Citation: Xuan Wu, Ming Liu, Cheng Zheng, Yingying Wang, Yujing Zheng, Yuna Qian, Zhiyong Liao, Guoyong Fang, Jianliang Shen. Solvent-mediated handedness inversed and amplified circularly polarized luminescence system based on camptothecin derivative[J]. Chinese Chemical Letters, ;2023, 34(2): 107590. doi: 10.1016/j.cclet.2022.06.013 shu

Solvent-mediated handedness inversed and amplified circularly polarized luminescence system based on camptothecin derivative

Xuan Wu ^{a, c} ,
Ming Liu ^b ,
Cheng Zheng ^d ,
Yingying Wang ^e ,
Yujing Zheng ^b ,
Yuna Qian ^{a, c} ,
Zhiyong Liao ^d ,
Guoyong Fang ^{e, f} ,
Jianliang Shen ^{a, b, c, *,}

a.
Wenzhou Institute, University of Chinese Academy of Sciences, Wenzhou 325000, China
b.
School of Ophthalmology and Optometry, School of Biomedical Engineering, Wenzhou Medical University, Wenzhou 325035, China
c.
Oujiang Laboratory (Zhejiang Lab for Regenerative Medicine, Vision and Brain Health), Wenzhou 325001, China
d.
College of Life and Environmental Science, Wenzhou University, Wenzhou 325000, China
e.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325000, China
f.
National Laboratory of Solid State Microstructures, Nanjing University, Nanjing 210093, China

shenjl@wiucas.ac.cn

Received Date: 15 April 2022
Revised Date: 1 June 2022
Accepted Date: 5 June 2022
Available Online: 10 June 2022

Figures(6)

To realize the handedness controllable circularly polarized luminescence (CPL) system remains challenging. Herein, the solvent-mediated CPL inversion and amplification systems were successfully constructed by camptothecin derivative (CPT-A). Due to the planar structure of N, N-dimethylformamide, it could co-assemble with CPT-A, resulting in the alteration of g_lum from ‒0.0082 to +0.0085 by increasing water content. While in the non-planar solvent (hexafluoroisopropanol), the g_lum was amplified to 0.034 with the increase in water content. Moreover, the CPT-A could react with the glutathione, resulting in the anticancer drug CPT to make it more toxic to the cancer cells. Overall, the handedness controllable CPL systems were realized by tuning the supramolecular self-assembly of a prodrug.
1. [1]
  K. Dhbaibi, L. Favereau, M. Srebro-Hooper, et al., Angew. Chem. Int. Ed.9 (2018) 735-742.
2. [2]
  M. Li, S.H. Li, D. Zhang, et al., Angew. Chem. Int. Ed. 57 (2018) 2889-2893. doi: 10.1002/anie.201800198
3. [3]
  R. Sethy, J. Kumar, R. Métivier, et al., Angew. Chem. Int. Ed. 56 (2017) 15053-15057. doi: 10.1002/anie.201707160
4. [4]
  G. Xia, L. Wang, H. Xia, et al., Chin. Chem. Lett. 33 (2022) 4253–4256. doi: 10.1016/j.cclet.2022.03.032
5. [5]
  H. Wang, H.K. Bisoyi, B.X. Li, et al., Angew. Chem. Int. Ed. 59 (2020) 2684-2687. doi: 10.1002/anie.201913977
6. [6]
  Z.G. Zheng, Y. Li, H.K. Bisoyi, et al., Nature 531 (2016) 352-356. doi: 10.1038/nature17141
7. [7]
  E. Ohta, H. Sato, S. Ando, et al., Nat. Chem. 3 (2011) 68-73. doi: 10.1038/nchem.900
8. [8]
  K. Maeda, K. Shimomura, T. Ikai, et al., Macromolecules 50 (2017) 7801-7806. doi: 10.1021/acs.macromol.7b01955
9. [9]
  Q. Ye, F. Zheng, E. Zhang, et al., Chem. Sci. 11 (2020) 9989-9993. doi: 10.1039/d0sc04179c
10. [10]
  Y. Zhang, J. Wang, H. Chen, et al., Chin. Chem. Lett. 33 (2022) 2473-2476. doi: 10.1016/j.cclet.2021.11.069
11. [11]
  X. Zhang, J. Yin, J. Yoon, Chem. Rev. 114 (2014) 4918-4959. doi: 10.1021/cr400568b
12. [12]
  K. Wang, J.H. Jordan, X.Y. Hu, L. Wang, Angew. Chem. Int. Ed. 59 (2020) 13712-13721. doi: 10.1002/anie.202000045
13. [13]
  Y.M. Zhang, Y.H. Liu, Y. Liu, Adv. Mater. 32 (2020) 1806158. doi: 10.1002/adma.201806158
14. [14]
  J. Zhou, L. Rao, G. Yu, et al., Chem. Soc. Rev. 50 (2021) 2839-2891. doi: 10.1039/d0cs00011f
15. [15]
  P. Xing, Y. Zhao, Acc. Chem. Res. 51 (2018) 2324-2334. doi: 10.1021/acs.accounts.8b00312
16. [16]
  L. Ji, Y. Sang, G. Ouyang, et al., Angew. Chem. Int. Ed. 58 (2019) 844-848. doi: 10.1002/anie.201812642
17. [17]
  G. Park, H. Kim, H. Yang, et al., Chem. Sci. 10 (2019) 1294-1301. doi: 10.1039/c8sc04509g
18. [18]
  X. Yang, J. Han, Y. Wang, P. Duan, Chem. Sci. 10 (2019) 172-178. doi: 10.1039/c8sc03806f
19. [19]
  T. Zhao, J. Han, X. Jin, et al., Angew. Chem. Int. Ed. 58 (2019) 4978-4982. doi: 10.1002/anie.201900052
20. [20]
  L. Yuan, Q.J. Ding, Z.L. Tu, et al., Chin. Chem. Lett. 33 (2022) 1459-1462. doi: 10.1016/j.cclet.2021.08.104
21. [21]
  C. Wang, T. Jiang, X. Ma, Chin. Chem. Lett. 31 (2020) 2921-2924. doi: 10.1016/j.cclet.2020.03.021
22. [22]
  W. Han, W. Xiang, Q. Li, et al., Chem. Soc. Rev. 50 (2021) 10025-10043. doi: 10.1039/d1cs00187f
23. [23]
  S.J.D. Lugger, S.J.A. Houben, Y. Foelen, et al., Chem. Rev. 122 (2022) 4946-4975. doi: 10.1021/acs.chemrev.1c00330
24. [24]
  L. Zhang, H.X. Wang, S. Li, M. Liu, Chem. Soc. Rev. 49 (2020) 9095-9120. doi: 10.1039/d0cs00191k
25. [25]
  X. Liu, W. Shao, Y. Zheng, et al., Chem. Commun. 53 (2017) 8596-8599. doi: 10.1039/C7CC04932C
26. [26]
  S.Z.F. Phua, C. Xue, W.Q. Lim, et al., Chem. Mater. 31 (2019) 3349-3358. doi: 10.1021/acs.chemmater.9b00439
27. [27]
  Y. Yang, Y.M. Zhang, D. Li, et al., Bioconjugate Chem. 27 (2016) 2834-2838. doi: 10.1021/acs.bioconjchem.6b00606
28. [28]
  M. Ma, W. Shang, P. Xing, et al., Carbohydr. Res. 402 (2015) 208-214. doi: 10.1016/j.carres.2014.09.008
29. [29]
  A. Steffen, C. Thiele, S. Tietze, et al., Chem. Eur. J. 13 (2007) 6801-6809. doi: 10.1002/chem.200700661
30. [30]
  Y. Yu, H. Xu, W. Zhang, et al., J. Photochem. Photobiol. Photobiol. A346 (2017) 215-220. doi: 10.1016/j.jphotochem.2017.06.001
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