3,6-O-[N-(2-Aminoethyl)-acetamide-yl]-chitosan exerts antibacterial activity by a membrane damage mechanism.
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.
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Feilong
F
Yan
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Qifeng
Q
Dang
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China. Electronic address: liucsouc@126.com.
Chengsheng
C
Liu
School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Jingquan
J
Yan
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Teng
T
Wang
Qingdao Aorun Biotechnology Co. Ltd., Room 602, Century Mansion, 39 Donghaixi Road, Qingdao 266071, PR China.
Bing
B
Fan
The Graduate School of Biotechnology, Korea University, Seoul 136-701, South Korea.
Dongsu
D
Cha
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Xiaoli
X
Li
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Shengnan
S
Liang
College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
Zhenzhen
Z
Zhang
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D002462:Cell Membrane / Q000187:drug effects* / Q000378:metabolism*; D048271:Chitosan / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D004553:Electric Conductivity; D004926:Escherichia coli / Q000166:cytology / Q000187:drug effects; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D008970:Molecular Weight; D012995:Solubility; D013211:Staphylococcus aureus / Q000166:cytology / Q000187:drug effects; D014867:Water / Q000737:chemistry
C000626079:3,6-O-(N-(2-aminoethyl)acetamide-yl)chitosan; D000900:Anti-Bacterial Agents; D014867:Water; D048271:Chitosan
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)