Reducing Escherichia coli growth on a composite biomaterial by a surface immobilized antimicrobial peptide

Buckholtz, Gavin A.; Reger, Nina; Anderton, William D.; Schimoler, Patrick J.; Roudebush, Shana L.; Meng, Wilson S.; Miller, Mark Carl; Gawalt, Ellen S.

doi:10.1016/j.msec.2016.04.021

Cited by 16 publications

(6 citation statements)

References 58 publications

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“…In fact, as mentioned in the introduction, norbornene is one of the most reactive enes within the thiol–ene reactions, and it has been found to undergo quantitative reaction even at very low concentrations as polymer end groups . Previous reports describe peptide conjugation (EPL-chitosan and AMP-dextran) in a 12 h reaction under UV light (365 nm, 20 mW cm –2 ) at RT. , Elsewhere, immobilization of cysteine-modified AMP (Inverso-CysHHC10, 1 mg mL –1 ) directly onto hydroxyapatite (HA) discs modified with an alkene-terminating organic acid (16-heptadecenoic acid) film was performed over 3 h under UV light and in the presence of Irgacure 2959, under inert conditions; this resulted in an AMP content of 8850 μg (around 5.8 μmol) per gram of modified HA . More recently, when using norbornene as an alkene donor, HHC10-Cys was linked to oxynorbornene modified alginate hydrogels using 5 min of a UV-triggered reaction on each side of the hydrogel, after a lengthy 24 h soaking step of the hydrogel in the AMP solution (1–4 mg mL –1 ), to allow the AMP to infiltrate within the hydrogel mesh .…”

Section: Resultsmentioning

confidence: 99%

“…40,41 Elsewhere, immobilization of cysteine-modified AMP (Inverso-CysHHC10, 1 mg mL −1 ) directly onto hydroxyapatite (HA) discs modified with an alkene-terminating organic acid (16heptadecenoic acid) film was performed over 3 h under UV light and in the presence of Irgacure 2959, under inert conditions; this resulted in an AMP content of 8850 μg (around 5.8 μmol) per gram of modified HA. 44 More recently, when using norbornene as an alkene donor, HHC10-Cys was linked to oxynorbornene modified alginate hydrogels using 5 min of a UV-triggered reaction on each side of the hydrogel, after a lengthy 24 h soaking step of the hydrogel in the AMP solution (1−4 mg mL −1 ), to allow the AMP to infiltrate within the hydrogel mesh. 45 The amount of initial AMP retained within the hydrogels varied between 91% and 37.5% depending on AMP concentration in solution.…”

Section: Resultsmentioning

confidence: 99%

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Thiol–Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials

Alves

Pereira

Costa

et al. 2022

ACS Appl. Polym. Mater.

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Covalent conjugation of antimicrobial peptides (AMP) is considered an effective approach to overcome their potential degradation in vivo. As the high cost of AMP-based therapies is one of the major hurdles toward their clinical application, it is urgently needed to explore high yield reactions. Herein, the highly efficient thiol–norbornene photoclick chemistry (TNPC) was explored for AMP grafting onto chitosan. Norbornenes were introduced onto chitosan (NorChit) in an aqueous/organic system, followed by UV-triggered conjugation of N- and C-terminus cysteine-modified Dhvar5 (NorChit-Dhvar5). Up to 0.38 norbornene groups per chitosan repeating unit and up to 43% conjugation yield in NorChit-Nt-Dhvar5 (80 μmol of Dhvar5/g) were achieved, while in NorChit-Ct-Dhvar5 conjugation yield was 30% (55 μmol of Dhvar5/g). Finally, NorChit-Dhvar5 ultrathin films showed up to a 35% reduction of total adhered Gram-positive Staphylococcus epidermidis and increased the adhesion and killing of Gram-negative Pseudomonas aeruginosa compared to unmodified chitosan. Moreover, NorChit-Dhvar5 was noncytotoxic to human neonatal dermal fibroblasts, according to ISO 10993-1. Overall, our findings indicate TNPC as a high yield strategy for AMP grafting onto norbornene-functionalized biopolymers toward the fabrication of antibacterial biomaterials.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Thiol–Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials

Alves

Pereira

Costa

et al. 2022

ACS Appl. Polym. Mater.

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“…As a positive control, amoxicillin only damaged bacterial cell walls of H. pylori, while cell membranes remained intact. Additionally, NPN bound to a phospholipid of the H. pylori cell membrane and produced blue fluorescence, which could be used to determine the degree of damage to bacterial cell membranes (39). With increasing concentrations of hydrogen peroxide, the intensity of blue fluorescence also increased, indicating that bacterial cell membranes of H. pylori were ruptured.…”

Section: Discussionmentioning

confidence: 99%

Hydrogen Peroxide-Mediated Oxygen Enrichment Eradicates Helicobacter pylori In Vitro and In Vivo

Dounan

Zhang

Cao

et al. 2020

Antimicrob Agents Chemother

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Helicobacter pylori is an important risk factor for gastric ulcers. However, antibacterial therapies increase the resistance rate and decrease the eradication rate of H. pylori. Inspired by the microaerophilic characteristics of H. pylori, we aimed at effectively establishing an oxygen-enriched environment to eradicate and prevent the recurrence of H. pylori. The effect and the mechanism of an oxygen-enriched environment in eradicating H. pylori and preventing the recurrence were explored in vitro and in vivo. During oral administration and after drug withdrawal, H. pylori counts were evaluated by Giemsa staining in animal cohorts. An oxygen-enriched environment in which H. pylori could not survive was successfully established by adding hydrogen peroxide into several solutions and rabbit gastric juice. Hydrogen peroxide effectively killed H. pylori in Columbia blood agar and special peptone broth. Minimum inhibition concentrations and minimum bactericidal concentrations of hydrogen peroxide were both relatively stable after promotion of resistance for 30 generations, indicating that hydrogen peroxide did not easily promote resistance in H. pylori. In models of Mongolian gerbils and Kunming mice, hydrogen peroxide has been shown to significantly eradicate and effectively prevent the recurrence of H. pylori without toxicity and damage to the gastric mucosa. The mechanism of hydrogen peroxide causing H. pylori death was related to the disruption of bacterial cell membranes. The oxygen-enriched environment achieved by hydrogen peroxide eradicates and prevents the recurrence of H. pylori by damaging bacterial cell membranes. Hydrogen peroxide thus provides an attractive candidate for anti-H. pylori treatment.

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“…[25,34] While the use of thiol-mediated coupling strategies has been previously reported for the chemical attachment of AMPs, many of these are tethered to bulk materials or supports such as hydrogels, [35,36] fibers, [37] or metals/ceramics. [38,39] Immobilization to colloidal particles on the other hand affords the therapeutic agent to be incorporated in other materials, or to be deposited onto a surface as a coating, [18] or added to other systems containing colloids presenting other biological signals. [40] As such, the results presented herein use thiol-mediated conjugation reactions for the tethering of PEG and AMPs to silica microparticles, while assessing immobilization efficiency and antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Enhancing the Activity of Surface Immobilized Antimicrobial Peptides Using Thiol‐Mediated Tethering to Poly(ethylene glycol)

Boden

Dart

Liao

et al. 2023

Macromolecular Bioscience

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Considering the need for versatile surface coatings that can display multiple bioactive signals and chemistries, the use of more novel surface modification methods is starting to emerge. Thiol‐mediated conjugation of biomolecules is shown to be quite advantageous for such purposes due to the reactivity and chemoselectivity of thiol functional groups. Herein, the immobilization of poly(ethylene glycol) (PEG) and antimicrobial peptides (AMPs) to silica colloidal particles based on thiol‐mediated conjugation techniques, along with an assessment of the antimicrobial potential of the functionalized particles against Pseudomonas aeruginosa and Staphylococcus aureus is investigated. Immobilization of PEG to thiolated Si particles is performed by either a two‐step thiol–ene “photo‐click” reaction or a “one‐pot” thiol–maleimide type conjugation using terminal acrylate or maleimide functional groups, respectively. It is demonstrated that both immobilization methods result in a significant reduction in the number of viable bacterial cells compared to unmodified samples after the designated incubation periods with the PEG‐AMP‐modified colloidal suspensions. These findings provide a promising outlook for the fabrication of multifunctional surfaces based upon the tethering of PEG and AMPs to colloidal particles through thiol‐mediated biocompatible chemistry, which has potential for use as implant coatings or as antibacterial formulations that can be incorporated into wound dressings to prevent or control bacterial infections.

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Reducing Escherichia coli growth on a composite biomaterial by a surface immobilized antimicrobial peptide

Cited by 16 publications

References 58 publications

Thiol–Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials

Thiol–Norbornene Photoclick Chemistry for Grafting Antimicrobial Peptides onto Chitosan to Create Antibacterial Biomaterials

Hydrogen Peroxide-Mediated Oxygen Enrichment Eradicates Helicobacter pylori In Vitro and In Vivo

Enhancing the Activity of Surface Immobilized Antimicrobial Peptides Using Thiol‐Mediated Tethering to Poly(ethylene glycol)

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