Hydrophilic acrylic biomaterials derived from vitamin E with antioxidant properties

Abstract

Hydrogels based on polymeric derivatives of vitamin E for biomedical purposes have been prepared by copolymerization reaction of the alpha-tocopheryl methacrylate (V) with 2-hydroxyethyl methacrylate (H) in a range of composition between 5-20 wt % of V. The swelling behavior of the hydrogels in water, alkaline, and acidic media showed a slight decrease in the equilibrium water content with the content of V in the copolymer although in all cases it was superior to an EWC > 20%. The diffusion mechanism followed a Fickian behavior in all media. The values of the diffusion coefficients were in the range 2.5-1.6 10(-7) cm2/s. The states of water in the hydrogels were determined by DSC. A decrease in the content of freezing water was obtained with the V content for all media, and for all compositions lower values of freezing water were obtained in acidic or basic pHs than in distilled water. The copolymeric xerogels, analyzed by contact angle measurements, deviated from those expected taking into consideration those of the homopolymers and the average fraction of the monomers in the copolymer. The polar contribution dropped with the introduction of a small content (4 wt %) of the vitamin E-containing monomer, and it reached a value similar to that of poly-V for a composition of 49 wt % of V in the copolymer. This behavior is accounted for by the segregation of the macromolecular chains of both kinds of monomers, due mainly to differences in their polarity, molecular weights, and the reactivity of both monomers. Finally, thermogravimetric analysis showed a higher thermal (antioxidant) stability of the poly-V with respect to poly-H, giving rise to a residue of 18 wt %. The V-containing copolymers also showed an improved stability (antioxidant behavior), indicating the possibility of the V unit's interfering with the oxidative process, based on free-radical species, and, therefore, with the aging process at the cellular level.

Polystyrene surface coated with vitamin E modulates human granulocyte adhesion and MMP-9 release

“…The Vit.E anti-oxidative and anti-inflammatory properties have been extensively utilized to improve the biostability and the biocompatibility of different biomaterials. In fact Vit.E has been used in the production of amphiphilic monomers [11] and it has been added to different biocompatible materials such as poly(etherurethane urea) elastomers [12], acrylic bone cements [13], and recently to ultrahigh molecular weight polyethylene [14]. Another important application of Vit.E is the production of Vit.E-modified dialysis cellulose membrane for hemodialysis [15] to reduce the neutrophil activation induced by cellulose contact [16][17][18].…”

From Natural Products to Polymeric Derivatives of “Eugenol”: A New Approach for Preparation of Dental Composites and Orthopedic Bone Cements

“…All these results indicate that the eugenyl side residue is very active as scavenger of the free radicals produced during the thermal treatment at temperatures higher than 250 °C and makes it clear that this effect could be kept in a similar way for the stabilization and inhibition of the free radicals produced by the decomposition of hydroperoxide compounds associated to inflammatory processes in the physiological medium. A similar behavior was found for the polyacrylic derivative of vitamin E 8 Evolution of water content with time of immersion in PBS and at 37 °C for EMA- co -EgMA copolymers.

9 Results of agar disc diffusion test of eugenol (1 and 1R), eugenyl methacrylate, EgMA, (2 and 2R), ethoxyeugenyl methacrylate, EEgMA, (3 and 3R), and ethyl methacrylate, EMA, (4 and 4R) against S. mutans CECT 479 after 24 h of incubation at 37 °C.

10 Comparison of dose−response curves (MTT assay) of eugenyl methacrylate (EgMA), ethoxyeugenyl methacrylate (EEgMA), and eugenol (Eg).

…”

Antioxidant Activity of Synthetic Polymers of Phenolic Compounds

“…Three main chemical approaches have been used for delivery of AO using the polymer backbone-In the first approach, antioxidant molecules have been functionalized with polymerizable groups [10], which can then be polymerized. As an example, Dziubla et al have synthesized a new class of poly(β-amino esters) with phenolic antioxidants incorporated in the polymer backbone [11].…”