Development of contact-killing non-leaching antimicrobial guanidyl-functionalized polymers via click chemistry

• Published in: RSC advances Vol. 7; no. 4; pp. 2493 - 24913
• Main Authors: Peng, Kaimei, Zou, Tao, Ding, Wei, Wang, Ruonan, Guo, Jinshan, Round, John Jay, Tu, Weiping, Liu, Chao, Hu, Jianqing
• Format: Journal Article
• Language: English
• Published: 01.01.2017
• Subjects: Antiinfectives and antibacterials; Conjugation; Covalence; Escherichia coli; Guanidines; Killing; Leaching; Polyurethane resins; Staphylococcus aureus; Toxicity
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c7ra02706k

An expedient and efficient method applied to synthesize click-suitable penta-substituted guanidines at room temperature is hereby described. The guanidine containing polyurethanes (PU-TMGs) were prepared via click reaction (copper catalyzed alkyne-azide [3 + 2] cycloaddition, CuAAC), which was performed either before or after polymerization to incorporate the guanidine. The guanidine-functionalized polymers exhibited strong contact-killing antibacterial activity against both Gram-negative and Gram-positive bacteria. There is around 99.9% killing of S. aureus and 98.0% killing of E. coli when TMG weight percentage content in PU-TMG is around 1%. Covalent conjugation of the guanidine groups to the polymers prevents leaching. The conjugation also reduces cytotoxicity of the materials and preserves long-term antimicrobial activity. A new contact-killing and non-leaching antimicrobial polymer was prepared by a robust, efficient and orthogonal click-chemistry.