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Preparation and antibacterial activity of Schiff bases from O-carboxymethyl chitosan and para-substituted benzaldehydes

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Abstract

Seven Schiff bases were synthesized from O-carboxymethyl chitosan (CMC) and para-substituted benzaldehydes. The Schiff bases were characterized through Fourier Transform Infrared Spectroscopy, Carbon-13 Nuclear Magnetic Resonance (13C NMR), Distortionless Enhancement of Polarization Transfer (DEPT) 135 NMR, elemental analysis, and acid–base titration. Antibacterial activities of the Schiff bases against Escherichia coli (E. coli, ATCC 35218) and Staphylococcus aureus (S. aureus, ATCC 25923) were measured through the optical density method. Antibacterial activity of the Schiff bases differs from the substituent at the para position of benzaldehyde, and decreases as the sequence OCH3 > CH3 > H > F > Cl > Br > NO2. The IC50 of the Schiff base from 4-methoxylbenzylaldehyde against E. coli and S. aureus is 30 and 34 ppm, respectively, much lower than that of chitosan (53, 48 ppm) and CMC (58, 60 ppm).

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Acknowledgments

The authors thank the financial support from the National Science Foundation of China (Project No. 50863002), Key Scientific and Technological Project of Haikou (Project No 2010-084), and the “Project 211” of Hainan University.

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Authors and Affiliations

  1. Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou, 570228, Hainan, China

    Xueqiong Yin, Junhua Chen, Wen Yuan, Qiang Lin, Li Ji & Fang Liu

  2. Key Laboratory of Tropical Medicinal Plant Chemistry Ministry of Education, Hainan Normal University, Haikou, 571158, Hainan, China

    Qiang Lin

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  1. Xueqiong Yin
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  2. Junhua Chen
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  3. Wen Yuan
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Correspondence to Xueqiong Yin.

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Yin, X., Chen, J., Yuan, W. et al. Preparation and antibacterial activity of Schiff bases from O-carboxymethyl chitosan and para-substituted benzaldehydes. Polym. Bull. 68, 1215–1226 (2012). https://doi.org/10.1007/s00289-011-0599-4

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  • DOI: https://doi.org/10.1007/s00289-011-0599-4

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