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Preparation and characterization of ortho-biguanidinyl benzoyl chitosan hydrochloride and its antibacterial activities

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Abstract

A novel derivative of chitosan (CTS), ortho-biguanidinyl benzoyl chitosan hydrochloride (o-BGBCH), was prepared with CTS and ortho-biguanidinyl benzoyl chloride, which was synthesized by acid chloride reaction of ortho-biguanidinyl benzonic acid hydrochloride (o-BGBA), as starting material in the medium consisted of methylsulfonic acid (MeSO3H) and dimethyl sulfoxide. Structure of o-BGBCH was characterized by FT-IR and 1H NMR, molecular weight of o-BGBCH was determined through gel permeation chromatography, and degree of substitution (DS) of guanidinylation of o-BGBCH was measured using elemental analysis technique. Meanwhile, the minimum inhibitory concentration of o-BGBCHs against Escherichia coli, a Gram-negative bacterium, and Staphylococcus aureus, a Gram-positive bacterium, were ascertained by agar plate method. Compared with CTS hydrochloride, o-BGBCHs had much stronger antimicrobial activities, and these activities improved with the increase of their DS of guanidinylation. When the DS of o-BGBCH reached or exceeded 32.7 %, its antibacterial activities against the tested bacteria were higher than that of Bromo-Geramium.

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Acknowledgments

We gratefully acknowledged the support of National Natural Science Foundation of P.R. China (No. 31170543), 973 Program in Natural Basic Research Program of P.R. China (No.2007CB936300) and Jiangsu Natural Science Foundation (BK 2009293). We also gratefully acknowledged the support of China Pharmaceutical University and Changzou University in analysis.

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Authors and Affiliations

  1. School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng, 224051, Jiangsu, People’s Republic of China

    Zhao-sheng Cai, Xue-mei Zhu, Lin-lin Zhao & Gui-yun Yue

  2. School of Materials Science and Engineering, Southeast University, Nangjing, 211189, Jiangsu, People’s Republic of China

    Zhao-sheng Cai & Yue-ming Sun

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  1. Zhao-sheng Cai
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Correspondence to Zhao-sheng Cai.

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Cai, Zs., Sun, Ym., Zhu, Xm. et al. Preparation and characterization of ortho-biguanidinyl benzoyl chitosan hydrochloride and its antibacterial activities. Polym. Bull. 70, 1085–1096 (2013). https://doi.org/10.1007/s00289-012-0883-y

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