Immobilization of an antimicrobial peptide on silicon surface with stable activity by click chemistry

He, Jingcai; Chen, Junjian; Hu, Guoqing; Wang, Lin; Zheng, Jian‐Guo; Zhan, Jiezhao; Zhu, Yuan; Zhong, Chunting; Shi, Xuetao; Liu, Sa; Wang, Yingjun; Li, Ren

doi:10.1039/c7tb02557b

Cited by 60 publications

(42 citation statements)

References 49 publications

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“…One such peptoid has also been synthesized as part of a surface grafted peptoid brush but a high level of overall bacterial attachment was observed . Natural AMPs such as hLf1‐11, LL‐37, and melamine have also been immobilized with varying results . These studies apply bioconjugation techniques such as maleimide‐thiol, amide, and alkyne–azide „click“ coupling to enable covalent surface immobilization.…”

Section: Figurementioning

confidence: 99%

“…PEG attachment was verified both by further increases of this C−O peak arising from the abundance of ether bonds in PEG, and by the appearance of the N1s N−C peak (401 eV) arising from the terminal amine of the PEG used (Figure B). Subsequent azide derivatization was confirmed by the appearance of a N−N=N − peak at 402.3 eV . Final peptoid coupling was confirmed by the substantial increase in peaks attributed to (kss) 4 : C1s C−C (284.8 eV) and amide (288.3 eV), and N1s N−C=O (399.5 eV) and NH 2 (400.8 eV) .…”

Section: Figurementioning

confidence: 99%

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Surface Design for Immobilization of an Antimicrobial Peptide Mimic for Efficient Anti‐Biofouling

Hasan

Lee

Tewari

et al. 2020

Chemistry A European J

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Microbial surface attachmentn egatively impacts aw ide range of devices from waterp urification membranes to biomedical implants. Mimics of antimicrobial peptides (AMPs) constituted from poly(N-substituted glycine) "peptoids" are of great interestast hey resist proteolysis andc an inhibitawide spectrum of microbes. We investigate how terminal modification of ap eptoid AMPmimic and its surface immobilization affect antimicrobial activity.W ea lso demonstrate ac onvenient surface modification strategyf or enablinga lkyne-azide "click" coupling on amino-functionalized surfaces. Our resultsv erifiedt hat the N-and C-terminal peptoid structures are not required for antimicrobiala ctivity.M oreover,o ur peptoid immobilization density and choice of PEG tether resulted in a "volumetric" spatials eparation between AMPst hat, compared to past studies,e nabledt he highest AMP surface activity relativet ob acterial attachment. Our analysis suggests the importance of spatialf lexibility for membrane activity and that AMP separation may be ac ontrolling parameterf or optimizing surface anti-biofouling.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Surface Design for Immobilization of an Antimicrobial Peptide Mimic for Efficient Anti‐Biofouling

Hasan

Lee

Tewari

et al. 2020

Chemistry A European J

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“…Therefore, new technologies are greatly demanded to solve the above‐mentioned disadvantages. So far, researchers have witnessed the advancement of antimicrobial polymer coatings to prevent microorganisms' adhesion and proliferation for combating BAI, by various approaches such as self‐assembly interactions, in situ surface immobilization, chemical vapor deposition, and plasma‐assisted surface grafting . However, the preparation of these coatings usually involves complicated steps, expensive materials, or harsh water/oxygen‐free environment .…”

Section: Methodsmentioning

confidence: 99%

Mussel‐Inspired, Surface‐Attachable Initiator for Grafting of Antimicrobial and Antifouling Hydrogels

Feng

et al. 2019

Macromol. Rapid Commun.

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In this work, a novel biomimetic surface‐attachable initiator is successfully synthesized by the conjugation of 3,4‐dihydroxyphenylacetic acid and thermal 2,2′‐azobis(2‐methylpropionamide) dihydrochloride (V‐50). The synthesized initiator (DOPV) can adhere to various material surfaces in a mussel‐inspired way and initiate the surface grafting polymerization. Hydrogel coatings are facilely prepared by the thermal‐initiated radical copolymerization of antimicrobial polyhexamethylene guanidine and antifouling polyethylene glycol oligomers. The developed hydrogel coatings not only show antimicrobial activity toward gram‐negative and gram‐positive bacteria but also demonstrate protein resistance, antibiofilm efficacy, hemocompatibility, and low cytotoxicity in vitro. Most importantly, the hydrogel coatings reveal excellent antimicrobial efficacy with a log reduction above 5 in a rodent subcutaneous infection model. These results demonstrate the potential fabrication of bio‐functional coatings for biomedical devices or implants through an inexpensive, facile, and environmentally friendly mussel‐inspired technique.

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“…The surface modification spans from chemical functionalization with small molecules that serve as initiators or reactive braces for self‐assembled monolayers (SAM). Common functionalization is based on highly reactive molecules that undergo high yielding chemistry, such as EDC/NHS, “Click,” thiol–ene, and Sn2 chemistry . Since the polymer chains are produced in advance, high control over the brush thickness is achieved by controlling the chain length.…”

Section: Planar Membrane Fabricationmentioning

confidence: 99%

“…The “grafting to” method generally relays on thinner and more flexible chains, that react with the surface in high yielding reactions, which are commonly “click” reactions (Figure A) . In fewer cases, “Click” chemistry has also been used in the grafting of bulkier macromolecules like dendrimers or hyper branched polymers to a surface .…”

Section: Planar Membrane Fabricationmentioning

confidence: 99%

Self‐Assembled Polymeric Membranes and Nanoassemblies on Surfaces: Preparation, Characterization, and Current Applications

Chimisso

Maffeis

Hürlimann

et al. 2019

Macromolecular Bioscience

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Biomembranes play a crucial role in a multitude of biological processes, where high selectivity and efficiency are key points in the reaction course. The outstanding performance of biological membranes is based on the coupling between the membrane and biomolecules, such as membrane proteins. Polymer‐based membranes and assemblies represent a great alternative to lipid ones, as their presence not only dramatically increases the mechanical stability of such systems, but also opens the scope to a broad range of chemical functionalities, which can be fine‐tuned to selectively combine with a specific biomolecule. Tethering the membranes or nanoassemblies on a solid support opens the way to a class of functional surfaces finding application as sensors, biocomputing systems, molecular recognition, and filtration membranes. Herein, the design, physical assembly, and biomolecule attachment/insertion on/within solid‐supported polymeric membranes and nanoassemblies are presented in detail with relevant examples. Furthermore, the models and applications for these materials are highlighted with the recent advances in each field.

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Immobilization of an antimicrobial peptide on silicon surface with stable activity by click chemistry

Abstract: We click an antimicrobial peptide onto a silicon substrate to protect it from enzymolysis using a polySBMA spacer.

Cited by 60 publications

References 49 publications

Surface Design for Immobilization of an Antimicrobial Peptide Mimic for Efficient Anti‐Biofouling

Surface Design for Immobilization of an Antimicrobial Peptide Mimic for Efficient Anti‐Biofouling

Mussel‐Inspired, Surface‐Attachable Initiator for Grafting of Antimicrobial and Antifouling Hydrogels

Self‐Assembled Polymeric Membranes and Nanoassemblies on Surfaces: Preparation, Characterization, and Current Applications

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