Unsaturated fatty acids lactose esters: cytotoxicity, permeability enhancement and antimicrobial activity

Abstract

Sugar based surfactants conjugated with fatty acid chains are an emerging broad group of highly biocompatible and biodegradable compounds with established and potential future applications in the pharmaceutical, cosmetic and food industries. In this work, we investigated absorption enhancing and antimicrobial properties of disaccharide lactose, monoesterified with unsaturated fatty acids through an enzymatic synthetic approach. After chemical and cytotoxicity characterizations, their permeability enhancing activity was demonstrated using intestinal Caco-2 monolayers through transepithelial electrical resistance (TEER) and permeability studies. The synthesized compounds, namely lactose palmitoleate (URB1076) and lactose nervonate (URB1077), were shown to exhibit antimicrobial activity versus eight pathogenic species belonging to Gram-positive, Gram-negative microorganisms and fungi.

Keywords: (Z)-6′-O-Hexadec-9-enoyl lactose (lactose palmitoleate, URB1076); (Z)-6′-O-Tetracos-15-enoyl lactose (lactose nervonate, URB1077); Antimicrobial agents; Lactose esters; Nervonic acid; Palmitoleic acid; Permeability enhancers; Sugar-based surfactants.