Modification of Bacterial Cellulose with Quaternary Ammonium Compounds Based on Fatty Acids and Amino Acids and the Effect on Antimicrobial Activity

In the present work, bacterial cellulose (BC) membranes have been modified with bioactive compounds based on long chain dimer of C18 linoleic acid, referred to as the dilinoleic acid (DLA) and tyrosine (Tyr), a natural amino acid capable of forming noncovalent cation-pi interactions with positively charged ethylene diamine (EDA). This new compound, [EDA]-[DLA-Tyr], has been synthesized by simple coupling reaction, and its chemical structure was characterized by H-1 NMR and Fourier transform infrared spectroscopy. The antimicrobial activity of a new compound against S. aureus and S. epidermidis, two cocci associated with skin and wound infections, was assessed. The [EDA][DLA-Tyr] impregnated BC exhibited strong and long-term antimicrobial activity against both staphylococcal species. The results showed a 57-66% and 56-60% reduction in S. aureus and S. epidermidis viability, respectively, depending on [EDA][DLA-Tyr] concentration used. Importantly, [EDA] [DLA-Tyr] molecules were released gradually from the BC pellicle, while a reference antibiotic, erythromycine (ER), did not show any antibacterial activity against S. aureus and S. epidermidis after 48 h of soaking in deionized water. Thus, a combination of [EDA] [DLA-Tyr] and BC could be a promising new class of wound dressing displaying both biocompatibility and antimicrobial activity.