Metastable hydrogels from aromatic dipeptides

Conte, Maria Paola; Singh, Neeloo; Sasselli, Ivan R.; Escuder, Beatriu; Ulijn, Rein V.

doi:10.1039/c6cc05821c

Cited by 59 publications

(56 citation statements)

References 45 publications

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“…68 and TEM adapted from ref. 69 ) and the single amino-acid phenylalanine (crystal structure CCDC 985094 and TEM micrograph of phenylalanine at 4 mg/ml was taken as described in the Methods). b-g Inhibition of metabolite aggregation by polyphenol-based inhibitors.…”

Section: Spectroscopic Monitoring Of Metabolite Amyloid Assemblymentioning

confidence: 99%

Differential inhibition of metabolite amyloid formation by generic fibrillation-modifying polyphenols

et al. 2018

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The formation of ordered amyloid fibrils by proteins and polypeptides is associated with human disorders. A recent extension of the amyloidogenic building block family includes several small metabolites, which form assemblies with structural and functional similarities to well-established amyloids. Here we investigate whether generic amyloid polyphenolic inhibitors can also restrict the formation of metabolite fibrils. We reveal that epigallocatechin gallate and tannic acid inhibit amyloid-like fibrillation of adenine, phenylalanine, and tyrosine. Moreover, the compounds reduce the cytotoxicity triggered by these assemblies. In contrast, acetylsalicylic acid, used as a control does not have an inhibitory effect. The compounds' differential effects at various time points is consistent with molecular dynamics simulations, providing information about the inhibition mechanisms and inhibitors' key interactions with the monomeric and subsequent crystalline fibril states. Taken together, we provide additional evidence for the fundamental similarities between protein-and metabolite-based amyloids, the inhibition process and dynamics of association.

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Section: Spectroscopic Monitoring Of Metabolite Amyloid Assemblymentioning

confidence: 99%

Differential inhibition of metabolite amyloid formation by generic fibrillation-modifying polyphenols

et al. 2018

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“…The prototype of this new class of molecules is the short and well‐known diphenylalanine (FF) homopeptide . Through a combination of π–π stacking and hydrogen‐bonding, different method of preparation, specific pH values or solvent, FF is able to self‐organize in different kinds of nano and macro morphologies (hollow nanotubes, fibers, vesicles, metastable hydrogels or organogels). These nanostructures have been investigated for their mechanical, electrochemical and optical properties .…”

Section: Introductionmentioning

confidence: 99%

Structural Characterization of Self‐Assembled Tetra‐Tryptophan Based Nanostructures: Variations on a Common Theme

et al. 2018

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Over the years, a large number of multidisciplinary investigations has unveiled that the self-assembly of short peptides and even of individual amino acids can generate a variety of different biomaterials. In this framework, we have recently reported that polyethylene glycol (PEG) conjugates of short homopeptides, containing aromatic amino acids such as phenylalanine (Phe, F) and naphthylalanine (Nal), are able to form elongated fibrillary aggregates having interesting chemical and physical properties. We here extend these analyses characterizing the self-assembling propensity of PEG -W4, a PEG adduct of the tetra-tryptophan (W4) sequence. A comprehensive structural characterization of PEG -W4 was obtained, both in solution and at the solid state, through the combination of spectroscopic, microscopic, X-ray scattering and computational techniques. Collectively, these studies demonstrate that this peptide is able to self-assemble in fibrillary networks characterized by a cross β-structure spine. The present findings clearly demonstrate that aromatic residues display a general propensity to induce self-aggregation phenomenon, despite the significant differences in the physicochemical properties of their side chains.

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“…Finally, the final (often overlooked) parameter is aging. A number of reports of how gels can change in different ways have been reported, [42][43][44] but it is extremely common for the time at which the gels were analyzed not to be mentioned. Some interesting observations include gel-to-gel transitions, 44,45 syneresis, 46,47 and transient network formation.…”

Section: Introductionmentioning

confidence: 99%

Low-Molecular-Weight Gels: The State of the Art

Draper

Adams

2017

Chem

516

469

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Low-molecular-weight gels are currently a hugely important class of materials that are attracting significant interest. These gels are formed when small molecules self-assemble into one-dimensional structures that entangle and cross-link to form a network that is capable of immobilizing the solvent. Here, we critically discuss the current state of the art and highlight two key areas where we believe there is significant untapped potential. The first is the observation that the properties of the gels are highly process dependent, which means that it is possible to access materials with very different properties from a single gelator. Second, using multiple gelators offers the opportunity to prepare materials with a high degree of information content and with a wider range of properties. We aim to spark thought and discussion on these aspects. INTRODUCTIONLow-molecular-weight gels (LMWGs), or supramolecular gels, are a fascinating and useful class of material. The gels arise from the self-assembly of small molecules into long, anisotropic structures, most commonly fibers. [1][2][3][4][5] At a sufficiently high concentration, these fibers entangle or otherwise form cross-links, leading to the network that is able to immobilize the solvent through surface tension and capillary forces. 1,2 These gels differ from permanently covalently cross-linked polymer gels because the cross-linking can be reversed by the input of energy, for example, by heating. 6 LMWGs have been around for many years but are receiving considerable current interest. 4 They are also used in industrial products, 7 although this seems rarely discussed in the academic literature.In addition to the industrial applications, many recent advances and uses are being described. [8][9][10][11][12] The specific self-assembly leading to gel formation can be exploited. For example, the fiber formation is a result of molecular stacking, meaning that the self-assembly leads to aggregates that can be suitable for optoelectronic applications. 13,14 The ready reversibility of gelation can be exploited, for example, to release cells from gels on demand in a manner that does not lead to cell death. 15 Ready gel formation by a simple trigger can also be used to allow easy and efficient gel loading. [16][17][18] Unsurprisingly, therefore, there is significant interest in these materials ( Figure 1). This is a fascinating area and in many ways holds attention because of the difficulties in probing and understanding the gels. The gels arise from assembly across many length scales, and understanding all of these is difficult. At the molecular level, the molecules must interact in a manner that leads to the formation of suitable aggregates that can eventually entangle. Thus, one-dimensional growth must be favored. From this perspective, it is very frustrating that it is often extremely difficult to predict whether a molecule will form a gel or not; indeed, gelation has been described as an empirical science. 4 Structurally similar small molecules can exhibitThe Bigger Pict...

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Metastable hydrogels from aromatic dipeptides

Cited by 59 publications

References 45 publications

Differential inhibition of metabolite amyloid formation by generic fibrillation-modifying polyphenols

Differential inhibition of metabolite amyloid formation by generic fibrillation-modifying polyphenols

Structural Characterization of Self‐Assembled Tetra‐Tryptophan Based Nanostructures: Variations on a Common Theme

Low-Molecular-Weight Gels: The State of the Art

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