Citation: Zhang Tianhui, Yao Jiuxu, Tian Jiamei, Deng Mingxiao, Zhuang Xiuli, Xiao Chunsheng. Synthesis of polypeptide bearing 1, 4-dithiane pendants for ROS-responsive drug release[J]. Chinese Chemical Letters, ;2020, 31(5): 1129-1132. doi: 10.1016/j.cclet.2019.07.010 shu

Synthesis of polypeptide bearing 1, 4-dithiane pendants for ROS-responsive drug release

Zhang Tianhui ^a,b ,
Yao Jiuxu ^c ,
Tian Jiamei ^c ,
Deng Mingxiao ^c ,
Zhuang Xiuli ^a,b,e,*, ,
Xiao Chunsheng ^a,d,e,*,

a.
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
University of Science and Technology of China, Hefei 230026, China
c.
Department of Chemistry, Northeast Normal University, Changchun 130021, China
d.
State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200433, China
e.
Jilin Biomedical Polymers Engineering Laboratory, Changchun 130022, China

zhuangxl@ciac.ac.cn

xiaocs@ciac.ac.cn

Received Date: 8 May 2019
Revised Date: 10 June 2019
Accepted Date: 3 July 2019
Available Online: 3 July 2019

Figures(5)

Stimuli-responsive polypeptides have been intensively investigated for controlled drug release, owing to their favorable biocompatibility and biodegradability. In this work, we designed and synthesized a new kind of polypeptide bearing 1, 4-dithiane pendants for reactive oxygen species (ROS)-responsive drug release. The polypeptide-based block copolymer was facilely synthesized by ring-opening polymerization (ROP) of 1, 4-dithian-substituted L-glutamate N-carboxyanhydride (DTG-NCA) monomer using an amino-terminated poly(ethylene glycol) methyl ether (mPEG-NH₂) as the macromolecular initiator. The resultant block copolymer, mPEG-b-PDTG, could self-assemble into uniform micelles in aqueous medium owing to its amphiphilic structure. Then, the H₂O₂-triggered oxidation behaviors of the mPEG-b-PDTG micelles were studied by dynamic light scattering (DLS), FT-IR and turbidimetric assay. It was revealed that the oxidation of thioether into sulfoxide in the side chains would result in disassembly of the micelles. Furthermore, the ROS-responsive drug release behavior of the mPEG-b-PDTG micelles was verified by using Nile Red as a model drug. MTT assay also proved that mPEG-b-PDTG was non-toxic in B16F10 and L929 cells. Therefore, such a new class of oxidation-responsive polypeptide might provide a promising platform for ROS-responsive drug delivery.
- Polypeptides,
- ROS-responsive,
- Self-assembly,
- Thioether,
- Drug release
1. [1]
  C.L. He, X.L. Zhuang, Z.H. Tang, H.Y. Tian, X.S. Chen, Adv. Health. Mater. 1(2012) 48-78. doi: 10.1002/adhm.201100008
2. [2]
  C. Deng, J. Wu, R. Cheng, et al., Prog. Polym. Sci. 39(2014) 330-364. doi: 10.1016/j.progpolymsci.2013.10.008
3. [3]
  H. Lu, J. Wang, Z. Song, et al., Chem. Commun. 50(2014) 139-155. doi: 10.1039/C3CC46317F
4. [4]
  W. Shen, P. He, C. Xiao, X. Chen, Adv. Health. Mater. 7(2018) 1800354. doi: 10.1002/adhm.201800354
5. [5]
  J. Zha, X. Jiang, Chin. Chem. Lett. 29(2018) 1079-1087. doi: 10.1016/j.cclet.2018.05.026
6. [6]
  C. Xiao, J. Ding, C. He, X. Chen, Acta Polym. Sin. (2018) 45-55.
7. [7]
  J. Huang, A. Heise, Chem. Soc. Rev. 42(2013) 7373-7390. doi: 10.1039/c3cs60063g
8. [8]
  T.J. Deming, Chem. Rev. 116(2016) 786-808. doi: 10.1021/acs.chemrev.5b00292
9. [9]
  Y. Gao, C. Dong, Chin. Chem. Lett. 29(2018) 927-930. doi: 10.1016/j.cclet.2017.09.042
10. [10]
  C.C. Winterbourn, Nat. Chem. Biol. 4(2008) 278-286. doi: 10.1038/nchembio.85
11. [11]
  P.D. Ray, B.W. Huang, Y. Tsuji, Cell. Signal. 24(2012) 981-990. doi: 10.1016/j.cellsig.2012.01.008
12. [12]
  D. Trachootham, J. Alexandre, P. Huang, Nat. Rev. Drug Discov. 8(2009) 579-591. doi: 10.1038/nrd2803
13. [13]
  M. Schieber, Navdeep S. Chandel, Curr. Biol. 24(2014) R453-R462. doi: 10.1016/j.cub.2014.03.034
14. [14]
  C.C. Song, F.S. Du, Z.C. Li, J. Mater. Chem. B 2(2014) 3413-3426. doi: 10.1039/C3TB21725F
15. [15]
  C. Tapeinos, A. Pandit, Adv. Mater. 28(2016) 5553-5585. doi: 10.1002/adma.201505376
16. [16]
  Q. Xu, C. He, C. Xiao, X. Chen, Macromol. Biosci. 16(2016) 635-646. doi: 10.1002/mabi.201500440
17. [17]
  J. Wang, Y. Zhang, E. Archibong, F.S. Ligler, Z. Gu, Adv. Biosyst.1(2017) 1700084. doi: 10.1002/adbi.201700084
18. [18]
  W. Tao, Z. He, Asian J. Pharm. Sci. 13(2018) 101-112. doi: 10.1016/j.ajps.2017.11.002
19. [19]
  J.R. Kramer, T.J. Deming, J. Am. Chem. Soc. 134(2012) 4112-4115. doi: 10.1021/ja3007484
20. [20]
  X. Fu, Y. Shen, W. Fu, Z. Li, Macromolecules. 46(2013) 3753-3760. doi: 10.1021/ma400678w
21. [21]
  J.R. Kramer, T.J. Deming, J. Am. Chem. Soc. 136(2014) 5547-5550. doi: 10.1021/ja500372u
22. [22]
  X. Fu, Y. Ma, J. Sun, Z. Li, RSC Adv. 6(2016) 70243-70250. doi: 10.1039/C6RA17427B
23. [23]
  X.H. Fu, Y.N. Ma, J. Sun, Z.B. Li, Chinese J. Polym. Sci. 34(2016) 1436-1447. doi: 10.1007/s10118-016-1861-x
24. [24]
  Q. Xu, C. He, K. Ren, C. Xiao, X. Chen, Adv. Health. Mater. 5(2016) 1979-1990. doi: 10.1002/adhm.201600292
25. [25]
  S. Yu, C. Wang, J. Yu, et al., Adv. Mater. 30(2018) 1801527. doi: 10.1002/adma.201801527
26. [26]
  C. Xiao, C. Zhao, P. He, et al., Macromol. Rapid Comm. 31(2010) 991-997. doi: 10.1002/marc.200900821
27. [27]
  C. Xiao, J. Ding, L. Ma, et al., Polym. Chem. 6(2015) 738-747. doi: 10.1039/C4PY01156B
28. [28]
  P. Carampin, E. Lallana, J. Laliturai, et al., Macromol. Chem. Phys. 213(2012) 2052-2061. doi: 10.1002/macp.201200264
29. [29]
  C. Wang, H. Sang, Y. Wang, et al., Nano Lett. 18(2018) 7045-7051. doi: 10.1021/acs.nanolett.8b03015
30. [30]
  X. Li, Y. Zhang, Z. Ma, et al., Chin. Chem. Lett. 30(2019) 489-493. doi: 10.1016/j.cclet.2018.03.019
31. [31]
  S. Gao, G. Tang, D. Hua, et al., J. Mater. Chem. B 7(2019) 709-729. doi: 10.1039/C8TB02491J
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