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通过生物衍生的三环氧杂降冰片烯内酰胺衍生物的开环易位聚合制备抗菌聚合物

Antimicrobial Polymer via ROMP of a Bioderived Tricyclic Oxanorbornene Lactam Derivative.

作者信息

Yassin Mohamed A, Komber Hartmut, Naguib Mohamed, Abdelraof Mohamed, Appelhans Dietmar, Voit Brigitte

机构信息

Leibniz-Institut für Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, Germany.

Chemical Industries Research Institute, National Research Centre, El Buhouth St. 33, 12622 Giza, Egypt.

出版信息

ACS Appl Bio Mater. 2025 Feb 17;8(2):1720-1731. doi: 10.1021/acsabm.4c01924. Epub 2025 Jan 20.

Abstract

The rapid emergence of multidrug-resistant (MDR) bacteria represents a critical global health threat, underscoring the urgent need for alternative antimicrobial strategies beyond conventional antibiotics. In this study, we report the synthesis of novel biobased antimicrobial polymers bearing quaternary ammonium salts, derived from sustainable feedstocks, maleic anhydride, dimethylaminobenzaldehyde, and furfurylamine. The functional tricyclic oxanorbornene lactam monomer is polymerized via ring opening metathesis polymerization, yielding well-defined polymers with controlled molar masses and low dispersity. Structural characterization is performed using 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and the polymerization kinetics is monitored by online H NMR spectroscopy. The quaternized biobased polymers demonstrate potent broad-spectrum antimicrobial activity against three clinically isolated MDR bacterial strains. They exhibit minimum inhibitory concentrations (MICs) that are significantly lower than those of several conventional antibiotics while also showing low hemolytic activity toward mammalian cells. This study highlights the potential of bioderived ROMP polymers as promising, sustainable antimicrobial polymers for combating the growing threat of antimicrobial resistance.

摘要

多重耐药(MDR)细菌的迅速出现是对全球健康的重大威胁,凸显了除传统抗生素之外迫切需要其他抗菌策略。在本研究中,我们报告了一种新型的含季铵盐的生物基抗菌聚合物的合成,该聚合物由可持续原料马来酸酐、二甲基氨基苯甲醛和糠胺衍生而来。功能性三环氧化降冰片烯内酰胺单体通过开环易位聚合反应进行聚合,得到具有可控摩尔质量和低分散度的结构明确的聚合物。使用一维和二维核磁共振(NMR)光谱进行结构表征,并通过在线H NMR光谱监测聚合动力学。季铵化生物基聚合物对三种临床分离的MDR细菌菌株表现出强大的广谱抗菌活性。它们的最低抑菌浓度(MIC)显著低于几种传统抗生素,同时对哺乳动物细胞的溶血活性也很低。本研究强调了生物衍生的开环易位聚合聚合物作为有前景的可持续抗菌聚合物,用于应对日益增长的抗菌耐药性威胁的潜力。

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