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Synthesis and Characterization of Lactobionic Acid Grafted Phenylalanyl-Glycyl-Chitosan

  • Li, He-Ping ;
  • Li, Shan ;
  • Wang, Zhou-Dong ;
  • Qin, Long
  • Received : 2011.06.29
  • Accepted : 2011.09.14
  • Published : 2011.12.20

Abstract

In order to enhance the target action of chitosan-based drug, this paper firstly prepared phenylalanyl-glycylchitosan (Phe-Gly-CS) by grafting the key intermediate, bromoacetyl-phenylalanine (BA-Phe) onto chitosan. Then the target sugar molecule, lactobionic acid (LA), was grafted to Phe-Gly-CS and the topic compound lactobionic acid grafted phenylalanyl-glycyl-chitosan (Phe-Gly-CS-LA) was finally obtained in a yield of 78.8%. The product were characterized by FTIR, MS and 1H NMR. The preparing condition of BA-Phe was optimized as follows: the best pH was 10-11, the optimum temperature was $-4^{\circ}C$, the reaction time was 1.5 h.

Keywords

Grafted chitosan;Drug carrier;prepare;Lactobionic acid

References

  1. Sui, W. P.; Chen, G. H.; Gao, X. C.; Shang, C. Q.; Sun, M. K. Chem. J. Chinese Univ. 2001, 22, 133.
  2. Jia, J. T.; Dong, C. D.; Zhang, W. L.; Cui, Y. X.; Liu, J. P. Pharmaceutical and Biomedical Analysis 2011, 55, 342. https://doi.org/10.1016/j.jpba.2011.01.044
  3. Lin, W. J.; Chen, T. D.; Liu, C. W. Polymer 2009, 50, 4166. https://doi.org/10.1016/j.polymer.2009.06.076
  4. Kumar, M. N.; Muzzarelli, R.A.; Muzzarelli, C.; Sashiwa, H.; Domb, A. J. Chem. Rev. 2004, 104, 6017. https://doi.org/10.1021/cr030441b
  5. Patale, R. L.; Patravale, V. B. Carbohydr. Polym. 2011, 85, 105. https://doi.org/10.1016/j.carbpol.2011.02.001
  6. Knapczyk, L. K. J.; Krzck, J.; Brzeski, M.; Nirnberg, E.; Schenk, D.; Struszcyk, H. Chitin and Chitosan: Sources, Chemistry, Biochemistry, Physical Properties and Applications; In Requirements of Chitosan for Pharmaceutical and Biomedical Applications; G. Skak-Braek, T. Anthonsen, P. Sandford, Eds.; Elsevier: London, 1989, p 657.
  7. Illum, L. Pharm. Res. 1998, 15, 1326. https://doi.org/10.1023/A:1011929016601
  8. Felt, O.; Buri, P.; Gurny, R. Drug. Dev. Ind. Pharm. 1998, 24, 979. https://doi.org/10.3109/03639049809089942
  9. Bhattarai, N.; Gunn, J.; Zhang, M. Q. Advanced Drug Delivery Reviews 2010, 62, 83. https://doi.org/10.1016/j.addr.2009.07.019
  10. Lao, S. B.; Zhang, Z. X.; Xu, H. H.; Jiang, G. B. Carbohydr. Polym. 2010, 82, 1136. https://doi.org/10.1016/j.carbpol.2010.06.044
  11. Yoo, H. S.; Lee, J. E.; Chung, H.; Kwon, I. C.; Jeong. S. Y. J. Control Release 2005, 103, 235. https://doi.org/10.1016/j.jconrel.2004.11.033
  12. Amidi, M.; Romeijn, S. G.; Borchard, G.; Junginger, H. E.; Hennink, W.E.; Jiskoot, W. J. Control Release 2006, 111, 107. https://doi.org/10.1016/j.jconrel.2005.11.014
  13. Kim, J. H.; Kim, Y. S.; Park, K.; Lee, S.; Nam, H. Y.; Min, K. H.; Jo, H. G.; Park, J. H.; Choi, K.; Jeong, S. Y.; Park, R. W.; Kim, I. S.; Kim, K.; Kwon, I. C. Control Release 2008, 127, 41. https://doi.org/10.1016/j.jconrel.2007.12.014
  14. Overington, J. P.; Al-Lazikani, B.; Hopkins, A. L. Drug Discov. 2006, 5, 993. https://doi.org/10.1038/nrd2199
  15. Park, J. H.; Saravanakumar, G.; Kim, K.; Kwon, I. C. Advanced Drug Delivery Reviews 2010, 62, 28. https://doi.org/10.1016/j.addr.2009.10.003
  16. Li, M. L.; Xu, Y. J.; Jiang, L. Q.; Chen, L. G. Chemistry 2006, 3, 179.
  17. Batista, M. K. S.; Pinto, L. F.; Gomes, C. A. R.; Gomes, P. Carbohydr. Polym. 2006, 64, 299. https://doi.org/10.1016/j.carbpol.2005.11.040
  18. Gomes, P.; Gomes, C. A. R.; Batista, M. K. S.; Pinto, L. F. P.; Silva, A. P. Carbohydr. Polym. 2008, 71, 54. https://doi.org/10.1016/j.carbpol.2007.05.015
  19. Park, J. H.; Cho, Y. W.; Chung, H.; Kwon, I. C.; Jeong, S. Y. Biomacromolecules 2003, 4, 1087. https://doi.org/10.1021/bm034094r
  20. Sun, L.; Dai, J. H.; Baker, G. L.; Bruening, M. L. Chem. Mater. 2006, 18, 4033. https://doi.org/10.1021/cm060554m

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  2. Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation vol.33, pp.2, 2013, https://doi.org/10.1016/j.foodhyd.2013.03.016

Acknowledgement

Supported by : National Natural Science Foundation of China, Natural Science Foundation of Hunan Province of China