Ionic coupling of hyaluronic acid with ethyl N-lauroyl l-arginate (LAE): Structure, properties and biocide activity of complexes

• Published in: Carbohydrate polymers 2018-10, Vol.197, p.109-116
• Main Authors: Gamarra, Ana, Missagia, Beatriz, Urpí, Lourdes, Morató, Jordi, Muñoz-Guerra, Sebastián
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antimicrobial polymers; Arginine - analogs & derivatives; Arginine - chemistry; Arginine - pharmacology; Bactericide surfactants; biocide activity; Biopolímers; Enginyeria química; Ethyl alpha-N-lauroyl L-arginate; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; hyaluronic acid; Hyaluronic Acid - chemistry; Hyaluronic Acid - pharmacology; Hyaluronic acid ionic complexes; ionic complexes; Ions - chemistry; Ions - pharmacology; LAE; Microbial Sensitivity Tests; Molecular Structure; Particle Size; Polyuronic acid; Àrees temàtiques de la UPC
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2018.05.057

[Display omitted] •Coupling of HyA with the biocide compound LAE led to stable ionic complexes.•Complexes were arranged in a biphasic structure with order at nanometric scale.•Upon incubation in water, complexes dissociated with release of LAE.•Complexes were able to form non-water soluble consistent films.•Films displayed biocide activity against both Gram-positive and Gram-negative bacteria. Ethyl αN-lauroyl l-arginate hydrochloride (LAE) was coupled with hyaluronic acid (HyA) to form ionic complexes with LAE to HyA ratios of 1:1 and 1:2. The complexes were extensively characterized by FTIR and NMR spectroscopies and their thermal properties evaluated by thermogravimetry and calorimetry. Thin films prepared from these complexes by casting displayed a smectic-like structure based on an ordered arrangement of LAE and HyA layers with a nanometric periodicity of 3.8–3.9 nm. Films immersed in water at pH 7.4 and 5.5 dissociated to deliver free LAE to the environment and reaching the equilibrium in few hours. The biocide activity of these films against both Gram-positive and Gram-negative bacteria was preliminary assessed by the liquid medium method, and shown to be notable in both cases. The antibacterial property of the complexes was found to increase with the content of LAE and to be particularly efficient against Gram-negative S. enterica bacteria.