Bioactive Seed Layer for Surface‐Confined Self‐Assembly of Peptides

Vigier‐Carrière, Cécile; Garnier, Tony; Wagner, Déborah; Lavalle, Philippe; Rabineau, Morgane; Hemmerlé, Joseph; Senger, Bernard; Schaaf, Pierre; Boulmedais, Fouzia; Jierry, Loı̈c

doi:10.1002/ange.201504761

Cited by 20 publications

(9 citation statements)

References 26 publications

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“…The Fmoc-FFpY peptide is known to transform into Fmoc-FFY in the presence of AP which then self-assembles to form a gel. 48 Here, we show that the hydrogelation of Fmoc-FFpY can occur by electrostatic interactions with polycation chains without dephosphorylation whereas Fmoc-FFpY solution by itself does not gel even after several days. A phase diagram was established using the inverted tube test, a commonlyaccepted method for screening whether a gel has been formed ( Figure S1a in Supporting Information, SI).…”

Section: Resultsmentioning

confidence: 67%

Supramolecular Hydrogel Induced by Electrostatic Interactions between Polycation and Phosphorylated-Fmoc-Tripeptide

et al. 2020

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Supramolecular hydrogels formed through non-covalent interactions of low molecular weight hydrogelators (LMWH) show great potential applications in different fields, such as delivery of therapeutics, injectable biomaterials, catalysis or materials chemistry. Generally, the self-assembly of LMWH is triggered by a sol-gel process through an external stimulus able to switch their solubility, such as temperature, pH or solvent change and chemical or enzymatic reactions. In this work, we introduced a new strategy to trigger and control the self-assembly of Fmoc-FFpY peptides: by direct electrostatic interactions with a polycation without dephosphorylation of the peptides. The resulting hydrogels show enhanced mechanical properties in comparison to gels of Fmoc-FFpY induced by enzymatic dephosphorylation. Peptide self-assembly yields -sheets, revealed by circular dichroism and infrared spectroscopy. Characteristic distances predicted by geometry optimization in the gas phase are in agreement with X-ray scattering data and TEM observations. It is proposed that core-shell cylinders are formed in which polycation chains decorate the micellar structures of Fmoc-FFpY peptides through electrostatic interactions between the charged amine groups of the polycations and the phosphate groups of the peptides. Since the gels form quickly and have superior mechanical properties, applications as injectable biomaterials are foreseen. This work opens a route towards a new class of self-assembled hydrogels, where Fmoc tripeptides can be self-assembled with specific polycations to obtain, for example, antimicrobial hydrogels.

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Section: Resultsmentioning

confidence: 67%

Supramolecular Hydrogel Induced by Electrostatic Interactions between Polycation and Phosphorylated-Fmoc-Tripeptide

et al. 2020

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“…This decrease continued more slowly over 12 h without levelling off, suggesting a continuing gelation process over this period of time (Figure S4) . AFM, SEM, HPLC composition analysis, and fluorescence emission intensity measurements confirmed the nanofibrous architecture of the hydrogel made up of the hydrogelator Fmoc‐GFFYGHY with Fmoc groups stacking together through π–π interactions in the resulting assembly (Figures S5–S7) . Cryo‐SEM analysis was realized on CASH grown up from a silica wafer.…”

Section: Figurementioning

confidence: 79%

“…We immobilized an enzyme that is able to transform non‐self‐assembling precursors present in solution into self‐assembling building blocks on the surface . The confinement of these building blocks at the material–water interface induces the growth of nanofibers anchored on the surface and underpinning the hydrogel …”

Section: Figurementioning

confidence: 99%

Supported Catalytically Active Supramolecular Hydrogels for Continuous Flow Chemistry

et al. 2019

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Inspired by biology, one current goal in supramolecular chemistry is to control the emergence of new functionalities arising from the self‐assembly of molecules. In particular, some peptides can self‐assemble and generate exceptionally catalytically active fibrous networks able to underpin hydrogels. Unfortunately, the mechanical fragility of these materials is incompatible with process developments, relaying this exciting field to academic curiosity. Here, we show that this drawback can be circumvented by enzyme‐assisted self‐assembly of peptides initiated at the walls of a supporting porous material. We applied this strategy to grow an esterase‐like catalytically active supramolecular hydrogel (CASH) in an open‐cell polymer foam, filling the whole interior space. Our supported CASH material is highly efficient towards inactivated esters and enables the kinetic resolution of racemates. This hybrid material is robust enough to be used in continuous flow reactors, and is reusable and stable over months.

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“…3-Maleimidopropionic acid N-hydroxysuccinimide ester (MalOSu) was prepared according to the literature [47]. The details are given in the Additional file 1, Synthesis S4.…”

Section: Synthesis Of the Surface Linkermentioning

confidence: 99%

Dual functional β-peptide polymer-modified resin beads for bacterial killing and endotoxin adsorption

Qian

Shen

Deng

et al. 2019

BMC Mat

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Background: Bacterial infections and endotoxin contaminations are serious problems in the production/manufacture of food, water, drinks, and injections. The development of effective materials to kill bacteria and adsorb endotoxins, particularly those caused by gram-negative bacteria, represents a major step toward improved safety. As synthetic mimic of host defense peptides, β-peptide polymers are not susceptible to bacterial resistance and exhibit potent bacteria-killing abilities upon antibiotic-resistant bacteria. This study investigated the potential of synthetic β-peptide polymer-modified polyacrylate (PA) beads to kill bacteria and remove endotoxin, i.e. lipopolysaccharide (LPS), produced by these bacteria.Results: Synthetic β-peptide polymer-modified PA beads displayed strong antimicrobial activity against Escherichia coli and methicillin-resistant Staphylococcus aureus, as well as excellent biocompatibility. In addition, these β-peptide polymer-modified beads removed around 90% of the endotoxins, even at 200 EU/mL of LPS, a very high concentration of LPS.Conclusions: β-peptide polymer-modified PA beads are efficient in bacterial killing and endotoxin adsorption. Hence, these modified beads demonstrate the potential application in the production/manufacture of food, water, drinks, and injections.

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Bioactive Seed Layer for Surface‐Confined Self‐Assembly of Peptides

Cited by 20 publications

References 26 publications

Supramolecular Hydrogel Induced by Electrostatic Interactions between Polycation and Phosphorylated-Fmoc-Tripeptide

Supramolecular Hydrogel Induced by Electrostatic Interactions between Polycation and Phosphorylated-Fmoc-Tripeptide

Supported Catalytically Active Supramolecular Hydrogels for Continuous Flow Chemistry

Dual functional β-peptide polymer-modified resin beads for bacterial killing and endotoxin adsorption

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