Citation: Qian Ren, Xue Dai, Ran Cen, Yang Luo, Mingyang Li, Ziyun Zhang, Qinghong Bai, Zhu Tao, Xin Xiao. A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution[J]. Chinese Chemical Letters, ;2024, 35(12): 110022. doi: 10.1016/j.cclet.2024.110022 shu

A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Institute of Applied Chemistry, Guizhou University, Guiyang 550025, China

xxiao@gzu.edu.cn

Received Date: 9 February 2024
Revised Date: 1 May 2024
Accepted Date: 16 May 2024
Available Online: 17 May 2024

Figures(5)

In recent years, host-guest interactions of macrocycles have emerged as a promising approach to effectively enhance pure organic room-temperature phosphorescence by inhibiting the nonradiative relaxation while isolating the effects of oxygen and water molecules. In this work, a supramolecular assembly Q[8]-BCPI was constructed by 6-bromoisoquinoline derivative (BCPI) and cucurbit[8]uril (Q[8]). The assembly produced intense green room temperature phosphorescence (RTP) emission and enabled supramolecular recognition and detection of l-tryptophan (L-Trp) and l-tyrosine (L-Tyr). Moreover, the Q[8]-BCPI assembly showed good biocompatibility and low biotoxicity, and had a good staining effect on HeLa cells.
- Cucurbituril,
- Isobromoquinoline,
- Pure organic room-temperature phosphorescent,
- Cell imaging,
- Amino acid
1. [1]
  Y.Y. Si, Y.Y. Zhao, W.B. Dai, et al., Chin. J. Chem. 41 (2023) 1575–1582. doi: 10.1002/cjoc.202200838
2. [2]
  H. Gao, Z. Gao, D. Jiao, et al., Small 17 (2021) 2005449. doi: 10.1002/smll.202005449
3. [3]
  W.L. Zhou, W. Lin, Y. Chen, et al., Chem. Sci. 13 (2022) 7976–7989. doi: 10.1039/d2sc01770a
4. [4]
  B.B. Ding, X. Ma, H. Tian, Acc. Mater. Res. 4 (2023) 827–838. doi: 10.1021/accountsmr.3c00090
5. [5]
  F. Gu, X. Ma, Chem. Eur. J. 28 (2022) e202104131. doi: 10.1002/chem.202104131
6. [6]
  H. Ju, H. Zhang, L.X. Hou, et al., J. Am. Chem. Soc. 145 (2023) 3763–3773. doi: 10.1021/jacs.2c13264
7. [7]
  Y. Zhu, Z. Feng, Z. Yan, et al., Sens. Actuators B Chem. 371 (2022) 132529. doi: 10.1016/j.snb.2022.132529
8. [8]
  S. Kuila, K.V. Rao, S. Garain, et al., Angew. Chem. Int. Ed. 57 (2018) 17115–17119. doi: 10.1002/anie.201810823
9. [9]
  X.K. Ma, Q.W. Cheng, X.L. Zhou, et al., JACS Au 3 (2023) 2036–2043. doi: 10.1021/jacsau.3c00255
10. [10]
  D. Li, Z. Liu, M. Fang, et al., ACS Nano 17 (2023) 12895–12902. doi: 10.1021/acsnano.3c04971
11. [11]
  H.J. Wang, W.W. Xing, Z.H. Yu, et al., Adv. Opt. Mater. 10 (2022) 2201903. doi: 10.1002/adom.202201903
12. [12]
  W. Zhu, H. Xing, E. Li, et al., Macromolecules 55 (2022) 9802–9809. doi: 10.1021/acs.macromol.2c00680
13. [13]
  P. Wei, X. Zhang, J. Liu, et al., Angew. Chem. Int. Ed. 59 (2020) 9293–9298. doi: 10.1002/anie.201912155
14. [14]
  H. Zhu, J. Liu, Y. Wu, et al., J. Am. Chem. Soc. 145 (2023) 11130–11139. doi: 10.1021/jacs.3c00711
15. [15]
  J. Wang, Z. Huang, X. Ma, et al., Angew. Chem. Int. Ed. 59 (2020) 9928–9933. doi: 10.1002/anie.201914513
16. [16]
  C. Li, Q. Guo, J. Zhu, et al., Res. Chem. Intermed. 49 (2023) 2755–2768. doi: 10.1007/s11164-023-05009-3
17. [17]
  C. Li, X. Li, Q. Wang, Chin. Chem. Lett. 33 (2022) 877–880. doi: 10.1016/j.cclet.2021.08.011
18. [18]
  D. Yang, M. Liu, X. Xiao, et al., Coord. Chem. Rev. 434 (2021) 213733. doi: 10.1016/j.ccr.2020.213733
19. [19]
  W. Zhang, Y. Luo, J. Zhao, et al., Chin. Chem. Lett. 33 (2021) 2455–2458. doi: 10.1007/s10461-021-03208-w
20. [20]
  R. Cen, M. Liu, H. Xiao, et al., Sens. Actuators B Chem. 378 (2022) 133126.
21. [21]
  Y. Luo, W. Zhang, M. Liu, et al., Chin. Chem. Lett. 32 (2020) 367–370.
22. [22]
  J.H. Hu, Y. Huang, R. Carl, et al., Coord. Chem. Rev. 489 (2023) 215194. doi: 10.1016/j.ccr.2023.215194
23. [23]
  R.H. Gao, L.X. Chen, K. Chen, et al., Coord. Chem. Rev. 348 (2017) 1–24. doi: 10.1016/j.ccr.2017.07.017
24. [24]
  W. Zhang, Y. Luo, Y. Zhou, et al., Dyes Pigments 176 (2020) 108235. doi: 10.1016/j.dyepig.2020.108235
25. [25]
  M. Liu, R. Cen, J. Li, et al., Angew. Chem. Int. Ed. 61 (2022) e202207209. doi: 10.1002/anie.202207209
26. [26]
  M. Liu, R. Cen, J.H. Lu, et al., Chin. Chem. Lett. 33 (2021) 2469–2472. doi: 10.1080/01635581.2020.1830126
27. [27]
  Y. Luo, W. Zhang, J. Zhao, et al., Chin. Chem. Lett. 34 (2022) 107780.
28. [28]
  A. Hennig, H. Bakirci, W.M. Nau, Nat. Methods 4 (2007) 629–632. doi: 10.1038/nmeth1064
29. [29]
  H. Barbero, N.A. Thompson, E. Masson, J. Am. Chem. Soc. 142 (2020) 867–873. doi: 10.1021/jacs.9b09751
30. [30]
  X. Yang, Q. Cheng, V. Monnier, et al., Angew. Chem. Int. Ed. 60 (2021) 6617–6623. doi: 10.1002/anie.202014399
31. [31]
  X. Yang, F. Liu, Z. Zhao, et al., Chin. Chem. Lett. 29 (2018) 1560–1566. doi: 10.1016/j.cclet.2018.01.032
32. [32]
  L. Xu, L. Zou, H. Chen, et al., Dyes Pigments 142 (2017) 300–305. doi: 10.1016/j.dyepig.2017.03.044
33. [33]
  B.S. Kanti, P.S. Kumar, B. Supratim, Chem. Commun. 59 (2023) 10396–10399. doi: 10.1039/D3CC02836D
34. [34]
  W. Zhang, Y. Luo, C. Liu, et al., ACS Appl. Mater. Interfaces 14 (2022) 51429–51437. doi: 10.1021/acsami.2c16567
35. [35]
  C. Li, J. Zhu, Q. Wang, Dyes Pigments, 204 (2022) 110368. doi: 10.1016/j.dyepig.2022.110368
36. [36]
  M. Singh, K. Liu, S. Qu, et al., Adv. Opt. Mater. 9 (2021) 2002197. doi: 10.1002/adom.202002197
37. [37]
  X.K. Ma, Y. Liu, Acc. Chem. Res. 17 (2021) 3403–3414. doi: 10.1021/acs.accounts.1c00336
38. [38]
  S.K. Bhaumik, R. Biswas, S. Banerjee, Chem. Asian J. 16 (2021) 2195–2210. doi: 10.1002/asia.202100594
39. [39]
  D.A. Xu, Q.Y. Zhou, X. Dai, et al., Chin. Chem. Lett. 33 (2022) 851–854. doi: 10.1016/j.cclet.2021.08.001
40. [40]
  X. Yu, W. Liang, Q. Huang, et al., Chem. Commun. 55 (2019) 3156–3159. doi: 10.1039/c9cc00097f
41. [41]
  H.J. Yu, Q. Zhou, X. Dai, et al., J. Am. Chem. Soc. 34 (2021) 13887–13894. doi: 10.1021/jacs.1c06741
42. [42]
  W.W. Xing, H.J. Wang, Z. Liu, et al., Adv. Opt. Mater. 11 (2023) 2202588. doi: 10.1002/adom.202202588
43. [43]
  Y.H. Liu, Y. Liu, J. Mater. Chem. B, 10 (2022) 8058–8063. doi: 10.1039/d2tb01494g
44. [44]
  J. Yang, X. Hu, M. Fan, et al., Org. Chem. Front. 10 (2023) 422–429. doi: 10.1039/d2qo01831d
45. [45]
  C. Liu, X. Xiao, X.L. Ni, Dyes Pigments 212 (2023) 111152. doi: 10.1016/j.dyepig.2023.111152
46. [46]
  H.J. Yu, Q. Zhou, X. Dai, et al., J. Am. Chem. Soc. 143 (2021) 13887–13894. doi: 10.1021/jacs.1c06741
47. [47]
  H.G. Nie, Z. Wei, X.L. Ni, et al., Chem. Rev. 122 (2022) 9032–9077. doi: 10.1021/acs.chemrev.1c01050
48. [48]
  X.K. Ma, W. Zhang, Z. Liu, et al., Adv. Mater. 33 (2021) 2007476. doi: 10.1002/adma.202007476
49. [49]
  X.L. Ni, X. Xiao, H. Cong, et al., Chem. Soc. Rev. 42 (2013) 9480–9508. doi: 10.1039/c3cs60261c
50. [50]
  A. Bahadoran, M.K. Jabarabadi, Z.H. Mahmood, et al., Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 268 (2022) 118863.
51. [51]
  J. Xiong, S. He, Z. Wang, et al., J. Hazard. Mater. 429 (2022) 128316. doi: 10.1016/j.jhazmat.2022.128316
52. [52]
  J. Zhang, X. Lu, Y. Lei, et al., Nanoscale 9 (2017) 15606–15611. doi: 10.1039/C7NR03673F
53. [53]
  S. Ghosh, J. Krishnan, S.S. Hossain, et al., ACS Appl. Mater. Interfaces 15 (2023) 26843–26851. doi: 10.1021/acsami.3c04278
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