Table of Contents
International Journal of Carbohydrate Chemistry
Volume 2016 (2016), Article ID 6046232, 10 pages
http://dx.doi.org/10.1155/2016/6046232
Research Article

Synthesis and Antimicrobial Activity of N-(6-Carboxyl Cyclohex-3-ene Carbonyl) Chitosan with Different Degrees of Substitution

1Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, El-Shatby, Alexandria 21545, Egypt
2Department of Plant Protection, Faculty of Agriculture, Damanhour University, Damanhur 22516, Egypt

Received 29 June 2016; Revised 15 September 2016; Accepted 28 September 2016

Academic Editor: Shin-ichiro Shoda

Copyright © 2016 Mohamed E. I. Badawy and Entsar I. Rabea. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. K. S. Pillai, W. Paul, and C. P. Sharma, “Chitin and chitosan polymers: chemistry, solubility and fiber formation,” Progress in Polymer Science, vol. 34, no. 7, pp. 641–678, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. P. K. Dutta, J. Duta, and V. S. Tripathi, “Chitin and Chitosan: chemistry, properties and applications,” Journal of Scientific and Industrial Research, vol. 63, no. 1, pp. 20–31, 2004. View at Google Scholar · View at Scopus
  3. R. A. A. Muzzarelli, Chitin, Elsevier, New York, NY, USA, 2013.
  4. S. Chandrkrachang, “The application of chitin and chitosan in agriculture in Thailand,” Advances in Chitin Science, vol. 5, pp. 458–462, 2002. View at Google Scholar
  5. E. I. Rabea, M. E.-T. Badawy, C. V. Stevens, G. Smagghe, and W. Steurbaut, “Chitosan as antimicrobial agent: applications and mode of action,” Biomacromolecules, vol. 4, no. 6, pp. 1457–1465, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. M. E. I. Badawy and E. I. Rabea, “A biopolymer chitosan and its derivatives as promising antimicrobial agents against plant pathogens and their applications in crop protection,” International Journal of Carbohydrate Chemistry, vol. 2011, Article ID 460381, 29 pages, 2011. View at Publisher · View at Google Scholar
  7. F. Shahidi, J. K. V. Arachchi, and Y.-J. Jeon, “Food applications of chitin and chitosans,” Trends in Food Science & Technology, vol. 10, no. 2, pp. 37–51, 1999. View at Publisher · View at Google Scholar · View at Scopus
  8. Q. Liu, C. Wu, H. Cai, N. Hu, J. Zhou, and P. Wang, “Cell-based biosensors and their application in biomedicine,” Chemical Reviews, vol. 114, no. 12, pp. 6423–6461, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Kumar, D. McGlade, and J. Lawler, “Functionalized chitosan derived novel positively charged organic-inorganic hybrid ultrafiltration membranes for protein separation,” RSC Advances, vol. 4, no. 42, pp. 21699–21711, 2014. View at Publisher · View at Google Scholar · View at Scopus
  10. B. Krajewska, “Application of chitin- and chitosan-based materials for enzyme immobilizations: a review,” Enzyme and Microbial Technology, vol. 35, no. 2-3, pp. 126–139, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. K. Xing, X. Zhu, X. Peng, and S. Qin, “Chitosan antimicrobial and eliciting properties for pest control in agriculture: a review,” Agronomy for Sustainable Development, vol. 35, no. 2, pp. 569–588, 2015. View at Publisher · View at Google Scholar · View at Scopus
  12. A. El Hadrami, L. R. Adam, I. El Hadrami, and F. Daayf, “Chitosan in plant protection,” Marine Drugs, vol. 8, no. 4, pp. 968–987, 2010. View at Publisher · View at Google Scholar · View at Scopus
  13. I. M. Helander, E.-L. Nurmiaho-Lassila, R. Ahvenainen, J. Rhoades, and S. Roller, “Chitosan disrupts the barrier properties of the outer membrane of Gram-negative bacteria,” International Journal of Food Microbiology, vol. 71, no. 2-3, pp. 235–244, 2001. View at Publisher · View at Google Scholar · View at Scopus
  14. N. R. Sudarshan, D. G. Hoover, and D. Knorr, “Antibacterial action of chitosan,” Food Biotechnology, vol. 6, no. 3, pp. 257–272, 1992. View at Publisher · View at Google Scholar · View at Scopus
  15. R. C. Goy, S. T. B. Morais, and O. B. G. Assis, “Evaluation of the antimicrobial activity of chitosan and its quaternized derivative on E. Coli and S. aureus growth,” Brazilian Journal of Pharmacognosy, vol. 26, no. 1, pp. 122–127, 2016. View at Publisher · View at Google Scholar · View at Scopus
  16. N. M. Alves and J. F. Mano, “Chitosan derivatives obtained by chemical modifications for biomedical and environmental applications,” International Journal of Biological Macromolecules, vol. 43, no. 5, pp. 401–414, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. M. E. I. Badawy and E. I. Rabea, “Synthesis and antifungal property of N-(aryl) and quaternary N-(aryl) chitosan derivatives against Botrytis cinerea,” Cellulose, vol. 21, no. 4, pp. 3121–3137, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. M. El Badawy, “Chemical modification of chitosan: synthesis and biological activity of new heterocyclic chitosan derivatives,” Polymer International, vol. 57, no. 2, pp. 254–261, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. R. Jayakumar, M. Prabaharan, R. L. Reis, and J. F. Mano, “Graft copolymerized chitosan—present status and applications,” Carbohydrate Polymers, vol. 62, no. 2, pp. 142–158, 2005. View at Publisher · View at Google Scholar · View at Scopus
  20. H.-C. Ge and D.-K. Luo, “Preparation of carboxymethyl chitosan in aqueous solution under microwave irradiation,” Carbohydrate Research, vol. 340, no. 7, pp. 1351–1356, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. H. Sashiwa, N. Kawasaki, A. Nakayama et al., “Chemical modification of chitosan. Part 15: synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate,” Carbohydrate Research, vol. 338, no. 6, pp. 557–561, 2003. View at Publisher · View at Google Scholar · View at Scopus
  22. E. I. Rabea, M. E. I. Badawy, T. M. Rogge et al., “Enhancement of fungicidal and insecticidal activity by reductive alkylation of chitosan,” Pest Management Science, vol. 62, no. 9, pp. 890–897, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. R. de Oliveira Pedro, C. C. Schmitt, and M. G. Neumann, “Syntheses and characterization of amphiphilic quaternary ammonium chitosan derivatives,” Carbohydrate Polymers, vol. 147, pp. 97–103, 2016. View at Publisher · View at Google Scholar
  24. M. E. I. Badawy, E. I. Rabea, T. M. Rogge et al., “Synthesis and fungicidal activity of new N,O-acyl chitosan derivatives,” Biomacromolecules, vol. 5, no. 2, pp. 589–595, 2004. View at Publisher · View at Google Scholar · View at Scopus
  25. S. Hirano, Y. Ohe, and H. Ono, “Selective N-acylation of chitosan,” Carbohydrate Research, vol. 47, no. 2, pp. 315–320, 1976. View at Publisher · View at Google Scholar · View at Scopus
  26. M. Shibano, S. Nishida, Y. Saito, H. Kamitakahara, and T. Takano, “Facile synthesis of acyl chitosan isothiocyanates and their application to porphyrin-appended chitosan derivative,” Carbohydrate Polymers, vol. 113, pp. 279–285, 2014. View at Publisher · View at Google Scholar · View at Scopus
  27. T. Satoh, L. Vladimirov, M. Johmen, and N. Sakairi, “Preparation and thermal dehydration of N-(carboxy)acyl chitosan derivatives with high stereoregularity,” Chemistry Letters, vol. 32, no. 4, pp. 318–319, 2003. View at Publisher · View at Google Scholar · View at Scopus
  28. R. Yamaguchi, Y. Arai, T. Itoh, and S. Hirano, “Preparation of partially N-succinylated chitosans and their cross-linked gels,” Carbohydrate Research, vol. 88, no. 1, pp. 172–175, 1981. View at Publisher · View at Google Scholar · View at Scopus
  29. H. Sashiwa, Y. Shigemasa, and R. Roy, “Homogeneous N,O-acylation of chitosan in dimethyl sulfoxide with cyclic acid anhydrides,” Chemistry Letters, no. 10, pp. 1186–1187, 2000. View at Google Scholar · View at Scopus
  30. S. Hirano, M. Zhang, B. G. Chung, and S. K. Kim, “N-acylation of chitosan fibre and the N-deacetylation of chitin fibre and chitin-cellulose blended fibre at a solid state,” Carbohydrate Polymers, vol. 41, no. 2, pp. 175–179, 2000. View at Publisher · View at Google Scholar · View at Scopus
  31. S. Hirano and T. Moriyasu, “N-(carboxyacyl)chitosans,” Carbohydrate Research, vol. 92, no. 2, pp. 323–327, 1981. View at Publisher · View at Google Scholar · View at Scopus
  32. S. Hirano, Y. Yamaguchi, and M. Kamiya, “Novel N-saturated-fatty-acyl derivatives of chitosan soluble in water and in aqueous acid and alkaline solutions,” Carbohydrate Polymers, vol. 48, no. 2, pp. 203–207, 2002. View at Publisher · View at Google Scholar · View at Scopus
  33. M. E. I. Badawy and E. I. Rabea, “Characterization and antimicrobial activity of water-soluble N-(4-carboxybutyroyl) chitosans against some plant pathogenic bacteria and fungi,” Carbohydrate Polymers, vol. 87, no. 1, pp. 250–256, 2012. View at Publisher · View at Google Scholar · View at Scopus
  34. G. G. Allan and M. Peyron, “Molecular weight manipulation of chitosan II: prediction and control of extent of depolymerization by nitrous acid,” Carbohydrate Research, vol. 277, no. 2, pp. 273–282, 1995. View at Publisher · View at Google Scholar · View at Scopus
  35. G. G. Allan and M. Peyron, “Molecular weight manipulation of chitosan I: kinetics of depolymerization by nitrous acid,” Carbohydrate Research, vol. 277, no. 2, pp. 257–272, 1995. View at Publisher · View at Google Scholar · View at Scopus
  36. P. J. Flory, Principles of Polymer Chemistry, Cornell University Press, 1953.
  37. C. Tanford, Physical Chemistry of Macromolecules, John Wiley & Sons, New York, NY, USA, 1961.
  38. M. Sugimoto, M. Morimoto, H. Sashiwa, H. Saimoto, and Y. Shigemasa, “Preparation and characterization of water-soluble chitin and chitosan derivatives,” Carbohydrate Polymers, vol. 36, no. 1, pp. 49–59, 1998. View at Publisher · View at Google Scholar · View at Scopus
  39. J. N. Eloff, “A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria,” Planta Medica, vol. 64, no. 8, pp. 711–713, 1998. View at Publisher · View at Google Scholar · View at Scopus
  40. D. M. Yajko, J. J. Madej, M. V. Lancaster et al., “Colorimetric method for determining MICs of antimicrobial agents for Mycobacterium tuberculosis,” Journal of Clinical Microbiology, vol. 33, no. 9, pp. 2324–2327, 1995. View at Google Scholar · View at Scopus
  41. M. E. I. Badawy, E. I. Rabea, and N. E. M. Taktak, “Antimicrobial and inhibitory enzyme activity of N-(benzyl) and quaternary N-(benzyl) chitosan derivatives on plant pathogens,” Carbohydrate Polymers, vol. 111, pp. 670–682, 2014. View at Publisher · View at Google Scholar · View at Scopus
  42. D. J. Finney, Probit Analysis, Cambridge University Press, 3rd edition, 1971. View at MathSciNet
  43. A. Hirai, H. Odani, and A. Nakajima, “Determination of degree of deacetylation of chitosan by 1H NMR spectroscopy,” Polymer Bulletin, vol. 26, no. 1, pp. 87–94, 1991. View at Publisher · View at Google Scholar · View at Scopus
  44. H. Sashiwa and Y. Shigemasa, “Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins,” Carbohydrate Polymers, vol. 39, no. 2, pp. 127–138, 1999. View at Publisher · View at Google Scholar · View at Scopus
  45. E. I. Rabea, M. E. I. Badawy, W. Steurbaut, and C. V. Stevens, “In vitro assessment of N-(benzyl)chitosan derivatives against some plant pathogenic bacteria and fungi,” European Polymer Journal, vol. 45, no. 1, pp. 237–245, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. Z. Zhong, B. Aotegen, H. Xu, and S. Zhao, “Structure and antimicrobial activities of benzoyl phenyl-thiosemicarbazone-chitosans,” International Journal of Biological Macromolecules, vol. 50, no. 4, pp. 1169–1174, 2012. View at Publisher · View at Google Scholar · View at Scopus
  47. Z. Zhong, B. Aotegen, H. Xu, and S. Zhao, “The influence of chemical structure on the antimicrobial activities of thiosemicarbazone-chitosan,” Cellulose, vol. 21, no. 1, pp. 105–114, 2014. View at Publisher · View at Google Scholar · View at Scopus
  48. R. Jia, Y. Duan, Q. Fang, X. Wang, and J. Huang, “Pyridine-grafted chitosan derivative as an antifungal agent,” Food Chemistry, vol. 196, pp. 381–387, 2016. View at Publisher · View at Google Scholar · View at Scopus
  49. E. I. Rabea, “In vitro assessment of antimicrobial property of O-(phenoxyacetic) chitosan compounds on plant pathogens,” Journal of Chitin and Chitosan Science, vol. 2, no. 4, pp. 293–298, 2014. View at Publisher · View at Google Scholar
  50. Z. Guo, R. Xing, S. Liu et al., “The influence of molecular weight of quaternized chitosan on antifungal activity,” Carbohydrate Polymers, vol. 71, no. 4, pp. 694–697, 2008. View at Publisher · View at Google Scholar · View at Scopus
  51. A. El Ghaouth, J. Arul, A. Asselin, and N. Benhamou, “Antifungal activity of chitosan on post-harvest pathogens: induction of morphological and cytological alterations in Rhizopus stolonifer,” Mycological Research, vol. 96, no. 9, pp. 769–779, 1992. View at Publisher · View at Google Scholar
  52. J. García-Rincón, J. Vega-Pérez, M. G. Guerra-Sánchez, A. N. Hernández-Lauzardo, A. Peña-Díaz, and M. G. Velázquez-Del Valle, “Effect of chitosan on growth and plasma membrane properties of Rhizopus stolonifer (Ehrenb.:Fr.) Vuill,” Pesticide Biochemistry and Physiology, vol. 97, no. 3, pp. 275–278, 2010. View at Publisher · View at Google Scholar · View at Scopus
  53. M. R. Avadi, A. M. M. Sadeghi, A. Tahzibi et al., “Diethylmethyl chitosan as an antimicrobial agent: synthesis, characterization and antibacterial effects,” European Polymer Journal, vol. 40, no. 7, pp. 1355–1361, 2004. View at Publisher · View at Google Scholar · View at Scopus
  54. R. G. Cuero, G. Osuji, and A. Washington, “N-carboxymethylchitosan inhibition of aflatoxin production: role of zinc,” Biotechnology Letters, vol. 13, no. 6, pp. 441–444, 1991. View at Publisher · View at Google Scholar · View at Scopus