DOI QR코드

DOI QR Code

Synthesis and Hydroxyl Radicals Scavenging Activity of 2-Pyridine-acetyl-N-trimethyl Chitosan Chloride

Li, Rongchun

  • Received : 2012.02.06
  • Accepted : 2012.06.13
  • Published : 2012.08.20

Abstract

A novel chitosan derivative with double quaternary ammonium salt-2-pyridine-acetyl-N-trimethyl chitosan chloride (PATMCS) was synthesized and the antioxidant activity of PATMCS against hydroxyl radicals was assessed. The results indicated that PATMCS had potent hydroxyl scavenging activity. The $IC_{50}$ of PATMCS was 0.13 mg/mL. PATMCS showed 100% scavenging effect at a dose of 0.8 mg/mL which markedly better than that of N-trimethyl chitosan chloride (TMCS). It was confirmed that quaternary chitosan derivatives showed potent antioxidant activity. PATMCS has double quaternary ammonium salt structure in the molecules. Therefore, the antioxidant activity of PATMCS was better than TMCS. The above results are theoretically fundamental for further development and making use of chitosan resources to prepare new antioxidants.

Keywords

Double quaternary chitosan;Synthesis;Antioxidant activity

References

  1. Lim, S. H.; Hudson, S. M. Carbohydr. Res. 2004, 39, 313.
  2. Krajewska, B. Sep. Purif. Technol. 2005, 41, 305. https://doi.org/10.1016/j.seppur.2004.03.019
  3. Kim, K. W.; Thomas, R. L. Food Chem. 2007, 101, 308. https://doi.org/10.1016/j.foodchem.2006.01.038
  4. Muzzarelli, R. A. A.; Tanfani, F. Carbohydr. Polym. 1985, 5, 297. https://doi.org/10.1016/0144-8617(85)90037-2
  5. Domard, A.; Rinaudo, M.; Terrassin, C. International Journal of Biological Macromolecules 1986, 8, 105. https://doi.org/10.1016/0141-8130(86)90007-3
  6. Guo, Z.; Liu, H.; Chen, X.; Ji, X.; Li, P. Bioorg. Med. Chem. Lett. 2006, 16, 6348. https://doi.org/10.1016/j.bmcl.2006.09.009
  7. Liu, J.; Sun, H.; Dong, F.; Xue, Q.; Wang, G.; Qin, S.; Guo, Z. Carbohydr. Polym. 2009,78, 439. https://doi.org/10.1016/j.carbpol.2009.04.030
  8. Halliwell, B.; Gutteridge, J. M. C. Methods Enzymol. 1990, 86, 1.
  9. Snyman, D.; Hanmman, J. H.; Kotze, J. S.; Rollings J. E.; Kotze, A. F. Carbohydr. Polym. 2002, 50, 145. https://doi.org/10.1016/S0144-8617(02)00008-5
  10. Britto, D.; Assis, O. B. G. International Journal of Biological Macromolecules 2007, 41, 198. https://doi.org/10.1016/j.ijbiomac.2007.02.005
  11. Jia, Z.; Shen, D.; Xu, W. Carbohydr. Res. 2001, 333, 1. https://doi.org/10.1016/S0008-6215(01)00112-4
  12. Liu, Z. R.; Zhao, J. X. Journal of Qingdao University of Science and Technology 2006, 27, 317.
  13. Baumann, H.; Faust, V. Carbohydr. Res. 2001, 331, 43. https://doi.org/10.1016/S0008-6215(01)00009-X
  14. Panicker, C. Y.; Varghese, H. T.; Philip, D.; Nogueira, H. I. S. Spectrochim. Acta, Part A 2006, 64, 744. https://doi.org/10.1016/j.saa.2005.06.048
  15. Chruszcz, K.; Baranska, M.; Czarniecki, K.; Boduszek, B.; Proniewicz, L. M. J. Mol. Struct. 2003, 648, 215. https://doi.org/10.1016/S0022-2860(03)00025-5
  16. Heras, A.; Rodriguez, N. M.; Ramos, V. M.; Agullu, E. Carbohydr. Polym. 2001, 44, 1. https://doi.org/10.1016/S0144-8617(00)00195-8
  17. Guo, Z.; Xing, R.; Liu, S.; Yu, H.; Wang, P.; Li C.; Li, P. Bioorg. Med. Chem. Lett. 2005, 15, 4600. https://doi.org/10.1016/j.bmcl.2005.06.095

Cited by

  1. Evaluation of net antioxidant activity of mono- and bis-Mannich base hydrochlorides and 3-keto-1,5-bisphosphonates from their ProAntidex parameter vol.1091, 2015, https://doi.org/10.1016/j.molstruc.2015.02.071
  2. Preparation and Characterization of Quaternized Chitosan Derivatives and Assessment of Their Antioxidant Activity vol.23, pp.3, 2018, https://doi.org/10.3390/molecules23030516