Статья
2017

Voltammetric, spectroscopic and thermal studies on the binding of some heterocyclic azo compounds with α- and β-cyclodextrins: pH effect and association affinity


N. Özdemir N. Özdemir , E. Biçer E. Biçer
Российский электрохимический журнал
https://doi.org/10.1134/S102319351705007X
Abstract / Full Text

The binding abilities of α- and β-cyclodextrins (α-CD and β-CD) with some heterocyclic azo compounds (1,1'-(azodicarbonyl)dipiperidine (ADP) and azodicarboxylic dimorpholide (ADM)) were studied at different pHs (4, 7.4 and 10) by UV-Vis spectroscopy and square-wave voltammetry techniques. The association constants (K i) and stoichiometries of the binding of these azo compounds with α-CD and β-CD were determined by using square-wave voltammetry technique. These bindings were formed with a stoichiometry of 1: 1 in solution. The solid samples, obtained from the mixtures (molar ratio of 1: 1) of these azo dyes and CDs in aqueous phase were analyzed by FT-IR spectroscopy and thermal analysis methods. Thermal analysis results showed that ADP and ADM formed the inclusion complexes with α-CD; however, the binding of the azo dyes with β-CD gave non-inclusion complexes.

Author information
  • Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Atakum-Samsun, Turkey

    N. Özdemir & E. Biçer

References
  1. Liu, L. and Guo, Q.-X., J. Incl. Phenom. Macrocycl. Chem., 2002, vol. 42, p. 1.
  2. Roik, N.V. and Belyakova, L.A., Phys. Chem. Solid State, 2011, vol. 12, p. 168.
  3. Wenz, G., Angew. Chem., Int. Ed. Eng., 1994, vol. 33, p. 803.
  4. Breslow, R., Science, 1982, vol. 218, p. 532.
  5. Saenger, W., Angew. Chem., Int. Ed. Eng., 1980, vol. 19, p. 344.
  6. Rekharsky, M.V. and Inoue, Y., Chem. Rev., 1998, vol. 98, p. 1875.
  7. Liu, Y., Zhao, Y.-L., Zhang, H.-Y., Fan, Z., Wen, G.-D., and F. Ding, J. Phys. Chem. B, 2004, vol. 108, p. 8836.
  8. Huskens, J., Deij, M.A., and Reinhoudt, D.N., Angew. Chem. Int. Ed., 2002, vol. 41, p. 4467.
  9. Franchi, P., Lucarini, M., and Pedulli, G.F., Angew. Chem. Int. Ed., 2003, vol. 42, p. 1842.
  10. Lucarini, M., Mezzina, E., and Pedulli, G.F., Eur. J. Org. Chem., 2000, vol. 23, p. 3927.
  11. Brewster, R.E., Teresa, B.F., and Schuh, M.D., J. Phys. Chem. A, 2003, vol. 107, p. 10521.
  12. Yamauchi, A., Hayashita, T., Kato, A., Nishizawa, S., Watanabe, M., and Teramae, N., Anal. Chem., 2000, vol. 72, p. 5841.
  13. Tong, A.-J., Yamauchi, A., Hayashita, T., Zhang, Z.-Y., Smith, B.D., and Teramae, N., Anal. Chem., 2001, vol. 73, p. 1530.
  14. Yamauchi, A., Hayashita, T., Nishizawa, S., Watanabe, M., and Teramae, N., J. Am. Chem. Soc., 1999, vol. 121, p. 2319.
  15. Hayashita, T., Qing, D., Minagawa, M., Lee, J.C., Ku, C.H., and Teramae, N., Chem. Commun., 2003, p. 2160.
  16. Balş, G. and Simu, G.M., Annals of the Faculty of Engineering Hunedoara, Int. J. Eng., 2009, vol. 7, no. 3, p. 107.
  17. Voncina, B., Vivod, V., and Jausovec, D., Dyes Pigments, 2007, vol. 74, p. 642.
  18. Loftsson, T., Jarho, P., Másson, M., and Järvinen, T., Expert Opin. Drug Deliv., 2005, vol. 2, p. 335.
  19. Loftsson, T., Másson, M., and Brewster, M.E., J. Pharm. Sci., 2004, vol. 93, p. 1091.
  20. de Jesus, M.B., Fraceto, L.F., Martini, M.F., Pickholz, M., Ferreira, C.V., and de Paula, E., J. Pharm. Pharmacol., 2012, vol. 64, p. 832.
  21. Brewster, M.E. and Loftsson, T., Adv. Drug Deliver. Rev., 2007, vol. 59, p. 645.
  22. Yilmaz, A., Yilmaz, E., Yilmaz, M., and Bartsch, R.A., Dyes Pigments, 2007, vol. 74, p. 54.
  23. Anderson, S., Claridge, T.D.W., and Anderson, H.L., Angew. Chem. Int. Ed. Eng., 1997, vol. 36, p. 1310.
  24. Yoshida, N., J. Chem. Soc., Perkin Trans., 1995, vol. 2, p. 2249.
  25. Sanchez, A.M. and de Rossi, R.H., J. Org. Chem., 1996, vol. 61, p. 3446.
  26. Hirai, H., Toshima, N., and Uenoyama, S., Bull. Chem. Soc. Jpn., 1985, vol. 58, p. 1156.
  27. Liu, W., Bian, S., Li, L., Samuelson, L., Kumar, J., and Tripathy, S., Chem. Mater., 2000, vol. 12, p. 1577.
  28. Takei, M., Yui, H., Hirose, Y., and Sawada, T., J. Phys. Chem. A, 2001, vol. 105, p. 11395.
  29. Matsue, T., Osa, T., and Evans, D.H., J. Incl. Phenom. Macro., 1984, vol. 2, p. 547.
  30. Wang, X.-P., Pan, J.-H., Shuang, S.-M., and Zhang, Y., Supramol. Chem., 2002, vol. 14, p. 419.
  31. Li, Y.-Q., Guo, Y.-J., and Pan, J.-H., J. Incl. Phenom. Macro., 2006, vol. 56, p. 237.
  32. Bersier, P.M., Bersier, J., and Klingert, B., Electroanalysis, 1991, vol. 3, p. 443.
  33. Jones, S.P. and Parr, G.D., Int J. Pharm., 1986, vol. 33, p. 105.
  34. Maazaoui, R. and Abderrahim, R., Int. J. Adv. Res., 2015, vol. 3, p. 1030.
  35. Radi, A. and Eissa, S., Open Chem. Biomed. Meth. J., 2010, vol. 3, p. 74.
  36. Omanović, D. and Branica, M., Croat. Chem. Acta, 1998, vol. 71, p. 421.
  37. Li, J., Yan, D., and Chen, Q., Sci. China, Ser. B, 2002, vol. 45, p. 73.
  38. Zhao, G.C., Zhu, J.J., Zhang, J.J., and Chen, H.Y., Anal. Chim. Acta, 1999, vol. 394, p. 337.
  39. Ibrahim, M.S., Shehatta, I.S., and Al-Nayeli, A.A., J. Pharm. Biomed. Anal., 2002, vol. 28, p. 217.
  40. Caballero, J., Zamora, C., Aguayo, D., Yanez, C., and Gonzalez-Nilo, F.D., J. Phys. Chem. B, 2008, vol. 112, p. 10194.
  41. Matsui, Y., Sawada, H., Mochido, K., and Date, Y., B. Chem. Soc. Jpn., 1975, vol. 48, p. 3446.
  42. Carter, M.T., Rodriguez, M., and Bard, A.J., J. Am. Chem. Soc., 1989, vol. 111, p. 8901.
  43. Li, P.Z., Wao, M.Y., and Zhu, T.T., Chin. J. Anal. Chem., 1994, vol. 22, p. 58.
  44. Yaw, C.W., Tan, W.T., Tan, W.S., Ng, C.H., Yap, W.B., Rahman, N.H., and Zidan, M., Int. J. Electrochem. Sci., 2012, vol. 7, p. 4692.
  45. Karim, Z. and Adnan, R., Arch. Environ. Sci., 2012, vol. 6, p. 1.
  46. Deligkiozi, I., Voyiatzis, E., Tsolomitis, A., and Papadakis, R., Dyes Pigments, 2015, vol. 113, p. 709.
  47. Khouri, S.J., Abdel-Rahim, I.A., and Shamaileh, E.M., J. Incl. Phenom. Macro., 2013, vol. 77, p. 105.
  48. Pushpa, R.G., Annaselvi, A.G., and Subramaniam, P., Int. J. Agricult. Food Sci., 2013, vol. 3, p. 90.
  49. Sowrirajan, C., Yousuf, S., and Israel Vijayaraj, M.V.E., Turk. J. Chem., 2014, vol. 38, p. 725.
  50. Hazra, S., Hossain, M., and Kumar, G.S., J. Incl. Phenom. Macro., 2014, vol. 78, p. 311.
  51. Yan, J., Wu, D., Ma, X., Wang, L., Xu, K., and Li, H., Carbohyd. Polym., 2015, vol. 131, p. 65.
  52. Patil, D.R., Ingole, P.G., Singh, K., and Dalal, D.S., Res. J. Chem. Sci., 2012, vol. 2, p. 60.
  53. Kemelbekov, U., Luo, Y., Orynbekova, Z., Rustembekov, Z., Haag, R., Saenger, W., and Pralivey, K., J. Incl. Phenom. Macro., 2011, vol. 69, p. 181.
  54. Choi, S.H., Kim, S.Y., Ryoo, J.J., Park, J.Y., and Lee K.P., Anal. Sci., 2001, vol. 17, p. 1785.
  55. Premakumari, J., Allan Gnana Roy, G., Antony Muthu Prabhu, A., Venkatesh, G., Subramanian, V.K., and Rajendiran, N., J. Solution Chem., 2011, vol. 40, p. 327.
  56. Lu, Y., Liu, S., Zhao, Y., Zhu, L., and Yu, S., Acta Pharm., 2014, vol. 64, p. 211.
  57. Araújo, M.V.G., Vieira, E.K.B., Lázaro, G.S., Conegero, L.S., Ferreira, O.P., Almeida, L.E., Barreto, L.S., Costa, N.B., Jr., and Gimenez, I.F., Bioorg. Med. Chem., 2007, vol. 15, p. 5752.
  58. Meier, M.M., Luiz, M.T.B., Szpoganicz, B., and Soldi, V., Thermochim. Acta, 2001, vol. 375, p. 153.
  59. Yılmaz, V.T., Karadağ, A., and İçbudak, H., Thermochim. Acta, 1995, vol. 261, p. 107.
  60. Ma, S., Shi, Y., Wang, J., and Shang, X., World J. Pharm. Res., 2014, vol. 3, p. 38.
  61. Khalafi, L. and Rafiee, M., Cyclodextrin based spectral changes, in An Integrated View of the Molecular Recognition and Toxinology–From Analytical Procedures to Biomedical Applications, Radis-Baptista, G., Ed., Rijeka: InTech, 2013, Ch. 19, pp. 471–493.
  62. Villiers, A., C. R. Hebd. Seances Acad. Sci., 1891, vol. 112, p. 536.
  63. Roy, M.N., Ekka, D., Saha, S., and Roy, M.C., RSC Adv., 2014, vol. 4, p. 42383.
  64. Li, Y.-Q., Guo, Y.-J., Li, X.-F., and Pan, J.-H., Dyes Pigments, 2007, vol. 74, p. 67.