Citation: Yibin Zhou, Hao Tang, Hanlun Wu, Xiaomei Jiang, Lingyun Wang, Derong Cao. Supramolecular cyclization induced emission enhancement in a pillar[5]arene probe for discrimination of spermine[J]. Chinese Chemical Letters, ;2024, 35(1): 108626. doi: 10.1016/j.cclet.2023.108626 shu

Supramolecular cyclization induced emission enhancement in a pillar[5]arene probe for discrimination of spermine

State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China

haotang@scut.edu.cn

drcao@scut.edu.cn

Received Date: 17 March 2023
Revised Date: 24 May 2023
Accepted Date: 29 May 2023
Available Online: 1 June 2023

Figures(6)

Early diagnosis and treatment of cancer requires the development of tools that are both sensitive and selective in detecting spermine. In this study, we presented a "supramolecular cyclization-induced emission enhancement" strategy for the sensitive and selective detection of spermine. A new pillar[5]arene probe (P1) demonstrated excellent solution/solid dual-state emission properties, and the addition of certain spermine (Spm) resulted in fluorescence enhancement due to the synergy of multiple weak interactions that restricted the free motion of P1 in the P1⊃Spm complex. This mechanism was further confirmed by time-resolved spectroscopy, DFT calculations, and IGM analysis. With its low limit of detection and high selectivity, P1 is a promising tool for measuring spermine in artificial urine samples.
- Spermine,
- Pillar[5]arene,
- Probe,
- Supramolecular chemistry,
- Supramolecular cyclization induced emission enhancement
1. [1]
  C. Stefanelli, F. Bonavita, I. Stanic, et al., FEBS Lett. 437 (1998) 233–236. doi: 10.1016/S0014-5793(98)01239-3
2. [2]
  A. Bibillo, M. Figlerowicz, R. Kierzek, Nucl. Acids Res. 27 (1999) 3931–3937. doi: 10.1093/nar/27.19.3931
3. [3]
  C. Moinard, L. Cynober, J.-.P. de Bandt, Clin. Nutr. 24 (2005) 184–197. doi: 10.1016/j.clnu.2004.11.001
4. [4]
  R.A. C.asero, L.J. M.arton, Nat. Rev. Drug. Disc. 6 (2007) 373–390. doi: 10.1038/nrd2243
5. [5]
  D.H. Russell, Nat. New Biol. 233 (1971) 144–145. doi: 10.1038/newbio233144a0
6. [6]
  H.E. Flores, A.W. Galston, Plant Physiol. 69 (1982) 701–706. doi: 10.1104/pp.69.3.701
7. [7]
  Y. Ma, G. Liu, M. Du, et al., Electrophoresis 25 (2004) 1473–1484. doi: 10.1002/elps.200405895
8. [8]
  J.T. Fletcher, B.S. Bruck, Sens. Actuators B Chem. 207 (2015) 843–848. doi: 10.1016/j.snb.2014.10.116
9. [9]
  B. Lee, R. Scopelliti, K. Severin, Chem. Commun. 47 (2011) 9639–9641. doi: 10.1039/c1cc13604f
10. [10]
  W. Li, L. Wang, T. Sun, et al., Commun. Biol. 4 (2021) 803. doi: 10.1038/s42003-021-02317-5
11. [11]
  H. Nohta, H. Satozono, K. Koiso, et al., Anal. Chem. 72 (2000) 4199–4204. doi: 10.1021/ac0002588
12. [12]
  L. Wang, S. Xin, C. Zhang, et al., J. Mater. Chem. B 9 (2021) 9383–9394. doi: 10.1039/d1tb01791h
13. [13]
  M. Barros, S. Ceballos, P. Arroyo, et al., Chemosensors 10 (2021) 8. doi: 10.3390/chemosensors10010008
14. [14]
  S.M. T.awfik, J. Shim, D. Biechele-Speziale, et al., Sens. Actuators B: Chem. 257 (2018) 734–744. doi: 10.1016/j.snb.2017.10.172
15. [15]
  B. Bao, L. Yuwen, X. Zheng, et al., J. Mater. Chem. 20 (2010) 9628–9634. doi: 10.1039/c0jm01467b
16. [16]
  A. Satrijo, S.E. Kooi, T.M. Swager, Macromolecules 40 (2007) 8833–8841. doi: 10.1021/ma071659t
17. [17]
  J. Wang, Q. Zhang, Z. De Liu, et al., Analyst 137 (2012) 5565–5570. doi: 10.1039/c2an35952a
18. [18]
  C.F. Chow, M.H. L.am, W.Y. W.ong, Anal. Chem. 85 (2013) 8246–8253. doi: 10.1021/ac401513j
19. [19]
  G. Munzi, S. Failla, S. Di Bella, Analyst 146 (2021) 2144–2151. doi: 10.1039/d0an02336a
20. [20]
  A.A. B.hosle, M. Banerjee, N. Barooah, et al., J. Photochem. Photobiol. A: Chem. 426 (2022) 113770. doi: 10.1016/j.jphotochem.2022.113770
21. [21]
  Z. Kostereli, K. Severin, Chem. Commun. 48 (2012) 5841–3. doi: 10.1039/c2cc32228e
22. [22]
  B. Lu, L. Wang, X. Ran, et al., Biosensors 12 (2022) 633. doi: 10.3390/bios12080633
23. [23]
  H. Tian, X. Yu, J. Yao, et al., Chem. Commun. 57 (2021) 1806–1809. doi: 10.1039/d0cc07814j
24. [24]
  J. Tu, S. Sun, Y. Xu, Chem. Commun. 52 (2016) 1040–1043. doi: 10.1039/C5CC07861J
25. [25]
  G. Jiang, W. Zhu, Q. Chen, et al., Sens. Actuators B: Chem. 261 (2018) 602–607. doi: 10.1016/j.snb.2018.01.197
26. [26]
  X.Y. Lou, Y.W. Y.ang, Adv. Mater. 32 (2020) 2003263. doi: 10.1002/adma.202003263
27. [27]
  K. Wang, J.H. Jordan, K. Velmurugan, et al., Angew. Chem. Int. Ed. 60 (2021) 9205–9214. doi: 10.1002/anie.202010150
28. [28]
  K. Wang, X. Tian, J.H. J.ordan, et al., Chin. Chem. Lett. 33 (2022) 89–96. doi: 10.1016/j.cclet.2021.06.026
29. [29]
  L. Wu, C. Han, X. Jing, et al., Chin. Chem. Lett. 32 (2021) 3322–3330. doi: 10.1016/j.cclet.2021.04.046
30. [30]
  L. Xu, Z. Wang, R. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 9908–9913. doi: 10.1002/anie.201907678
31. [31]
  W.L. Zhou, Y. Chen, W. Lin, et al., Chem. Commun. 57 (2021) 11443–11456. doi: 10.1039/d1cc04672a
32. [32]
  H. Zhu, Q. Li, L.E. Khalil-Cruz, et al., Sci. China Chem. 64 (2021) 688–700. doi: 10.1007/s11426-020-9932-9
33. [33]
  L. Xu, R. Wang, H. Tang, et al., J. Mater. Chem. A 10 (2022) 11332–11339. doi: 10.1039/d1ta10959f
34. [34]
  J. Chen, H. Ni, Z. Meng, et al., Nat. Commun. 10 (2019) 3546. doi: 10.1038/s41467-019-11553-7
35. [35]
  D. Dai, Z. Li, J. Yang, et al., J. Am. Chem. Soc. 141 (2019) 4756–4763. doi: 10.1021/jacs.9b01546
36. [36]
  X. Jiang, L. Wang, X. Ran, et al., Biosensors 12 (2022) 571. doi: 10.3390/bios12080571
37. [37]
  Q. Lin, Z.H. Wang, T.T. Huang, et al., J. Mater. Chem. C 9 (2021) 3863–3870. doi: 10.1039/d0tc05922f
38. [38]
  Y. Luo, W. Zhang, Q. Ren, et al., Chin. Chem. Lett. 33 (2022) 5120–5123. doi: 10.1016/j.cclet.2022.04.028
39. [39]
  D. Cao, H. Meier, Chin. Chem. Lett. 30 (2019) 1758–1766. doi: 10.1016/j.cclet.2019.06.026
40. [40]
  Y. Zhou, H. Tang, Z.H. L.i, et al., Chem. Commun. 57 (2021) 13114–13117. doi: 10.1039/d1cc05153a
41. [41]
  X. Shu, S. Chen, J. Li, et al., Chem. Commun. 48 (2012) 2967–2969. doi: 10.1039/c2cc00153e
42. [42]
  P. Gilli, L. Pretto, V. Bertolasi, et al., Acc. Chem. Res. 42 (2009) 33–44. doi: 10.1021/ar800001k
43. [43]
  T. Lu, F. Chen, J. Comput. Chem. 33 (2012) 580–592. doi: 10.1002/jcc.22885
44. [44]
  N. Kaur, S. Chopra, G. Singh, et al., J. Mater. Chem. B 6 (2018) 4872–4902. doi: 10.1039/c8tb00732b
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沈阳化工大学材料科学与工程学院沈阳 110142