Synthesis,Characterization, and Antibacterial Activity of Quaternized of N-Aromatic Chitosan Derivatives

Article Preview

Abstract:

The quaternized of N-aryl chitosan (CTS) derivatives containing different aromatic moieties were synthesized by two steps, N-aromatic Schiff and the quaternization. The chemical structures of all chitosan derivatives, N-vanillin Schiff’s base chitosan (NVCh), N-cinnamaldehyde Schiff’s base chitosan (NCCh), N-benzaldehyde Schiff’s base CTS (NBCh), and their quaternized of N-aromatic CTS derivatives were characterized by ATR-FTIR. The water solubility of the N-aromatic Schiff’s base CTS derivatives had very poor water solubility. But after quaternized, the water solubility of CTS derivatives was obviously improved. The antibacterial studies of these CTS derivatives were carried out by the inhibition zone diameters methods against E.coli (Gram-negative), S.aurueus and P.aeruginosa (Gram-positive) bacteria, and against V.Aspergillus niger (fungal). It was found that the quaternized NVSCTS showed higher antibacterial activity than quaternized NCCh and quaternized NVBCh at the almost same DQ and ES level. In comparison to each of the chemical structure, it was found that the phenol hydroxyl group effect on antibacterial activity was even higher than that of positive charge density of CTS.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

1202-1208

Citation:

Online since:

November 2011

Export:

Price:

[1] Rabea, E. I., Badawy, M. E. T., Stevens, C. V., Smagge, G., & Steurbaut, W. Chitosan as antimicrobial agent: Application and mode of action. Biomacromolecules, 4(2003), 1457–1465.

DOI: 10.1021/bm034130m

Google Scholar

[2] Xiaoxiao Jin, Jiangtao Wang, Jie Bai. Synthesis and antimicrobial activity of the Schiff base from chitosan and citral. Carbohyd. Res. 344 (2009) : 825–829.

DOI: 10.1016/j.carres.2009.01.022

Google Scholar

[3] Zhishen Jia, Dongfeng shen, Weiliang Xu. Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohyd. Res. 333 (2001) 1–6.

DOI: 10.1016/s0008-6215(01)00112-4

Google Scholar

[4] Sajomsang, W., Tantayanon, S., Tangpasuthadol, V., & Daly, W. H. Degradation of chitosan during synthesis of N-benzyl chitosan Quat-188. The second mathematics and physical science graduate conference, (2006): 35–36.

Google Scholar

[5] Warayuth Sajomsang, Supawan Tantayanon, Varawut Tangpasuthadol, William H. Daly. Quaternization of N-aryl chitosan derivatives: synthesis, characterization and antibacterial activity. Carbohyd. Res 344 (2009) : 2502–2511.

DOI: 10.1016/j.carres.2009.09.004

Google Scholar

[6] Warayuth Sajomsang, Pattarapond Gonil, Somsak Saesoo. Synthesis and characterization of N-aryl chitosan derivatives. International Journal of Biological Macromolecules 43 (2008): 79–87.

DOI: 10.1016/j.ijbiomac.2008.03.010

Google Scholar

[7] Yajun Xie, Xiaofei Liu, Qiang Chen. Synthesis and characterization of water-soluble chitosan derivate and its antibacterial activity. Carbohyd Polymer. 69 (2007) : 142–147.

DOI: 10.1016/j.carbpol.2006.09.010

Google Scholar