Citation: Liu Xin, Wang Kaiya, Externbrink Marlen, Niemeyer Jochen, Giese Michael, Hu Xiao-Yu. Control of secondary structure and morphology of peptide-guanidiniocarbonylpyrrole conjugates by variation of the chain length^☆[J]. Chinese Chemical Letters, ;2020, 31(5): 1239-1242. doi: 10.1016/j.cclet.2019.10.036 shu

Control of secondary structure and morphology of peptide-guanidiniocarbonylpyrrole conjugates by variation of the chain length^☆

a.
School of Material Science&Engineering, Nanjing University of Aeronautics&Astronautics, Nanjing 210016, China
b.
Qinghai Provincial Key Laboratory of Tibetan Medicine Research and Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, China
c.
Institute for Organic Chemistry, University of Duisburg-Essen, Essen 45117, Germany
d.
College of Pharmacy, Nantong University, Nantong 226001, China

^☆

huxy@nuaa.edu.cn

huxy@nju.edu.cn

Received Date: 23 September 2019
Revised Date: 16 October 2019
Accepted Date: 28 October 2019
Available Online: 2 November 2019

Figures(7)

Peptide amphiphiles with well-organized secondary structure are an important family of molecules that are known to assemble into a variety of nanostructures. In this work, we present three guanidiniocarbonylpyrrole (GCP) containing peptide amphiphiles, which show versatile morphology and secondary structure changes as a result of different chain lengths and in different concentration regimes. The random coil conformation, α-helix, and β-sheet are obtained for peptide 1, peptide 2, and peptide 3, respectively under neutral aqueous conditions. Furthermore, all peptide amphiphiles can aggregate to form nanoparticles at low concentrations. However, at high concentrations, peptide 1 selfassembles into left-handed twisted helical fibers, while longer bamboo-like morphology can be observed exclusively for peptide 2. For peptide 3, freshly prepared samples show uniform spherical morphology, whereas an obvious morphological transition from original nanoparticles to disordered fibers was realized after incubating for one week. These fascinating morphology changes were determined by the combination of circular dichroism, dynamic light scattering, transmission electron microscopy, atomic force microscopy, and theoretical calculations.
- Peptide amphiphiles,
- Secondary structures,
- Supramolecular self-assembly,
- Nanostructures,
- pH-responsiveness
1. [1]
  A.L. Boyle, D.N. Woolfson, Chem. Soc. Rev. 40(2011) 4295-4306. doi: 10.1039/c0cs00152j
2. [2]
  H. Acar, S. Srivastava, E.J. Chung, et al., Adv. Drug Deliv. Rev. 110(2017) 65-79.
3. [3]
  Y. Xu, M. Tian, H. Zhang, et al., Chin. Chem. Lett. 29(2018) 1093-1097. doi: 10.1016/j.cclet.2018.03.032
4. [4]
  Y. Sun, A. Zhan, S. Zhou, et al., Chin. Chem. Lett. 30(2019) 1435-1439. doi: 10.1016/j.cclet.2019.05.001
5. [5]
  D. Mandal, A.N. Shirazi, K. Parang, Org. Biomol. Chem. 12(2014) 3544-3561. doi: 10.1039/C4OB00447G
6. [6]
  M.T. Jeena, L. Palanikumar, E. Min Go, et al., Nat. Commun. 8(2017) 26. doi: 10.1038/s41467-017-00047-z
7. [7]
  I.W. Hamley, Chem. Rev. 112(2012) 5147-5192. doi: 10.1021/cr3000994
8. [8]
  F. Chiti, C.M. Dobson, Annu. Rev. Biochem. 75(2006) 333-366. doi: 10.1146/annurev.biochem.75.101304.123901
9. [9]
  D.J. Selkoe, Nat. Cell Biol. 6(2004) 1054-1061. doi: 10.1038/ncb1104-1054
10. [10]
  G. Wei, Z. Su, N.P. Reynolds, et al., Chem. Soc. Rev. 46(2017) 466-4708.
11. [11]
  Y. Jiang, H. Long, Y. Zhu, Y. Zeng, Chin. Chem. Lett. 29(2018) 1067-1073. doi: 10.1016/j.cclet.2018.05.028
12. [12]
  C.J. Bruns, J.F. Stoddart, Nat. Nanotechnol. 8(2013) 9-10. doi: 10.1038/nnano.2012.239
13. [13]
  J.C. Stendahl, M.S. Rao, M.O. Guler, S.I. Stupp, Adv. Funct. Mater. 16(2006) 499-508. doi: 10.1002/adfm.200500161
14. [14]
  M.P. Hendricks, K. Sato, L.C. Palmer, S.I. Stupp, Acc. Chem. Res. 50(2017) 2440-2448. doi: 10.1021/acs.accounts.7b00297
15. [15]
  C. Schmuck, M. Schwegmann, J. Am. Chem. Soc. 127(2005) 3373-3379. doi: 10.1021/ja0433469
16. [16]
  J. Hatai, C. Schmuck, Acc. Chem. Res. 52(2019) 1709-1720. doi: 10.1021/acs.accounts.9b00142
17. [17]
  X.Y. Hu, M. Ehlers, T. Wang, et al., Chem. -Eur. J. 24(2018) 9754-9759. doi: 10.1002/chem.201801315
18. [18]
  M. Rad-Malekshahi, L. Lempsink, M. Amidi, W.E. Hennink, E. Mastrobattista, Bioconjug. Chem. 27(2016) 3-18. doi: 10.1021/acs.bioconjchem.5b00487
19. [19]
  C.J.C. Edwards-Gayle, I.W. Hamley, Org. Biomol. Chem. 15(2017) 5867-5976. doi: 10.1039/C7OB01092C
20. [20]
  C.A. Chantell, M.A. Onaiyekan, M. Menakuru, J. Pept. Sci. 18(2012) 88-91. doi: 10.1002/psc.1419
21. [21]
  S.M. Kelly, N.C. Price, Curr. Protein Pept. Sci. 1(2000) 349-384. doi: 10.2174/1389203003381315
22. [22]
  P. Jana, M. Ehlers, E. Zellermann, K. Samanta, C. Schmuck, Angew. Chem. Int. Ed. 55(2016) 15287-15291. doi: 10.1002/anie.201608069
23. [23]
  E. Yashima, N. Ousaka, D. Taura, et al., Chem. Rev. 116(2016) 13752-13990. doi: 10.1021/acs.chemrev.6b00354
24. [24]
  Y. Hu, R. Lin, P. Zhang, et al., ACS Nano 10(2016) 880-888. doi: 10.1021/acsnano.5b06011
25. [25]
  H. Cui, T. Muraoka, A.G. Cheetham, S.I. Stupp, Nano Lett. 9(2009) 945-951. doi: 10.1021/nl802813f
26. [26]
  S. Aravinda, N. Shamala, C. Das, et al., J. Am. Chem. Soc. 125(2003) 5308-5315. doi: 10.1021/ja0341283
27. [27]
  A. Perczel, Z. Gáspári, I.G. Csizmadia, J. Comput. Chem. 26(2005) 1155-1168. doi: 10.1002/jcc.20255
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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

Control of secondary structure and morphology of peptide-guanidiniocarbonylpyrrole conjugates by variation of the chain length☆

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通讯作者: 陈斌, bchen63@163.com

Control of secondary structure and morphology of peptide-guanidiniocarbonylpyrrole conjugates by variation of the chain length^☆