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

Abstract

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-π 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 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.

Development and biological evaluation of Ti6Al7Nb scaffold implants coated with gentamycin-saturated bacterial cellulose biomaterial

“…xylinus bacteria. The main advantages of BC are lack of cytotoxicity and immune response after introduction into the body, high capacity for adsorption of fluids, microfibrillar structure and a simple and relatively inexpensive way of manufacture [ 10 , 14 , 28 ]. So far, BC has been successfully used in many fields of bio-medical applications [ 10 , 29 ].…”

“…In this context, another beneficial BC feature is its high retention ratio. Thanks to this parameter, BC may be saturated with high concentration of anti-inflammatory and antimicrobial drugs, including antibiotics [ 2 – 4 , 13 , 14 ]. Such saturation allows to protect the implant and the surrounding bone from microbial contamination and subsequent biofilm formation.…”

Biological Activity of Quaternary Ammonium Salts and Their Derivatives

“…An interesting potential medical application may be the dressings based on bacterial cellulose and QASs. Preliminary studies have shown the possibility of obtaining a wound dressing that would simultaneously exhibit antimicrobial activity and biocompatibility [68]. An interesting and promising solution is also the use of QAS-modified polyurethane foams for the production of dressings.…”

Dodecenylsuccinic anhydride modified collagen hydrogels loaded with simvastatin as skin wound dressings

“…Moreover, when bacteria come into contact with the hydrocarbonated tails exposed in the gel, death may occur as a consequence of wall disruption. It has also been reported that bacterial cellulose wound dressings carrying long‐chain unsaturated fatty acids are promising antimicrobial agents of natural origin with a broad spectrum of activity (Żywicka, Fijałkowski, Junka, & Grzesiak, ).…”