Citation: Meng Du, Ming Li, Wangze Song, Nan Zheng. Metal-free multicomponent polymerization toward cationic polyamidines[J]. Chinese Chemical Letters, ;2022, 33(5): 2643-2647. doi: 10.1016/j.cclet.2021.09.031 shu

Metal-free multicomponent polymerization toward cationic polyamidines

Meng Du ¹ ,
Ming Li ¹ ,
Wangze Song ^*, ,
Nan Zheng ^*,

State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China

wzsong@dlut.edu.cn

nzheng@dlut.edu.cn

Received Date: 6 August 2021
Accepted Date: 7 September 2021
Available Online: 11 September 2021

Figures(6)

Cationic polymers, also known as polycations, are considered to be the most potential non-viral gene carriers due to their unique advantages such as the ability to bind the negative charge of nucleic acid molecules. Multicomponent polymerization (MCP) is a one-step, tandem strategy to construct complex structures based on multicomponent reactions. Herein, we developed a metal-free MCP method based on three monomers of p-dinitrovinylbenzene (p-DNVB), 1, 1-dimethylethyl N, N-dibromocarbamate (BocNBr₂), and bis-secondary-amines with a ratio of 1:2:1, to access a library of Boc-substituted polyamidines with well-defined structures and suitable molecular weights (M_w ranging from 4400 Da to 11, 000 Da) in high yields (up to 85%) under mild conditions. Upon the removal of Boc groups, a series of water-soluble polymers with cationic property were prepared and their gene binding capability was further evaluated.
- Multicomponent polymerization,
- Metal-free,
- Cationic polymer,
- Polyamidine,
- Water-soluble
1. [1]
  C.G. Neochoritis, T. Zhao, A. Doemling, Chem. Rev. 119 (2019) 1970-2042. doi: 10.1021/acs.chemrev.8b00564
2. [2]
  J. Zhang, W. Xie, S. Ye, J. Wu, Org. Chem. Front. 6 (2019) 2254-2259. doi: 10.1039/c9qo00520j
3. [3]
  M. Giustiniano, A. Basso, V. Mercalli, et al., Chem. Soc. Rev. 46 (2017) 1295-1357.
4. [4]
  T. Yao, B. Wang, B. Ren, X. Qin, T. Li, Chem. Commun. 57 (2021) 4247-4250. doi: 10.1039/d1cc01226f
5. [5]
  K. Yang, F. Zhang, T. Fang, et al., Nat. Commun. 12 (2021) 441. doi: 10.1038/s41467-020-20727-7
6. [6]
  Q. Liu, H. Xu, Y. Li, et al., Nat. Commun. 12 (2021) 19. doi: 10.1038/s41467-020-20205-0
7. [7]
  I.H. Lee, H. Kim, T.L. Choi, J. Am. Chem. Soc. 135 (2013) 3760-3763. doi: 10.1021/ja312592e
8. [8]
  B.J. Yao, W.X. Wu, L.G. Ding, Y.B. Dong, J. Org. Chem. 86 (2021) 3024-3032. doi: 10.1021/acs.joc.0c02423
9. [9]
  J. He, N. Zheng, D. Xie, Y. Zheng, W. Song, Polym. Chem. 11 (2020) 1198-1210. doi: 10.1039/c9py01576k
10. [10]
  S.C. Solleder, M.A.R. Meier, Angew. Chem., Int. Ed. 53 (2014) 711-714. doi: 10.1002/anie.201308960
11. [11]
  S. Oelmann, S.C. Solleder, M.A.R. Meier, Polym. Chem. 7 (2016) 1857-1860. doi: 10.1039/C5PY02030A
12. [12]
  H. Wu, B. Yang, Y. Zhao, et al., Polym. Chem. 7 (2016) 4867-4872. doi: 10.1039/C6PY00781C
13. [13]
  C.Y.K. Chan, N.W. Tseng, J.W.Y. Lam, et al., Macromolecules. 46 (2013) 3246-3256. doi: 10.1021/ma4005346
14. [14]
  J.Y. Quek, T.P. Davis, A.B. Lowe, Chem. Soc. Rev. 42 (2013) 7326-7334. doi: 10.1039/c3cs60065c
15. [15]
  J. Tanabe, D. Taura, N. Ousaka, E. Yashima, J. Am. Chem. Soc. 139 (2017) 7388-7398. doi: 10.1021/jacs.7b03317
16. [16]
  M.B. Tehrani, S. Emami, M. Asadi, et al., J. Med. Chem. 57 (2014) 759-764. doi: 10.1021/jm401492x
17. [17]
  M.J. Wang, X.B. Zhao, D. Wu, et al., J. Agric. Food Chem. 62 (2014) 5429-5442. doi: 10.1021/jf501108j
18. [18]
  T.R.M. Rauws, B.U.W. Maes, Chem. Soc. Rev. 41 (2012) 2463-2497. doi: 10.1039/c1cs15236j
19. [19]
  L. Xu, H. Li, Z. Liao, et al., Org. Lett. 17 (2015) 3434-3437. doi: 10.1021/acs.orglett.5b01435
20. [20]
  C.G. Saluste, R.J. Whitby, M. Furber, Angew. Chem. Int. Ed. 39 (2000) 4156-4158. doi: 10.1002/1521-3773(20001117)39:22<4156::AID-ANIE4156>3.0.CO;2-B
21. [21]
  Q. Dai, Y. Jiang, J.T. Yu, J. Cheng, Chem. Commun. 51 (2015) 16645-16647. doi: 10.1039/C5CC06771E
22. [22]
  K.D. Veeranna, K.K. Das, S. Baskaran, Angew. Chem. Int. Ed. 56 (2017) 16197-16201. doi: 10.1002/anie.201708138
23. [23]
  Z. Zhang, B. Huang, G. Qiao, et al., Angew. Chem. Int. Ed. 56 (2017) 4320-4323. doi: 10.1002/anie.201700539
24. [24]
  T. Otani, X. Jiang, K. Cho, et al., Adv. Synth. Catal. 357 (2015) 1483-1492. doi: 10.1002/adsc.201401186
25. [25]
  N. Zheng, D.K. Cudjoe, W. Song, Macromol. Rapid Commun. 42 (2021) 2000464. doi: 10.1002/marc.202000464
26. [26]
  E. Tsuchida, T. Tomono, J. Polym. Sci. Part A: Polym. Chem. 11 (1973) 723-735. doi: 10.1002/pol.1973.170110403
27. [27]
  B. Guo, B. Gao, H. Yu, et al., J. Environ. Sci. 51 (2017) 305-314. doi: 10.1016/j.jes.2016.08.002
28. [28]
  R. Tang, W. Ji, C. Wang, Polymer (Guildf) 52 (2011) 921-932. doi: 10.1016/j.polymer.2010.12.057
29. [29]
  S.J. Hwang, N.C. Bellocq, M.E. Davis, Bioconjug. Chem. 12 (2001) 280-290. doi: 10.1021/bc0001084
30. [30]
  M. Zhou, J. Li, C. Tian, et al., J. Org. Chem. 84 (2019) 1015-1024. doi: 10.1021/acs.joc.8b02998
31. [31]
  H. Sun, J. Han, P.V. Kattamuri, et al., J. Org. Chem. 78 (2013) 1171-1175. doi: 10.1021/jo302727v
32. [32]
  C. Xu, J. Du, L. Ma, et al., Tetrahedron. 69 (2013) 4749-4757. doi: 10.1016/j.tet.2013.02.084
33. [33]
  H. Uchida, K. Miyata, M. Oba, et al., J. Am. Chem. Soc. 133 (2011) 15524-15532. doi: 10.1021/ja204466y
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