Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

被引:32
作者
Appel, Ralph [1 ,2 ]
Tacke, Sebastian [3 ]
Klingauf, Juergen [3 ]
Besenius, Pol [1 ,2 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
[2] Ctr Nanotechnol CeNTech, D-48149 Munster, Germany
[3] Univ Munster, Inst Med Phys & Biophys, Dept Cellular Biophys, D-48149 Munster, Germany
关键词
AMINO-ACIDS; SUPRAMOLECULAR POLYMER; DISCOTIC AMPHIPHILES; GOLD NANOPARTICLES; DESIGN; GROWTH; VIRUS; WATER; HYDROGELATORS; AGGREGATION;
D O I
10.1039/c4ob02185a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the synthesis of a series of anionic dendritic peptide amphiphiles of increasing hydrophobic character. By establishing state diagrams we describe their pH and ionic strength triggered self-assembly into supramolecular nanorods in water and highlight the impact of hydrophobic shielding in the supramolecular polymerisation process. Via the incorporation of fluorinated peptide side chains the pH-triggered monomer to polymer transition at physiological ionic strength is shifted from pH 5.0 to pH 7.4. We thereby show that compensating attractive non-covalent interactions and hydrophobic effects with repulsive electrostatic forces, a concept we refer to as frustrated growth, is a sensitive tool in order to manipulate one-dimensional supramolecular polymerisation processes in water.
引用
收藏
页码:1030 / 1039
页数:10
相关论文
共 100 条
[1]   A new method for maintaining homogeneity during liquid-hydrogel transitions using low molecular weight hydrogelators [J].
Adams, Dave J. ;
Butler, Michael F. ;
Frith, William J. ;
Kirkland, Mark ;
Mullen, Leanne ;
Sanderson, Paul .
SOFT MATTER, 2009, 5 (09) :1856-1862
[2]   STUDIES ON ASSEMBLY OF A SPHERICAL PLANT VIRUS .1. STATES OF AGGREGATION OF ISOLATED PROTEIN [J].
ADOLPH, KW ;
BUTLER, PJG .
JOURNAL OF MOLECULAR BIOLOGY, 1974, 88 (02) :327-&
[3]   The Synthesis of Dendritic EDOT-Peptide Conjugates and their Multistimuli-Responsive Self-Assembly into Supramolecular Nanorods and Fibers in Water [J].
Ahlers, Patrick ;
Frisch, Hendrik ;
Spitzer, Daniel ;
Vobecka, Zuzana ;
Vilela, Filipe ;
Besenius, Pol .
CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (08) :2052-2057
[4]   Functional Supramolecular Polymers [J].
Aida, T. ;
Meijer, E. W. ;
Stupp, S. I. .
SCIENCE, 2012, 335 (6070) :813-817
[5]   Fine structure analysis of a protein folding transition state; distinguishing between hydrophobic stabilization and specific packing [J].
Anil, B ;
Sato, S ;
Cho, JH ;
Raleigh, DP .
JOURNAL OF MOLECULAR BIOLOGY, 2005, 354 (03) :693-705
[6]   Control over Self-Assembly through Reversible Charging of the Aromatic Building Blocks in Photofunctional Supramolecular Fibers [J].
Baram, Jonathan ;
Shirman, Elijah ;
Ben-Shitrit, Netanel ;
Ustinov, Alona ;
Weissman, Haim ;
Pinkas, Iddo ;
Wolf, Sharon G. ;
Rybtchinski, Boris .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14966-+
[7]   A Fast pH-Switchable and Self-Healing Supramolecular Hydrogel Carrier for Guided, Local Catheter Injection in the Infarcted Myocardium [J].
Bastings, Maartje M. C. ;
Koudstaal, Stefan ;
Kieltyka, Roxanne E. ;
Nakano, Yoko ;
Pape, A. C. H. ;
Feyen, Dries A. M. ;
van Slochteren, Frebus J. ;
Doevendans, Pieter A. ;
Sluijter, Joost P. G. ;
Meijer, E. W. ;
Chamuleau, Steven A. J. ;
Dankers, Patricia Y. W. .
ADVANCED HEALTHCARE MATERIALS, 2014, 3 (01) :70-78
[8]  
Baumeister B, 2002, HELV CHIM ACTA, V85, P2740, DOI 10.1002/1522-2675(200209)85:9<2740::AID-HLCA2740>3.0.CO
[9]  
2-C
[10]   Peptide functionalised discotic amphiphiles and their self-assembly into supramolecular nanofibres [J].
Besenius, P. ;
Goedegebure, Y. ;
Driesse, M. ;
Koay, M. ;
Bomans, P. H. H. ;
Palmans, A. R. A. ;
Dankers, P. Y. W. ;
Meijer, E. W. .
SOFT MATTER, 2011, 7 (18) :7980-7983