Bulletin of the Korean Chemical Society

  • 제34권7호
  • /
  • Pages.2016-2022
  • /
  • 2013
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Characterization of Cationic and Anionic Cyclodextrin Oligomers and Their Use in Layer-by-Layer Film Formation

  • Yang, Sung Yun (Department of Polymer Science and Engineering, Chungnam National University) ;
  • Hoonor, Rekha (Department of Polymer Science and Engineering, Chungnam National University) ;
  • Jin, Hye-Seung (Department of Polymer Science and Engineering, Chungnam National University) ;
  • Kim, Jeongkwon (Department of Chemistry, Chungnam National University)
  • 투고 : 2013.04.02
  • 심사 : 2013.04.09
  • 발행 : 2013.07.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Ionically modified ${\beta}$-cyclodextrins, which have excellent water-solubility, have been interested in purification technology as well as drug carrier system. The present study summarizes the synthesis and characterization of cationic and anionic ${\beta}$-cyclodextrin (${\beta}$-CyD) products using by polycondensation. The oligo (${\beta}$-CyD)s are synthesized from ${\beta}$-CyD, epichlorohydrin (EP) and choline chloride (CC; for cationic polymer) or chloroacetic acid (CAA; for anionic polymer) through one step polycondenstaion process. Unlike the previous studies, we successfully purified the ionic ${\beta}$-CyD condensation products from the ${\beta}$-CyD reaction mixtures and accomplished a great level of structural analysis. The detailed structural analysis of these ionic ${\beta}$-CyD compounds is done by $^1H$ NMR, MALDI-TOF as well as GPC analysis and confirms the formation of oligomers with a few units of ${\beta}$-CyD. We found that the sequence of reactant addition also could effect on the molecular weight of the resulting product as well as the molar ratio of the reactants. Finally, we used the cationic and anionic ${\beta}$-CyD oligomers for fabricating multilayer films by layer-layer process.

키워드

참고문헌

  1. Del Valle, E. M. Process Biochemistry 2004, 39, 1033. https://doi.org/10.1016/S0032-9592(03)00258-9
  2. Breslow, R.; Dong, S. D. Chemical Reviews 1998, 98, 1997. https://doi.org/10.1021/cr970011j
  3. Li, S.; Purdy, W. C. Chemical Reviews 1992, 92, 1457. https://doi.org/10.1021/cr00014a009
  4. Fanali, S. Electrophoresis 2009, 30, S203. https://doi.org/10.1002/elps.200900056
  5. Hedges, A. R. Chemical Reviews 1998, 98, 2035. https://doi.org/10.1021/cr970014w
  6. Hirayama, F.; Uekama, K. Advanced Drug Delivery Reviews 1999, 36, 125. https://doi.org/10.1016/S0169-409X(98)00058-1
  7. Szente, L.; Szejtli, J. Advanced Drug Delivery Reviews 1999, 36, 17. https://doi.org/10.1016/S0169-409X(98)00092-1
  8. Arima, H.; Yunomae, K.; Miyake, K.; Irie, T.; Hirayama, F.; Uekama, K. Journal of Pharmaceutical Sciences 2001, 90, 690. https://doi.org/10.1002/jps.1025
  9. Yang, S. Y.; Green, M. M.; Schultz, G.; Jha, S. K.; Muller, A. H. E. Journal of the American Chemical Society 1997, 119, 12404. https://doi.org/10.1021/ja972789s
  10. Yang, S. Y.; Schultz, G.; Green, M. M.; Morawetz, H. Macromolecules 1999, 32, 2577. https://doi.org/10.1021/ma9818533
  11. Yang, S. Y.; Seo, J. Y. Colloids and Surfaces A-Physicochemical and Engineering Aspects 2008, 313, 526.
  12. Lee, K. H.; K., D. Y.; Yang, S. Y. Macromolecular Research 2013, 21(2), 127. https://doi.org/10.1007/s13233-013-1058-x
  13. Yang, S. Y.; Mendelsohn, J. D.; Rubner, M. F. Biomacromolecules 2003, 4, 987. https://doi.org/10.1021/bm034035d
  14. Renard, E.; Deratani, A.; Volet, G.; Sebille, B. European Polymer Journal 1997, 33, 49. https://doi.org/10.1016/S0014-3057(96)00123-1
  15. Renard, E.; Barnathan, G.; Deratani, A.; Sebille, B. Macromolecular Symposia 1997, 122, 229. https://doi.org/10.1002/masy.19971220136
  16. Li, J.; Xiao, H.; Li, J.; Zhong, Y. International Journal of Pharmaceutics 2004, 278, 329. https://doi.org/10.1016/j.ijpharm.2004.03.026
  17. Qian, L.; Guan, Y.; Xiao, H. International Journal of Pharmaceutics 2008, 357, 244. https://doi.org/10.1016/j.ijpharm.2008.01.018
  18. Xin, J. Y.; Guo, Z. Z.; Chen, X. Y.; Jiang, W. F.; Li, J. S.; Li, M. L. International Journal of Pharmaceutics 2010, 386, 221. https://doi.org/10.1016/j.ijpharm.2009.11.024
  19. Jeong, H. J.; Pyun, W. H.; Yang, S. Y. Macromolecular Rapid Communications 2009, 30, 1109. https://doi.org/10.1002/marc.200900205
  20. J., K.-M.; An, Y.-J.; Park, H.; Yang, S. Y. Macromolecular Research 2013, 21(4), 343. https://doi.org/10.1007/s13233-013-1070-1
  21. Duan, L. J.; Kim, M. J.; Liu, Y.; Kim, J.; Chung, D. J. Macromolecular Research 2012, 20, 117. https://doi.org/10.1007/s13233-012-0091-5

피인용 문헌

  1. Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2013-2014 vol.37, pp.4, 2018, https://doi.org/10.1002/mas.21530
  2. Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers vol.10, pp.None, 2014, https://doi.org/10.3762/bjoc.10.319
  3. CD Oxyanions as a Tool for Synthesis of Highly Anionic Cyclodextrin Polymers vol.12, pp.12, 2013, https://doi.org/10.3390/polym12122845