Citation: Maomao He, Zongwei Zhang, Ziyue Jiao, Meiyu Yan, Pengcheng Miao, Zhiyong Wei, Xuefei Leng, Yang Li, Jiangli Fan, Wen Sun, Xiaojun Peng. Redox-responsive phenyl-functionalized polylactide micelles for enhancing Ru complexes delivery and phototherapy[J]. Chinese Chemical Letters, ;2023, 34(3): 107574. doi: 10.1016/j.cclet.2022.05.088 shu

Redox-responsive phenyl-functionalized polylactide micelles for enhancing Ru complexes delivery and phototherapy

Maomao He ^a ,
Zongwei Zhang ^a ,
Ziyue Jiao ^a ,
Meiyu Yan ^a ,
Pengcheng Miao ^a ,
Zhiyong Wei ^a ,
Xuefei Leng ^a ,
Yang Li ^{a, *,} ,
Jiangli Fan ^{a, b} ,
Wen Sun ^{a, b, *,} ,
Xiaojun Peng ^a

a.
State Key Laboratory of Fine Chemicals, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian University of Technology, Dalian 116024, China
b.
Ningbo Institute of Dalian University of Technology, Ningbo 315016, China

liyang@dlut.edu.cn

sunwen@dlut.edu.cn

Received Date: 2 April 2022
Revised Date: 27 May 2022
Accepted Date: 31 May 2022
Available Online: 3 June 2022

Figures(7)

Poly(ethylene glycol)-poly(lactic acid) block copolymer (PEG-PLA) is one of the most widely used biomedical polymers in clinical drug delivery owing to its biocompatibility and biodegradability. However, endowing PEG-PLA micelles with high drug loading, self-assembly stability and fast intracellular drug release is still challenging. Redox-responsive diblock copolymers (MPEG-SS-PMLA) of poly(ethylene glycol) and phenyl-functionalized poly(lactic acid) with disulfide bond as the linker are synthesized to prepare PLA-based micelles that demonstrate excellent colloidal stability and high Ru loading. Notably, MPEG-SS-PMLA achieved a remarkably high Ru loading efficiency of 84.3% due to the existence of strong π-π stacking between phenyl and Ru complex. MPEG-SS-PMLA exhibited good colloidal stability in physiological condition but quickly destabilized by reductive tumor microenvironment. Interestingly, about 74% of Ru complex was released under 10 mmol/L GSH concentration. Ru-loaded MEPG-SS-PMLA showed efficient delivery and release of Ru complex into MCF-7 cancer cells, achieving enhanced in vitro and in vivo antitumor activity of photodynamic therapy. This feasible functionalization method of MPEG-PLA has appeared to be a clinically viable platform for controlled delivery therapeutic agents and enhanced phototherapy.
- PEG-PLA micelles,
- Phenyl functionalization,
- Redox-responsive,
- Ru complexes,
- Delivery
1. [1]
  S. Zhou, X. Hu, R. Xia, et al. Angew. Chem. Int. Ed. 59 (2020) 23198-23205. doi: 10.1002/anie.202008732
2. [2]
  T.C. Pham, V.N. Nguyen, Y. Choi, S. Lee, J. Yoon. Chem. Rev. 121 (2021) 13454-13619. doi: 10.1021/acs.chemrev.1c00381
3. [3]
  J. Tian, B. Huang, M.H. Nawaz, W. Zhang. Coord. Chem. Rev. 420 (2020) 213410. doi: 10.1016/j.ccr.2020.213410
4. [4]
  R. Cao, W. Sun, Z. Zhang, et al. Chin. Chem. Lett. 31 (2020) 3127-3130. doi: 10.1016/j.cclet.2020.06.031
5. [5]
  F. Heinemann, J. Karges, G. Gasser, et al., Acc. Chem. Res. 50 (2017) 2727-2736. doi: 10.1021/acs.accounts.7b00180
6. [6]
  A. Raza, S.A. Archer, S.D. Fairbanks, et al., J. Am. Chem. Soc. 142 (2020) 4639-4647. doi: 10.1021/jacs.9b11313
7. [7]
  Z. Lv, H. Wei, Q. Li, et al., Chem. Sci. 9 (2018) 502-512. doi: 10.1039/C7SC03765A
8. [8]
  N. Soliman, L.K. McKenzie, J. Karges, E. Bertrand, et al., Chem. Sci. 11 (2020) 2657-2663. doi: 10.1039/c9sc05976h
9. [9]
  N. Soliman, G. Gasser, C.M. Thomas, Adv. Mater. 32 (2020) 2003294. doi: 10.1002/adma.202003294
10. [10]
  E. Villemin, Y.C. Ong, C.M. Thomas, et al., Nat. Rev. Chem. 3 (2019) 261-282. doi: 10.1038/s41570-019-0088-0
11. [11]
  K. Ariga, Small Sci. 1 (2020) 2000032.
12. [12]
  J. Shen, H.C. Kim, J. Wolfram, et al., Nano Lett. 17 (2017) 2913-2920. doi: 10.1021/acs.nanolett.7b00132
13. [13]
  X. Li, Y. Zhang, H. Chen, J. Sun, F. Feng, ACS Appl. Mater. Interfaces 8 (2016) 22756-22761. doi: 10.1021/acsami.6b07038
14. [14]
  M. Appold, C. Mari, C. Lederle, et al., Polym. Chem. 8 (2017) 890-900. doi: 10.1039/C6PY02026G
15. [15]
  M. He, F. Chen, D. Shao, et al., Biomaterials 275 (2021) 120915. doi: 10.1016/j.biomaterials.2021.120915
16. [16]
  M. He, G. He, P. Wang, et al., Adv. Sci. 8 (2021) 2103334. doi: 10.1002/advs.202103334
17. [17]
  X. Zeng, Y. Wang, J. Han, et al., Adv. Mater. 32 (2020) 2004766. doi: 10.1002/adma.202004766
18. [18]
  T.A. Bauer, J. Eckrich, N. Wiesmann, et al., J. Mater. Chem. B 9 (2021) 8211-8223. doi: 10.1039/d1tb01336j
19. [19]
  G. Boeuf, G.V. Roullin, J. Moreau, et al., ChemPlusChem 79 (2014) 171-180. doi: 10.1002/cplu.201300242
20. [20]
  W. Sun, S. Li, B. Haupler, et al., Adv. Mater. 29 (2017) 1603702. doi: 10.1002/adma.201603702
21. [21]
  N. Kamaly, B. Yameen, J. Wu, et al., Chem. Rev. 116 (2016) 2602-2663. doi: 10.1021/acs.chemrev.5b00346
22. [22]
  C. Sun, Y. Liu, J. Du, et al., Angew. Chem. Int. Ed. 55 (2016) 1010-1014. doi: 10.1002/anie.201509507
23. [23]
  T. Sim, J.E. Kim, N.H. Hoang, et al., Drug Deliv. 25 (2018) 1362-1371. doi: 10.1080/10717544.2018.1477865
24. [24]
  X. Guo, X. Wei, Y. Jing, et al., Adv. Mater. 27 (2015) 6450-6456. doi: 10.1002/adma.201502865
25. [25]
  S. Aryal, C.M. Hu, L. Zhang, ACS Nano 4 (2010) 251-258. doi: 10.1021/nn9014032
26. [26]
  J. Wang, S. Li, Y. Han, et al., Front. Pharmacol. 9 (2018) 202. doi: 10.3389/fphar.2018.00202
27. [27]
  Q. Jin, Y. Deng, X. Chen, J. Ji, ACS Nano 13 (2019) 954-977. doi: 10.1021/acsnano.8b07746
28. [28]
  Y. Wang, N. Gong, C. Ma, et al., Nat. Commun. 12 (2021) 1-16. doi: 10.1038/s41467-020-20314-w
29. [29]
  Z. Liu, T. Cao, Y. Xue, et al., Angew. Chem. Int. Ed. 59 (2020) 3711-3717. doi: 10.1002/anie.201914434
30. [30]
  X. Wei, Y. Wang, X. Xiong, et al., Adv. Funct. Mater. 26 (2016) 8266-8280. doi: 10.1002/adfm.201603336
31. [31]
  H. Qi, Y. Xu, P, Hu, et al., Chin. Chem. Lett. 33 (2022) 1131-1140. doi: 10.1016/j.cclet.2021.09.026
32. [32]
  X. Gu, Y. Wei, Q. Fan, et al., J. Control. Release 301 (2019) 110-118. doi: 10.1016/j.jconrel.2019.03.005
33. [33]
  K. Liang, J.E. Chung, S.J. Gao, et al., Adv. Mater. 30 (2018) 1706963. doi: 10.1002/adma.201706963
34. [34]
  Y. Liang, X. Deng, L. Zhang, et al., Biomaterials 71 (2015) 1-10. doi: 10.1016/j.biomaterials.2015.08.032
35. [35]
  D. Xi, N. Xu, X. Xia, et al., Adv. Mater. 34 (2021) 2106797.
36. [36]
  X. You, L. Wang, L. Wang, J. Wu. Adv. Funct. Mater. 31 (2021) 2100805. doi: 10.1002/adfm.202100805
37. [37]
  K. Ou, X. Xu, X. Guan, et al., Adv. Funct. Mater. 30 (2020) 1907857. doi: 10.1002/adfm.201907857
38. [38]
  R. Zhang, R. Nie, T. Fang, et al., Biomacromolecules 23 (2021) 1-19.
39. [39]
  D. Li, R. Zhang, G. Liu, Y. Kang, J. Wu, Adv. Healthc. Mater. 20 (2020) 2000605. doi: 10.1002/adhm.202000605
40. [40]
  L. Tu, Z. Liao, Z. Luo, et al., Exploration 1 (2021) 20210023. doi: 10.1002/exp.20210023
41. [41]
  Q. Zhao, C. Huang, F. Li, Chem. Soc. Rev. 40 (2011) 2508-2524. doi: 10.1039/c0cs00114g
42. [42]
  X. Zhou, M. Xiao, V. Ramu, et al., J. Am. Chem. Soc. 142 (2020) 10383-10399. doi: 10.1021/jacs.0c01369
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