Selective homodimerization of unprotected peptides using hybrid hydroxydimethylsilane derivatives

Echalier, Cécile; Kalistratova, Aleksandra; Ciccione, Jeremie; Lebrun, Aurélien; Legrand, Baptiste; Naydenova, Emilia; Gagne, Didier; Fehrentz, Jean‐Alain; Marie, Jacky; Amblard, Muriel; Mehdi, Ahmad; Martinez, Jean; Subra, Gilles

doi:10.1039/c6ra06075g

Cited by 7 publications

(3 citation statements)

References 27 publications

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“…Compound 4 was dissolved in water (1/1000 TFA)/ethanol, 30/5, v/v solution at a 30 × 10 −3 m concentration. Noteworthy we demonstrated that dimethylhydroxysilane peptides did not form dimers through intermolecular reaction in acidic solutions . Pieces of catheters were activated by oxygen plasma and immediately incubated in this solution at 60 °C for 12 h. As a control experiment, pieces of catheters were also incubated in a solution of the unsilylated fluorescein derivative 3 .…”

Section: Antibacterial Hybrid Peptidementioning

confidence: 94%

“…Several chlorodimethylsilylated peptides were already prepared by our group as precursors for G protein‐coupled receptor (GPCR) ligand dimers. These peptide may undergo dimerization upon freeze drying or precipitation but are only observed in monomeric form when treated in acidic conditions, enabling their purification by classical RP HPLC in water/acetonitrile (with TFA, 1/1000, v/v) solvent system. The hybrid peptide 2 “ready to use” was purified and characterized (See the Supporting Information).…”

Section: Antibacterial Hybrid Peptidementioning

confidence: 99%

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Simple and Specific Grafting of Antibacterial Peptides on Silicone Catheters

Pinese

Jebors

Echalier

et al. 2016

Adv Healthcare Materials

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To fight against nosocomial infection initiated by colonization of medical devices, a strategy enabling the direct and fast functionalization of silicone surfaces is proposed. This strategy proceeds in a site-specific way using original hybrid silylated antibacterial peptides. This safe and up-scalable method guarantees a covalent and robust immobilization with the correct orientation of the bioactive moiety. Importantly it also avoids multi-step chemical modifications of the surface or multi-layer polymer coatings. As proof of concept, antibacterial silicone catheter has been prepared whose immediate and long term efficiency is superior by comparison to similar silver-embedded materials.

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Section: Antibacterial Hybrid Peptidementioning

confidence: 94%

Section: Antibacterial Hybrid Peptidementioning

confidence: 99%

Simple and Specific Grafting of Antibacterial Peptides on Silicone Catheters

Pinese

Jebors

Echalier

et al. 2016

Adv Healthcare Materials

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“…Other examples of silylated peptides include peptides with biological activity (anti-angiogenic, ( Ciccione et al, 2016 ; Maurel et al, 2021 ), regulatory, ( Jebors et al, 2015 ; Echalier et al, 2016b ), antibacterial ( Masurier et al, 2018 )), catalytic activity ( Jebors et al, 2013b ) or enzyme-responsive degradation. ( Maggini et al, 2016 ).…”

Section: Bioink Silylated Componentsmentioning

confidence: 99%

Silylated biomolecules: Versatile components for bioinks

Montheil

Simon

Noël

et al. 2022

Front. Bioeng. Biotechnol.

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Physical hydrogels prepared from natural biopolymers are the most popular components for bioinks. However, to improve the mechanical properties of the network, in particular its durability for long-lasting tissue engineering applications or its stiffness for bone/cartilage applications, covalent chemical hydrogels have to be considered. For that purpose, biorthogonal reactions are required to allow the inclusion of living cells within the bioink reservoir before the 3D printing procedure. Interestingly, such reactions also unlock the possibility to further multifunctionalize the network, adding bioactive moieties to tune the biological properties of the resulting printed biomaterial. Surprisingly, compared to the huge number of studies disclosing novel bioink compositions, no extensive efforts have been made by the scientific community to develop new chemical reactions meeting the requirements of both cell encapsulation, chemical orthogonality and versatile enough to be applied to a wide range of molecular components, including fragile biomolecules. That could be explained by the domination of acrylate photocrosslinking in the bioprinting field. On the other hand, proceeding chemoselectively and allowing the polymerization of any type of silylated molecules, the sol-gel inorganic polymerization was used as a crosslinking reaction to prepare hydrogels. Recent development of this strategy includes the optimization of biocompatible catalytic conditions and the silylation of highly attractive biomolecules such as amino acids, bioactive peptides, proteins and oligosaccharides. When one combines the simplicity and the versatility of the process, with the ease of functionalization of any type of relevant silylated molecules that can be combined in an infinite manner, it was obvious that a family of bioinks could emerge quickly. This review presents the sol-gel process in biocompatible conditions and the various classes of relevant silylated molecules that can be used as bioink components. The preparation of hydrogels and the kinetic considerations of the sol-gel chemistry which at least allowed cell encapsulation and extrusion-based bioprinting are discussed.

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