Amphiphilic copolymers containing 2-hydroxyethyl methacrylate (HEMA) and methyl methacrylate (MMA) units were synthesized by controlled atom transfer radical polymerization (ATRP) applying bromoester modified retinol (RETBr) as a novel initiator. Analogous series of copolymers with adjustable hydrophilic-hydrophobic balance was obtained with the use of a standard initiator, i.e. ethyl α-bromoisobutyrate (EBriB). The self-assembling particles, prepared by the solvent evaporation, were loaded with vitamin C (VitC) or ferulic acid (FA). The hydrophilic/hydrophobic ratio in the copolymer was indicated as a crucial factor to regulate efficiencies of encapsulation processes in the range of 53-98%. In vitro release of bioactive substance was carried out in phosphate buffer solution (PBS) at pH 7.4 with the maximum amount of VitC after 1h (27-62%) or FA within 2 h (71-97%). The polymeric systems with satisfactory encapsulation characteristics and release profiles are attractive micellar carriers of antioxidants, which, due to their activities could be also delivered using the popular approaches in cosmetology like masks, under-eye patches, or wraps.
The new polymeric systems for delivery in cosmetology applications were prepared using self-assembling amphiphilic graft copolymers. The synthesis based on “click” chemistry reaction included grafting of azide-functionalized polyethylene glycol (PEG-N3) onto multifunctional polymethacrylates containing alkyne units. The latter ones were obtained via atom transfer radical polymerization (ATRP) of alkyne-functionalized monomers, e.g., ester of hexynoic acid and 2-hydroxyethyl methacrylate (AlHEMA) with methyl methacrylate (MMA), using bromoester-modified retinol (RETBr) as the initiator. Varying the content of alkyne moieties adjusted by initial monomer ratios of AlHEMA/MMA was advantageous for the achievement of a well-defined grafting degree. The designed amphiphilic graft copolymers P((HEMA-graft-PEG)-co-MMA), showing tendency to micellization in aqueous solution at room temperature, were encapsulated with arbutin (ARB) or vitamin C (VitC) with high efficiencies (>50%). In vitro experiments carried out in the phosphate-buffered saline solution (PBS) at pH 7.4 indicated the maximum release of ARB after at least 20 min and VitC within 10 min. The fast release of the selected antioxidants and skin-lightening agents by these micellar systems is satisfactory for applications in cosmetology, where they can be used as the components of masks, creams, and wraps.
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