3,6-O-[N-(2-Aminoethyl)-acetamide-yl]-chitosan exerts antibacterial activity by a membrane damage mechanism

Abstract

A novel chitosan derivative, 3,6-O-[N-(2-aminoethyl)-acetamide-yl]-chitosan (AACS), was successfully prepared to improve water solubility and antibacterial activity of chitosan. AACS had good antibacterial activity, with minimum inhibitory concentrations of 0.25mg/mL, against Escherichia coli and Staphylococcus aureus. Cell membrane integrity, electric conductivity and NPN uptake tests showed that AACS caused quickly increasing the release of intracellular nucleic acids, the uptake of NPN, and the electric conductivity by damaging membrane integrity. On the other hand, hydrophobicity, cell viability and SDS-PAGE experiments indicated that AACS was able to reduce the surface hydrophobicity, the cell viability and the intracellular proteins through increasing membrane permeability. SEM observation further confirmed that AACS could kill bacteria via disrupting their membranes. All results above verified that AACS mainly exerted antibacterial activity by a membrane damage mechanism, and it was expected to be a new food preservative.

Keywords: 3,6-O-[N-(2-Aminoethyl)-acetamide-yl]-chitosan; Acetic acid (PubChem CID: 176); Antibacterial activity; Antibacterial mechanism; Benzaldehyde (PubChem CID: 240); Chitosan; Chitosan (PubChem CID: 71853); EDC·HCl (PubChem CID: 2723939); Ethanol (PubChem CID: 702); Ethylenediamine (PubChem CID: 3301); HEPES sodium salt (PubChem CID: 2724248); Hexadecane (PubChem CID: 110066); Membrane disruption; Monochloroacetic acid (PubChem CID: 300); N-Phenyl-1-naphthylamine (PubChem CID: 7013).