Facile synthesis and characterization of biodegradable antimicrobial poly(ester-carbonate)

被引:34
|
作者
Zhu, Weipu [1 ]
Wang, Ying [1 ]
Sun, Shuai [1 ]
Zhang, Qiujin [1 ]
Li, Xiaodong [2 ]
Shen, Zhiquan [1 ]
机构
[1] Zhejiang Univ, MOE Key Lab Macromol Synth & Functionalizat, Dept Polymer Sci & Engn, Hangzhou 310027, Peoples R China
[2] Zhejiang Univ, Affiliated Stomatol Hosp, Sch Med, Hangzhou 310068, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANSFER RADICAL POLYMERIZATION; BIOLOGICALLY-ACTIVE POLYMERS; EPSILON-CAPROLACTONE POLYMER; RING-OPENING POLYMERIZATION; CROSS-LINKED COPOLYMERS; QUATERNARY AMMONIUM; PHOSPHONIUM GROUPS; STAINLESS-STEEL; GENE DELIVERY; NERVE GUIDE;
D O I
10.1039/c2jm30331k
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Biodegradable antimicrobial poly(ester-carbonate)s were prepared facilely via a simple two-step process with low cost. First, poly(5,5-dibromomethyl trimethylene carbonate-co-epsilon-caprolactone) (PDBTCL) with pendant bromo groups was synthesized by the direct ring-opening copolymerization of 5,5-dibromomethyl trimethylene carbonate (DBTC) and epsilon-caprolactone (CL) in the presence of stannous octanoate (Sn(Oct)(2)) as catalyst. Then, the quaternization reaction between PDBTCL and a series of N,N-dimethyl alkylamines was performed under mild conditions, resulting in biodegradable poly(ester-carbonate) s with pendant ammonium salts (QPDBTCL). The chemical structure and composition of QPDBTCLs were characterized by H-1 NMR. The influences of alkyl chain length and charge density on the antimicrobial activity of QPDBTCLs against Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria were evaluated by OD600 and zone of inhibition methods. It was observed that QPDBTCLs with long alkyl chain on the ammonium groups exhibit significantly higher antimicrobial activity than those with short alkyl chain for both Gram-negative and Gram-positive bacteria. QPDBTCL with quaternary N,N-dimethyldodecylammonium groups shows strong antimicrobial activity even with very low charge density (4.3 mol%). This kind of biodegradable antimicrobial material may have potential applications as biomaterials.
引用
收藏
页码:11785 / 11791
页数:7
相关论文
共 50 条
  • [1] Properties of cellulose ester/biodegradable poly (ester-carbonate) blend
    Lee, Seung-Hwan
    Wang, Siqun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3680 - U3681
  • [2] Ester-carbonate interchange reaction in the solid state: synthesis of poly(ester-carbonate)
    Hait, SB
    Sivaram, S
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 1998, 199 (12) : 2689 - 2697
  • [3] Preparation and properties of biodegradable network poly(ester-carbonate) elastomers
    Nagata, Minoru
    Tanabe, Takeru
    Sakai, Wataru
    Tsutsumi, Naoto
    POLYMER, 2008, 49 (06) : 1506 - 1511
  • [4] Synthesis, Characterization, and Antimicrobial Evaluation of Random Poly(ester-Carbonate)s Bearing Pendant Primary Amine in the Main Chain
    Dong, Peng
    Feng, Jing
    Li, Sujuan
    Sun, Tingli
    Shi, Qingshan
    Xie, Xiaobao
    POLYMERS, 2020, 12 (11) : 1 - 13
  • [5] Preparation and characterization of polyester- and poly(ester-carbonate)-paclitaxel conjugates
    Sobczak, Marcin
    Korzeniowska, Agnieszka
    Gos, Piotr
    Kolodziejski, Waclaw L.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) : 3047 - 3051
  • [6] An Improved Approach to Poly(Ester-Carbonate) Conjugates
    Mo, Guojun
    Yue, Jun
    Ma, Ping'an
    Huang, Yubin
    Chen, Xuesi
    Jing, Xiabin
    JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION, 2012, 23 (1-4) : 375 - 389
  • [7] Synthesis and Properties of Biodegradable Multiblock Poly(ester-carbonate) Comprising of Poly(L-lactic acid) and Poly(butylene carbonate) with Hexamethylene Diisocyanate as Chain-Extender
    Wang, Jin
    Zheng, Liuchun
    Li, Chuncheng
    Zhu, Wenxiang
    Zhang, Dong
    Guan, Guohu
    Xiao, Yaonan
    JOURNAL OF APPLIED POLYMER SCIENCE, 2014, 131 (05)
  • [8] Synthesis of poly(ester-carbonate) with a pendant acetylcholine analog for promoting neurite growth
    Xing, Bongming
    Ma, Lie
    Gao, Changyou
    ACTA BIOMATERIALIA, 2014, 10 (10) : 4127 - 4135
  • [9] Synthesis, characterization of poly(ester-amide) biodegradable and evaluation of their antimicrobial activity
    Khane, Yasmine
    Lahcene, Belarbi
    Benali, Mouffok
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2016, 6 (02): : 1104 - 1111
  • [10] Synthesis and preliminary biological evaluation of novel functionalised poly(ethylene glycol)-block-poly(ester-carbonate) copolymers as biodegradable polymeric carriers
    Vincenzi, V
    Ferruti, P
    Ford, J
    Duncan, R
    MACROMOLECULAR BIOSCIENCE, 2001, 1 (04) : 164 - 169