Layer-by-Layer Hydrogen-Bonded Antioxidant Films of Linear Synthetic Polyphenols

Hlushko, Raman; Ankner, John F.; Sukhishvili, Svetlana A.

doi:10.1021/acs.macromol.9b02512

Cited by 16 publications

(29 citation statements)

References 73 publications

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“…Oxidized EGCG by tyrosinase can be coupled with primary amines on the glycol chitosan. However, upon completion of hydrogel formation, unconjugated or unreacted EGCGs may be retained within the hydrogel structure [ 31 , 32 ]. These EGCGs may be entrapped within a cross-linked hydrogel network and are prone to sustained release from the hydrogel (via diffusion).…”

Section: Discussionmentioning

confidence: 99%

Enzyme-mediated one-pot synthesis of hydrogel with the polyphenol cross-linker for skin regeneration

Kim

et al. 2020

Materials Today Bio

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Polyphenols can trigger immunity that activates intracellular anti-inflammatory signaling and prevents external infections. In this study, we report the fabrication of chitosan-based hydrogels with epigallocatechin gallate (EGCG) using enzyme-mediated one-pot synthesis. The tyrosinase-mediated oxidative reaction of the phenolic rings of EGCG with the primary amines on chitosan results in stable EGCG-chitosan hydrogels. The EGCG concentrations contributed to the cross-linking density and physical properties of EGCG-chitosan hydrogels. Furthermore, EGCG-chitosan hydrogels maintained intrinsic properties such as antibacterial and antioxidant effects. When endotoxin-activated RAW 264.7 macrophage cells were cultured with EGCG-chitosan hydrogels, the hydrogels reduced the inflammatory response of the RAW 264.7 cells. Furthermore, subcutaneous implantation of EGCG-chitosan hydrogels reduced endogenous macrophage and monocyte activation. When the EGCG-chitosan hydrogels were applied to a full-skin defect wound, they facilitated skin regeneration. Our study demonstrates that the one-pot synthesized EGCG-chitosan hydrogels can be applied in broad tissue regeneration applications that require immune modulation.

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Section: Discussionmentioning

confidence: 99%

Enzyme-mediated one-pot synthesis of hydrogel with the polyphenol cross-linker for skin regeneration

Kim

et al. 2020

Materials Today Bio

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“…Ji et al [50] prepared ciprofloxacin/ polyallylamine hydrochloride/SiO 2 /polyallylamine hydrochloride (abbreviated as CIP/PAH/SiO 2 /PAH) multilayers on the surface of AZ31 Mg alloy by spin-spray LbL assembly. The presence of SiO 2 NPs not only improved the corrosion resistance of the substrate, but also endowed the coating with self-healing properties in which the particles can locate and effectively diffuse to the area of nanoscale cracks to repair the damaged regions [51]. The degradable graphene oxide (GO) is another optional assembly unit to improve corrosion resistance due to its high aspect ratio.…”

Section: Reviewmentioning

confidence: 99%

“…SCIENCE CHINA Materials functional films by this assembly technique has also been studied in many fields [51,59]. Nevertheless, there are few reports on preparing hydrogen bonding-driven LbLassembled coating on Mg alloys.…”

Section: Reviewmentioning

confidence: 99%

“…It is envisioned that in future studies, a novel biomedical coating could be developed using the influence of pH value and other factors on hydrogen bonding. When the patient recovers, a slight increase in pH value will lead to the failure of "hydrogen bond coating" and accelerate the degradation of Mg implants, so as to achieve the effect of both the recovery of the patient and the degradation of the implant [51,58,59].…”

Section: Reviewmentioning

confidence: 99%

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Advances in layer-by-layer self-assembled coatings upon biodegradable magnesium alloys

Shao

et al. 2021

Sci. China Mater.

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Magnesium (Mg) and its alloys are considered as ideal biodegradable materials due to their excellent mechanical properties and biocompatibility. In order to improve the surface properties to allow better adaptation to the surrounding tissue of the body, surface modification has played a significant role in satisfying multiple clinical requirements such as corrosion resistance, biocompatibility, and antibacterial ability. Here, layer-by-layer (LbL) self-assembly, which can be applied for biodegradable Mg alloys due to its extensive choice of usable units, holds great promise among all the surface techniques. In this review, the mechanisms of the driving force (i.e., electrostatic interaction, hydrogen bonding, charge transfer interaction and covalent bonding), cuttingedge advances in preparation methods (e.g., dipping, spraying, and spinning) and the functional properties (corrosion resistance, antibacterial activity, and biocompatibility) that could be achieved by the LbL coatings are summarized. A reasonable trend of the potential development of LbL for bio-Mg alloys is also proposed at the end of this article.

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“…51,52 We demonstrated that the structure of the polyphenol rings has a strong effect on the film growth regime, film internal structure, and the ability of these assemblies to scavenge radicals. 53 In this work, we aim to understand the underlying dynamics driving these behaviors. Using NR to track infusion of deuterated PEO chains into linear and exponential hydrogen-bonded LbL films, in situ ellipsometry to monitor kinetics of mass deposition during film construction, and AFM to track healing of tip-indented films upon exposure to water, we have uncovered differences in chain diffusivity between film components during film construction and correlate these with the film growth mode and the structure of the polyphenol ring in hydrogen-bonded linear polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

Dynamics and Self-Healing of Layer-by-Layer Hydrogen-Bonded Films of Linear Synthetic Polyphenols

2021

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This work explores the dynamics of hydrogen-bonded layer-by-layer (LbL) films of linear synthetic polyphenols (lPPh’s) with different backbone and pendant group structures. The polymers feature repeat units with catechol-like or gallol-like polyphenol rings, namely, poly(3,4-dihydroxybenzyl methacrylamide) (P2HMA), poly(3,4-dihydroxybenzyl acrylamide) (P2HAA), poly(3,4,5-trihydroxybenzyl acrylamide) (P3HAA), and poly(3,4,5-trihydroxybenzyl methacrylamide) (P3HMA), and were assembled with linear poly(ethylene oxide) (PEO). The structure of the lPPh’s has a major effect on the diffusivity of LbL films, and chain dynamics is asymmetric for lPPh- and PEO-terminated films during film construction. Specifically, diffusivity of polyphenols in the direction perpendicular to the substrate varied from values below ∼10–17 cm2 s–1 to ∼10–14 cm2 s–1 for lPPh’s of the P2 and P3 families, as assessed by in situ ellipsometry during film assembly. The uptake of the most diffusive P3HMA exhibits subdiffusive behavior with an anomalous diffusion exponent β ≈ 0.3. Similarly, large differences in film dynamics were revealed by neutron reflectometry, which detected fast penetration of deuterated PEO (dPEO) through the entire film with a diffusion coefficient >10–12 cm2 s–1 through P3HMA/PEO films but accumulation of dPEO only at the film surface for all other lPPh/PEO systems during the first 10 min of exposure to dPEO. The observed trends in film dynamics were consistent with strongly exponential growth of P3HMA/PEO films and largely linear deposition of nondiffusive P2/PEO systems. Finally, the self-healing behavior of lPPh/PEO films in an aqueous environment was quantified by in situ atomic force microscopy experiments, which revealed robust self-healing of P3/PEO films occurring on a time scale of minutes and an absence of film healing for P2/PEO films.

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Layer-by-Layer Hydrogen-Bonded Antioxidant Films of Linear Synthetic Polyphenols

Cited by 16 publications

References 73 publications

Enzyme-mediated one-pot synthesis of hydrogel with the polyphenol cross-linker for skin regeneration

Enzyme-mediated one-pot synthesis of hydrogel with the polyphenol cross-linker for skin regeneration

Advances in layer-by-layer self-assembled coatings upon biodegradable magnesium alloys

Dynamics and Self-Healing of Layer-by-Layer Hydrogen-Bonded Films of Linear Synthetic Polyphenols

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