Citation: 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 Chimica Sinica, ;2016, 74(3): 241-250. doi: 10.6023/A15120780 shu

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

1.
College of Materials Science and Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640

Corresponding author: Du Fangkai, dufangkai501@163.com Wu Shuizhu, shzhwu@scut.edu.cn
Received Date: 15 December 2015

Fund Project: the National Key Basic Research Program of China 2013CB834702NSFC 21474031, 21174040, 21025415China Postdoctoral Science Foundation 2015M572305

Figures(11)

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.
- targeted,
- fluorescence,
- prodrug,
- carbon dots,
- controlled drug releasing
1. [1]
  Finkel, T.; Serrano, M.; Blasco, M. A. Nature 2007, 448, 767.
2. [2]
  Davis, M. E.; Chen, Z.; Shin, D. M. Nat. Rev. Drug Discovery 2008, 7, 771.
3. [3]
4. [4]
  Pecot, C. V.; Calin, G. A.; Coleman, R. L.; Lopez-Berestein, G.; Sood, A. K. Nat. Rev. Cancer 2011, 11, 59.
5. [5]
  Modi, S.; Swetha, M. G.; Goswami, D.; Gupta, G. D.; Mayor, S.; Krishnan, Y. Nat. Nanotechnol. 2009, 4, 325.
6. [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. [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. [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. [9]
10. [10]
  Liu, C. J.; Zhang, P.; Tian, F.; Li, W. C.; Li, F.; Liu, W. G. J. Mater. Chem. 2011, 21, 13163.
11. [11]
  Baker, S. N.; Baker, G. A. Angew. Chem., Int. Ed.2010, 49, 6726.
12. [12]
13. [13]
  Wang, F.; Xie, Z.; Zhang, H.; Liu, C. Y.; Zhang, Y. G. Adv. Funct. Mater. 2011, 21, 1027.
14. [14]
15. [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. [16]
17. [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. [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. [19]
  Zhou, L.; Li, Z. H.; Liu, Z.; Ren, J. S.; Qu, X. G. Langmuir 2013, 29, 6396.
20. [20]
  Pandey, S.; Thakur, M.; Mewada, A.; Anjarlekar, D.; Mishra, N.; Sharon, M. J. Mater. Chem. B 2013, 1, 4972.
21. [21]
  Fan, J. Q.; Fang, G.; Zeng, F.; Wang, X. D.; Wu, S. Z. Small 2013, 9, 613.
22. [22]
  Peng, H.; Travas, S. J. Chem. Mater. 2009, 21, 5563.
23. [23]
  Allen, H. M.; Cullis, P. R. Adv. Drug Delivery Rev. 2013, 65, 36.
24. [24]
  Zhang, P.; Li, W. C.; Zhai, X. Y.; Liu, C. J.; Dai, L. M.; Liu, W. G. Chem. Commun. 2012, 48, 10431.
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沈阳化工大学材料科学与工程学院沈阳 110142