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Antifouling silicones based on surface-modifying additive amphiphiles.

ABSTRACT: Surface modifying additives (SMAs), which may be readily blended into silicones to improve anti-fouling behavior, must have excellent surface migration potential and must not leach into the aqueous environment. In this work, we evaluated the efficacy of a series of poly(ethylene oxide) (PEO)-based SMA amphiphiles which varied in terms of crosslinkability, siloxane tether length (m) and diblock versus triblock architectures. Specifically, crosslinkable, diblock PEO-silane amphiphiles with two oligodimethylsiloxane (ODMS) tether lengths [(EtO)3Si-(CH2)3-ODMS m -PEO8, m = 13 and 30] were compared to analogous non-crosslinkable, diblock (H-Si-ODMS m -PEO8) and triblock (PEO8-ODMS m -PEO8) SMAs. Prior to water conditioning, while all modified silicone coatings exhibited a high degree of water-driven surface restructuring, that prepared with the non-crosslinkable diblock SMA (m = 13) was the most hydrophilic. After conditioning, all modified silicone coatings were similarly hydrophilic and remained highly protein resistant, with the exception of PEO8-ODMS 30 -PEO8. Notably, despite twice the PEO content, triblock SMAs were not superior to diblock SMAs. For diblock SMAs, it was shown that water uptake and leaching were also similar whether or not the SMA was crosslinkable.

SUBMITTER: Rufin MA

PROVIDER: S-EPMC6822677 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Antifouling silicones based on surface-modifying additive amphiphiles.

Rufin Marc A MA Ngo Bryan Khai D BKD Barry Mikayla E ME Page Vanessa M VM Hawkins Melissa L ML Stafslien Shane J SJ Grunlan Melissa A MA

Green materials 20170301 1

Surface modifying additives (SMAs), which may be readily blended into silicones to improve anti-fouling behavior, must have excellent surface migration potential and must not leach into the aqueous environment. In this work, we evaluated the efficacy of a series of poly(ethylene oxide) (PEO)-based SMA amphiphiles which varied in terms of crosslinkability, siloxane tether length (m) and diblock versus triblock architectures. Specifically, crosslinkable, diblock PEO-silane amphiphiles with two oli ...[more]

PMID: 31673356

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Project description:Antifouling properties of materials play crucial roles in many important applications such as biomedical implants, marine antifouling coatings, biosensing, and membranes for separation. Poly(ethylene glycol) (or PEG) containing polymers and zwitterionic polymers have been shown to be excellent antifouling materials. It is believed that their outstanding antifouling activity comes from their strong surface hydration. On the other hand, it is difficult to develop underwater glues, although adhesives with strong adhesion in a dry environment are widely available. This is related to dehydration, which is important for adhesion for many cases while water is the enemy of adhesion. In this research, we applied sum frequency generation (SFG) vibrational spectroscopy to investigate buried interfaces between mussel adhesive plaques and a variety of materials including antifouling polymers and control samples, supplemented by studies on marine animal (mussel) behavior and adhesion measurements. It was found that PEG containing polymers and zwitterionic polymers have very strong surface hydration in an aqueous environment, which is the key for their excellent antifouling performance. Because of the strong surface hydration, mussels do not settle on these surfaces even after binding to the surfaces with rubber bands. For control samples, SFG results indicate that their surface hydration is much weaker, and therefore mussels can generate adhesives to displace water to cause dehydration at the interface. Because of the dehydration, mussels can foul on the surfaces of these control materials. Our experiments also showed that if mussels were forced to deposit adhesives onto the PEG containing polymers and zwitterionic polymers, interfacial dehydration did not occur. However, even with the strong interfacial hydration, strong adhesion between mussel adhesives and antifouling polymer surfaces was detected, showing that under certain circumstances, interfacial water could enhance the interfacial bio-adhesion.

Project description:Rapid, facile, and noncovalent cell membrane modification with alkyl-grafted anionic polymers was sought as an approach to enhance intracellular delivery and bioactivity of cationic peptides. We synthesized a library of acrylic acid-based copolymers containing varying amounts of an amine-reactive pentafluorophenyl acrylate monomer followed by postpolymerization modification with a series of alkyl amines to afford precise control over the length and density of aliphatic alkyl side chains. This synthetic strategy enabled systematic investigation of the effect of the polymer structure on membrane binding, potentiation of peptide cell uptake, pH-dependent disruption of lipid bilayers for endosome escape, and intracellular bioavailability. A subset of these polymers exhibited pKa of ∼6.8, which facilitated stable membrane association at physiological pH and rapid, pH-dependent endosomal disruption upon endocytosis as quantified in Galectin-8-YFP reporter cells. Cationic cell penetrating peptide (CPP) uptake was enhanced up to 15-fold in vascular smooth muscle cells in vitro when peptide treatment was preceded by a 30-min pretreatment with lead candidate polymers. We also designed and implemented a new and highly sensitive assay for measuring the intracellular bioavailability of CPPs based on the NanoLuciferase (NanoLuc) technology previously developed for measuring intracellular protein-protein interactions. Using this split luciferase class of assay, polymer pretreatment enhanced intracellular delivery of the CPP-modified HiBiT peptide up to 30-fold relative to CPP-HiBiT without polymer pretreatment (p < 0.05). The overall structural analyses show that polymers containing 50:50 or 70:30 molar ratios of carboxyl groups to alkyl side chains of 6-8 carbons maximized peptide uptake, pH-dependent membrane disruption, and intracellular bioavailability and that this potentiation effect was maximized by pairing with CPPs with high cationic charge density. These results demonstrate a rapid, mild method for polymer modification of cell surfaces to potentiate intracellular delivery, endosome escape, and bioactivity of cationic peptides.

Dataset Information

Antifouling silicones based on surface-modifying additive amphiphiles.

Publications

Antifouling silicones based on surface-modifying additive amphiphiles.

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