Citation: Yang Zhuting, Peng Yan, Qiu Liyan. pH-Responsive supramolecular micelle based on host-guest interaction of poly(β-amino ester) derivatives and adamantyl-terminated poly(ethylene glycol) for cancer inhibition[J]. Chinese Chemical Letters, ;2018, 29(12): 1839-1844. doi: 10.1016/j.cclet.2018.11.009 shu

pH-Responsive supramolecular micelle based on host-guest interaction of poly(β-amino ester) derivatives and adamantyl-terminated poly(ethylene glycol) for cancer inhibition

Ministry of Educational(MOE) Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China

lyqiu@zju.edu.cn

Received Date: 24 September 2018
Revised Date: 2 November 2018
Accepted Date: 5 November 2018
Available Online: 15 December 2018

Figures(6)

Supramolecular structures have received growing attention and been widely applied in many fields. Herein, we synthesized hydrophobic β-cyclodextrin-contained poly(β-amino ester) (PAE-β-CD) and hydrophilic adamantyl-terminated poly (ethylene glycol) (PEG-AD) to form a supramolecular micelle via the host-guest interaction. The micelle displayed pH responsive structure change due to the transform of hydrophobic PAE core to hydrophilic form in weakly acid condition. After the anticancer drug curcumin (Cur) was loaded into the micelle, the drug release behavior of the Cur-loaded micelle was studied, and it turned out that the Cur-loaded supramolecular micelle could effectively unload the drug at pH 5.5. Furthermore, the antitumor efficiency of the Cur-loaded micelle was also examined both in vitro and in vivo, indicating considerable inhibition ratio as high as 62.14% against mouse sarcoma 180.
- Supramolecules,
- Micelle,
- Poly(β-amino ester),
- pH-Sensitive,
- β-Cyclodextrin,
- Curcumin
1. [1]
  G.C. Yu, W. Yu, L. Shao, et al., Adv. Funct. Mater. 26 (2016) 8999-9008. doi: 10.1002/adfm.v26.48
2. [2]
  K. Yang, L. Feng, Z. Liu, Adv. Drug Deliv. Rev. 105 (2016) 228-241. doi: 10.1016/j.addr.2016.05.015
3. [3]
  S. Tang, Q.S. Meng, H.P. Sun, et al., Biomaterials 114 (2017) 44-53. doi: 10.1016/j.biomaterials.2016.06.005
4. [4]
  C. Gao, F. Tang, G.Y. Gong, et al., Nanoscale 9 (2017) 12533-12542. doi: 10.1039/C7NR03611F
5. [5]
  C. Zhang, T. An, D. Wang, et al., J. Control. Release 226 (2016) 193-204. doi: 10.1016/j.jconrel.2016.02.030
6. [6]
  D.Q. Chen, G.Q. Zhang, R.M. Li, et al., J. Am. Chem. Soc. 140 (2018) 7373-7376. doi: 10.1021/jacs.7b12025
7. [7]
  L. Peng, Z.L. Wang, A.C. Feng, et al., Polymer 88 (2016) 112-122. doi: 10.1016/j.polymer.2016.02.023
8. [8]
  P.D. Thornton, R.J. Mart, R.V. Ulijn, Adv. Mater. 19 (2007) 1252-1256.
9. [9]
  Z. Zhang, J.X. Ding, X.F. Chen, et al., Polym. Chem. 4 (2013) 3265-3271. doi: 10.1039/c3py00141e
10. [10]
  P. Shen, L.Y. Qiu, New J. Chem. 42 (2018) 3593-3601. doi: 10.1039/C7NJ05042A
11. [11]
  Q.N. Bui, Y. Li, M.S. Jang, et al., Macromolecules 48 (2015) 4046-4054. doi: 10.1021/acs.macromol.5b00423
12. [12]
  G.H. Gao, J.W. Lee, M.K. Nguyen, et al., J. Control Release 155 (2011) 11-17. doi: 10.1016/j.jconrel.2010.09.012
13. [13]
  N. Segovia, P. Dosta, A. Cascante, V. Ramos, S. Borrós, Acta Biomater. 10 (2014) 2147-2158. doi: 10.1016/j.actbio.2013.12.054
14. [14]
  G.C. Yu, X.Y. Zhou, Z.B. Zhang, et al., J. Am. Chem. Soc. 134 (2012) 19489-19497. doi: 10.1021/ja3099905
15. [15]
  M.V. Rekharsky, Y. Inoue, Chem. Rev. 98 (1998) 1875-1918. doi: 10.1021/cr970015o
16. [16]
  C. Li, G.F. Luo, H.Y. Wang, et al., J. Phys. Chem. C 115 (2011) 17651-17659. doi: 10.1021/jp203940s
17. [17]
  C. Xie, P. Zhang, Z.K. Zhang, et al., Nanoscale 7 (2015) 12572-12580. doi: 10.1039/C5NR02861B
18. [18]
  H. Han, D.E. Liu, H. Lu, W.X. Gu, H. Gao, RSC Adv. 4 (2014) 40882-40891. doi: 10.1039/C4RA07175A
19. [19]
  Y. Wang, D.D. Li, H.B. Wang, et al., Chem. Commun. 50 (2014) 9390-9392. doi: 10.1039/C4CC03978E
20. [20]
  D. Harries, D.C. Rau, V.A. Parsegian, J. Am. Chem. Soc. 127 (2005) 2184-2190. doi: 10.1021/ja045541t
21. [21]
  M.Y. Guo, M. Jiang, Soft Matter 5 (2009) 495-500. doi: 10.1039/B813556H
22. [22]
  J.M. Zhang, J.J. Li, Z. Shi, et al., Acta Biomater. 58 (2017) 349-364. doi: 10.1016/j.actbio.2017.04.029
23. [23]
  R. Ji, J. Cheng, T. Yang, et al., Biomacromolecules 15 (2014) 3531-3539. doi: 10.1021/bm500711c
24. [24]
  D.E. Liu, H. Han, H.G. Lu, et al., RSC Adv. 4 (2014) 37130-37137. doi: 10.1039/C4RA04432K
25. [25]
  G.B. Zhu, X.H. Zhang, P.B. Gai, J.H. Chen, ChemPlusChem 77 (2012) 844-849. doi: 10.1002/cplu.201200144
26. [26]
  X. Song, J.L. Zhu, Y.T. Wen, et al., J. Colloid Interface Sci. 490 (2017) 372-379. doi: 10.1016/j.jcis.2016.11.056
27. [27]
  P. Zhang, X.P. Qian, Z.K. Zhang, et al., ACS Appl. Mater. Interfaces 9 (2017) 5768-5777. doi: 10.1021/acsami.6b14464
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