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Vol. 28 No. 8 (2016): Vol 28 Issue 8

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Inclusion Complexes of Folic Acid with Polyamine-Modified b-Cyclodextrins: Characterization, Solubilization and Inclusion Mode

https://doi.org/10.14233/ajchem.2016.19896
Kun Liu
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China
Manshuo Liu
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China
Hudie Xie
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China
Bin Han
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China
Yulin Zhao
Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming 650500, P.R. China
Bo Yang
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China

Corresponding Author(s) : Bo Yang

yangb6910@sina.com

Asian Journal of Chemistry, Vol. 28 No. 8 (2016): Vol 28 Issue 8

Abstract

The formation of inclusion complexes between folic acid with three types of polyamine-modified b-cyclodextrins (1-3) was studied in solution and steady state by means of fluorescence spectroscopy, NMR, XRD and DSC. The stoichiometric ratio and stability constant was determined by Job’s plot and fluorescence titrations method, respectively. The results showed that 1:2 complexes are formed for folic acid with hosts b-cyclodextrins (1-3). From the ROESY data, benzene ring and pteridine ring of folic acid was found to be inserted to the cavity of b-cyclodextrin. Due to excellent enhancement of water solubility and thermal stability of folic acid with addition of hosts (1-3), this study will provide useful information for its application as herbal medicine.

Keywords

Folic acid Polyamine-modified b-cyclodextrins Inclusion complex Solubilization
Liu, K., Liu, M., Xie, H., Han, B., Zhao, Y., & Yang, B. (2016). Inclusion Complexes of Folic Acid with Polyamine-Modified b-Cyclodextrins: Characterization, Solubilization and Inclusion Mode. Asian Journal of Chemistry, 28(8), 1855–1860. https://doi.org/10.14233/ajchem.2016.19896
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References
  1. M. Lucock, Mol. Genet. Metab., 71, 121 (2000); doi:10.1006/mgme.2000.3027.
  2. I.R. Younis, M.K. Stamatakis, P.S. Callery and P.J. Meyer-Stout, Int. J. Pharm., 367, 97 (2009); doi:10.1016/j.ijpharm.2008.09.028.
  3. A. Vora, A. Riga, D. Dollimore and K.S. Alexander, Thermochim. Acta, 392-393, 209 (2002); doi:10.1016/S0040-6031(02)00103-X.
  4. A. Vora, A. Riga, D. Dollimore and K.J. Alexander, J. Therm. Anal. Calorim., 75, 709 (2004); doi:10.1023/B:JTAN.0000027167.14746.28.
  5. B.F. Cole, J.A. Baron, R.S. Sandler, R.W. Haile, D.J. Ahnen, R.S. Bresalier, G. McKeown-Eyssen, R.W. Summers, R.I. Rothstein, C.A. Burke, D.C. Snover, T.R. Church, J.I. Allen, D.J. Robertson, G.J. Beck, J.H. Bond, T. Byers, J.S. Mandel, L.A. Mott, L.H. Pearson, E.L. Barry, J.R. Rees, N. Marcon, F. Saibil, P.M. Ueland and E.R. Greenberg, JAMA, 297, 2351 (2007); doi:10.1001/jama.297.21.2351.
  6. C.L. Relton, M.S. Pearce and L. Parker, Br. J. Nutr., 93, 593 (2005); doi:10.1079/BJN20041395.
  7. M.L. Taylor, S.M. Carney, G.M. Goodwin and J.R. Geddes, J. Psychopharmacol., 18, 251 (2004); doi:10.1177/0269881104042630.
  8. A. Garcia and K. Zanibbi, Can. Med. Assoc. J., 171, 897 (2004); doi:10.1503/cmaj.1031586.
  9. R.R. McLean, P.F. Jacques, J. Selhub, K.L. Tucker, E.J. Samelson, K.E. Broe, M.T. Hannan, L.A. Cupples and D.P. Kiel, N. Engl. J. Med., 350, 2042 (2004); doi:10.1056/NEJMoa032739.
  10. J.B.J. van Meurs, R.A.M. Dhonukshe-Rutten, S.M.F. Pluijm, M. van der Klift, R. de Jonge, J. Lindemans, L.C.P.G.M. de Groot, A. Hofman, J.C.M. Witteman, J.P.T.M. van Leeuwen, M.M.B. Breteler, P. Lips, H.A.P. Pols and A.G. Uitterlinden, N. Engl. J. Med., 350, 2033 (2004); doi:10.1056/NEJMoa032546.
  11. P. Garin-Chesa, I. Campbell, P.E. Saigo and J.L. Jr, Am. J. Pathol., 142, 557 (1993).
  12. W.A. Henne, D.D. Doorneweerd, A.R. Hilgenbrink, S.A. Kularatne and P.S. Low, Bioorg. Med. Chem. Lett., 16, 5350 (2006); doi:10.1016/j.bmcl.2006.07.076.
  13. J.W. Lee, J.Y. Lu, P.S. Low and P.L. Fuchs, Bioorg. Med. Chem., 10, 2397 (2002); doi:10.1016/S0968-0896(02)00019-6.
  14. C.P. Lemon and P.S. Low, J. Biol. Chem., 267, 24966 (1992).
  15. M.X. Zhao, H.F. Huang, Q. Xia, L.N. Ji and Z.-W. Mao, J. Mater. Chem., 21, 10290 (2011); doi:10.1039/c1jm11066g.
  16. B. Sahoo, K.S.P. Devi, R. Banerjee, T.K. Maiti, P. Pramanik and D. Dhara, ACS Appl. Mater. Interfaces, 5, 3884 (2013); doi:10.1021/am400572b.
  17. X. Guo, C.L. Shi, J. Wang, S.B. Di and S.B. Zhou, Biomaterials, 34, 4544 (2013); doi:10.1016/j.biomaterials.2013.02.071.
  18. K. Watanabe, M. Kaneko and Y. Maitani, Int. J. Nanomed., 7, 3679 (2012); doi:10.2147/IJN.S32853.
  19. M. Ceborska, M. Zimnicka, M. Pietrzak, A. Troc, M. Koźbial and J. Lipkowski, Org. Biomol. Chem., 10, 5186 (2012); doi:10.1039/c2ob25683e.
  20. K.F. Uekama, I.T. Hirayama and T. Irie, Chem. Rev., 98, 2045 (1998); doi:10.1021/cr970025p.
  21. B. Yang, J. Lin, J.Y. Chen and Y. Liu, Bioorg. Med. Chem., 17, 6311 (2009); doi:10.1016/j.bmc.2009.07.060.
  22. M.G. Hartell, R. Hicks, A.K. Bhattacharjee, B.W. Koser, K. Carvalho and J.E. Van Hamont, J. Pharm. Sci., 93, 2076 (2004); doi:10.1002/jps.20106.
  23. H.S. Choi, A. Yamashita, T. Ooya, N. Yui, H. Akita, K. Kogure, R. Ito and H. Harashima, ChemBioChem, 6, 1986 (2005); doi:10.1002/cbic.200500242.
  24. X.M. Yang, Y.L. Zhao, Y.J. Chen, X.L. Liao, C.Z. Gao, D. Xiao, Q.X. Qin, D. Yi and B. Yang, Mater. Sci. Eng. C, 33, 2386 (2013); doi:10.1016/j.msec.2013.02.002.
  25. A.R. Khan, P. Forgo, K.J. Stine and V.T. D’Souza, Chem. Rev., 98, 1977 (1998); doi:10.1021/cr970012b.
  26. Y. Liu, G.S. Chen, L. Li, H.Y. Zhang, D.X. Cao and Y.J. Yuan, J. Med. Chem., 46, 4634 (2003); doi:10.1021/jm034148f.
  27. Y. Zhao, Y.C. Yang, H. Shi, H.Y. Zhu, R. Huang, C.M. Chi and Y. Zhao, Helv. Chim. Acta, 93, 1136 (2010); doi:10.1002/hlca.200900345.
  28. J. Bügler, N.A.J.M. Sommerdijk, A.J.W.G. Visser, A. van Hoek, R.J.M. Nolte, J.F.J. Engbersen and D.N. Reinhoudt, J. Am. Chem. Soc., 121, 28 (1999); doi:10.1021/ja9828657.
  29. H. Wang, R. Cao, C.F. Ke, Y. Liu, T. Wada and Y. Inoue, J. Org. Chem., 70, 8703 (2005); doi:10.1021/jo051073+.
  30. B.J. Shen, L.H. Tong and D.S. Jin, Synth. Commun., 21, 635 (1991); doi:10.1080/00397919108020830.
  31. Y. Liu, Y. Chen, L. Li, H.Y. Zhang, S.X. Liu and X.D. Guan, J. Org. Chem., 66, 8518 (2001); doi:10.1021/jo0159789.
  32. I.V.M.V. Enoch and S. Yousuf, J. Solution Chem., 42, 470 (2013); doi:10.1007/s10953-013-9965-1.
  33. S. Li and W.C. Purdy, Chem. Rev., 92, 1457 (1992); doi:10.1021/cr00014a009.
  34. J.F. Ayala-Zavala, L. Del-Toro-Sánchez, E. Alvarez-Parrilla and G.A. González-Aguilar, J. Food Sci., 73, R41 (2008); doi:10.1111/j.1750-3841.2008.00705.x.
  35. K. Miyajima, H. Komatsu, K. Inoue, T. Handa and M. Nakagaki, Bull. Chem. Soc. Jpn., 63, 6 (1990); doi:10.1246/bcsj.63.6.
  36. Y. Liu, G.S. Chen, Y. Chen and J. Lin, Bioorg. Med. Chem., 13, 4037 (2005); doi:10.1016/j.bmc.2005.03.051.
  37. I. Correia, N. Bezzenine, N. Ronzani, N. Platzer, J.C. Beloeil and B.T. Doan, J. Phys. Org. Chem., 15, 647 (2002); doi:10.1002/poc.528.
  38. M.J. ONeil, The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, People’s Health Publishing House: Beijing, China, edn 14 (2006).
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