Turning peptides in comb silicone polymers

Abstract

We have recently reported on a new class of silicone-peptide' biopolymers obtained by polymerization of di-functionalized chlorodimethylsilyl hybrid peptides. Herein, we describe a related strategy based on dichloromethylsilane-derived peptides, which yield novel polymers with a polysiloxane backbone, comparable with a silicone-bearing pendent peptide chains. Interestingly, polymerization is chemoselective toward amino acids side-chains and proceeds in a single step in very mild conditions (neutral pH, water, and room temperature). As potential application, a cationic sequence was polymerized and used for antibacterial coating.

New Antiadhesive Hydrophobic Polysiloxanes

“…The premise for this approach was the fact that carboxylic acids, including ibuprofen [25] and acetic acid [26,27], are regarded as non-antibiotic drugs and are well-known for their antimicrobial behaviour. Polysiloxanes with amide linkers in their side chains resemble, to some extent, antibacterial silicones modified with peptides [28,29]. The functionalization of polysiloxanes with mercaptoethyl residues was inspired by the well-known ability of thiols to take part in the disruption of proteins through oxidation into S-S bonds and/or SH-induced S-S interchange reactions [30,31].…”

Direct Synthesis of Peptide‐Containing Silicones: A New Way to Bioactive Materials

“…Peptides 2 and 3 were first synthesized on a solid support, by using Rink amide and 2‐chloro chlorotrityl PS resin, respectively. Peptide 3 was silylated on the solid support, while peptide 2 was cleaved and then silylated in solution, according to a well‐established procedure …”

“…In contrast, direct strategies can be envisioned to obtain peptide‐containing silicone. We have already reported on the polymerization of peptides using silane chemistry to get linear and comblike peptide–polymers assembled through Si−O−Si bonds without any dichlorodimethylsilane (DCDMS) copolymerization (Figure ) . However, these hybrid peptide polymers are limited by their modest degrees of polymerization (DP<30) despite the similarities in their backbone, and they did not show comparable physicochemical properties to PDMS.…”

Sol-gel and peptides: an attractive route to unprecedented biomaterials

“…We already used this sol-gel process to prepare peptide-functionalized fluorescent silica nanoparticles [10,11], grafting of wound-healing or antibacterial peptides on silicone catheter, [12] dressings [13] and titanium [14] and comb-like and silicone linear polymers were prepared. [15,16] At pH 7, the sol gel process needs to be catalyzed with a nucleophilic compound to faster the gelation. We selected sodium fluoride at low and non-toxic concentration (< 0.3 mg/ml) to perform the hydrolysis of alkoxysilane and subsequent condensation reactions (Fig.…”