Synthesis and determination of in vitro biological activity of novel fulleropyrrolidines containing vanilin subunit

Abstract

Due to the presence of a large number of double bonds, fullerene C60 shows good antioxidant and moderate anti-inflammatory properties. At the same time, natural product vanillin, thanks to its phenolic subunit expresses the same activities, although in a lesser extent. Willing to obtain novel fulleropyrrolidines with improved biological activity, we explored the synthesis of hybrid structures containing fullerene and vanillin. The Prato reaction of the glycine derivative, vanillin and the fullerene C60 provided desired products in satisfactory yields. DPPH radical scavenging activity and β-carotene-linoleic acid bleaching assay were used to determine antioxidant activity, while for evaluation of anti-inflammatory activity, ovalbumin (OVA) and bovine serum albumin (BSA) thermal denaturation inhibition assays were used. Obtained fulleropyrrolidines showed significantly better biological activity in comparison with starting compound.