Citation: Zhang Xuan, Gao Jushan, Zhao Xiaoye, Liu Zhaotie, Liu Zhongwen, Wang Ke, Li Guo, Jiang Jinqiang. Hyperbranched polymer micelles with triple-stimuli backbone-breakable iminoboronate ester linkages[J]. Chinese Chemical Letters, ;2020, 31(7): 1822-1826. doi: 10.1016/j.cclet.2020.03.018 shu

Hyperbranched polymer micelles with triple-stimuli backbone-breakable iminoboronate ester linkages

Zhang Xuan ^a ,
Gao Jushan ^b ,
Zhao Xiaoye ^b ,
Liu Zhaotie ^a ,
Liu Zhongwen ^a ,
Wang Ke ^b,*, ,
Li Guo ^a,*, ,
Jiang Jinqiang ^a,*,

a.
Key Laboratory of Syngas Conversion of Shaanxi Province, Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China
b.
School of Pharmacy, Health Science Center, Xi'an Jiaotong University, Xi'an 710061, China

perpetual1003@mail.xjtu.edu.cn

liguo@snnu.edu.cn

jiangjq@snnu.edu.cn

Received Date: 9 January 2020
Revised Date: 5 March 2020
Accepted Date: 6 March 2020
Available Online: 6 March 2020

Figures(6)

Hyperbranched polymers have attracted increasing interests due to their unique structure-related advantages and have been utilized as drug carriers for controlled delivery. However, it is still challenging to prepare multi stimuli-responsive hyperbranched polymers to sense and response the complex yet delicate changes in physiological environment. Herein, we propose a triple-stimuli backbone-breakable hyperbranched polymer (HBP(OEG-IB)), which is prepared via the convenient iminoboronate multicomponent reaction of α, w-di(1, 2-diol)s oligo(ethylene glycol), tris(3-aminopropyl)amine and 2-formylphenylboronic acid. Upon the stimulation of CO₂, lactic acid and glutathione, micelles formed by HBP(OEG-IB) could be disrupted via the dissociation of iminoboronate ester bond to subsequent release incorporated camptothecin (CPT). Cell experiments show that the HBP(OEG-IB) is non-toxic but can enhance the therapeutic effect of CPT thanks to the effect of the protonated tertiary amino groups. The demonstration made in this work can enrich the design of responsive HBPs and can be readily applied to other systems with tunable responsive properties and functions.
- Hyperbranched polymer,
- Multi-stimuli responsiveness,
- Iminoboronate esters,
- CPT,
- Drug delivery
1. [1]
  D.L. Wang, Y. Jin, X.Y. Zhu, et al., Prog. Polym. Sci. 64(2017) 114-153. doi: 10.1016/j.progpolymsci.2016.09.005
2. [2]
  T. Nishikubo, H. Kudo, K. Maruyama, et al., Polym. J. 38(2006) 447-456. doi: 10.1295/polymj.38.447
3. [3]
  Z. Wei, J.H. Yang, Z.Q. Liu, et al., Adv. Funct. Mater. 25(2015) 1352-1359. doi: 10.1002/adfm.201401502
4. [4]
  B. Yu, X.S. Jiang, R. Wang, et al., Macromolecules 43(2010) 10457-10465. doi: 10.1021/ma1023632
5. [5]
  Y.Y. Zhuang, H.P. Deng, Y. Su, et al., Biomacromolecules 17(2016) 2050-2062. doi: 10.1021/acs.biomac.6b00262
6. [6]
  L. Yang, H. Sun, Y. Liu, et al., Angew. Chem. Int. Ed. 57(2018) 17048-17052. doi: 10.1002/anie.201809753
7. [7]
  H. Li, W.Z. Chen, F.F. Xu, et al., Macromol. Rapid Comm. 39(2018) 1800053. doi: 10.1002/marc.201800053
8. [8]
  Y. Huang, F. Qiu, L.Y. Shen, et al., ACS Nano 10(2016) 10489-10499. doi: 10.1021/acsnano.6b06450
9. [9]
  Z.F. Jia, G.L. Li, Q. Zhu, et al., Chem. -Eur. J. 15(2009) 7593-7600. doi: 10.1002/chem.200900345
10. [10]
  H. Chen, Z.F. Jia, D.Y. Yan, et al., Macromol. Chem. Phys. 208(2007) 1637-1645. doi: 10.1002/macp.200700049
11. [11]
  J.Y. Liu, Y. Pang, W. Huang, et al., Macromolecules 43(2010) 8416-8423. doi: 10.1021/ma1015819
12. [12]
  G.X. Cao, G. Li, Q. Yang, et al., Macromol. Rapid Commun. 39(2018) 1700684. doi: 10.1002/marc.201700684
13. [13]
  W.X. Gao, Y.L. Hu, L. Xu, et al., Chin. Chem. Lett. 29(2018) 1795-1798. doi: 10.1016/j.cclet.2018.05.022
14. [14]
  Y.P. Li, W.W. Xiao, K. Xiao, et al., Angew. Chem. Int. Ed. 51(2012) 2864-2869. doi: 10.1002/anie.201107144
15. [15]
  O.R. Cromwell, J. Chung, Z.B. Guan, J. Am. Chem. Soc. 137(2015) 6492-6495. doi: 10.1021/jacs.5b03551
16. [16]
  A.P. Bapat, D. Roy, J.G. Ray, et al., J. Am. Chem. Soc. 133(2011) 19832-19838. doi: 10.1021/ja207005z
17. [17]
  S. Delpierre, B. Willocq, G. Manini, et al., Chem. Mater. 31(2019) 3736-3744. doi: 10.1021/acs.chemmater.9b00750
18. [18]
  P.M.S.D. Cal, J.B. Vicente, E. Pires, et al., J. Am. Chem. Soc. 134(2012) 10299-10305. doi: 10.1021/ja303436y
19. [19]
  S.R. Chaudhari, N. Suryaprakash, J. Org. Chem. 77(2012) 648-651. doi: 10.1021/jo202334d
20. [20]
  R.J. Ma, C. Zhang, Y. Liu, et al., RSC Adv. 7(2017) 21328-21335. doi: 10.1039/C7RA01742A
21. [21]
  A. Pettignano, S.Grijalvo, M. Haring, et al., Chem. Commun. 53(2017) 3350-3353. doi: 10.1039/C7CC00765E
22. [22]
  Y. Xu, Y.Y. Lu, L. Wang, et al., Colloid. Surface. B 141(2016) 318-326. doi: 10.1016/j.colsurfb.2016.01.044
23. [23]
  X.Y. Xu, H. Shang, T.Y. Zhang, et al., Int. J. Pharm. 548(2018) 649-658. doi: 10.1016/j.ijpharm.2018.07.020
24. [24]
  Y. Ding, C. Du, J.W. Qian, et al., Polym. Chem. 9(2018) 3488-3498. doi: 10.1039/C8PY00579F
25. [25]
  L. Qiu, L.F. Zhao, C.F. Xing, et al., Chin. Chem. Lett. 29(2018) 301-304. doi: 10.1016/j.cclet.2017.09.048
26. [26]
  G.C. Yu, X.L. Zhao, J. Zhou, et al., J. Am. Chem. Soc. 140(2018) 8005-8019. doi: 10.1021/jacs.8b04400
27. [27]
  F.M.F. Santos, A.I. Matos, A.E. Ventura, et al., Angew. Chem. 129(2017) 9474-9478. doi: 10.1002/ange.201703492
28. [28]
  R.M.R.M. Lopes, A.E. Ventura, L.C. Silva, et al., Chem. -Eur. J. 24(2018) 12495-12499. doi: 10.1002/chem.201802515
29. [29]
  M. Masui, H. Takata, T. Kominami, Electrophoresis 23(2002) 2087-2095. doi: 10.1002/1522-2683(200207)23:13<2087::AID-ELPS2087>3.0.CO;2-R
30. [30]
  V.A. Sethuraman, Y.H. Bae, J. Control. Release 118(2007) 216-224. doi: 10.1016/j.jconrel.2006.12.008
31. [31]
  X.X. Shi, M.L. Hou, X.Q. Ma, et al., Biomacromolecules 20(2019) 1190-1202. doi: 10.1021/acs.biomac.8b01566
1. [1]
  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
2. [2]
  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
3. [3]
  Xingqun Pu , Rongrong Liu , Yuting Xie , Chenjing Yang , Jingyi Chen , Baoling Guo , Chun-Xia Zhao , Peng Zhao , Jian Ruan , Fangfu Ye , David A Weitz , Dong Chen . One-step preparation of biocompatible amphiphilic dimer nanoparticles with tunable particle morphology and surface property for interface stabilization and drug delivery. Chinese Chemical Letters, 2025, 36(3): 109820-. doi: 10.1016/j.cclet.2024.109820
4. [4]
  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
5. [5]
  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
6. [6]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
7. [7]
  Jiaqi Huang , Renjiang Kong , Yanmei Li , Ni Yan , Yeyang Wu , Ziwen Qiu , Zhenming Lu , Xiaona Rao , Shiying Li , Hong Cheng . Feedback enhanced tumor targeting delivery of albumin-based nanomedicine to amplify photodynamic therapy by regulating AMPK signaling and inhibiting GSTs. Chinese Chemical Letters, 2024, 35(8): 109254-. doi: 10.1016/j.cclet.2023.109254
8. [8]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
9. [9]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
10. [10]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
11. [11]
  Yuanzheng Wang , Chen Zhang , Shuyan Han , Xiaoli Kong , Changyun Quan , Jun Wu , Wei Zhang . Cancer cell membrane camouflaged biomimetic gelatin-based nanogel for tumor inhibition. Chinese Chemical Letters, 2024, 35(11): 109578-. doi: 10.1016/j.cclet.2024.109578
12. [12]
  Yinglan Yu , Sajid Hussain , Jianping Qi , Lei Luo , Xuemei Zhang . Mechanisms and applications: Cargos transport to basolateral membranes in polarized epithelial cells. Chinese Chemical Letters, 2024, 35(12): 109673-. doi: 10.1016/j.cclet.2024.109673
13. [13]
  Han Wu , Yumei Wang , Zekai Ren , Hailin Cong , Youqing Shen , Bing Yu . The nanocarrier strategy for crossing the blood-brain barrier in glioma therapy. Chinese Chemical Letters, 2025, 36(4): 109996-. doi: 10.1016/j.cclet.2024.109996
14. [14]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
15. [15]
  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
16. [16]
  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
17. [17]
  Wenjun Yang , Qiaoling Tan , Wenjiao Xie , Xiaoyu Pan , Youyong Yuan . Construction and Characterization of Calcium Alginate Microparticle Drug Delivery System: A Novel Design and Teaching Practice in Polymer Experiments. University Chemistry, 2025, 40(3): 371-380. doi: 10.12461/PKU.DXHX202405150
18. [18]
  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
19. [19]
  Chunlei Dai , Liying Wang , Xinru You , Yi Zhao , Zhong Cao , Jun Wu . Coffee-derived self-anti-inflammatory polymer as drug nanocarrier for enhanced rheumatoid arthritis treatment. Chinese Chemical Letters, 2025, 36(3): 109869-. doi: 10.1016/j.cclet.2024.109869
20. [20]
  Yi Cao , Xiaojiao Ge , Yuanyuan Wei , Lulu He , Aiguo Wu , Juan Li . Tumor microenvironment-activatable neuropeptide-drug conjugates enhanced tumor penetration and inhibition via multiple delivery pathways and calcium deposition. Chinese Chemical Letters, 2024, 35(4): 108672-. doi: 10.1016/j.cclet.2023.108672

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(801)
HTML views(81)

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