N-octadecyl lactose-amide modified microemulsions as targeting delivery carrier for α-linolenic acid: In vitro evaluation and interaction mechanism

Abstract

Targeting delivery for nutritional factor is increasingly paid in research field of agricultural and food science. In this present work, a novel asialoglycoprotein receptor (ASGPR)-targeted α-linolenic acid (ALA)-loaded microemulsions (MEs) for hepatocellular carcinoma (HCC) was designed. The N-octadecyl lactose-amide (NOL) was synthesized and used as active targeting ligand. The structure of NOL was characterized by Fourier transform infrared spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR). The load-ALA MEs as delivery carrier with or without NOL were evaluated by in vitro release and viability effect to hepa1-6 cells. Notably, NOL-modified MEs loading ALA (NOL-ALA-ME) consisted of spheroidal droplets with a particle size of 10–20 nm. Compared with the no-targeted ligand MEs, NOL-ALA-ME possessed a sustained release characteristic in vitro. Due to specific ligand-receptor interactions, NOL-ALA-ME demonstrated a more remarkable selective toxicity to Hepa1-6 cells. Molecular docking of ligand and receptor compounds indicated a docking score of −5.4 kcal/mol, meaning a strong targeting binding force between ligand and receptor, theoretically supports the results of cell experiments. These findings could offer significant insight into MEs as targeting delivery carrier, which may be regarded as a promising strategy for functional enhancement of active components in agricultural and food industry.