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
1. [1]
  Shuang Liang , Jianjun Yao , Dan Liu , Mengli Zhou , Yong Cui , Zhaohui Wang . Tumor-responsive covalent organic polymeric nanoparticles enhancing STING activation for cancer immunotherapy. Chinese Chemical Letters, 2025, 36(3): 109856-. doi: 10.1016/j.cclet.2024.109856
2. [2]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
3. [3]
  Wen Xiao , Fazhan Wang , Yangzhuo Gu , Xi He , Na Fan , Qian Zheng , Shugang Qin , Zhongshan He , Yuquan Wei , Xiangrong Song . PEG400-mediated nanocarriers improve the delivery and therapeutic efficiency of mRNA tumor vaccines. Chinese Chemical Letters, 2024, 35(5): 108755-. doi: 10.1016/j.cclet.2023.108755
4. [4]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
5. [5]
  Yunjie Dang , Yanru Feng , Xiao Chen , Chaoxing He , Shujie Wei , Dingyang Liu , Jinlong Qi , Huaxing Zhang , Shaokun Yang , Zhiyun Niu , Bai Xiang . Development of a multi-level pH-responsive lipid nanoplatform for efficient co-delivery of siRNA and small-molecule drugs in tumor treatment. Chinese Chemical Letters, 2024, 35(12): 109660-. doi: 10.1016/j.cclet.2024.109660
6. [6]
  Makhloufi Zoulikha , Zhongjian Chen , Jun Wu , Wei He . Approved delivery strategies for biopharmaceuticals. Chinese Chemical Letters, 2025, 36(2): 110225-. doi: 10.1016/j.cclet.2024.110225
7. [7]
  Chun-Yun Ding , Ru-Yuan Zhang , Yu-Wu Zhong , Jiannian Yao . Binary and heterostructured microplates of iridium and ruthenium complexes: Preparation, characterization, and thermo-responsive emission. Chinese Journal of Structural Chemistry, 2024, 43(10): 100393-100393. doi: 10.1016/j.cjsc.2024.100393
8. [8]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
9. [9]
  Fengjie Liu , Fansu Meng , Zhenjiang Yang , Huan Wang , Yuehong Ren , Yu Cai , Xingwang Zhang . Exosome-biomimetic nanocarriers for oral drug delivery. Chinese Chemical Letters, 2024, 35(9): 109335-. doi: 10.1016/j.cclet.2023.109335
10. [10]
  Yiran Tao , Chunlei Dai , Zhaoxiang Xie , Xinru You , Kaiwen Li , Jun Wu , Hai Huang . Redox responsive polymeric nanoparticles enhance the efficacy of cyclin dependent kinase 7 inhibitor for enhanced treatment of prostate cancer. Chinese Chemical Letters, 2024, 35(8): 109170-. doi: 10.1016/j.cclet.2023.109170
11. [11]
  Hui Zhang , Rong Feng , Wanyi Yu , Hongbei Wei , Tianhong Wu , Peng Zhang , Wenhai Bian , Xin Li , Di Gao , Guojun Weng , Zhe Yang , Tony D. James , Xiaolong Sun . Evaluating the global thiols redox state in living cells using a reducing sulfur species responsive fluorescence switching platform. Chinese Chemical Letters, 2025, 36(4): 110528-. doi: 10.1016/j.cclet.2024.110528
12. [12]
  Qin Yu , Haisheng He , Jianping Qi , Yi Lu , Wei Wu . Oral delivery of insulin by barbed microneedles actuated by intestinal peristalsis. Chinese Chemical Letters, 2024, 35(9): 109888-. doi: 10.1016/j.cclet.2024.109888
13. [13]
  Jing Zhang , Charles Wang , Yaoyao Zhang , Haining Xia , Yujuan Wang , Kun Ma , Junfeng Wang . Application of magnetotactic bacteria as engineering microrobots: Higher delivery efficiency of antitumor medicine. Chinese Chemical Letters, 2024, 35(10): 109420-. doi: 10.1016/j.cclet.2023.109420
14. [14]
  Yujie Li , Ya-Nan Wang , Yin-Gen Luo , Hongcai Yang , Jinrui Ren , Xiao Li . Advances in synthetic biology-based drug delivery systems for disease treatment. Chinese Chemical Letters, 2024, 35(11): 109576-. doi: 10.1016/j.cclet.2024.109576
15. [15]
  Weiyu Chen , Zenghui Li , Chenguang Zhao , Lisha Zha , Junfeng Shi , Dan Yuan . Enzyme-modulate conformational changes in amphiphile peptide for selectively cell delivery. Chinese Chemical Letters, 2024, 35(12): 109628-. doi: 10.1016/j.cclet.2024.109628
16. [16]
  Ningyue Xu , Jun Wang , Lei Liu , Changyang Gong . Injectable hydrogel-based drug delivery systems for enhancing the efficacy of radiation therapy: A review of recent advances. Chinese Chemical Letters, 2024, 35(8): 109225-. doi: 10.1016/j.cclet.2023.109225
17. [17]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
18. [18]
  Dexuan Xiao , Tianyu Chen , Tianxu Zhang , Sirong Shi , Mei Zhang , Xin Qin , Yunkun Liu , Longjiang Li , Yunfeng Lin . Transdermal treatment for malignant melanoma by aptamer-modified tetrahedral framework nucleic acid delivery of vemurafenib. Chinese Chemical Letters, 2024, 35(4): 108602-. doi: 10.1016/j.cclet.2023.108602
19. [19]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
20. [20]
  Haijun Shen , Yi Qiao , Chun Zhang , Yane Ma , Jialing Chen , Yingying Cao , Wenna Zheng . A matrix metalloproteinase-sensitive hydrogel combined with photothermal therapy for transdermal delivery of deferoxamine to accelerate diabetic pressure ulcer healing. Chinese Chemical Letters, 2024, 35(12): 110283-. doi: 10.1016/j.cclet.2024.110283

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(442)
HTML views(40)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142