Development of a quaternized chitosan with enhanced antibacterial efficacy

Abstract

The antibacterial activity of a water-soluble chitosan derivative prepared by chemical modification to quaternary ammonium compound N,N,N-trimethylchitosan (TC) was investigated against four selected waterborne pathogens: Aeromonas hydrophila ATCC 35654, Yersinia enterocolitica ATCC 9610, Listeria monocytogenes ATCC 19111 and Escherichia coli O157:H7 ATCC 32150. An inactivation of 4 log CFU/ml of all waterborne pathogens was noted for the quaternized chitosan as compared with chitosan over a short contact time (30 min) and low dosage (4.5 ppm) at ambient temperature. A marked increase in glucose level, protein content and lactate dehydrogenase (LDH) activity was observed concurrently in the cell supernatant to be a major bactericidal mechanism. The results suggest that the TC derivative may be a promising commercial substitute for acid-soluble chitosan for rapid and effective disinfection of water.

Antimicrobial Chitosan and Chitosan Derivatives: A Review of the Structure–Activity Relationship

“…However, fully quaternized TMC (DS = 1) can only be obtained by treating the O -protected chitosan precursor (TBDMS-chitosan) with MeI and Cs 2 CO 3 in NMP as the reagents (2c) . Quaternary ammonium groups have been introduced into unmodified chitosan by reaction with epoxides, such as glycidyl-trimethylammonium chloride (2d, 2e), by reacting chitosan with alkyl halides, such as 3-chloro-2-hydroxypropyltrimethylammonium chloride (2f), or by reductive alkylation followed by methylation (2g) . The use of several protecting groups has also been observed in the synthesis of quaternary chitosan derivatives.…”

The Microstructure, Antibacterial and Antitumor Activities of Chitosan Oligosaccharides and Derivatives

“…In general, CH 3 I/NaOH treatment of COSs can yield amino quaternization, such as in N, N, N-trimethyl COSs (TMCs, Figure 4a), and the quaternization group prepared by this method is characterized by three methyl groups attached to the N atom. If substituent quaternization inconsistencies are desired on the N atom, reductive alkylation followed by methylation can be implemented [42]; substituted alkyl groups on N atoms depend on the alkyl structure of the aldehydes selected for reductive alkylation, so more diversified N-quaternized COSs can be obtained (Figure 4b). In addition, according to the pH of the reaction conditions, epoxides such as glycidyl trimethylammonium chloride can introduce quaternary ammonium groups in different positions when reacting with COSs (Figure 4c,d) [43,44].…”

Manufacture and performance of ethylamine hydroxyethyl chitosan/cellulose fiber in N -methylmorpholine- N -oxide system

“…5 reached 63.5 mg/ml. Due to the hydration of NH 3 + , in aqueous NMMO, EHCs exhibit favorable solubility which benefits to spinning [28]. Table 2 shows the polydispersity index (PDI) and solubility of EHCs synthesized from original chitosan with various molecular weights, thereinto EHCs were synthesized under NO.…”