDI-TOF MS、HPLC和聚丙烯酰胺凝胶电泳(PAGE)表征. 研究证明, 通过调节DNA-树状聚脂肪醚杂化体的结构和组装的溶剂体系, 可以得到各种不同的有序聚集体(球形胶束、纳米纤维等), 这些组装形貌均通过透射电镜(TEM)、原子力显微镜(AFM)和动态光散射(DLS)进行表征; 荧光包裹实验和DNA互补配对实验不仅证明了疏水树状聚脂肪醚位于组装体内核、DNA处于外壳的组装机理, 也说明这类DNA-树状聚脂肪醚杂化体将在疏水药物运输和纳米技术等领域具有潜在的应用.

关键词: DNA-树状分子, 两亲分子, 自组装, 球形胶束, 纤维

A new kind of amphiphilic DNA-aliphatic polyether dendron hybrids consisting of a flexible hydrophobic polyether dendron and a single stranded DNA are synthesized, which are characterized by MALDI-TOF mass spectroscopy, HPLC and polyacrylamide gel electrophoresis (PAGE). In aqueous solution, as DNA length shortens from 24 mer to 18 mer, to 12 mer, to 6 mer, the hydrophilic DNA content in the DNA-aliphatic polyether dendron hybrid decreases, the morphology of the aggregates change from spherical micelles to nanofibers, and to irregular clusters. These different assemblies from DNA-aliphatic polyether dendron hybrids in aqueous solution are depended on the hydrophobic/hydrophilic ratio between the polyether dendron skeleton and DNA strand. However, when adding 1/10 (V/V) organic solvents such as dichloromethane (DCM), diethyl ether (EtOEt) or tetrahydrofuran (THF) into aqueous solution and after the assembling process that the sample solution is heated to 90 ℃ for 30 min and subsequently cooled to room temperature overnight, the third generation dendron conjugated 18 mer DNA hybrid could assemble into nanofibers. Meanwhile, in the THF/H₂O (1∶10, V/V) mixed solvents, with the same assembling process, as different dendron generations (the second or third generation) and different DNA lengths (6 mer, 12 mer, 18 mer or 24 mer) in the hybrids, all these hybrids could assemble into long nanofibers. The assembled structures have been characterized by transmission electron microscopy (TEM), atomic force microscope (AFM), dynamic light scattering (DLS) and fluorescent experiments. Subsequently, we verified the assembling mechanism that the spherical micelles and nanofibers contain a hydrophobic dendron core and a hydrophilic DNA shell by hydrophobic fluorescent molecule Nile Red encapsulation experiment and precise DNA hybridization to load gold nanoparticles at a size of 10 nm. The hybridization property of DNA at the shell associated with the encapsulation ability of dendron at the inner core indicated the potential application in gene or drug delivery and nanotechnology.

Key words: DNA-dendron, amphiphile, self-assembly, spherical micelle, nanofiber

引用此文

赵智勇, 吴芬, 杨忠强, 刘冬生, 范青华. DNA-树状聚脂肪醚杂化体的合成及组装性能研究[J]. 化学学报, 2013, 71(04): 549-554.

Zhao Zhiyong, Wu Fen, Yang Zhongqiang, Liu Dongsheng, Fan Qing-Hua. Synthesis and Self-Assembly of DNA-Aliphatic Polyether Dendron Hybrids[J]. Acta Chimica Sinica, 2013, 71(04): 549-554.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Israelachvili, J. Intermolecular & Surface Forces, 2nd ed., Academic Press, London, 1991; (b) Blanazs, A.; Armes, S. P.; Ryan, A. J. Macromol. Rapid Commun. 2009, 30, 267.

[2] Fuks, G.; Talom, R. M.; Gauffre, F. Chem. Soc. Rev. 2011, 40, 2475.

[3] (a) Gauthier, M. A.; Klok, H. A. Chem. Commun. 2008, 2591; (b) Klok, H. A. Macromolecules 2009, 42, 7990; (c) König, H. M.; Kilbinger, A. F. M. Angew. Chem., Int. Ed. 2007, 46, 8334; (d) Krishna, O. D.; Kiick, K. L. Biopolymers 2010, 94, 32; (e) Van Hest, J. C. M. Polym. Rev. 2007, 47, 63.

[4] (a) Alemdaroglu, F. E.; Herrmann, A. Org. Biomol. Chem. 2007, 5, 1311; (b) Kwak, M.; Herrmann, A. Angew. Chem., Int. Ed. 2010, 49, 8574.

[5] Lemaitre, M.; Bayard, B.; Lebleu, B. Proc. Natl. Acad. Sci. U. S. A. 1987, 84, 648.

[6] (a) Alemdaroglu, F. E.; Ding, K.; Berger, R.; Herrmann, A. Angew. Chem., Int. Ed. 2006, 45, 4206; (b) Zhao, Z.; Wang, L.; Liu, Y.; Yang, Z.; He, Y.-M.; Li, Z.; Fan, Q.-H.; Liu, D. Chem. Commun. 2012, 48, 9753.

[7] Li, Z.; Zhang, Y.; Fullhart, P.; Mirkin, C. A. Nano Lett. 2004, 4, 1055.

[8] (a) Seeman, N. C. J. Theor. Biol. 1982, 99, 237; (b) Seeman, N. C. Nature 2003, 421, 427.

[9] Costioli, M. D.; Fisch, I.; Garret-Flaudy, F.; Hilbrig, F.; Freitag, R. Biotechnol. Bioeng. 2003, 81, 535.

[10] Tong, G.; Lawlor, J. M.; Tregear, G. W.; Haralambidis, J. J. Org. Chem. 1993, 58, 2223.

[11] (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications, Wiley-VCH, Weinheim, 2001; (b) Jiang, D.-L.; Sato, T.; Aida, T. Chin. J. Polym. Sci. 2001, 19, 161; (c) Li, Y.; He, Y.-M.; Li, Z.-W.; Zhang, F.; Fan, Q.-H. Org. Biomol. Chem. 2009, 7, 1890; (d) Li, P.; Zeng, Y.; Chen, J.; Li, Y.; Li, Y. Acta Chim. Sinica 2012, 70, 1611. (李鹏, 曾毅, 陈金平, 李迎迎, 李嫕, 化学学报, 2012, 70, 1611.)

[12] (a) Caminade, A.-M.; Turrin, C.-O.; Majoral, J.-P. Chem.-Eur. J. 2008, 14, 7422; (b) DeMattei, C. R.; Huang, B.; Tomalia, D. A. Nano Lett. 2004, 4, 771; (c) Carneiro, K. M. M.; Aldaye, F. A.; Sleiman, H. F. J. Am. Chem. Soc. 2010, 132, 679; (d) Sun, Y.; Liu, H.; Xu, L.; Wang, L.; Fan, Q.-H.; Liu, D. Langmuir 2010, 26, 12496; (e) Chen, P.; Sun, Y.; Liu, H.; Xu, L.; Fan, Q.-H.; Liu, D. Soft Matter 2010, 6, 2143.

[13] Wang, L.; Feng, Y.; Sun, Y.; Li, Z.; Yang, Z.; He, Y.-M.; Fan, Q.-H.; Liu, D. Soft Matter 2011, 7, 7187.

[14] (a) Grayson, S. M.; Fréchet, J. M. J. J. Am. Chem. Soc. 2000, 122, 10335; (b) Jayaraman, M.; Fréchet, J. M. J. J. Am. Chem. Soc. 1998, 120, 12996.

[15] Wang, L.; Feng, Y.; Yang, Z.; He, Y.-M.; Fan, Q.-H.; Liu, D. Chem. Commun. 2012, 48, 3715.

[16] Yang, M.; Wang, W.; Yuan, F.; Zhang, X.; Li, J.; Liang, F.; He, B.; Minch, B.; Wegner, G. J. Am. Chem. Soc. 2005, 127, 15107.

[17] Jeong, J. H.; Park, T. G. Bioconjugate Chem. 2001, 12, 917.

[18] Tinland, B.; Pluen, A.; Sturm, J.; Weill, G. Macromolecules 1997, 30, 5763.

[19] Cho, B. K.; Jain, A.; Nieberle, J.; Mahajan, S.; Wiesner, U.; Gruner, S. M.; Turk, S.; Rader, H. J. Macromolecules 2004, 37, 4227.

[20] Fö1rster, S.; Hermsdorf, N.; Leube, W.; Schnablegger, H.; Regenbrecht, M.; Akari, S. J. Phys. Chem. B 1999, 103, 6657.

[21] Yu, K.; Eisenberg, A. Macromolecules 1996, 29, 6359. Percec, V.; Wilson, D. A.; Leowanawat, P.; Wilson, C. J.; Hughes, A. D.; Kaucher, M. S.; Hammer, D. A.; Levine, D. H.; Kim, A. J.; Bates, F. S.; Davis, K. P.; Lodge, T. P.; Klein, M. L.; DeVane, R. H.; Aqad, E.; Rosen, B. M.; Argintaru, A. O.; Sienkowska, M. J.; Rissanen, K.; Nummelin, S.; Ropponen, J. Science 2010, 328, 1009.

DNA-树状聚脂肪醚杂化体的合成及组装性能研究

Synthesis and Self-Assembly of DNA-Aliphatic Polyether Dendron Hybrids

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	胡立伟, 刘宪虎, 刘春太, 宋延林, 李明珠. 光子晶体结构色材料的自组装制备与应用^★[J]. 化学学报, 2023, 81(7): 809-819.
[2]	王凯晴, 袁硕, 徐王东, 霍丹, 杨秋林, 侯庆喜, 于得海. ZIF-8@B-CNF复合气凝胶的制备及其吸附性能研究[J]. 化学学报, 2023, 81(6): 604-612.
[3]	赵天成, 蒋鸿宇, 张琨, 徐一帆, 康欣悦, 胥鉴宸, 周旭峰, 陈培宁, 彭慧胜. 基于环烷烃/乙醇混合碳源高性能碳纳米管纤维的连续化制备[J]. 化学学报, 2023, 81(6): 565-571.
[4]	李兰英, 陶晴, 闻艳丽, 王乐乐, 郭瑞妍, 刘刚, 左小磊. 多聚腺嘌呤DNA探针及其生物传感应用^★[J]. 化学学报, 2023, 81(6): 681-690.
[5]	苏东芮, 任小康, 于沄淏, 赵鲁阳, 王天宇, 闫学海. 酪氨酸衍生物调控酶催化路径可控合成功能黑色素^★[J]. 化学学报, 2023, 81(11): 1486-1492.
[6]	溥旭, 李泽娟, 石隽秋, 朱云卿, 杜建忠. 器官靶向的聚合物核酸载体研究进展^★[J]. 化学学报, 2023, 81(10): 1438-1446.
[7]	Jamshid Kadirkhanov, 钟峰, 张文建, 洪春雁. 聚合诱导自组装制备多腔室囊泡以及成核链段中亲溶剂片段的影响[J]. 化学学报, 2022, 80(7): 913-920.
[8]	牛犇, 翟振宇, 郝肖柯, 任婷莉, 李从举. 基于ZIF-8/PAN复合薄膜的柔性丙酮气体传感器[J]. 化学学报, 2022, 80(7): 946-955.
[9]	王志琴, 项博, 黄晓宇, 陆国林, 冯纯. 磷钨酸对对苯撑乙烯撑寡聚物-b-聚(2-乙烯基吡啶)自晶种行为的影响^※[J]. 化学学报, 2022, 80(3): 297-302.
[10]	殷东, 商宏怡, 余文浩, 向仕凯, 胡平, 赵可清, 冯春, 汪必琴. 三唑环修饰的苯并菲二羧酸酯和酰亚胺: 合成、液晶及凝胶性[J]. 化学学报, 2022, 80(10): 1376-1384.
[11]	郝肖柯, 翟振宇, 孙亚昕, 李从举. 柔性可水洗的Zr-MOFs复合纳米纤维薄膜的制备和性能表征[J]. 化学学报, 2022, 80(1): 49-55.
[12]	金艳梅, 蒙叶, 李远, 史建华, 邓雷. 对称二环己基取代六元瓜环与3-吡啶甲酰肼的超分子自组装[J]. 化学学报, 2022, 80(1): 44-48.
[13]	王旭生, 杨胥, 陈春辉, 李红芳, 黄远标, 曹荣. 石墨烯量子点/铁基金属-有机骨架复合材料高效光催化二氧化碳还原^※[J]. 化学学报, 2022, 80(1): 22-28.
[14]	张欣欣, 刘荣, 王蕾, 付宏刚. 细菌纤维素基柔性锌离子电池正极的构筑及性能研究[J]. 化学学报, 2021, 79(5): 670-677.
[15]	王静, 王锦. 气凝胶维度结构设计与功能化应用的研究进展[J]. 化学学报, 2021, 79(4): 430-442.