Self-assembly and application of diphenylalanine-based nanostructures.

Micro- and nanostructures fabricated from biological building blocks have attracted tremendous attention owing to their potential for application in biology and in nanotechnology. Many biomolecules, including peptides and proteins, can interact and self-assemble into highly ordered supramolecular architectures with functionality. By imitating the processes where biological peptides or proteins are assembled in nature, one can delicately design and synthesize various peptide building blocks composed of several to dozens of amino acids for the creation of biomimetic or bioinspired nanostructured materials. This tutorial review aims to introduce a new kind of peptide building block, the diphenylalanine motif, extracted with inspiration of a pathogenic process towards molecular self-assembly. We highlight recent and current advances in fabrication and application of diphenylalanine-based peptide nanomaterials. We also highlight the preparation of such peptide-based nanostructures as nanotubes, spherical vesicles, nanofibrils, nanowires and hybrids through self-assembly, the improvement of their properties and the extension of their applications.

[1]  J. Fei,et al.  Self‐Assembly of Peptide‐Inorganic Hybrid Spheres for Adaptive Encapsulation of Guests , 2010, Advanced materials.

[2]  Junbai Li,et al.  Solvent-induced structural transition of self-assembled dipeptide: from organogels to microcrystals. , 2010, Chemistry.

[3]  Chan Beum Park,et al.  Synthesis of diphenylalanine/polyaniline core/shell conducting nanowires by peptide self-assembly. , 2009, Angewandte Chemie.

[4]  S. Kim,et al.  Highly entangled hollow TiO2nanoribbons templating diphenylalanine assembly , 2009 .

[5]  Mi Zhou,et al.  Self-assembled peptide-based hydrogels as scaffolds for anchorage-dependent cells. , 2009, Biomaterials.

[6]  Chan Beum Park,et al.  Photoluminescent Peptide Nanotubes , 2009 .

[7]  Joanna Aizenberg,et al.  Biological and Biomimetic Materials , 2009 .

[8]  Z. Ou-Yang,et al.  Concentration-induced shape transition of nano-aggregates in solution , 2008 .

[9]  Samuel I Stupp,et al.  Biomimetic systems for hydroxyapatite mineralization inspired by bone and enamel. , 2008, Chemical reviews.

[10]  Chan Beum Park,et al.  High‐Temperature Self‐Assembly of Peptides into Vertically Well‐Aligned Nanowires by Aniline Vapor , 2008 .

[11]  Junbai Li,et al.  Self-assembly of peptide-based colloids containing lipophilic nanocrystals. , 2008, Small.

[12]  Qiang He,et al.  Microcapsules Containing a Biomolecular Motor for ATP Biosynthesis , 2008 .

[13]  Qiang He,et al.  Reversible transitions between peptide nanotubes and vesicle-like structures including theoretical modeling studies. , 2008, Chemistry.

[14]  Chan Beum Park,et al.  Solid-Phase Growth of Nanostructures from Amorphous Peptide Thin Film: Effect of Water Activity and Temperature , 2008 .

[15]  E. Gazit,et al.  Amyloids: not only pathological agents but also ordered nanomaterials. , 2008, Angewandte Chemie.

[16]  A. Ajayaghosh,et al.  Organogels as scaffolds for excitation energy transfer and light harvesting. , 2008, Chemical Society reviews.

[17]  E. Kumacheva,et al.  Patterning surfaces with functional polymers. , 2008, Nature materials.

[18]  Andrew M. Smith,et al.  Designing peptide based nanomaterials. , 2008, Chemical Society reviews.

[19]  L. Adler-Abramovich,et al.  Controlled patterning of peptide nanotubes and nanospheres using inkjet printing technology , 2008, Journal of peptide science : an official publication of the European Peptide Society.

[20]  Bing Xu,et al.  Enzymatic hydrogelation of small molecules. , 2008, Accounts of chemical research.

[21]  Junbai Li,et al.  Organogels Based on Self-Assembly of Diphenylalanine Peptide and Their Application To Immobilize Quantum Dots , 2008 .

[22]  Rein V. Ulijn,et al.  Fmoc‐Diphenylalanine Self Assembles to a Hydrogel via a Novel Architecture Based on π–π Interlocked β‐Sheets , 2008 .

[23]  Katsuhiko Ariga,et al.  Challenges and breakthroughs in recent research on self-assembly , 2008, Science and technology of advanced materials.

[24]  E. Gazit,et al.  Alignment of Aromatic Peptide Tubes in Strong Magnetic Fields , 2007 .

[25]  Yeliang Wang,et al.  Ordering of dipeptide chains on Cu surfaces through 2D cocrystallization. , 2007, Journal of the American Chemical Society.

[26]  S. Kim,et al.  Liquid Crystalline Peptide Nanowires , 2007 .

[27]  Bing Xu,et al.  Intracellular hydrogelation of small molecules inhibits bacterial growth. , 2007, Angewandte Chemie.

[28]  Bing Xu,et al.  Intracellular Enzymatic Formation of Nanofibers Results in Hydrogelation and Regulated Cell Death , 2007 .

[29]  Junbai Li,et al.  Synthesis and in vitro behavior of multivalent cationic lipopeptide for DNA delivery and release in HeLa cells. , 2007, Bioconjugate chemistry.

[30]  Ehud Gazit,et al.  Self-assembled peptide nanostructures: the design of molecular building blocks and their technological utilization. , 2007, Chemical Society reviews.

[31]  A. De Vita,et al.  Tracking the chiral recognition of adsorbed dipeptides at the single-molecule level. , 2007, Angewandte Chemie.

[32]  S. Allen,et al.  Using the bending beam model to estimate the elasticity of diphenylalanine nanotubes. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[33]  Y. Rosenberg,et al.  Formation of Well‐Organized Self‐Assembled Films from Peptide Nanotubes , 2007 .

[34]  Qiang He,et al.  Transition of cationic dipeptide nanotubes into vesicles and oligonucleotide delivery. , 2007, Angewandte Chemie.

[35]  Carl Henrik Görbitz,et al.  Microporous organic materials from hydrophobic dipeptides. , 2007, Chemistry.

[36]  Bing Xu,et al.  Using β-lactamase to trigger supramolecular hydrogelation , 2007 .

[37]  Stephen Z. D. Cheng,et al.  Temperature-induced reversible morphological changes of polystyrene-block-poly(ethylene oxide) micelles in solution. , 2007, Journal of the American Chemical Society.

[38]  E. Gazit,et al.  Controlled patterning of aligned self-assembled peptide nanotubes , 2006, Nature nanotechnology.

[39]  Xiaojun Zhao,et al.  Molecular designer self-assembling peptides. , 2006, Chemical Society reviews.

[40]  Ehud Gazit,et al.  Fabrication of coaxial metal nanocables using a self-assembled peptide nanotube scaffold. , 2006, Nano letters.

[41]  Meital Reches,et al.  Rigid, Self‐Assembled Hydrogel Composed of a Modified Aromatic Dipeptide , 2006 .

[42]  Carl Henrik Görbitz,et al.  The structure of nanotubes formed by diphenylalanine, the core recognition motif of Alzheimer's beta-amyloid polypeptide. , 2006, Chemical communications.

[43]  L. Adler-Abramovich,et al.  Direct observation of the release of phenylalanine from diphenylalanine nanotubes. , 2006, Journal of the American Chemical Society.

[44]  A. Miller,et al.  Nanostructured Hydrogels for Three‐Dimensional Cell Culture Through Self‐Assembly of Fluorenylmethoxycarbonyl–Dipeptides , 2006 .

[45]  Bing Xu,et al.  Using a kinase/phosphatase switch to regulate a supramolecular hydrogel and forming the supramolecular hydrogel in vivo. , 2006, Journal of the American Chemical Society.

[46]  Rein V Ulijn,et al.  Enzyme-triggered self-assembly of peptide hydrogels via reversed hydrolysis. , 2006, Journal of the American Chemical Society.

[47]  J. Bünzli,et al.  Taking advantage of luminescent lanthanide ions. , 2005, Chemical Society reviews.

[48]  H. Matsui,et al.  Peptide‐Based Nanotubes and Their Applications in Bionanotechnology , 2005, Advanced materials.

[49]  Meital Reches,et al.  Peptide nanotube-modified electrodes for enzyme-biosensor applications. , 2005, Analytical chemistry.

[50]  David Barlam,et al.  Self-assembled peptide nanotubes are uniquely rigid bioinspired supramolecular structures. , 2005, Nano letters.

[51]  Clément Sanchez,et al.  Biomimetism and bioinspiration as tools for the design of innovative materials and systems , 2005, Nature materials.

[52]  Sivakumar R. Challa,et al.  Synthesis of peptide-nanotube platinum-nanoparticle composites. , 2004, Chemical communications.

[53]  Meital Reches,et al.  Formation of Closed-Cage Nanostructures by Self-Assembly of Aromatic Dipeptides , 2004 .

[54]  Shuguang Zhang.  Fabrication of novel biomaterials through molecular self-assembly , 2003, Nature Biotechnology.

[55]  Meital Reches,et al.  Casting Metal Nanowires Within Discrete Self-Assembled Peptide Nanotubes , 2003, Science.

[56]  Jean-Marie Lehn,et al.  Toward complex matter: Supramolecular chemistry and self-organization , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[57]  Shuguang Zhang,et al.  Molecular self-assembly of surfactant-like peptides to form nanotubes and nanovesicles , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[58]  G. Whitesides,et al.  Self-Assembly at All Scales , 2002, Science.

[59]  H. Möhwald,et al.  Dynamic Observations of the Hydrolysis of a DPPC Monolayer at the Air/Water Interface Catalyzed by Phospholipase A2 , 2000 .

[60]  Katsuhiko Ariga,et al.  Regulation of β-Sheet Structures within Amyloid-Like β-Sheet Assemblage from Tripeptide Derivatives , 1998 .

[61]  Naito,et al.  Equilibrium shapes of smectic-A phase grown from isotropic phase. , 1993, Physical review letters.

[62]  Rein V Ulijn,et al.  Enzyme-assisted self-assembly under thermodynamic control. , 2009, Nature nanotechnology.

[63]  Leroy Cronin,et al.  Polyoxometalate clusters, nanostructures and materials: from self assembly to designer materials and devices. , 2007, Chemical Society reviews.

[64]  Meital Reches,et al.  Novel electrochemical biosensing platform using self-assembled peptide nanotubes. , 2005, Nano letters.