Synthesis and supramolecular behavior study of a novel amphiphilic compound for idebenone encapsulation

Abstract

The synthesis of a new amphiphilic compound obtained from galactose and glycerol monostearate is described, applying an efficient and environmentally friendly technique as is click reactions. The physicochemical characterization was carried out using nuclear magnetic resonance and high resolution mass spectrometry. Indeed, the novel compound enhances the solubility of idebenone, a hydrophobic active pharmaceutical ingredient. Transmission electron microscopy and molecular dynamics simulation were used to visualize the self-aggregated molecules, and dynamic light scattering to analyze the size of the supramolecular structure that shows nano-sized aggregates, with dimensions of up to 200 nm. The cytotoxicity and biocompatibility assay using murine macrophage RAW 264.7 cells showed no cytotoxicity at the 0.1 and 0.05 mg/ml concentration tested. Water solubility of idebenone increased sixteen-fold in the presence of the synthesized compound. Idebenone loading suggests that amphiphilic compound could be used as a potential drug delivery system in medicinal applications.