Antibacterial activity of quaternary ammonium chitosan containing mono or disaccharide moieties: preparation and characterization.
The 9 quaternary ammonium chitosans containing monosaccharides or disaccharides moieties were successfully synthesized by reductive N-alkylation then quaternized by N-(3-chloro-2-hydroxypropyl) trimethylammonium chloride (Quat-188). The chemical structures of quaternary ammonium chitosan derivatives were characterized by ATR-FTIR and (1)H NMR spectroscopy. The degree of N-substitution (DS) and the degree of quaternization (DQ) were determined by (1)H NMR spectroscopic method. It was found that the DS was in the range of 12-40% while the DQ was in the range of 90-97%. The results indicated that the O-alkylation was occured in this condition. Moreover, all quaternary ammonium chitosan derivatives were highly water-soluble at acidic, basic, and neutral pH. Minimum inhibitory concentration (MIC) antibacterial studies of these materials were carried out on Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive) bacteria compared to quaternary ammonium N-octyl and N-benzyl chitosan derivatives. The quaternary ammonium mono and disaccharide chitosan derivatives showed very high MIC values which were in the range of 32 to >256 microg/mL against both bacteria. Also it was found that the antibacterial activity decreased with increasing the DS. This was due to the increased hydrophilicity of mono and disaccharide moieties. On the other hand, the low MIC values (8-32 microg/mL) were obviously observed when the DS of quaternary ammonium N-octyl and N-benzyl chitosan derivatives was lower than 18%. The results showed that the presence of hydrophobic moiety such as the N-benzyl group enhanced the antibacterial activity compared to the hydrophilic moiety against both bacteria.
National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathumthani 12120, Thailand. warayuth@nanotec.or.th
Warayuth
W
Sajomsang
Pattarapond
P
Gonil
Supawan
S
Tantayanon
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D048271:Chitosan / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004187:Disaccharides / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D004187:Disaccharides; D009005:Monosaccharides; D020005:Propanols; D000644:Quaternary Ammonium Compounds; D048271:Chitosan; C496948:(3-chloro-2-hydroxypropyl)trimethylammonium chloride