Aromatic-aromatic interactions induce the self-assembly of pentapeptidic derivatives in water to form nanofibers and supramolecular hydrogels

Journal of the American Chemical Society
Manlung MaBing Xu

Abstract

In this paper we report the conjugation of an aromatic moiety (pyrene (P), fluorene (F), or naphthalene (N)) to pentapeptides GAGAS (1), GVPVP (2), VPGVG (3), VTEEI (4), VYGGG (5), and YGFGG (6) to afford peptidic derivatives for exploring pentapeptide-based hydrogels as potential biomaterials. Most of these compounds (1F, 1P, 2F, 2P, 4F, 4P, 4N, 5F, 5N, 6F, 6P, and 6N) behave as molecular hydrogelators and can form hydrogels at minimum concentrations of gelation from 0.5 to 2.8 wt %. The fluorescence spectra of the hydrogels exhibit a significant red shift, indicating the interactions between the aromatic moieties in those hydrogels. The circular dichroism spectra indicate that the self-assembly of the hydrogelators affords helical or beta-sheet-like structures. Transmission and scanning electron microscopic examination reveals the nanofiber networks of these hydrogelators. In addition, rheological measurements show fair to excellent viscoelastic properties of these hydrogels. The balance of intermolecular aromatic-aromatic interactions and hydrogen bonds of these hydrogelators leads to their self-assembly in water and the formation of nanofibers as the matrixes of hydrogels. A total of 6 of these 18 pentapeptide derivatives--...Continue Reading

References

Jan 1, 1978·Annual Review of Biochemistry·P Y Chou, G D Fasman
Sep 28, 1990·Science·R Langer
Jan 1, 1972·Biopolymers·V Madison, J Schellman
May 14, 1993·Science·R Langer, J P Vacanti
May 9, 2000·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·V JenningS H Gohla
Jun 7, 2000·Proceedings of the National Academy of Sciences of the United States of America·T C HolmesS Zhang
Jan 12, 2001·Journal of Molecular Biology·B LiV Daggett
Feb 13, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·K BurgessH U Saragovi
Nov 17, 2001·Chemical Reviews·K Y Lee, D J Mooney
Nov 27, 2001·Science·J D HartgerinkS I Stupp
Jan 5, 2002·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Ehud Gazit
Aug 5, 1997·Chemical Reviews·Brian Linton, Andrew D. Hamilton
Feb 20, 2002·Chemical Reviews·Pierre Terech, Richard G. Weiss
Apr 4, 2002·Proceedings of the National Academy of Sciences of the United States of America·Sylvain VautheyShuguang Zhang
Apr 4, 2002·Proceedings of the National Academy of Sciences of the United States of America·Jeffrey D HartgerinkSamuel I Stupp
Sep 13, 2002·Journal of the American Chemical Society·Shigeki KiyonakaItaru Hamachi
Apr 26, 2003·Science·Meital Reches, Ehud Gazit
Aug 22, 2003·Proceedings of the National Academy of Sciences of the United States of America·Céline ValéryFranck Artzner
Oct 2, 2003·Nature Biotechnology·Shuguang Zhang
Nov 6, 2003·Journal of the American Chemical Society·Yan ZhangBing Xu
Nov 20, 2003·Journal of the American Chemical Society·Bi-Huang Hu, Phillip B Messersmith
Mar 11, 2004·Chemical Reviews·Lara A Estroff, Andrew D Hamilton
Aug 18, 2004·Current Opinion in Structural Biology·Karthikan Rajagopal, Joel P Schneider
Jan 18, 2005·Journal of Controlled Release : Official Journal of the Controlled Release Society·R Herrero-VanrellJ C Rodríguez-Cabello
Jan 27, 2005·Journal of the American Chemical Society·Heather A BehannaSamuel I Stupp
May 19, 2005·Journal of the American Chemical Society·John D TovarSamuel I Stupp
Sep 15, 2005·Journal of Controlled Release : Official Journal of the Controlled Release Society·Iqbal MassodiDrazen Raucher
Sep 21, 2005·Chemical Society Reviews·Neralagatta M Sangeetha, Uday Maitra
Dec 1, 2005·Journal of the American Chemical Society·Lisa A HainesJoel P Schneider
Jan 26, 2006·Journal of the American Chemical Society·Sophie ToledanoRein V Ulijn
Feb 9, 2006·Chemical Communications : Chem Comm·Zhimou YangBing Xu

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Citations

Jul 9, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Ye ZhangBing Xu
Aug 6, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Derek M RyanBradley L Nilsson
Oct 15, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Claire TangAlberto Saiani
Oct 1, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Maria L Muro-SmallAnne J McNeil
Oct 8, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Junfeng ShiBing Xu
Apr 28, 2011·Chemical Communications : Chem Comm·Weiping Wang, Ying Chau
Jun 28, 2011·Chemical Communications : Chem Comm·Yi KuangBing Xu
Apr 28, 2012·Chemical Communications : Chem Comm·Steven C BremmerMatthew B Soellner
Mar 31, 2011·Beilstein Journal of Organic Chemistry·Junfeng ShiBing Xu
Nov 5, 2013·Antioxidants & Redox Signaling·Jianwu ZhangZhimou Yang
Mar 14, 2013·Biomacromolecules·Erica L BakotaJeffrey D Hartgerink
Feb 5, 2016·ACS Applied Materials & Interfaces·Wei JiChuanliang Feng
Jan 14, 2016·Journal of Molecular Modeling·Dušan N SredojevićSnežana D Zarić
Jan 16, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·S BartocciM Mba
May 21, 2015·Colloids and Surfaces. B, Biointerfaces·Steven KirkhamJanne Ruokolainen
Jan 15, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Nitin Chaudhary, Ramakrishnan Nagaraj
Sep 4, 2015·ACS Applied Materials & Interfaces·Xiao-Qiu DouChuanliang Feng
Jul 9, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Shuwei LinYonggang Yang
Jan 24, 2017·Advanced Materials·Xiao-Qiu Dou, Chuan-Liang Feng
Sep 10, 2014·Chemical Society Reviews·Scott Fleming, Rein V Ulijn
Feb 25, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Akash Saini, Virander S Chauhan
Feb 28, 2014·Advanced Healthcare Materials·Yi KuangBing Xu
Oct 16, 2015·Chemical Communications : Chem Comm·Raoul PeltierHongyan Sun
Sep 29, 2015·Chemical Communications : Chem Comm·Bridget MiloreyReinhard Schweitzer-Stenner
Dec 15, 2016·Chemical Communications : Chem Comm·Yajun YinWenying Zhong
May 20, 2015·Chemical Communications : Chem Comm·Hai Qian, Ivan Aprahamian
Sep 5, 2015·Chemical Communications : Chem Comm·Ying ZhouWenying Zhong
Oct 13, 2015·Organic & Biomolecular Chemistry·Wei WangYan Zhang
May 3, 2016·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Dan YuanBing Xu
Jul 29, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Meryem Hatip KocMustafa O Guler
Jul 18, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Rajkumar MisraHosahudya N Gopi

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