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Carbohydr Polym ; 277: 118882, 2022 Feb 01.
Article in English | MEDLINE | ID: mdl-34893285

ABSTRACT

Hydrophobized chitosan derivatives, hexyl chitosan (HCS), dodecyl chitosan (DCS), and phthaloyl chitosan (PhCS) of approximately 30 and 50% degree of substitution (%DS) reacted with glycidyltrimethylammonium chloride (GTMAC) to incorporate hydrophilic positively charged groups of N-[(2-hydroxyl-3-trimethylammonium)propyl] and yielded amphiphilic quaternized chitosan derivatives. They can assemble into spherical nanoparticles with a hydrodynamic diameter of ~100-300 nm and positive ζ-potential values (+15 to +56). Their anti-biofilm efficacy was evaluated against the dental caries pathogen, Streptococcus mutans. Among all derivatives, the one having 30%DS of hexyl group and prepared by reacting with 1 mol equivalent of GTMAC (H30CS-GTMAC) showed the best performance in terms of its aqueous solubility, the lowest minimum inhibitory concentration (138 µg/mL) and the minimum bactericidal concentration (275 µg/mL) which are superior to the unmodified chitosan. Its equivalent anti-biofilm efficacy to that of chlorhexidine suggests that it can be a greener antibacterial agent for oral care formulations.


Subject(s)
Anti-Bacterial Agents/pharmacology , Biofilms/drug effects , Chitosan/pharmacology , Streptococcus mutans/drug effects , Surface-Active Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Carbohydrate Conformation , Chitosan/chemical synthesis , Chitosan/chemistry , Microbial Sensitivity Tests , Particle Size , Surface-Active Agents/chemical synthesis , Surface-Active Agents/chemistry
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