title: 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.
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy.
authors.forename: Simone
authors.initials: S
authors.lastname: Lucarini
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Fagioli
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy.
authors.forename: Raffaella
authors.initials: R
authors.lastname: Campana
authors.affiliation: School of Pharmacy, University of Lincoln, Brayford Pool, Lincoln LN6 7TS, UK.
authors.forename: Hannah
authors.initials: H
authors.lastname: Cole
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Duranti
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy.
authors.forename: Wally
authors.initials: W
authors.lastname: Baffone
authors.affiliation: School of Pharmacy, University of Lincoln, Brayford Pool, Lincoln LN6 7TS, UK.
authors.forename: Driton
authors.initials: D
authors.lastname: Vllasaliu
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento, 6, Urbino (PU) 61029, Italy. Electronic address: luca.casettari@uniurb.it.
authors.forename: Luca
authors.initials: L
authors.lastname: Casettari
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D018938:Caco-2 Cells; D002176:Candida albicans / Q000187:drug effects; D004952:Esters; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D006801:Humans; D007785:Lactose / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D010539:Permeability
chemical_list: D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D004952:Esters; D005231:Fatty Acids, Unsaturated; D007785:Lactose
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