Synthesis and characterization of thiazolium chitosan derivative with enhanced antimicrobial properties and its use as component of chitosan based films

Abstract

In this work, chemical modification of chitosan using cationic thiazolium groups was investigated with the aim to improve water solubility and antimicrobial properties of chitosan. Enzymatic synthesis and ethyl-3-(3- dimethylaminopropyl) carbodiimide/N-hydroxysuccinimide (EDC/NHS) chemistry were employed to synthesize and attach to chitosan through the amine groups the molecule bearing thiazolium moieties, quaternized 4- (2-(4-methylthiazol-5-yl) ethoxy)-4-oxobutanoic acid (MTBAQ). On the basis of Fourier transform infrared spectroscopy (FTIR), elemental analysis and solid state nuclear magnetic resonance (ssNMR), around 95 % of the available amine groups of chitosan (of 25 % degree of acetylation) reacted. The resulting derivative was water soluble at physiological pH and exhibit excellent antimicrobial activity against Listeria innocua, Staphylococcus epidermidis, Staphylococcus aureus and Methicillin Resistant S. aureus Gram-positive bacteria (MIC = 8–32 μg/ mL), whereas its efficiency decreases against fungi Candida albicans and Eschericia coli Gram-negative bacterium. Subsequently, the thiazolium chitosan derivative was employed as antimicrobial component (up to 7 wt%) of chitosan/glycerol based films. The incorporation of the chitosan derivative does not modify significantly the characteristics of the film in terms of thermal and mechanical properties, while enhances considerably the antimicrobial activity.