Effects of fluoro substitutions and electrostatic interactions on the self-assembled structures and hydrogelation of tripeptides: tuning the mechanical properties of co-assembled hydrogels.

Soft Matter
Abdelreheem Abdelfatah SaddikHsin-Chieh Lin

Abstract

A series of FFK tripeptides capped with phenylacetic acid of various fluoro-substitutions at the N-terminus has been synthesized and examined for self-assembly under aqueous conditions. The material properties of the FFK tripeptides dramatically changed from precipitate to hydrogel phase upon increasing the number of fluorine atoms. Peptides linked with benzyl (B-FFK) or monofluoro-benzyl (MFB-FFK) groups rapidly form solid precipitates under physiological pH conditions. The trifluoro-decorated compound (TFB-FFK) self-assembled into a metastable hydrogel which slowly transformed into a solid precipitate upon standing. A stable hydrogel formation was noticed in the case of the pentafluorobenzyl-diphenylalanyllysine (PFB-FFK) compound. TEM analysis indicates that the PFB-FFK peptide assembled into twisted nanofibril structures, which are predominantly stabilized by strong quadrupole π-stacking interactions and electrostatic interactions of amino acid side chains. Furthermore, the combination of PFB-FFK and PFB-FFD peptides was also investigated for hydrogelation and the self-assembly of such systems resulted in the formation of untwisted 1D nanofibril structures. Supramolecular coassembled hydrogels of variable stiffness have als...Continue Reading

References

Dec 22, 1999·Progress in Biophysics and Molecular Biology·J L Arrondo, F M Goñi
Oct 11, 2001·Proceedings of the National Academy of Sciences of the United States of America·A AggeliN Boden
Nov 27, 2001·Science·J D HartgerinkS I Stupp
Mar 20, 2003·Angewandte Chemie·Emmanuel A MeyerFrançois Diederich
Jan 12, 2005·Chemical Society Reviews·Katharina ReichenbächerJurg Hulliger
Jul 21, 2005·Bioconjugate Chemistry·Sumit S MahajanWilliam M Atkins
Aug 10, 2007·Acta Biochimica Et Biophysica Sinica·Jilie Kong, Shaoning Yu
Sep 27, 2007·Journal of the American Chemical Society·He DongJeffrey D Hartgerink
Mar 26, 2008·Chemical Society Reviews·Rein V Ulijn, Andrew M Smith
Jun 23, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Claire TangAlberto Saiani
Apr 28, 2010·Chemical Society Reviews·Congqi Yan, Darrin J Pochan
Mar 16, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Derek M RyanBradley L Nilsson
Sep 29, 2011·Angewandte Chemie·Xinming LiBing Xu
Jun 23, 2012·Accounts of Chemical Research·Shuguang Zhang
Sep 27, 2012·Biophysical Journal·Rustem I LitvinovJohn W Weisel
Jan 1, 2014·ACS Applied Materials & Interfaces·Chunqiu ZhangXing-Jie Liang
Oct 31, 2014·Chemical Communications : Chem Comm·Adam D MartinPall Thordarson
Dec 6, 2014·Chemical Communications : Chem Comm·Jaclyn Raeburn, Dave J Adams
Dec 31, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Wathsala Liyanage, Bradley L Nilsson
Apr 19, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Mohamed ElsawyAlberto Saiani
Aug 5, 2016·Chemical Society Reviews·Juan WangXuehai Yan
Jan 10, 2017·Biomacromolecules·Jie GaoAlberto Saiani
Feb 14, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Emily R DraperDave J Adams
Apr 14, 2018·ACS Applied Materials & Interfaces·Satish Kumar TallojHsin-Chieh Lin
Nov 21, 2018·Journal of Biomedical Materials Research. Part a·Alessandra ScelsiAntonietta Pepe
Jul 14, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Fangyi ZhaoZhengzhong Shao

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Citations

Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marco Scarel, Silvia Marchesan

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Methods Mentioned

BETA
NMR
circular dichroism
X-ray

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