Citation: Yang Jingge, Li Yang, Wang Xiaoai, Wang Dong, Sun Yawei, Wang Jiqian, Xu Hai. Self-Assembly of Cyclic Dipeptides and Their Fluorescent Properties[J]. Acta Chimica Sinica, ;2019, 77(12): 1279-1286. doi: 10.6023/A19090331 shu

Self-Assembly of Cyclic Dipeptides and Their Fluorescent Properties

Center for Bioengineering & Biotechnology, College of Chemical Engineering, China University of Petroleum(East China), Qingdao 266580

Corresponding author: Wang Jiqian, jqwang@upc.edu.cn Xu Hai, xuh@upc.edu.cn
Received Date: 7 September 2019
Available Online: 21 December 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21573287, 21673293, U1832108)the National Natural Science Foundation of China U1832108the National Natural Science Foundation of China 21673293the National Natural Science Foundation of China 21573287

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Cyclic dipeptide (CDP) is a kind of the smallest cyclic peptide with two amino acids cyclization through amide bonds. The two amide bonds with four hydrogen bonding sites give CDPs a high self-assembly propensity, mainly driven by the hydrogen bonding interactions. In this paper, we have designed four CDPs, c-SF, c-SY, c-SH and c-DF, and studied their self-assembly performance in aqueous solution with circular dichroism spectroscopy (CD) and atomic force microscopy (AFM), including the effects of pH and zinc ion coordination on self-assembly. The fluorescence properties of CDP self-assemblies have also been studied. CD results showed that c-SF, c-SY and c-DF adopted a β-sheet conformation, while c-SH was random coil secondary structure at the concentration of 2.0 mmol/L and pH 5.0. AFM results showed that c-SF, c-SY and c-DF could form nanofibers with different diameters ranged from 1.0 to 3.0 nm. In addition, c-SY self-assembled hierarchically over time. Not only the nanofiber diameter gradually increased, but also the nanofibers entangled into 3D networks. Although c-SH did not self-assemble at the concentration of 3.0 mmol/L and pH 7.0, it could form monolayers with the induction of zinc ion at pH 9.0. The self-assemblies of each CDP had different multiple fluorescent emission peaks with excitation of different wavelengths. Especially, c-SF emitted green fluorescent light under UV light of 365 nm. The fluorescent emission intensity of CDPs was much stronger than their corresponding linear dipeptides. It was assumed that the diketopiperazine structure contributed to the fluorescence enhancement. Moreover, the fluorescent emission intensity of CDP self-assemblies was much higher than that of their free molecules, which meant that the ordered aggregation made a significant contribution to the fluorescent properties. Both the coordination of zinc ions with the imidazole groups on histidine and the oxidation of phenolic hydroxyl groups in tyrosine could enhance the fluorescent emission intensity of CDPs. It was assumed that CDP molecules stacked one by one to form nanofibers during self-assembly. The diketopiperazine ring of CDPs and its self-assembly endowed CDPs with special fluorescent properties.
- cyclic dipeptide,
- diketopiperazine,
- self-assembly,
- nanofiber,
- fluorescence
1. [1]
  Wang, J.; Zou, Q.-L.; Yan, X.-H. Acta Chim. Sinica 2017, 75, 933 (in Chinese).
2. [2]
  Yan, X.; Zhu, P.; Li, J. Chem. Soc. Rev. 2010, 39, 1877. doi: 10.1039/b915765b
3. [3]
  Wang, J.-X.; Qin, S.-Y.; Cai, T.-T.; Zhang, X.-Z.; Zhuo, R.-X. Chem. J. Chin. Univ. 2014, 36, 201 (in Chinese).
4. [4]
  Han, S.; Cao, S.; Wang, Y.; Wang, J.; Xia, D.; Xu, H.; Zhao, X.; Lu, J. Chem.-Eur. J. 2011, 17, 13095. doi: 10.1002/chem.201101970
5. [5]
  Li, Q.; Jia, Y.; Li, J.-B. Acta Chim. Sinica 2019, 77, 1173 (in Chinese).
6. [6]
  MaassenVanDenBrink, A.; Terwindt, G. M.; van den Maagdenberg, A M. J. M. Genome Med. 2018, 10, 10. doi: 10.1186/s13073-018-0524-7
7. [7]
  Inaba, H.; Matsuura, K. Chem. Rec. 2019, 19, 843. doi: 10.1002/tcr.201800149
8. [8]
  Apter, B.; Lapshina, N.; Handelman, A.; Rosenman, G. J. Pept. Sci. 2019, 25, 3164. doi: 10.1002/psc.3164
9. [9]
  Yang, W.-T.; Guo, W.-S.; Zhang, B.-B.; Chang, J. Acta Chim. Sinica 2014, 72, 1209 (in Chinese).
10. [10]
  Wang, Z.-Y.; Cai, Y.-B.; Yi, L.-N.; Gao, J.; Yang, Z.-M. Chin. J. Chem. 2017, 35, 1057. doi: 10.1002/cjoc.201600813
11. [11]
  Kwak, J.; Lee, S. Y. Langmuir 2013, 29, 4477. doi: 10.1021/la4003252
12. [12]
  Elmes, R. B. P.; Jolliffe, K. A. Chem. Commun. 2015, 51, 4951. doi: 10.1039/C4CC10095F
13. [13]
  Prasad, C. Peptides 1995, 16, 151. doi: 10.1016/0196-9781(94)00017-Z
14. [14]
  Benedetti, E.; Corradini, P.; Pedone, C. J. Phys. Chem. 1969, 73, 2891. doi: 10.1021/j100843a018
15. [15]
  Corey, R. B. J. Am. Chem. Soc. 1938, 60, 1598. doi: 10.1021/ja01274a023
16. [16]
  Manchineella, S.; Govindaraju, T. ChemPlusChem 2017, 82, 88. doi: 10.1002/cplu.201600450
17. [17]
  Govindaraju, T. Supramol. Chem. 2011, 23, 759. doi: 10.1080/10610278.2011.628393
18. [18]
  Govindaraju, T.; Pandeeswar, M.; Jayaramulu, K.; Jaipuria, G.; Atreya, H. S. Supramol. Chem. 2011, 23, 487. doi: 10.1080/10610278.2010.550685
19. [19]
  Palmore, G. T. R.; Luo, T. J. M.; McBride-Wieser, M. T.; Picciotto, E. A.; Reynoso-Paz, C. M. Chem. Mater. 1999, 11, 3315. doi: 10.1021/cm990400p
20. [20]
  Di Blasio, B.; Pavone, V.; Nastri, F.; Isernia, C.; Saviano, M.; Pedone, C.; Cucinotta, V.; Impellizzeri, G.; Rizzarelli, E.; Vecchio, G. Natl. Acad. Sci. U. S. A. 1992, 89, 7218. doi: 10.1073/pnas.89.15.7218
21. [21]
  Bergeron, R. J.; Phanstiel IV, O.; Yao, G. W.; Milstein, S.; Weimar, W. R. J. Am. Chem. Soc. 1994, 116, 8479. doi: 10.1021/ja00098a007
22. [22]
  Bellezza, I.; Peirce, M. J.; Minelli, A. Trends Mol. Med. 2014, 20, 551. doi: 10.1016/j.molmed.2014.08.003
23. [23]
  González, O.; Ortíz-Castro, R.; Díaz-Pérez, C.; Díaz-Pérez, A. L.; Magaña-Dueñas, V.; López-Bucio, J.; Campos-García, J. Microb. Ecol. 2017, 73, 616. doi: 10.1007/s00248-016-0896-4
24. [24]
  Nishanth Kumar, S.; Dileep, C.; Mohandas, C.; Nambisan, B.; Ca, J. J. Pept. Sci. 2014, 20, 173. doi: 10.1002/psc.2594
25. [25]
  Van der Merwe, E.; Huang, D.; Peterson, D.; Kilian, G.; Milne, P. J.; Van de Venter, M.; Frost, C. Peptides 2008, 29, 1305. doi: 10.1016/j.peptides.2008.03.010
26. [26]
  Yang, M.; Yuan, C.; Shen, G.; Chang, R.; Xing, R.; Yan, X. J. Colloid Interface Sci. 2019, 557, 458. doi: 10.1016/j.jcis.2019.09.049
27. [27]
  Tao, K.; Makam, P.; Aizen, R.; Gazit, E. Science 2017, 358, 9756. doi: 10.1126/science.aam9756
28. [28]
  Tao, K.; Fan, Z.; Sun, L.; Makam, P.; Tian, Z.; Ruegsegger, M.; Shaham-Niv, S.; Hansford, D.; Aizen, R.; Pan, Z.; Galster, S.; Ma, J.-J.; Yan, F.; Si, M.-S.; Qu, S.-N.; Zhang, M.-J.; Gazit, E.; Li, J.-B. Nat. Commun. 2018, 9, 3217. doi: 10.1038/s41467-018-05568-9
29. [29]
  Seo, M. J.; Song, J.; Kantha, C.; Khazi, M. I.; Kundapur, U.; Heo, J. M.; Kim, J. M. Langmuir 2018, 34, 8365. doi: 10.1021/acs.langmuir.8b00743
30. [30]
  Yang, M.; Xing, R.; Shen, G.; Yuan, C.; Yan, X. Colloids Surf., A 2019, 572, 259. doi: 10.1016/j.colsurfa.2019.04.020
31. [31]
  Zong, Q.-Y.; Geng, H.-M.; Wang, L.; Ye, L.; Zhang, A.-Y.; Shao, Z.-Q.; Feng, Z.-G. Acta Chim. Sinica 2015, 73, 423 (in Chinese).
32. [32]
  Tucker, M. J.; Oyola, R.; Gai, F. Biopolymers 2006, 83, 571. doi: 10.1002/bip.20587
33. [33]
  Fan, Z.; Sun, L.; Huang, Y.; Wang, Y.; Zhang, M. Nat. Nanotechnol. 2016, 11, 388. doi: 10.1038/nnano.2015.312
34. [34]
  Wang, C.; Zhang, L.; Yang, J.; Yang, J.; Wang, D.; Sun, Y.; Wang, J. Appl. Surf. Sci. 2018, 453, 173. doi: 10.1016/j.apsusc.2018.04.240
35. [35]
  Wang, J.; Zhang, L.; Yang, J.; Yan, H.; Li, X.; Wang, C.; Wang, D.; Sun, Y.; Xu, H. Langmuir 2019, 35, 5617. doi: 10.1021/acs.langmuir.9b00265
36. [36]
  Zou, R.; Wang, Q.; Wu, J.; Schmuck, C.; Tian, H. Chem. Soc. Rev. 2015, 44, 5200. doi: 10.1039/C5CS00234F
37. [37]
  Faller, P.; Hureau, C.; Berthoumieu, O. Inorg. Chem. 2013, 52, 12193. doi: 10.1021/ic4003059
38. [38]
  Ren, X.; Zou, Q.; Yuan, C.; Chang, R.; Xing, R.; Yan, X. Angew. Chem., Int. Ed. 2019, 58, 5872. doi: 10.1002/anie.201814575
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