Low-Fouling and Antibacterial Polymer Brushes via Surface-Initiated Polymerization of a Mixed Zwitterionic and Cationic Monomer

Burmeister, Nils; Zorn, Eilika; Preuss, Lena; Timm, Donovan; Scharnagl, Nico; Rohnke, Marcus; Wicha, Sebastian G.; Streit, Wolfgang R.; Maison, Wolfgang

doi:10.1021/acs.langmuir.3c02657

Cited by 4 publications

(3 citation statements)

References 72 publications

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“…This negative charge was probably because of the preferential adsorption of hydroxide ions on the hydrophobic polyethylene surface, as many researchers discussed. 30–33 The membrane surface became neutral with increasing grafting amount. The existence of PMEA probably prohibited such adsorptions.…”

Section: Resultsmentioning

confidence: 99%

Poly(2-methoxyethyl acrylate)-grafted microfiltration membranes exhibiting low-fouling properties in the presence of salt species

Akamatsu,

Sano,

Okada

et al. 2024

RSC Appl. Interfaces

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Section: Resultsmentioning

confidence: 99%

Poly(2-methoxyethyl acrylate)-grafted microfiltration membranes exhibiting low-fouling properties in the presence of salt species

Akamatsu,

Sano,

Okada

et al. 2024

RSC Appl. Interfaces

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“…In particular, the PP/PDA/MPF-MTF coating showed a better stability than other polymer coatings. This stability could be due to its dual functionality, combining an antibacterial polymer containing quaternary ammonium groups with antifouling zwitterionic polymer, along with an increased count of covalent cross-linking and cation−π interaction between electron-rich π-system and cationic groups …”

Section: Resultsmentioning

confidence: 99%

Mussel-Inspired Polymer-Based Coating Technology for Antifouling and Antibacterial Properties

Imbia,

Ounkaew,

Mao

et al. 2024

Langmuir

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Zwitterionic coatings provide a promising antifouling strategy against biofouling adhesion. Quaternary ammonium cationic polymers can effectively kill bacteria on the surface, owing to their positive charges. This strategy can avoid the release of toxic biocides, which is highly desirable for constructing coatings for biomedical devices. The present work aims to develop a facile method by covalently grafting zwitterionic and cationic copolymers containing aldehydes to the remaining amine groups of selfpolymerized dopamine. Reversible addition−fragmentation chain transfer polymerization was used to copolymerize either zwitterionic 2-methacryloyloxyethyl phosphorylcholine monomer (MPC) or cationic 2-(methacryloyloxy)ethyl trimethylammonium monomer (META) with 4-formyl phenyl methacrylate monomer (FPMA), and the formed copolymers poly(MPC-st-FPMA) and poly(META-st-FPMA) are denoted as MPF and MTF, respectively. MPF and MTF copolymers were then covalently grafted onto the amino groups of polydopamine-coated surfaces. PDA/MPF/MTF-coated surfaces exhibited antibacterial and antifouling properties against S. aureus, E. coli, and bovine serum albumin protein. In addition, they showed excellent viability of normal human lung fibroblast cells MRC-5. We expect the facile surface modification strategy discussed here to be applicable to medical device manufacturing.

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“…Decomposition reactions typically start at around 120–150 °C. N -Oxides are therefore less thermostable than other zwitterions . They might thus not be compatible with common standard sterilization protocols.…”

Section: Polymeric N-oxides For Drug Conjugation and Surface Engineeringmentioning

confidence: 99%

Medicinal Chemistry of Drugs with N-Oxide Functionalities

Kobus,

Friedrich,

Zorn

et al. 2024

J. Med. Chem.

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Molecules with N-oxide functionalities are omnipresent in nature and play an important role in Medicinal Chemistry. They are synthetic or biosynthetic intermediates, prodrugs, drugs, or polymers for applications in drug development and surface engineering. Typically, the N-oxide group is critical for biomedical applications of these molecules. It may provide water solubility or decrease membrane permeability or immunogenicity. In other cases, the N-oxide has a special redox reactivity which is important for drug targeting and/or cytotoxicity. Many of the underlying mechanisms have only recently been discovered, and the number of applications of N-oxides in the healthcare field is rapidly growing. This Perspective article gives a short summary of the properties of N-oxides and their synthesis. It also provides a discussion of current applications of N-oxides in the biomedical field and explains the basic molecular mechanisms responsible for their biological activity. ■ SIGNIFICANCE Relevance of N-oxides for Medicinal Chemistry:• N + −O − bonds are highly polar and form strong hydrogen bonds. They may be inert or reactive in biological systems depending on their substituents.• N-Oxide groups can be used to increase the solubility of drugs and decrease membrane permeability.• Many heteroaromatic and aniline-derived N-oxides are reduced enzymatically in vivo and find applications as hypoxia-activated prodrugs.• Polymeric N-oxides have excellent blood compatibility, are nonimmunogenic and are nonadhesive for microorganisms (stealth materials).

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Low-Fouling and Antibacterial Polymer Brushes via Surface-Initiated Polymerization of a Mixed Zwitterionic and Cationic Monomer

Cited by 4 publications

References 72 publications

Poly(2-methoxyethyl acrylate)-grafted microfiltration membranes exhibiting low-fouling properties in the presence of salt species

Poly(2-methoxyethyl acrylate)-grafted microfiltration membranes exhibiting low-fouling properties in the presence of salt species

Mussel-Inspired Polymer-Based Coating Technology for Antifouling and Antibacterial Properties

Medicinal Chemistry of Drugs with N-Oxide Functionalities

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