Citation: Hu Jieni, Xu Yue, Zhang Yan. Amphiphilic random polycarbonate self-assemble into GSH/pH dual responsive micelle-like aggregates in water[J]. Chinese Chemical Letters, ;2019, 30(12): 2039-2042. doi: 10.1016/j.cclet.2019.05.017 shu

Amphiphilic random polycarbonate self-assemble into GSH/pH dual responsive micelle-like aggregates in water

Hu Jieni ^a ,
Xu Yue ^a ,
Zhang Yan ^a,b,*,

a.
Shanghai Key Laboratory of Advanced Polymeric Materials, Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
Key Laboratory of Smart Drug Delivery(Fudan University), Ministry of Education, Shanghai 201203, China

zhang_yan@ecust.edu.cn

Received Date: 20 March 2019
Revised Date: 30 April 2019
Accepted Date: 7 May 2019
Available Online: 7 December 2019

Figures(4)

Responsive polymers have been playing an increasingly important role in a wide variety of applications, such as biomedical materials and biosensors. Herein, we reported a dual-responsive polycarbonate (poly (MN-co-MSS)) based on the macrocyclic Sulfur/Nitrogen-substituted carbonate monomer (MSS/MN) via an enzyme-catalyzed ring-opening copolymerization and Lipase CA Novozym-435 as catalyst, with the disulfide and tertiary amine groups situated on the backbone. The structure of the random copolymers was confirmed by NMR and FTIR. In addition, size exclusion chromatography (SEC) results indicated that the copolymer had a symmetric peak and a relatively narrow polydispersity. Also, the random copolymers can self-assemble into micelle-like aggregates in water due to the hydrophilicity endowed by the amino groups, and the aggregates exhibited rich pH and GSH responsive behavior, which was verified by zeta masters instrument and dynamic light scattering (DLS). Moreover, transmission electron microscopy (TEM) demonstrated the morphology of the micellar aggregates and the variation subjected to the lower pH and GSH, and the responsive mechanism was elaborated. Therefore, these results highlighted a facile synthesis of the environment-responsive polymers and provided a novel GSH/pH responsive material platform for further application.
- Polycarbonate,
- Dual responsive,
- Micelles,
- Ring-opening polymerization,
- Random copolymers
1. [1]
  Z.G. Xu, S.Y. Liu, Y.J. Kang, M.F. Wang, ACS Biomater. Sci. Eng.1 (2015) 585-592. doi: 10.1021/acsbiomaterials.5b00119
2. [2]
  L.N. Gu, Z. Shen, S. Zhang, et al., Macromolecules 40 (2007) 4486-4493. doi: 10.1021/ma062083v
3. [3]
  W.H. Qian, T. Song, M. Ye, et al., Polym. Chem. 8 (2017) 4098. doi: 10.1039/C7PY00762K
4. [4]
  J. Zhu, H. Han, F.X. Li, et al., J. Colloid Interface Sci. 540 (2019) 634-646. doi: 10.1016/j.jcis.2018.12.091
5. [5]
  S.K. Ahn, J. Nam, J.H. Zhu, E. Lee, S.M. Kilbey, Polym. Chem. 9 (2018) 3279-3286. doi: 10.1039/C8PY00627J
6. [6]
  J. Nicolas, S. Mura, D. Brambilla, N. Mackiewicz, P. Couvreur, Des. Chem. Soc. Rev. 42 (2013) 1147-1235. doi: 10.1039/C2CS35265F
7. [7]
  S. Swaminathan, J. Garcia-Amoros, A. Fraix, et al., Chem. Soc. Rev. 43 (2014) 4167-4178. doi: 10.1039/C3CS60324E
8. [8]
  K. Kataoka, A. Harada, Y. Nagasaki, Adv. Drug Deliv. Rev. 64 (2012) 37-48. doi: 10.1016/j.addr.2012.09.013
9. [9]
  T. Terashima, T. Sugita, M. Sawamoto, Polym. J. 47 (2015) 667-677. doi: 10.1038/pj.2015.54
10. [10]
  M. Matsumoto, T. Terashima, K. Matsumoto, M. Takenaka, M. Sawamoto, J. Am. Chem. Soc. 139 (2017) 7164-7167. doi: 10.1021/jacs.7b03152
11. [11]
  Y. Koda, T. Terashima, M. Sawamoto, Macromolecules 49 (2016) 4534-4543. doi: 10.1021/acs.macromol.6b00998
12. [12]
  J.H. Ko, A. Bhattacharya, T. Terashima, M. Sawamoto, H.D. Maynard, Polym. Chem. 57 (2019) 352-359. doi: 10.1002/pola.29187
13. [13]
  G. Hattori, M. Takenaka, M. Sawamoto, T. Terashima, J. Am. Chem. Soc. 140 (2018) 8376-8379. doi: 10.1021/jacs.8b03838
14. [14]
  A. Martien, S. Cohen, T. Wilhelm, et al., Nat. Mater. 9 (2010) 101-113. doi: 10.1038/nmat2614
15. [15]
  C.L. Liu, C.H. Lin, C.C. Kuo, S.T. Lin, W.C. Chen, Prog. Polym. Sci. 36 (2011) 603-637. doi: 10.1016/j.progpolymsci.2010.07.008
16. [16]
  Y.C. Lee, Y.S. Sun, J.Y. Liou, W.T. Chuang, Polymer 53 (2012) 5972-5981. doi: 10.1016/j.polymer.2012.10.031
17. [17]
  L. Sun, W.M. Huang, Z. Ding, et al., Mater. Des. 33 (2012) 577-640. doi: 10.1016/j.matdes.2011.04.065
18. [18]
  Z.Q. Cao, G.J. Wang, Chem. Rec. 16 (2016) 1398-1435. doi: 10.1002/tcr.201500281
19. [19]
  T.Y. Wang, H.M. Zhu, H.G. Xue, Materials 9 (2016) 478. doi: 10.3390/ma9060478
20. [20]
  Y.W. Pei, A.B. Lowe, P.J. Roth, Macromol. Rapid Commun. 38 (2017) 1600528. doi: 10.1002/marc.201600528
21. [21]
  R. Cheng, F. Meng, C. Deng, H.A. Klok, Z. Zhong, Biomaterials 34 (2013) 3647. doi: 10.1016/j.biomaterials.2013.01.084
22. [22]
  M. Motornov, Y. Roiter, I. Tokarev, S. Minko, Prog. Polym. Sci. 35 (2010) 174.
23. [23]
  B. Yan, Y. Zhang, C. Wei, et al., Polym. Chem. 9 (2018) 904-911. doi: 10.1039/C7PY01908D
24. [24]
  N. Jommanee, C. Chanthad, K. Manokruang, Carbohyd. Polym.198 (2018) 486-494. doi: 10.1016/j.carbpol.2018.06.099
25. [25]
  Y. Zhang, Y. Xu, C. Wei, Mater. Today Chem. 4 (2017) 172-179. doi: 10.1016/j.mtchem.2017.03.004
26. [26]
  L.Zhang, Y.Wang, X.B.Zhang, etal., ACSAppl.Mater.Interfaces9 (2017)3388-3399. doi: 10.1021/acsami.6b14078
27. [27]
  J.Y. Teo, B. Eng, W. Chin, et al., Nanomed. -Nanotechnol. 13 (2017) 431-442. doi: 10.1016/j.nano.2016.09.016
28. [28]
  F.Y. Qiu, L. Yu, F.S. Du, Macromol. Rapid Commun. 38 (2017) 1700400-1700406. doi: 10.1002/marc.201700400
29. [29]
  J. Feng, R.X. Zhuo, X.Z. Zhang, Prog. Polym. Sci. 37 (2012) 211-236. doi: 10.1016/j.progpolymsci.2011.07.008
30. [30]
  H.F. Wang, H.Z. Jia, Y.F. Chu, et al., Macromol. Biosci. 14 (2014) 526-536. doi: 10.1002/mabi.201300414
31. [31]
  W. Su, H.F. Wang, J. Feng, et al., J. Mater. Chem. 21 (2011) 6327.
32. [32]
  X.L. Yang, X. Xing, J. Li, et al., RSC Adv. 9 (2019) 6003.
33. [33]
  M.N. Ganivada, P. Kumar, P. Kanjilal, et al., Polym. Chem. 7 (2016) 4237-4245. doi: 10.1039/C6PY00615A
34. [34]
  C. Wei, Y. Zhang, H. Xu, et al., J. Mater. Chem. B 4 (2016) 5059.
35. [35]
  H.M. Li, H. Jiang, M.N. Zhao, Y. Fu, X. Sun, Polym. Chem. 6 (2015) 1952-1960. doi: 10.1039/C4PY01623H
36. [36]
  H.F. Wang, H.Z. Jia, Y.F. Chu, et al., Macromol. Biosci. 14 (2014) 526-536. doi: 10.1002/mabi.201300414
37. [37]
  V.T. Huynh, P. de Souza, M.H. Stenze, Macromolecules 44 (2011) 7888-7900. doi: 10.1021/ma2016503
1. [1]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
2. [2]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
3. [3]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
4. [4]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
5. [5]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
6. [6]
  Tong Zhang , Chao Sun , Shubin Yang , Zimin Cai , Sifeng Zhu , Wendian Liu , Yun Luan , Cheng Wang . Inhalation of taraxasterol loaded mixed micelles for the treatment of idiopathic pulmonary fibrosis. Chinese Chemical Letters, 2024, 35(8): 109248-. doi: 10.1016/j.cclet.2023.109248
7. [7]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
8. [8]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
9. [9]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
10. [10]
  Yihan Zhou , Duo Gao , Yaying Wang , Li Liang , Qingyu Zhang , Wenwen Han , Jie Wang , Chunliu Zhu , Xinxin Zhang , Yong Gan . Worm-like micelles facilitate the intestinal mucus diffusion and drug accumulation for enhancing colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108967-. doi: 10.1016/j.cclet.2023.108967
11. [11]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
12. [12]
  Sixin Ai , Wenxiu Li , Huayong Zhu , Yang Wan , Weiying Lin . Viscosity-responsive signal amplification dual-modal probe triggered by cysteine/homocysteine for monitoring diabetic liver damages and repair processes. Chinese Chemical Letters, 2025, 36(3): 109904-. doi: 10.1016/j.cclet.2024.109904
13. [13]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
14. [14]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
15. [15]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
16. [16]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
17. [17]
  Zhenjie Yang , Chenyang Hu , Xuan Pang , Xuesi Chen . Sequence design in terpolymerization of ε-caprolactone, CO₂ and cyclohexane oxide: Random ester-carbonate distributions lead to large-span tunability. Chinese Chemical Letters, 2024, 35(5): 109340-. doi: 10.1016/j.cclet.2023.109340
18. [18]
  Hejie Zheng , Zhili Wang , Guizhen Luo , Cuicui Du , Xiaohua Zhang , Jinhua Chen . A novel PEC-EC dual-mode biosensing platform for dual target detection of miRNA-133a and cTnI. Chinese Chemical Letters, 2025, 36(4): 110131-. doi: 10.1016/j.cclet.2024.110131
19. [19]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(657)
HTML views(16)

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