Citation: Yiran Zhao, Jingyao Ma, Xia Yu, Min-Hui Li, Jun Hu. Tunable UCST thermoresponsive copolymers based on natural glycyrrhetinic acid[J]. Chinese Chemical Letters, ;2021, 32(1): 548-552. doi: 10.1016/j.cclet.2020.03.057 shu

Tunable UCST thermoresponsive copolymers based on natural glycyrrhetinic acid

Yiran Zhao ^a ,
Jingyao Ma ^a ,
Xia Yu ^a ,
Min-Hui Li ^{a, b, *} ,
Jun Hu ^{a, *,}

a.
Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China
b.
Institut de Recherche de Chimie Paris, Chimie ParisTech, PSL Research University, CNRS, Paris 75005, France

hujun82_1985@163.com

Received Date: 26 February 2020
Revised Date: 19 March 2020
Accepted Date: 22 March 2020
Available Online: 27 March 2020

Figures(5)

Water-soluble thermoresponsive polymers present either upper critical solution temperature (UCST) or lower critical solution temperature (LCST) depending on the location of their miscibility range with water at high temperatures or at low temperatures. Compared with LCST polymers, the water-soluble UCST polymers are still less explored until now. In this work three copolymers of P(AAm-co-GAA) were synthesized by copolymerizing two acrylamide monomers, acrylamide (AAm) and acrylamide functionalized with natural glycyrrhetinic acid (GAA), using reversible addition-fragmentation chain transfer (RAFT) polymerization. These copolymers exhibited the typical UCST thermoresponsive behavior, and their phase transition temperatures could be easily tuned to around 37 ℃ for potential biological applications. Moreover, the UCST of P(AAm-co-GAA) can be adjusted not only by the content of glycyrrhetinic acid (GA) and polymer concentrations, but also by the host-guest interactions between GA and cyclodextrins (β- and γ-CD). The suitable value of UCST and the biocompatible nature of GA and CDs may endow these copolymers with practical applications in biomedical chemistry
- Thermo-responsive polymer,
- UCST,
- Glycyrrhetinic acid,
- Natural product,
- Cyclodextrin
1. [1]
  N. Vanparijs, L. Nuhn, B.G. De Geest, Chem. Soc. Rev. 45 (2017) 1193-1239.
2. [2]
  W. Sun, Z. An, P. Wu, Macromolecules 50 (2017) 2175-2182. doi: 10.1021/acs.macromol.7b00020
3. [3]
  J. Niskanen, H. Tenhu, Polym. Chem. 8 (2017) 220-232. doi: 10.1039/C6PY01612J
4. [4]
  M. Heskins, J.E. Guillet, J. Macromol. Sci. Part. A: Chem. 2 (1968) 1441-1455. doi: 10.1080/10601326808051910
5. [5]
  H. Zhang, T. Marmin, É. Cuierrier, et al., Polym. Chem. 6 (2015) 6644-6650. doi: 10.1039/C5PY01126D
6. [6]
  J. Hunold, T. Wolf, F.R. Wurm, D. Hinderberger, Chem. Commun. 55 (2019) 3414-3417. doi: 10.1039/C8CC09788G
7. [7]
  S. Kuroyanagi, N. Shimada, S. Fujii, et al., J. Am. Chem. Soc. 141 (2019) 1261-1268. doi: 10.1021/jacs.8b10168
8. [8]
  T. Maji, S. Banerjee, Y. Biswas, T.K. Mandal, Macromolecules 48 (2015) 4957-4966. doi: 10.1021/acs.macromol.5b01099
9. [9]
  J. Seuring, S. Agarwal, ACS Macro Lett. 2 (2013) 597-600. doi: 10.1021/mz400227y
10. [10]
  J. Seuring, S. Agarwal, Macromol. Rapid Commun. 33 (2012) 1898-1920. doi: 10.1002/marc.201200433
11. [11]
  J. Seuring, S. Agarwal, Macromolecules 45 (2012) 3910-3918. doi: 10.1021/ma300355k
12. [12]
  H. Zhang, S. Guo, W. Fan, Y. Zhao, Macromolecules 49 (2016) 1424-1433. doi: 10.1021/acs.macromol.5b02522
13. [13]
  A. Palanisamy, S.A. Sukhishvili, Macromolecules 51 (2018) 3467-3476. doi: 10.1021/acs.macromol.8b00519
14. [14]
  G. Huang, H. Li, S.T. Feng, et al., Macromol. Chem. Phys. 216 (2015) 1014-1023. doi: 10.1002/macp.201400546
15. [15]
  O.V. Salomatina, A.V. Markov, E.B. Logashenko, et al., Bioorg. Med. Chem. 22 (2014) 585-593. doi: 10.1016/j.bmc.2013.10.049
16. [16]
  A. Saha, J. Adamcik, S. Bolisetty, S. Handschin, R. Mezzenga, Angew. Chem. Int. Ed. 54 (2015) 5408-5412. doi: 10.1002/anie.201411875
17. [17]
  B.G. Bag, R. Majumdar, RSC Adv. 2 (2012) 8623-8626. doi: 10.1039/c2ra21051g
18. [18]
  Y. Gao, J. Hao, J. Wu, et al., Nanoscale 7 (2015) 13568-13575. doi: 10.1039/C5NR03699B
19. [19]
  M. Zhang, H. Cheng, Z. Gong, et al., Adv. Funct. Mater. 27 (2017) 1703932-1703944. doi: 10.1002/adfm.201703932
20. [20]
  Q. Tian, C. Zhang, X. Wang, et al., Biomaterials 31 (2010) 4748-4756. doi: 10.1016/j.biomaterials.2010.02.042
21. [21]
  J. Hao, Y. Gao, Y. Li, et al., Chem. Asian. J. 12 (2017) 2231-2236. doi: 10.1002/asia.201700581
22. [22]
  J. Hao, Y. Gao, C. Zheng, et al., ACS Macro Lett. 7 (2018) 1131-1137. doi: 10.1021/acsmacrolett.8b00560
23. [23]
  Y. Li, J. Li, X. Zhao, et al., Chem. Eur. J. 22 (2016) 18435-18441. doi: 10.1002/chem.201603753
24. [24]
  C. Zhao, Z. Ma, X.X. Zhu, Prog. Polym. Sci. 90 (2019) 269-291. doi: 10.1016/j.progpolymsci.2019.01.001
25. [25]
  A. Harada, Y. Takashima, M. Nakahata, Acc. Chem. Res. 47 (2014) 2128-2140. doi: 10.1021/ar500109h
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