Patterned Polypeptoid Brushes

Schneider, Maximilian; Tang, Zian; Richter, Marcus; Marschelke, Claudia; Forster, Paul M.; Wegener, Erik; Amin, Ihsan; Zimmermann, Heike; Scharnweber, Dieter; Braun, Hans‐Georg; Luxenhofer, Robert; Jordan, Rainer

doi:10.1002/mabi.201500314

Cited by 34 publications

(29 citation statements)

References 56 publications

(67 reference statements)

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“…This structural difference implies the absence of intermolecular hydrogen bonds which results in an enhanced thermal and solution processability with respect to most biopolymers. SAMs of polypeptoids and glycopeptoids have been reported to significantly reduce the attachment of non‐specific proteins, cells and bacteria …”

Section: Amphiphilic Polypeptides and Peptide‐mimic Polymersmentioning

confidence: 99%

Amphiphilic Polymer Platforms: Surface Engineering of Films for Marine Antibiofouling

Galli

Martinelli

2017

Macromol. Rapid Commun.

119

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A range of amphiphilic polymers with diverse macromolecular architectures has been developed and incorporated into films and coatings with potential for marine antibiofouling applications, without resorting to addition of currently used biocidal, toxic agents. Novel "green" chemical technologies employ different building blocks to endow the polymer film with surface activity, functionality, structure, and reconstruction according to the outer environment as a result of a tailored amphiphilic character of the polymer platform. We emphasise how these features can interplay and add synergistically to affect antifouling and fouling-release against common, widespread marine micro- and macro-fouling organisms.

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Section: Amphiphilic Polypeptides and Peptide‐mimic Polymersmentioning

confidence: 99%

Amphiphilic Polymer Platforms: Surface Engineering of Films for Marine Antibiofouling

Galli

Martinelli

2017

Macromol. Rapid Commun.

119

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“…46,47 We therefore base our study on peptoid brushes that have previously been shown experimentally to exhibit excellent antifouling properties. 18,[48][49][50][51][52] In particular, we simulate the behavior of a zwitterionic peptoid containing pairs of residues with oppositely charged sidechains interspaced between uncharged residues, which was previously shown to exhibit lower protein adsorption and E. coli attachment than an uncharged counterpart at low to intermediate grafting densities. 18 Special attention is paid to the balance between charge, hydration, and molecular volume and chain density effects.…”

Section: Introductionmentioning

confidence: 99%

Atomistic Study of Zwitterionic Peptoid Antifouling Brushes

Cheung

Lau

2018

Langmuir

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Using molecular dynamics (MD) simulations, we study the molecular behavior and hydration properties of a set of zwitterionic "peptoid" brushes, grafted on a rutile surface, that has been previously reported to exhibit excellent resistance against protein adsorption and cell attachment. Peptoids are novel poly( N-substituted glycine) peptide mimics with the side chains attached to amide nitrogens. They constitute a unique model polymer system because hundreds of side chains have been demonstrated, and the exact chain length and sequence order of the residues/monomers may be specified in experiments. In this report, we vary the brush grafting density as well as the side chain/polymer molecular volume. We include in our study polysarcosine as an uncharged comparison with a small polymer chain cross-section. Sarcosine is the simplest peptoid residue with only a nominally hydrophobic methyl group as side chain, but is also reported to exhibit high antifouling performance. Overall, we show in detail how molecular volume and hydration effects are intertwined in a zwitterionic polymer brush. For example, the zwitterionic design significantly promotes extended chain conformations and could actually lower the overall electrostatic potential. Some properties promoted by the balanced charges, such as chain flexibility and hydration, increase more prominently at "low" to "intermediate" chain densities. These and other observations should provide insight on the molecular behavior of peptoids and inform the design of zwitterionic antifouling polymer brushes.

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“…This hybrid system combines the stealth‐like properties of polysarcosine with the multifunctionality of synthetic polypeptides . Polysarcosine has proven to be a highly protein‐resistant material, which is able to introduce stealth‐like properties to nano‐ or macroscopic surfaces, indicating to be an alternative to polyethylene glycol (PEG) . Polypept(o)ides are easily accessible by sequential nucleophilic ring opening polymerization (ROP) of α‐amino acid N ‐carboxyanhydrides (NCAs) and correspondingly of the N ‐substituted glycine N ‐carboxyanhydride (NNCA) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Stimuli‐Responsive Star‐Like Polypept(o)ides: Introducing Biodegradable PeptoStars

Holm

Weber

Heller

et al. 2017

Macromolecular Bioscience

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Star-like polymers are one of the smallest systems in the class of core crosslinked polymeric nanoparticles. This article reports on a versatile, straightforward synthesis of three-arm star-like polypept(o)ide (polysarcosine-block-polylysine) polymers, which are designed to be either stable or degradable at elevated levels of glutathione. Polypept(o)ides are a recently introduced class of polymers combining the stealth-like properties of the polypeptoid polysarcosine with the functionality of polypeptides, thus enabling the synthesis of materials completely based on endogenous amino acids. The star-like homo and block copolymers are synthesized by living nucleophilic ring opening polymerization of the corresponding N-carboxyanhydrides (NCAs) yielding polymeric stars with precise control over the degree of polymerization (X = 25, 50, 100), Poisson-like molecular weight distributions, and low dispersities (Đ = 1.06-1.15). Star-like polypept(o)ides display a hydrodynamic radius of 5 nm (μ < 0.05) as determined by dynamic light scattering (DLS). While star-like polysarcosines and polypept(o)ides based on disulfide containing initiators are stable in solution, degradation occurs at 100 × 10 m glutathione concentration. The disulfide cleavage yields the respective polymeric arms, which possess Poisson-like molecular weight distributions and low dispersities (Đ = 1.05-1.12). Initial cellular uptake and toxicity studies reveal that PeptoStars are well tolerated by HeLa, HEK 293, and DC 2.4 cells.

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Patterned Polypeptoid Brushes

Cited by 34 publications

References 56 publications

Amphiphilic Polymer Platforms: Surface Engineering of Films for Marine Antibiofouling

Amphiphilic Polymer Platforms: Surface Engineering of Films for Marine Antibiofouling

Atomistic Study of Zwitterionic Peptoid Antifouling Brushes

Synthesis and Characterization of Stimuli‐Responsive Star‐Like Polypept(o)ides: Introducing Biodegradable PeptoStars

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