Nanofiber formation of amphiphilic cyclic tri-β-peptide

Journal of Peptide Science

Volumn 16, Issue 2, 2010, Pages 110-114

  Ishihara, Yusuke ^a   Kimura, Shunsaku ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

amino acid; Amphiphilic peptide; Cyclic peptide; Nanofiber; Self assembly

Indexed keywords

AMINE; AMPHOPHILE; CARBOXYLIC ACID DERIVATIVE; CYCLOPEPTIDE; FORMIC ACID; NANOFIBER; TRIPEPTIDE DERIVATIVE; WATER;

ARTICLE; HYDROGEN BOND; MOLECULAR DYNAMICS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ASSEMBLY;

MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; NANOFIBERS; PEPTIDES, CYCLIC; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 74749097284     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1206     Document Type: Article

References (41)

1. Niu Z, Bruckman MA, Li S, Lee LA, Lee B, Pingali SV, Thiyagarajan P, Wang Q. Assembly of tobacco mosaic virus into fibrous and macroscopic bundled arrays mediated by surface aniline polymerization. Langmuire 2007; 23: 6719-6724.
2. Horne WS, Ashkenasy N, Ghadiri MR. Modulating charge transfer through cyclic D, L-α-peptide self-assembly. Chem. Eur. J. 2005; 11: 1137-1144.
3. Steinem C, Janshoff A, Vollmer MS, Ghadiri MR. Reversible photoisomerization of self-organized cylindrical peptide assemblies at air-water and solid interfaces. Langmuir 1999; 15: 3956-3964.
4. Dzenls Y. Spinning contaneous fibers for nanotechnology. Science 2004; 304: 1917-1919.
5. Lopez SF, Kim H, Choi EC, Delgado M, Granja JR, Khasanov A, Kraehenbuehl K, Weinberger DA, Wilcoxen KM, Ghadiri MR. Antibacterial agents based on the cyclic {D, L}-α-peptide architecture. nature 2001; 412: 452-455.
6. Zhang Y, Lim CT, Ramakrishna S, Huang ZM. Recent development of polymer nanofibers for biomedical and biotechnological applications. J.Mater. Sci. 2005; 16: 933-946.
7. Zhang S. Fabrication of novel biomaterials through molecular self assembly. Nat. Biotechnol. 2003; 21: 1171-1178.
8. Silva GA, Czeisler C, Niece KL, Beniash E, Harrington DA, Kessler JA, Stupp SI. Selective differentiation of neural progenitor cells by high epitope density nanofibers. Science 2004; 303: 1352-1355.
9. Ryadnov MG, Woolfson DN. Engineering the morphology of a self assembling protein fibre. Nat. Mater. 2003; 2: 329-332.
10. Zhao Y, Yokoi H, Tanaka M, Kinoshita T, Tan T. Self-assembled pH-responsive hydrogels composed of the RATEA16 peptide. Biomacromolecules 2008; 9: 1511-1518.
11. Murasato K, Matsuura K, Kimizuka N. Self-assembly of nanofiber with uniform width from wheel-type trigonal- beta-sheet-forming peptide. Biomacromolecules 2008; 9: 913-918.
12. Yang Y, Khoe U, Wang X, Horii A, Yokoi H, Zhang S. Designer self assembling peptide nanomaterials. Nano Today 2009; 4: 193-210.
13. Yang H, Fung S, Pritzker M, Chen P. Surface-assisted assembly of an ionic-complementary peptide: controllable growth of nanofibers. J. Am. Chem. Soc. 2007; 129: 12200-12210.
14. Lim Y,Moon K, Lee M. Recent advances in functional supramolecular nanostructuresassembledfrombioactive buildingblocks.Chem.Soc. Rev. 2009; 38: 925-934.
15. Zhao X, Zhang S. Designer self-assembling peptide materials. Macromol. Biosci. 2007; 7: 13-22.
16. Qiu F, Chen Y, Zhao X. Comparative studies on the self-assembling behaviors of cationic and catanionic surfactant-like peptides. J. Colloid and Interface Sci. 2009; 336: 477-484.
17. Marini DM, Hwang W, Lauffenburger DA, Zhang S, Kamm RD. Lefthandedhelical ribbonintermediates in the self-assembly of a β-sheet peptide. Nano lett 2002; 2: 295-299.
18. Aggeli A, Nyrkova IA, Bell M, Harding R, Carrick L, McLeish TCB, Semenov AN, Boden N. Hierarchical self-assembly of chiral rod-like molecules as a model for peptide β-sheet tapes, ribbons, fibrils, and fibers. Proc. Natl. Acad. Sci. 2001; 98: 11857-11862.
19. Aggeli A, Bell M, Boden N, Keen JN, Knowles PF, McLeish TCB, Pitkeathly M, Radford SE. Responsive gels formed by the spontaneous self-assembly of peptides into polymeric β-sheet tapes. Nature 1997; 386: 259-262.
20. Hartgerink JD, Beniash E, Stupp SI. Self-assembly andmineralization of peptide-amphiphile nanofibers. Science 2001; 294: 1684-1688.
21. Clark TD, Buriak JM, Kobayashi K, Isler MP, McRee DE, Ghadiri MR. Cylindrical β-sheet peptide assemblies. J. Am. Chem. Soc. 1998; 120: 8949-8962.
22. Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N. Self assembling organic nanotubes based on a cyclic peptide architecture. Nature 1993; 366: 324-327.
23. Horne WS, Stout CD, Ghadiri MR. A heterocyclic peptide nanotube. J. Am. Chem. Soc. 2003; 125: 9372-9376.
24. Rapaport H, Kim HS, Kjaer K, Howes PB, Cohen S, Nielsen JA, Ghadiri MR, Leiserowitz L, Lahav M. Crystalline cyclic peptide nanotubes at interfaces. J. Am. Chem. Soc. 1999; 121: 1186-1191.
25. Hartgerink JD, Granja JR, Milligan RA, Ghadiri MR. Self-assembling peptide nanotubes. J. Am. Chem. Soc. 1996; 118: 43-50.
26. Seebach D, Matthews JL, Meden A, Wessels T, Baerlocher C, McCusker LB. Cyclo-beta- peptides: structure and tubular stacking of cyclic tetramers of 3-aminobutanoic acid as determined from powder diffraction data. Helv. Chim. Acta. 1997; 80: 173-182.
27. Clark TD, Buehler LK, Ghadiri MR. Self-assembling cyclic β-peptide nanotubes as artificial transmmembrane ion channels. J. Am. Chem. Soc. 1998; 120: 651-656.
28. Hartgerink JD,Clark TD,Ghadiri MR. Peptide nanotubes and beyond. Chem. Eur. J. 1998; 4: 1367-1372.
29. Fujimura F, Hirata T, Horikawa Y, Sugiyama J, Morita T, Kimura S. Columnar assembly of cyclic β-amino acid functionalized with pyranose rings. Biomacromolecules 2006; 7: 2394-2400.
30. Fujimura F, Hirata T, Kimura S. Construction of nanotubes and their bundles from cyclic β-peptide. Pept. Sci. 2006; 360-360.
31. Wang C, Stewart RJ, KopeŠek J. Hybrid hydrogels assembled from synthetic polymers and coiled-coil protein domains. Nature 1999; 397: 417-420.
32. PetkaWA, Harden JL, McGrath KP, Wirtz D, Tirrell DA. Reversible hydrogels from self-assembling artificial proteins. Science 1998; 281: 389-392.
33. Zimenkov Y, Conticello VP, Guob L, Thiyagarajan P. Rational design of ananoscale helical scaffold derived from self-assembly of adimeric coiled coil motif. Tetrahedron 2004; 60: 7237-7246.
34. Paramonov SE, Jun HW, Hartgerink JD. Self-assembly of peptide amphiphile nanofibers: the roles of hydrogen bonding and amphiphilic packing. J. Am. Chem. Soc. 2006; 128: 7291-7298.
35. Nowak AP, Breedveld V, Pakstis L, Ozbas B, Pine DJ, Pochan D, Deming TJ. Rapidly recovering hydrogel scaffolds from self assembling diblock copolypeptide amphiphiles. Nature 2002; 417: 424-428.
36. Fujimura F, Fukuda M, Sugiyama J, Morita T, Kimura S. Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide. Org. Biomol. Chem. 2006; 4: 1896-1901.
37. Suhara Y, Hildreth JEK, Ichikawa Y. Synthesis of a new carbohydrate mimettics: "carbopeptide" containing A C-1 carboxylate and C-2 amono group. Tetrahedron Lett. 1996; 37: 1575-1578.
38. Fujimura F, Horikawa Y, Sugiyama J, Morita T, Kimura S. Double assembly composed of lectin association with columnar molecular assembly of cyclic tri-β-peptide having sugar units. Biomacromolecules 2007; 8: 611-616.
39. Krimm S, Bandekar J. in Adv. Protein Chem. (Eds: Anifinsen CB, Edsall JT, Richards FM) Academic Press: Orlando, 1986; pp 181-364.
40. Kanzaki T, Horikawa Y, Makino A, Sugiyama J, Kimura S. Nanotube and three-way nanotube formation with nonionic amphiphilic block peptides.Macromol. Biosci. 2008; 8: 1026-1033.
41. Kimura S. Molecular dipole engineering: New aspects of molecular dipoles in molecular architecture and their fuctions. Org. Biomol. Chem. 2008; 6: 1143-1148.