Enhanced water-solubility and antibacterial activity of novel chitosan derivatives modified with quaternary phosphonium salt
writer：Dan Zhu, Honghao Cheng, Jianna Li, Wenwen Zhang, Yuanyuan Shen, Shaojun Chen, Zaochuan Ge, Shiguo Ch
keywords：Chitosan,Quaternary phosphonium,Antibacterial,Water solubility
source：期刊
specific source：Materials Science and Engineering C: Materials for Biological Applications
Issue time：2016年
Chitosan (CS) has been widely recognized as an important biomaterial
due to its good antimicrobial activity, biocompatibility and biodegradability.
However, CS is insoluble in water in neutral and alkaline aqueous solution due
to the linear aggregation of chain molecules and the formation of
crystallinity. This is one of the key factors that limit its practical
applications. Therefore, improving the solubility of CS in neutral and alkaline
aqueous solution is a primary research direction for biomedical applications.
In this paper, a reactive antibacterial compound
(4-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-benzyl)-triphenyl-phosphonium bromide
(NHS-QPS) was synthesized for chemical modification of CS, and a series of
novel polymeric antimicrobial agents, Nquaternary phosphonium chitosan
derivatives (N-QPCSxy, x=1–2,y= 1–4) were obtained. The water solubilities and
antibacterial activities of N-QPCSxy against Escherichia coli and
Staphylococcus aureus were evaluated compare to CS. The water solubility of
N-QPCSxy was all better than that of CS at neutral pH aqueous solution, particularly,
N-QPCS14 can be soluble in water over the pH range of 3 to 12. The antibacterial
activities of CS derivatives were improved by introducing quaternary
phosphonium salt, and antibacterial activity of NQPCSxy increases with degree
of substitution. Overall, N-QPCS14 represents a novel antibacterial polymer material
with good antibacterial activity, waters solubility and low cytotoxicity.