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Development of direct contact-killing non-leaching antimicrobial polyurethanes through click chemistry

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Abstract

A robust, efficient, and orthogonal click chemistry (copper (I)-catalyzed alkyne-azide cycloaddition) was used to prepare an antimicrobial polymer and precisely control the conjugation ratio of antibiotic molecules to polymer. Antimicrobial polyurethanes with pendant benzisothiazolinone (PU-BIT) were synthesized using click chemistry to connect azide functional polyurethane (PU-N3) and alkyne functional benzisothiazolinone (BIT-Al). The direct contact-killing and non-leaching antimicrobial properties of PU-BIT were verified by both antimicrobial drop and disk diffusion. This approach provides a new methodology and platform for the development of contact-killing and non-leaching antimicrobial materials for a variety of practical applications. This research is the first to demonstrate that the broad-spectrum BIT antibiotic is a selective antibiotic for Gram-positive bacteria when covalently linked to a polymer. PU-BIT film containing 0.8 wt% BIT exhibited a selective antimicrobial performance with bactericidal efficacy of 91.6% and 30% against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli, respectively. The mechanism of the selective antimicrobial activity of PU-BIT is also discussed.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (21762036) and Foundation for High-level Talents in Qiannan Normal University for Nationalities and Qiankehe LH [2015]7706.

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  1. School of Chemistry and Chemical Engineering, Qiannan Normal University for Nationalities, Duyun, 558000, China

    Kaimei Peng, Xuexin Dai, Haili Mao, Hongtao Zou & Zaibo Yang

  2. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China

    Kaimei Peng, Weiping Tu & Jianqing Hu

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  1. Kaimei Peng
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  2. Xuexin Dai
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Peng, K., Dai, X., Mao, H. et al. Development of direct contact-killing non-leaching antimicrobial polyurethanes through click chemistry. J Coat Technol Res 15, 1239–1250 (2018). https://doi.org/10.1007/s11998-018-0068-1

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