Lipase-catalyzed synthesis of novel galactosylated cholesterol

In an organic phase system, an enzymes lipase was used as a catalyst to synthesize galactosylated cholesterol, (5-cholesten-3b-yl)[(4-O-β-d-galactopyranosyl)d-glucitol-6] sebacate (CHS-SE-LA), which contains galactose residues. Its chemical structure was characterized by ESI-MS, and NMR. For HepG2 cells, the cellular fluorescence intensities of liposomes modified with CHS-SE-LA (GAL-FL) were as much as 2.6-fold (p < 0.01) control liposomes (FL). Moreover, the presence of excess galactose significantly inhibited the uptake of GAL-FL suggesting ASGPR mediated uptake. In conclusion, the novel galactosylated ligand CHS-SE-LA was synthesized by lipase-catalyzation and revealed a great potential as drug carrier materials for hepatocyte-selective targeting.

A novel galactosyl ligand was synthesized via enzymatic esterification of sugar alcohol with high yield, simple procedure and mild conditions.Figure optionsDownload as PowerPoint slide