Amphiphilic block copolymers bearing hydrophobic γ-tocopherol groups with labile acetal bond

Abstract

High concentrations of-tocopherol (TCP) tend to show antioxidant, anti-inflammatory, and anticancer effects. In this study, we prepared polymer micelles under acidic conditions with a controlled release of ϒ TCP due to the decomposition of pendant acetal bonds. First, a precursor diblock copolymer composed of poly(ethylene glycol) (PEG) and acrylic acid (AA) was prepared. This was followed by the synthesis of an amphiphilic diblock copolymer (PEG54-P(AA/VE6/ ϒ TCP29)140), incorporated into hydrophobic ϒ TCP pendant groups attached to the main chain through an acetal bond. The prepared PEG54-P(AA/VE6/ ϒ TCP29)140 was further dispersed in water to form polymer micelles composed of hydrophobic cores that were generated from a hydrophobic block containing ϒ TCPs and hydrophilic shells on the surface. Under acidic conditions, ϒ TCP was then released from the core of the polymer micelles due to the decomposition of the pendant acetal bonds. In addition, polymer micelles swelled under acidic conditions due to hydration of the core.