PEG Grafted Polymethacrylates Bearing Antioxidants as a New Class of Polymer Conjugates for Application in Cosmetology

Odrobińska, Justyna; Neugebauer, Dorota

doi:10.3390/ma13163455

Cited by 5 publications

(8 citation statements)

References 47 publications

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“…The comparison of signal intensities in the 1 H NMR spectra provides further evidence for the formation of ester bonds between cellulose –OH groups and DDMAT carboxyl (–COOH) groups. The results showed after polymerization by PEGMA, the poly(PEGMA) peaks at (a) 1.2 ppm, (b) 1.8 ppm, (c) 3.4–3.5 ppm, and (d) 3.3 ppm. , This confirmed that all steps of synthesis were done successfully. Also, the ratio of PEGMA to cellulose was determined by using the integral calculation under the peak of about 1.2 ppm for poly(PEGMA) and about 4 ppm for cellulose.…”

Section: Resultssupporting

confidence: 57%

Investigation of the Effect of Poly[poly(ethylene glycol) methyl ether methacrylate] Addition on the Electrochemical Performance of Cellulose-Based Solid- and Gel-Polymer Electrolytes in Lithium-Ion Batteries

Safavi-Mirmahalleh,

Eliseeva,

Moghaddam

et al. 2023

ACS Appl. Energy Mater.

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Lithium-ion batteries based on polymer electrolytes have received much attention due to their potential for creating intrinsically safer and more flexible devices. However, their economic and environmental efficiency is one of the important issues in choosing materials to prepare these electrolytes. To overcome these problems, polymer electrolytes based on natural materials such as cellulose have been used due to their cheapness and availability, abundance, compatibility with the environment, and electrondonating groups in their structure. Also, cellulose modification by polymer is an important factor due to the increase of electron-donating groups and improvement of polymer electrolyte flexibility. In this study, a polymer electrolyte was synthesized by grafting ionconducting segments of poly(ethylene glycol) methyl ether methacrylate (PEGMA) onto cellulose through reversible addition-fragmentation chain-transfer (RAFT) polymerization. As a result, the increase in the PEGMA content led to enhanced ionic conductivity in both the solid and gel states. In solid-polymer electrolyte (SPE) samples, by increasing the PEGMA percentage from 10:1 (PEGMA/DDMAT) (DDMAT = 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid) to 90:1 (PEGMA/DDMAT), the ionic conductivity was increased from 3.9 × 10 −5 to 5.9 × 10 −4 S cm −1 , whereas some gel-polymer electrolyte (GPE) samples showed ionic conductivity values of 2.5 × 10 −4 and 2.4 × 10 −3 S cm −1 , respectively. Also, the prepared films presented good electrochemical properties, including considerable transference number (t + ) in the range of 0.35−0.80, a wide electrochemical stability window higher than 4.5 V, and good specific capacity (>330 mA h g −1 with capacity retention higher than 95% after 100 cycles at 0.2 C of LiCoO 2 /GPEs-SPEs/Gr).

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Section: Resultssupporting

confidence: 57%

Investigation of the Effect of Poly[poly(ethylene glycol) methyl ether methacrylate] Addition on the Electrochemical Performance of Cellulose-Based Solid- and Gel-Polymer Electrolytes in Lithium-Ion Batteries

Safavi-Mirmahalleh,

Eliseeva,

Moghaddam

et al. 2023

ACS Appl. Energy Mater.

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“…The differences in release profiles suggested the advantage of the "tailor-made" polymer carriers that could release the active substance under the appropriate conditions, which would depend on the specific use of the cosmetic or medical product. Comparing these micellar carriers with previously described conjugates also based on AlHEMA/MPEGMA copolymers, the latter ones bound less to the active substance, i.e., ferulic or lipoic acid (13-38%) [47]. Moreover, it took longer, up to 4 h, to release the usually lower amount of the conjugated bioactive molecules (~50%) than in the case of micelles.…”

Section: Resultsmentioning

confidence: 66%

Micellar Carriers Based on Amphiphilic PEG/PCL Graft Copolymers for Delivery of Active Substances

Odrobińska

Neugebauer

2020

Polymers

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Amphiphilic copolymers of alkyne functionalized 2-hydroxyethyl methacrylate (AlHEMA) and poly(ethylene glycol) methyl ether methacrylate (MPEGMA) with graft or V-shaped graft topologies were synthesized. The functionalization of poly(ε-caprolactone) (PCL) with azide group enabled attachment to P(AlHEMA-co-MPEGMA) copolymers via a “click” alkyne-azide reaction. The introduction of PCL as a second side chain type in addition to PEG resulted in heterografted copolymers with modified properties such as biodegradability. “Click” reactions were carried out with efficiencies between 17–70% or 32–50% (for lower molecular weight PCL, 4000 g/mol, or higher molecular weight PCL, 9000 g/mol, respectively) depending on the PEG grafting density. The graft copolymers were self-assembled into micellar superstructures with the ability to encapsulate active substances, such as vitamin C (VitC), arbutin (ARB) or 4-n-butylresorcinol (4nBRE). Drug loading contents (DLC) were obtained in the range of 5–55% (VitC), 39–91% (ARB) and 42–98% (4nBRE). In vitro studies carried out in a phosphate buffer saline (PBS) solution (at pH 7.4 or 5.5) gave the maximum release levels of active substances after 10–240 min depending on the polymer system. Permeation tests in Franz chambers indicated that the bioactive substances after release by micellar systems penetrated through the artificial skin membrane in small amounts, and a majority of the bioactive substances remained inside the membrane, which is satisfactory for most cosmetic applications.

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“…The resulting copolymers of alkyne-functionalized 2-hydroxyethyl methacrylate (AlHEMA) and methyl methacrylate (MMA) or poly(ethylene glycol) methyl ether methacrylate (MPEGMA), i.e., P(AlHEMA-co-MPEGMA) and P(AlHEMA-co-MMA), were subjected to a "click" reaction with azide functionalized polymers, i.e., biodegradable poly(ε-caprolactone) (PCL), hydrophilic poly(ethylene glycol) (PEG) or azide functionalized low-molecular weight active substances, such as FA and LA. PEG graft copolymers P((HEMA-graft-PEG)-co-MMA) [23] and P((HEMA-graft-PCL)-co-MPEGMA) [24] for micellar systems loaded with the active substance, i.e., ARB, and the conjugates varied with the "click" active substance such as P((HEMA-click-FA)-co-MPEGMA) and P((HEMA-click-LA)-co-MPEGMA) [25] were synthesized ( Figure 1). The active substances are classified as antioxidants and protect against UV radiation, reduce wrinkles and skin discoloration.…”

Section: Resultsmentioning

confidence: 99%

“…Spontaneously immortalized human epidermal keratinocytes (HaCaT) were purchased from CSL Cell Line Service GmbH (Eppelheim, Germany). Copolymers were synthesized and self-assembled to encapsulate active substance in aqueous solutions [23,24] or conjugated with FA and LA [25] according to previously described procedures.…”

Section: Methodsmentioning

confidence: 99%

“…These polymers showed the ability to self-assemble into micellar structures and encapsulate substances, such as arbutin (ARB). PEG graft polymers were conjugated with ferulic acid (FA) and lipoic acid (LA) [25]. An additional benefit of these polymers is the presence of retinol or 4-n-butylresorcinol as the terminal or center unit in the main chain, as it was also postulated for linear polymethacrylates [26,27].…”

Section: Introductionmentioning

confidence: 99%

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PEG Graft Polymer Carriers of Antioxidants: In Vitro Evaluation for Transdermal Delivery

2020

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The in vitro biochemical evaluation of the applicability of polymers carrying active substances (micelles and conjugates) was carried out. Previously designed amphiphilic graft copolymers with retinol or 4-n-butylresorcinol functionalized polymethacrylate backbone and poly(ethylene glycol) (PEG) side chains that included Janus-type heterografted copolymers containing both PEG and poly(ε-caprolactone) (PCL) side chains were applied as micellar carriers. The polymer self-assemblies were convenient to encapsulate arbutin (ARB) as the selected active substances. Moreover, the conjugates of PEG graft copolymers with ferulic acid (FA) or lipoic acid (LA) were also investigated. The permeability of released active substances through a membrane mimicking skin was evaluated by conducting transdermal tests in Franz diffusion cells. The biological response to new carriers with active substances was tested across cell lines, including normal human dermal fibroblasts (NHDF), human epidermal keratinocyte (HaCaT), as well as cancer melanoma (Me45) and metastatic human melanoma (451-Lu), for comparison. These polymer systems were safe and non-cytotoxic at the tested concentrations for healthy skin cell lines according to the MTT test. Cytometric evaluation of cell cycles as well as cell death defined by Annexin-V apoptosis assays and senescence tests showed no significant changes under action of the delivery systems, as compared to the control cells. In vitro tests confirmed the biochemical potential of these antioxidant carriers as beneficial components in cosmetic products, especially applied in the form of masks and eye pads.

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PEG Grafted Polymethacrylates Bearing Antioxidants as a New Class of Polymer Conjugates for Application in Cosmetology

Cited by 5 publications

References 47 publications

Investigation of the Effect of Poly[poly(ethylene glycol) methyl ether methacrylate] Addition on the Electrochemical Performance of Cellulose-Based Solid- and Gel-Polymer Electrolytes in Lithium-Ion Batteries

Investigation of the Effect of Poly[poly(ethylene glycol) methyl ether methacrylate] Addition on the Electrochemical Performance of Cellulose-Based Solid- and Gel-Polymer Electrolytes in Lithium-Ion Batteries

Micellar Carriers Based on Amphiphilic PEG/PCL Graft Copolymers for Delivery of Active Substances

PEG Graft Polymer Carriers of Antioxidants: In Vitro Evaluation for Transdermal Delivery

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