Preparation of a Multifunctional Nano-carrier System Based on Carbon Dots with pH-Triggered Drug Release

doi:10.6023/A15120780

Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (3): 241-250.DOI: 10.6023/A15120780 Previous Articles Next Articles

Article

基于碳点多功能纳米载药体系的制备及pH响应释药性能研究

杜方凯, 徐江生, 曾钫, 吴水珠

华南理工大学发光材料与器件国家重点实验室华南理工大学材料科学与工程学院广州 510640

投稿日期:2015-12-15 发布日期:2016-02-23
通讯作者: 杜方凯, 吴水珠 E-mail:dufangkai501@163.com;shzhwu@scut.edu.cn
基金资助:
项目受国家自然科学基金(Nos. 21474031, 21174040, 21025415)、中国博士后科学基金(No. 2015M572305)和国家重大科学研究计划(No. 2013CB834702)资助.

Preparation of a Multifunctional Nano-carrier System Based on Carbon Dots with pH-Triggered Drug Release

Du Fangkai, Xu Jiangsheng, Zeng Fang, Wu Shuizhu

College of Materials Science and Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640

Received:2015-12-15 Published:2016-02-23
Supported by:
Project supported by the NSFC (Nos. 21474031, 21174040, 21025415), China Postdoctoral Science Foundation (No. 2015M572305) and the National Key Basic Research Program of China (Project No. 2013CB834702).

A folated-functionalized nano-carrier system based on carbon dots was successfully synthesized for cancer cell-targeted drug delivery. In this report, using microwave-assisted assay the fluorescent CDots could be obtained via microwave-assisted pyrolysis of glycerol in the presence of 4,7,10-trioxa-1,13-tridecanediamine. The particle size of the CDots was confirmed by AFM and HR-TEM. The finding showed that the average diameter of CDots is about 4 nm. Incorporating (via a cleavable bond) an anticancer drug, which was Doxorubicin (DOX) in this study, and a targeting ligand (folic acid) onto carbon dot produces a more specific anticancer prodrug DOX-CDots-FA. The structure of the DOX-CDots-FA was characterized by ¹H NMR and UV-vis analysis. The loading content of DOX was determined by UV-vis analysis to be 13.5 wt%, and the content of the targeting ligand FA was calculated as 3.13 wt% based on ¹H NMR measurement. Particle size parameter of DOX-CDots-FA was determined by HR-TEM. The results showed that the average diameter of DOX-CDots-FA is about 6 nm. In addition, DOX-CDots-FA showed pH-dependent release, that is, the drug releases faster in pH=5.2 buffer solution than in pH=7.4 one. The cytotoxicity of DOX-CDots-FA, DOX-CDots nanoparticles and free DOX were evaluated and compared using HeLa and L929 cell lines. For the FR-positive HeLa cells, DOX-CDots-FA nanoparticles exhibit superior cytotoxicity as compared to DOX-CDots nanoparticles. These results showed that the FA moieties in DOX-CDots-FA nanoparticles play an important role in enhancing the cytotoxic effect as they increase the binding to FR-expressing cells. This high affinity binding subsequently increases their intracellular uptake as a result of receptor-mediated endocytosis. The FA molecules present on the surface of the nanoparticle prodrug do not have a remarkable effect on cellular uptake and/or cytotoxicity for FR-negative L929 cell lines. The confocal microscope studies revealed that FA-conjugated prodrug DOX-CDots-FA exhibited higher cellular uptake than FA-free nanosystem DOX-CDots which also led to higher cytotoxicity. Thus, multifunctional nano-carrier system could be a promising nanosize anticancer drug carrier with excellent targeting property.

Key words: targeted, fluorescence, prodrug, carbon dots, controlled drug releasing

Cite this article

Du Fangkai, Xu Jiangsheng, Zeng Fang, Wu Shuizhu. Preparation of a Multifunctional Nano-carrier System Based on Carbon Dots with pH-Triggered Drug Release[J]. Acta Chim. Sinica, 2016, 74(3): 241-250.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Finkel, T.; Serrano, M.; Blasco, M. A. Nature 2007, 448, 767.
[2] Davis, M. E.; Chen, Z.; Shin, D. M. Nat. Rev. Drug Discovery 2008, 7, 771.
[3] Pan, D. K.; Zhang, H. Acta Chim. Sinica 2011, 69, 1545. (盘登科, 张慧, 化学学报, 2011, 69, 1545.)
[4] Pecot, C. V.; Calin, G. A.; Coleman, R. L.; Lopez-Berestein, G.; Sood, A. K. Nat. Rev. Cancer 2011, 11, 59.
[5] Modi, S.; Swetha, M. G.; Goswami, D.; Gupta, G. D.; Mayor, S.; Krishnan, Y. Nat. Nanotechnol. 2009, 4, 325.
[6] Wu, Y. L.; Chen, W.; Meng, F. H.; Wang, Z. J.; Cheng, R.; Deng, C.; Liu, H. Y.; Zhong, Z. Y. J. Controlled Release 2012, 164, 338.
[7] Kaminskas, L. M.; McLeod, V. M.; Kelly, B. D.; Cullinane, C.; Sberna, G.; Williamson, M.; Boyd, B. J.; Owen, D. J.; Porter, C. J. Mol. Pharm. 2012, 9, 422.
[8] Xiao, Y.; Hong, H.; Javadi, A.; Engle, J. W.; Xu, W.; Yang, Y.; Zhang, Y.; Barnhart, T. E.; Cai, W.; Gong, S. Biomaterials 2012, 33, 3071.
[9] Liu, C. Y.; Hu, J. H.; Yang, D.; Yang, W. L. Acta Chim. Sinica 2009, 67, 843. (刘聪颖, 胡建华, 杨东, 杨武利, 化学学报, 2009, 67, 843.)
[10] Liu, C. J.; Zhang, P.; Tian, F.; Li, W. C.; Li, F.; Liu, W. G. J. Mater. Chem. 2011, 21, 13163.
[11] Baker, S. N.; Baker, G. A. Angew. Chem., Int. Ed.2010, 49, 6726.
[12] Yang, F.; Wang, L. L.; Guo, Z. H. Acta Chim. Sinica 2012, 70, 1283. (杨帆, 王伶俐, 郭志慧, 化学学报, 2012, 70, 1283.)
[13] Wang, F.; Xie, Z.; Zhang, H.; Liu, C. Y.; Zhang, Y. G. Adv. Funct. Mater. 2011, 21, 1027.
[14] Liu, T. T.; Peng, C.; Ma, Y. C.; Ouyang, J. Acta Chim. Sinica 2013, 71, 962. (刘亭廷, 彭程, 马云川, 欧阳津, 化学学报, 2013, 71, 962.)
[15] Yang, Y. H.; Cui, J. H.; Zheng, M. T.; Hu, C. F.; Tan, S. Z.; Xiao, Y.; Yang, Q.; Liu, Y. L. Chem. Commun. 2012, 48, 380.
[16] Li, T. F.; Li, Y. W.; Xiao, L.; Yu, H. T.; Fan, L. Z. Acta Chim. Sinica 2014, 72, 227. (李腾飞, 李昳玮, 肖璐, 余洪涛, 范楼珍, 化学学报, 2014, 72, 227.)
[17] Tang, J.; Kong, B.; Wu, H.; Xu, M.; Wang, Y. C.; Wang, Y. L.; Zhao, D. Y.; Zheng, G. F. Adv. Mater. 2013, 25, 6569.
[18] Choi, Y.; Kim, S.; Choi, M. H.; Ryoo, S. R.; Park, J.; Min, D. H.; Kim, B. S. Adv. Funct. Mater. 2014, 24, 5781.
[19] Zhou, L.; Li, Z. H.; Liu, Z.; Ren, J. S.; Qu, X. G. Langmuir 2013, 29, 6396.
[20] Pandey, S.; Thakur, M.; Mewada, A.; Anjarlekar, D.; Mishra, N.; Sharon, M. J. Mater. Chem. B 2013, 1, 4972.
[21] Fan, J. Q.; Fang, G.; Zeng, F.; Wang, X. D.; Wu, S. Z. Small 2013, 9, 613.
[22] Peng, H.; Travas, S. J. Chem. Mater. 2009, 21, 5563.
[23] Allen, H. M.; Cullis, P. R. Adv. Drug Delivery Rev. 2013, 65, 36.
[24] Zhang, P.; Li, W. C.; Zhai, X. Y.; Liu, C. J.; Dai, L. M.; Liu, W. G. Chem. Commun. 2012, 48, 10431.

基于碳点多功能纳米载药体系的制备及pH响应释药性能研究

Preparation of a Multifunctional Nano-carrier System Based on Carbon Dots with pH-Triggered Drug Release

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yinuo Wang, Shiyang Shao, Lixiang Wang. Recent Advances in Multiple Resonance Organic/Polymer Fluorescent Materials with Narrowband Emission^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1202-1214.
[2]	Feida Che, Xiaoming Zhao, Xin Zhang, Qi Ding, Xin Wang, Ping Li, Bo Tang. Fluorescence Imaging of Active Molecules Associated with Depression^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1255-1264.
[3]	Chen Li, Xiao Si, Jinbo Li, Yan Zhang. Chemical Modification and Delivery System of Small Interfering RNA Drugs^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1240-1254.
[4]	Fengjie Ge, Kaizhi Zhang, Qingpeng Cao, Hui Xu, Tao Zhou, Wenhao Zhang, Xinxin Ban, Xiaobo Zhang, Na Li, Peng Zhu. Design, Synthesis and Electroluminescence Performance of Flexible Fluorenyl Block Delayed Fluorescence Dimers [J]. Acta Chimica Sinica, 2023, 81(9): 1157-1166.
[5]	Hongyue Wu, Rui Guo, Hanwen Chi, Yonghe Tang, Sirui Song, Enxiang Ge, Weiying Lin. Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications [J]. Acta Chimica Sinica, 2023, 81(8): 905-911.
[6]	Xiao Wang, Xingwen Wang, Lehui Xiao. Nanocatalytic Mechanisms Investigated by Single Molecule Fluorescence Imaging at the Single-Particle Level [J]. Acta Chimica Sinica, 2023, 81(8): 1002-1014.
[7]	Wenshan Zheng, Guanbin Gao, Hao Deng, Taolei Sun. Room Temperature Synthesis and Near-infrared Fluorescence Performance Optimization of Ag₂Se@Ag₂S Core-shell Quantum Dots [J]. Acta Chimica Sinica, 2023, 81(7): 763-770.
[8]	Zhenyu Liu, Junfeng Rao, Shoujia Zhu, Bingyang Wang, Fan Yu, Quanyou Feng, Linghai Xie. Research Progress of Solution-Processed Self-Host Thermally Activated Delayed Fluorescence Materials [J]. Acta Chimica Sinica, 2023, 81(7): 820-835.
[9]	Yinfeng Wang, Meng Li, Chuanfeng Chen. Chiral Triptycene-Based Red Thermally Activated Delayed Fluorescence Polymers and Their Organic Light-Emitting Diodes^★ [J]. Acta Chimica Sinica, 2023, 81(6): 588-594.
[10]	Xin Lv, Yi Wu, Boran Zhang, Wei Guo. Design, Synthesis and Photodynamic Therapy of a H₂O₂-Activatable Near Infrared Borondipyrromethene （BODIPY） Photosensitizer [J]. Acta Chimica Sinica, 2023, 81(4): 359-370.
[11]	Shaoqin Zhang, Meiqing Li, Zhongjun Zhou, Zexing Qu. Theoretical Study on the Multiple Resonance Thermally Activated Delayed Fluorescence Process [J]. Acta Chimica Sinica, 2023, 81(2): 124-130.
[12]	Yanqin Huang, Lijun Li, Shupei Yang, Rui Zhang, Xingfen Liu, Quli Fan, Wei Huang. HA-AuNPs/FDF for Highly Sensitive Detection of Hyaluronidase, Tumor-targeting Fluorescence Cell Imaging and Phototherapy [J]. Acta Chimica Sinica, 2023, 81(12): 1687-1694.
[13]	Li Sun, Yajing Wang, Tao Li, Yingshu Guo, Shusheng Zhang. Au Nanocages Probes for Mitochondrial Imaging and Photothermal Damage Cells^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1301-1310.
[14]	Sirui Song, Yonghe Tang, Liangguang Sun, Rui Guo, Guanfan Jiang, Weiying Lin. Development of a Novel Fluorescent Probe Based on Coumarin Fluorophore for Polarity Detection and Its Imaging Applications [J]. Acta Chimica Sinica, 2022, 80(9): 1217-1222.
[15]	Jie Zhao, Zhiwen Wang, Huaqing Li, Qi Ai, Peiqing Cai, Junjie Si, Xin Yao, Xiaoguang Hu, Zugang Liu. Synthesis and Properties of Visible-light-driven Fluorescence Turn-on Diarylethenes Based on Benzo[b]naphtho[1,2-d]thiophene [J]. Acta Chimica Sinica, 2022, 80(9): 1223-1230.