Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles

Booth, Richard; Insua, Ignacio; Bhak, Ghibom; Montenegro, Javier

doi:10.1039/c8ob02243g

Cited by 11 publications

(16 citation statements)

References 60 publications

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“…We selected linear peptide amphiphiles as scaffolds for the assembly of fibrillar supramolecular architectures 36 , 38 , 39 . We employed a non-assembling peptide precursor, P C8 , that could readily react with a hydrophobic tail, T 8 , to generate in situ the self-assembling peptide amphiphile, P C8 T 8 (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Here we report the molecular and microscopic phenomena that resulted from the in situ generation of a peptide amphiphile via oxime condensation 36 , 37 of two dormant fragments, which triggered a physically autocatalytic reaction that induced the assembly of a microfibrillar network. Under confinement, these two coupled processes resulted in a series of unpredicted responses by aqueous microdroplets with their environment.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular fibrillation of peptide amphiphiles induces environmental responses in aqueous droplets

et al. 2021

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One-dimensional (1D) supramolecular polymers are commonly found in natural and synthetic systems to prompt functional responses that capitalise on hierarchical molecular ordering. Despite amphiphilic self-assembly being significantly studied in the context of aqueous encapsulation and autopoiesis, very little is currently known about the physico-chemical consequences and functional role of 1D supramolecular polymerisation confined in aqueous compartments. Here, we describe the different phenomena that resulted from the chemically triggered supramolecular fibrillation of synthetic peptide amphiphiles inside water microdroplets. The confined connection of suitable dormant precursors triggered a physically autocatalysed chemical reaction that resulted in functional environmental responses such as molecular uptake, fusion and chemical exchange. These results demonstrate the potential of minimalistic 1D supramolecular polymerisation to modulate the behaviour of individual aqueous entities with their environment and within communities.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Supramolecular fibrillation of peptide amphiphiles induces environmental responses in aqueous droplets

et al. 2021

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“…Design of a benzaldehyde-tethered peptide-type hydrogelator. According to pioneering examples where dynamic covalent oxime chemistry was used to form nanofiber and hydrogels [49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64] , we designed a new peptide-type hydrogelator, Ald-F(F)F, that has a benzaldehyde moiety as a reaction handle at the N-terminus of a self-assembled diphenylalanine sequence (Fig. 1b).…”

Section: Resultsmentioning

confidence: 99%

Control of seed formation allows two distinct self-sorting patterns of supramolecular nanofibers

et al. 2020

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Self-sorting double network hydrogels comprising orthogonal supramolecular nanofibers have attracted attention as artificially-regulated multi-component systems. Regulation of network patterns of self-sorted nanofibers is considered as a key for potential applications such as optoelectronics, but still challenging owing to a lack of useful methods to prepare and analyze the network patterns. Herein, we describe the selective construction of two distinct self-sorting network patterns, interpenetrated and parallel, by controlling the kinetics of seed formation with dynamic covalent oxime chemistry. Confocal imaging reveals the interpenetrated self-sorting network was formed upon addition of O-benzylhydroxylamine to a benzaldehyde-tethered peptide-type hydrogelator in the presence of lipid-type nanofibers. We also succeed in construction of a parallel self-sorting network through deceleration of seed formation using a slow oxime exchange reaction. Through careful observation, the formation of peptide-type seeds and nanofibers is shown to predominantly occur on the surface of the lipid-type nanofibers via highly dynamic and thermally-fluctuated processes.

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“…[5a-j] Despite much has been advanced with natural proteins, the confined self-assembly of artificial minimal systems that can be engineered by rational design has been much less explored. [6a-d] Bottom-up approaches towards synthetic mimics of natural supramolecular systems have recently exploited the encapsulation of artificial peptides [7] in protocell mimics, [8] such as giant vesicles, [9] capsules [10] or water-in-oil droplets. [11] However, despite the importance of the precise position of intracellular supramolecular networks, the control over the spatial adjustment of synthetic fibrillar networks has not been experimentally achieved.…”

Section: Introductionmentioning

confidence: 99%

Spatially Controlled Supramolecular Polymerization of Peptide Nanotubes by Microfluidics

Méndez‐Ardoy

Bayón‐Fernández

et al. 2020

Angew Chem Int Ed

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Despite the importance of spatially resolved self‐assembly for molecular machines, the spatial control of supramolecular polymerization with synthetic monomers had not been experimentally established. Now, a microfluidic‐regulated tandem process of supramolecular polymerization and droplet encapsulation is used to control the position of self‐assembled microfibrillar bundles of cyclic peptide nanotubes in water droplets. This method allows the precise preferential localization of fibers either at the interface or into the core of the droplets. UV absorbance, circular dichroism and fluorescence microscopy indicated that the microfluidic control of the stimuli (changes in pH or ionic strength) can be employed to adjust the packing degree and the spatial position of microfibrillar bundles of cyclic peptide nanotubes. Additionally, this spatially organized supramolecular polymerization of peptide nanotubes was applied in the assembly of highly ordered two‐dimensional droplet networks.

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Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles

Abstract: The oxime connection between linear peptides and hydrophobic aldehydes affords amphiphiles that are excellent biocompatible scaffolds for the hierarchical self-assembly of nano and micro fibrillar structures in aqueous media.

Cited by 11 publications

References 60 publications

Supramolecular fibrillation of peptide amphiphiles induces environmental responses in aqueous droplets

Supramolecular fibrillation of peptide amphiphiles induces environmental responses in aqueous droplets

Control of seed formation allows two distinct self-sorting patterns of supramolecular nanofibers

Spatially Controlled Supramolecular Polymerization of Peptide Nanotubes by Microfluidics

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