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
1. [1]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
2. [2]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
3. [3]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190
4. [4]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
5. [5]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
6. [6]
  Qihan Lin , Jiabin Xing , Yue-Yang Liu , Gang Wu , Shi-Jia Liu , Hui Wang , Wei Zhou , Zhan-Ting Li , Dan-Wei Zhang . taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119
7. [7]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
8. [8]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
9. [9]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
10. [10]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
11. [11]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
12. [12]
  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
13. [13]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
14. [14]
  Zihao Wang , Jing Xue , Zhicui Song , Jianxiong Xing , Aijun Zhou , Jianmin Ma , Jingze Li . Li-Zn alloy patch for defect-free polymer interface film enables excellent protection effect towards stable Li metal anode. Chinese Chemical Letters, 2024, 35(10): 109489-. doi: 10.1016/j.cclet.2024.109489
15. [15]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
16. [16]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
17. [17]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
18. [18]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
19. [19]
  Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
20. [20]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(715)
HTML views(70)

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