Supramolecular Self‐Assembly of <i>N</i>‐Acetyl‐Capped β‐Peptides Leads to Nano‐ to Macroscale Fiber Formation

Borgo, Mark P. Del; Mechler, Ádám; Traore, Daouda A K; Forsyth, Craig M.; Wilce, Jacqueline Anne; Wilce, Matthew Charles James; Aguilar, Marie Isabel; Perlmutter, Patrick

doi:10.1002/anie.201303175

Cited by 72 publications

(129 citation statements)

References 31 publications

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“…-peptide selfassembly by our group. [11][12][13] Despite the incorporation of a rigid p-aminobenzoic acid linker between the two b 3 -tripeptides, self-assembly was maintained in peptide 1. AFM analysis showed the presence of aggregates, from which a number of fibres grow into an architecture with relatively short fibres.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast, peptide 2 displayed extensive fibre formation similar to the architectures described previously for b 3 -peptides. [11][12][13]22 The morphology evident from AFM demonstrates that a flexible linker between the b-tripeptides does not hinder selfassembly and leads to longer fibres with greater coverage of the mica surface compared to 1.…”

Section: Resultsmentioning

confidence: 99%

“…2, 026104-1 APL BIOENGINEERING 2, 026104 (2018) We have recently reported the self-assembly of peptides comprised entirely of b 3 -amino acids. [11][12][13] These peptides possess an extra methylene group in their backbone and are commonly referred to as b-peptide foldamers. [14][15][16][17] Peptides containing acyclic b 3 -amino acids form a unique 14-helical structure that is not adopted by a-peptides, which, in combination with N-terminal acetylation, creates a self-assembly motif.…”

Section: Introductionmentioning

confidence: 99%

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β3-tripeptides act as sticky ends to self-assemble into a bioscaffold

et al. 2018

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Peptides comprised entirely of β 3 -amino acids, commonly referred to as β-foldamers, have been shown to self-assemble into a range of materials. Previously, β-foldamers have been functionalised via various side chain chemistries to introduce function to these materials without perturbation of the self-assembly motif. Here, we show that insertion of both rigid and flexible molecules into the backbone structure of the β-foldamer did not disturb the self-assembly, provided that the molecule is positioned between two β 3 -tripeptides. These hybrid β 3 -peptide flanked molecules self-assembled into a range of structures. α-Arginlyglycylaspartic acid (RGD), a commonly used cell attachment motif derived from fibronectin in the extracellular matrix, was incorporated into the peptide sequence in order to form a biomimetic scaffold that would support neuronal cell growth. The RGD-containing sequence formed the desired mesh-like scaffold but did not encourage neuronal growth, possibly due to over-stimulation with RGD. Mixing the RGD peptide with a β-foldamer without the RGD sequence produced a well-defined scaffold that successfully encouraged the growth of neurons and enabled neuronal electrical functionality. These results indicate that β 3 -tripeptides can form distinct self-assembly units separated by a linker and can form fibrous assemblies. The linkers within the peptide sequence can be composed of a bioactive α-peptide and tuned to provide a biocompatible scaffold.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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β3-tripeptides act as sticky ends to self-assemble into a bioscaffold

et al. 2018

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“…[3,4] Afterwards,m any groups demonstrated macroscopic assembly of hydrogel building blocks through supramolecular interactions. [5][6][7][8][9][10][11][12][13][14][15][16][17][18] To promote research on macroscopic supramolecular assemblies from the hydrogel systems to rigid building blocks,w eh ave proposed ageneral principle of aflexible spacing coating to realize selfassembly of macroscopic polydimethylsiloxane (PDMS) or polymethyl methacrylate building blocks. [19] However,a ll of the aforementioned work involved an external energy source such as shaking or rotating to drive the building blocks larger than 10 mmthat could hardly diffuse or collide with each other by molecular thermal motion.…”

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confidence: 99%

Precise Macroscopic Supramolecular Assembly by Combining Spontaneous Locomotion Driven by the Marangoni Effect and Molecular Recognition

2015

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Macroscopic supramolecular assembly bridges fundamental research on molecular recognition and the potential applications as bulk supramolecular materials. However, challenges remain to realize stable precise assembly, which is significant for further functions. To handle this issue, the Marangoni effect is applied to achieve spontaneous locomotion of macroscopic building blocks to reach interactive distance, thus contributing to formation of ordered structures. By increasing the density of the building blocks, the driving force for assembly transforms from a hydrophobic-hydrophobic interaction to hydrophilic-hydrophilic interaction, which is favorable for introducing hydrophilic coatings with supramolecular interactive groups on matched surfaces, consequently realizing the fabrication of stable precise macroscopic supramolecular assemblies.

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“…[1][2][3][4][5] Among them, stimuli-responsive self-assemblies have drawn particular attention due to feasibility of modulating structures, morphologies, and functions of these materials in the presence of external stimuli. [6][7][8][9] Polyoxomylatates (POMs) are typical clusters of nanometer-sized transition metal oxide that are emerging as useful materials for potential applications in diverse fields such as catalysis, material science, and sensing, etc.…”

Section: Introductionmentioning

confidence: 99%

Stimuli-Responsive Polyoxometalate/Ionic Liquid Supramolecular Spheres: Fabrication, Characterization, and Biological Applications

Gong

Wang

et al. 2016

Langmuir

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We report fabrication, characterization, and potential applications of polyoxometalate (POM)/ionic liquid (IL) supramolecular spheres in water for the first time. These supramolecular spheres have highly ordered structures and show excellent reversible self-assembly and tunable photoluminescence properties, which can be manipulated by adjusting pH of the aqueous solution. Specifically, the formation of POM/IL supramolecular spheres results in quenching of fluorescence emitted by Eu-POM because hopping of the d1 electron in the POM molecule is blocked by hydrogen bond existing between the oxygen atom of POM and the carboxylic acid group of IL. However, the fluorescence can be completely recovered by gradually increasing pH of the aqueous solution due to the pH-induced deprotonation of the carboxylic acid group of IL, which results in disassembly of the fabricated supramolecular spheres. Applications of these stimuli-responsive photoluminescent POM-based supramolecular materials are demonstrated in biological media. Dual signaling responses of turbidity and fluorescence are observed simultaneously in the detection of urease and heavy metals based on pH-induced disassembly of the supramolecular spheres during the biochemical events in aqueous solution. In addition, guest molecules are encapsulated into the supramolecular spheres, and controlled release of these entrapped molecules is demonstrated in the presence of external stimuli. This study shows potential of stimuli-responsive POM/IL supramolecular materials in biological applications.

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Supramolecular Self‐Assembly of N‐Acetyl‐Capped β‐Peptides Leads to Nano‐ to Macroscale Fiber Formation

Cited by 72 publications

References 31 publications

β3-tripeptides act as sticky ends to self-assemble into a bioscaffold

β3-tripeptides act as sticky ends to self-assemble into a bioscaffold

Precise Macroscopic Supramolecular Assembly by Combining Spontaneous Locomotion Driven by the Marangoni Effect and Molecular Recognition

Stimuli-Responsive Polyoxometalate/Ionic Liquid Supramolecular Spheres: Fabrication, Characterization, and Biological Applications

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