Effects of crosslink density in zwitterionic hydrogel coatings on their antifouling performance and susceptibility to silt uptake

Koc, Julian; Schönemann, Eric; Wanka, Robin; Aldred, Nick; Clare, Anthony S.; Gardner, Harrison; Swain, Geoffrey; Hunsucker, Kelli Z.; Laschewsky, André; Rosenhahn, Axel

doi:10.1080/08927014.2020.1796983

Cited by 25 publications

(33 citation statements)

References 64 publications

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“…The incorporation of 50% BMA reduced the uptake of silt to one third compared to pure PSPE which was an effect similar to the increase of the crosslinker content from 1% to 2%. [ 33 ]…”

Section: Discussionmentioning

confidence: 99%

Low Fouling Polysulfobetaines with Variable Hydrophobic Content

Schardt

Guajardo

Koc

et al. 2021

Macromol. Rapid Commun.

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Amphiphilic polymer coatings combining hydrophilic elements, in particular zwitterionic groups, and hydrophobic elements comprise a promising strategy to decrease biofouling. However, the influence of the content of the hydrophobic component in zwitterionic coatings on the interfacial molecular reorganization dynamics and the anti-fouling performance is not well understood. Therefore, coatings of amphiphilic copolymers of sulfobetaine methacrylate 3-[N-2'-(methacryloyloxy)ethyl-N,N-dimethyl]-ammonio propane-1-sulfonate (SPE) are prepared which contain increasing amounts of hydrophobic n-butyl methacrylate (BMA). Their fouling resistance is compared to that of their homopolymers PSPE and PBMA. The photo-crosslinked coatings form hydrogel films with a hydrophilic surface. Fouling by the proteins fibrinogen and lysozyme as well as by the diatom Navicula perminuta and the green algae Ulva linza is assessed in laboratory assays. While biofouling is strongly reduced by all zwitterionic coatings, the best fouling resistance is obtained for the amphiphilic copolymers. Also in preliminary field tests, the anti-fouling performance of the amphiphilic copolymer films is superior to that of both homopolymers. When the coatings are exposed to a marine environment, the reduced susceptibility to silt incorporation, in particular compared to the most hydrophilic polyzwitterion PSPE, likely contributes to the improved fouling resistance.

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“…The incorporation of 50% BMA reduced the uptake of silt to one third compared to pure PSPE which was an effect similar to the increase of the crosslinker content from 1% to 2%. [ 33 ]…”

Section: Discussionmentioning

confidence: 99%

Low Fouling Polysulfobetaines with Variable Hydrophobic Content

Schardt

Guajardo

Koc

et al. 2021

Macromol. Rapid Commun.

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“…As mentioned above, zwitterionic hydrogels, though lacking in bactericidal capacity, can prevent bacterial adhesion. Koc et al [ 122 ] designed various sulfobetaine hydrogel coatings on glass substrates, showing excellent resistance to microorganisms (2–8% related to butyl methacrylate (BMA) hydrogel coating) in severe conditions. Liu et al [ 123 ] prepared anti-bacterial hydrogel with copolymerization of sulfonated quaternization of 1-vinylimidazole (VIm) based zwitterions (VImSL) and [3(methacryloylamino)propyl]trimethyl ammonium chloride (MPTAmC).…”

Section: Biomedical Applications Of Zwitterionic Hydrogelsmentioning

confidence: 99%

Recent Advances in Zwitterionic Hydrogels: Preparation, Property, and Biomedical Application

Liu

Tang

et al. 2022

Gels

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Nonspecific protein adsorption impedes the sustainability of materials in biologically related applications. Such adsorption activates the immune system by quick identification of allogeneic materials and triggers a rejection, resulting in the rapid failure of implant materials and drugs. Antifouling materials have been rapidly developed in the past 20 years, from natural polysaccharides (such as dextran) to synthetic polymers (such as polyethylene glycol, PEG). However, recent studies have shown that traditional antifouling materials, including PEG, still fail to overcome the challenges of a complex human environment. Zwitterionic materials are a class of materials that contain both cationic and anionic groups, with their overall charge being neutral. Compared with PEG materials, zwitterionic materials have much stronger hydration, which is considered the most important factor for antifouling. Among zwitterionic materials, zwitterionic hydrogels have excellent structural stability and controllable regulation capabilities for various biomedical scenarios. Here, we first describe the mechanism and structure of zwitterionic materials. Following the preparation and property of zwitterionic hydrogels, recent advances in zwitterionic hydrogels in various biomedical applications are reviewed.

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“…To complement the "outside-in" strategy and to highlight its utility, a glycine spacer has been added between two lysine methacrylamide coupling partners, creating the N-Lys-Gly-Lys-C dimethacrylamide cross-linker (8) and between to serine coupling partners to create the N-Ser-Gly-Ser-C dimethacrylate (9). These compounds separate the zwitterionic units by seven atoms as the distance between charges, length of cross-linker, and cross-linker type are all important variables for understanding the polyampholyte properties.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…8 It has been suggested that further alterations to polyampholyte chemistries based on monomer length, shape, functional groups, and skeletal attachment can diversify physical properties in bulk polyampholyte and potential for increasing both non-fouling behavior and increase specific protein adhesion. 9 In the case of peptide-based zwitterionic cross-linkers, changes could include the relative polymer type (methacrylate vs. methacrylamide); position of the carboxylate and ammonium functionalities; and the length of the cross-linker.…”

mentioning

confidence: 99%

“…Herein, the "outside-in" strategy mentioned above has been extended to create a series of L-Lysine and L-Serine amino acid based dimethacrylamide and mixed methacrylate/ methacrylamide zwitterionic dipeptide crosslinkers (5)(6)(7) shown in Scheme 2. Moreover, this strategy was employed to build tripeptide zwitterionic cross-linkers (8)(9) as to extend the distance between the zwitterionic components, another key feature not amenable in the carboxy-or sulfobetaine based cross-linkers. While both methacrylation and peptide coupling are key to the development of these compounds, the choice of protecting groups was imperative due to the sensitivity of the methacrylate/methacrylamide group.…”

mentioning

confidence: 99%

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Outside-In Strategy for Peptide-Based Methacrylate and Methacrylamide Zwitterionic Cross-Linkers

Chakraborty¹,

Waynant²

2022

Synlett

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Polyampholyte hydrogels have shown promise as functional biomaterial platforms with resistance to nonspecific protein adsorption (non-biofouling). Yet there are few zwitterionic cross-linkers available to complement these materials and provide an extended charge density throughout the 3D network. Recent development of a peptide-based zwitterionic cross-linker has shown merit. Indeed, the use of functionalizable amino acids allows for a series of peptide-based zwitterionic methacrylate and methacrylamide cross-linkers. Methacrylate additions prior to peptide coupling provides an “outside-in” strategy when using natural L-Serine or L-Lysine as substrates to produce a series of methacrylate and methacrylamide combinations and expand the library of peptide-based cross-linkers. Herein such dipeptide combinations include Ser-Lys; Lys-Ser and Lys-Lys zwitterionic bis(methacrylate/methacrylamide) cross-linkers. Highlighting the utility of the method, and potential to increase the distance between zwitterionic components, the syntheses of tripeptide Lys-Gly-Lys dimethacrylamide and Ser-Gly-Ser dimethacrylate are also shown.

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Effects of crosslink density in zwitterionic hydrogel coatings on their antifouling performance and susceptibility to silt uptake

Cited by 25 publications

References 64 publications

Low Fouling Polysulfobetaines with Variable Hydrophobic Content

Low Fouling Polysulfobetaines with Variable Hydrophobic Content

Recent Advances in Zwitterionic Hydrogels: Preparation, Property, and Biomedical Application

Outside-In Strategy for Peptide-Based Methacrylate and Methacrylamide Zwitterionic Cross-Linkers

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