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Thermodynamic, IR spectral and X-ray diffraction studies of the “β-cyclodextrin-para-aminobenzoic acid” inclusion complex

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Abstract

The inclusion complex with stoichiometric composition 1:1 was formed as a result of intermolecular interactions between para-aminobenzoic acid and β-cyclodextrin. The stability constant of “β-cyclodextrin-para-aminobenzoic acid” inclusion complex at 289, 292 and 313 K was calculated by the Ketelar equation. The influence of temperature on the stability of “β-cyclodextrin-para-aminobenzoic acid” inclusion complex was also examined, and thermodynamic parameters involved in the complex formation (ΔG, ΔH, ΔS) were calculated. Supramolecular complex formation between para-aminobenzoic acid and β-cyclodextrin was confirmed by X-ray diffraction and IR spectroscopy studies.

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References

  1. Schradinger, F.: Uber thermophile Bakterien aus verschiedenen Speisen und Milch sowie uber einige Umsetzungsprodukte derselben in kohlenhydrathaltigen Nahrlosungen, darunter kristallisierte Polysaccharide Dextrin aus Starke. Z. Unters. Nahr. u. Genussm. 6, 865–880 (1903)

    Article  Google Scholar 

  2. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998)

    Article  CAS  Google Scholar 

  3. Liu, L., Guo, Q.-X.: The driving forces in the inclusion complexation of cyclodextrins. J. Incl. Phenom. 42, 1–14 (2002)

    Article  CAS  Google Scholar 

  4. Zouvelekis, D., Yannakopoulou, K., Mavridis, I.M., Antoniadou-Vyza, E.: The self-association of the drug acemetacin and its interactions and stabilization with β-cyclodextrin in aqueous solution as inferred from NMR spectroscopy and HPLC studies. Carbohydr. Res. 337, 1387–1395 (2002)

    Article  CAS  Google Scholar 

  5. Li, N.B., Luo, H.Q., Liu, S.P.: Resonance Rayleigh scattering study of the inclusion complexation of chloramphenicol with β-cyclodextrin. Talanta 66, 495–500 (2005)

    Article  CAS  Google Scholar 

  6. Zhang, Q.-F., Jiang, Z.-T., Guo, Y.-X., Li, R.: Complexation study of brilliant cresyl blue with β-cyclodextrin and its derivatives by UV–vis and fluorospectrometry. Spectrochim. Acta. 69, 65–70 (2008)

    Article  Google Scholar 

  7. Hergert, L.A., Escandar, G.M.: Spectrofluorimetric study of the β-cyclodextrin–ibuprofen complex and determination of ibuprofen in pharmaceutical preparations and serum. Talanta 60, 235–246 (2003)

    Article  CAS  Google Scholar 

  8. Redenti, E., Szente, L., Szejtli, J.: Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications. J. Pharm. Sci. 90, 979–986 (2001)

    Article  CAS  Google Scholar 

  9. Scholar, E.M., Pratt, W.B.: The Antimicrobial Drugs. University Press, Oxford (2000)

    Google Scholar 

  10. Xavier, S., MacDonald, S., Roth, J., Caunt, M., Akalu, A., Morais, D., Buckley, M.T., Liebes, L., Formenti, S.C., Brooks, P.C.: The vitamin-like dietary supplement para-aminobenzoic acid enhances the antitumor activity of ionizing radiation. Int. J. Radiat. Oncol. Biol. Phys. 65, 517–527 (2006)

    Article  CAS  Google Scholar 

  11. Pearson, D., Shaw, S.: Life extension: a practical scientific approach. Warner Books, New York (1982)

    Google Scholar 

  12. Zarafonetis, C.J., Dabich, L., Skovronski, J.J., DeVol, E.B., Negri, D., Yuan, W., Wolfe, R.: Retrospective studies in scleroderma: skin response to potassium para-aminobenzoate therapy. Clin. Exp. Rheumatol. 6, 261–268 (1988)

    CAS  Google Scholar 

  13. Sieve, B.F.: Clinical achromotrichia. Science 94, 257–258 (1941)

    Article  CAS  Google Scholar 

  14. Serpone, N., Salinaro, A., Emeline, A.V., Horikoshi, S., Hidaka, H.: An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical UVB/UVA active agents. Photochem. Photobiol. Sci. 1, 970–981 (2002)

    Article  CAS  Google Scholar 

  15. Stalin, T., Shanthi, B., Rani, P.V., Rajendiran, N.: Solvatochromism, prototropism and complexation of para-aminobenzoic acid. J. Incl. Phenom. Macrocycl. Chem. 55, 21–29 (2006)

    Article  CAS  Google Scholar 

  16. Shuang, S.M., Yang, Y., Pan, J.H.: Study on molecular recognition of para-aminobenzoic acid species by α-, β- and hydroxypropyl-β-cyclodextrin. Anal. Chim. Acta 458, 305–310 (2002)

    Article  CAS  Google Scholar 

  17. Sverdlova, O.V.: Electronic Spectra in Organic Chemistry. Khimiya, Leningrad (1973). (in Russian)

    Google Scholar 

  18. Atkins, P.W.: Physical Chemistry. Oxford University Press, Oxford (1978)

    Google Scholar 

  19. Rekharsky, M.V., Inoue, Y.: Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875–1918 (1998)

    Article  CAS  Google Scholar 

  20. Nakanishi, K.: Infrared absorption spectroscopy-practical. Nankodo Company Ltd, Tokyo (1962)

    Google Scholar 

  21. Von Plessing Rossel, C., Carreno, J.S., Rodriguez-Baeza, M., Alderete, J.B.: Inclusion complex of the antiviral drug acyclovir with cyclodextrin in aqueous solution and in solid phase. Quim. Nova. 23, 749–752 (2000)

    Google Scholar 

  22. Patil, A., Pore, Y., Kuchekar, B.: Effect of l-arginine on bicalutamide complexation with hydroxypropyl-β-cyclodextrin. Dig. J. Nanomater. Biostress 3, 89–98 (2008)

    Google Scholar 

  23. Ammar, H.O., Salama, H.A., Ghorab, M., Mahmoud, A.A.: Inclusion complexation of glimepiride in dimethyl-β-cyclodextrin. Asian J. Pharm. Sci. 2, 44–55 (2007)

    CAS  Google Scholar 

  24. Zhang, Y., Yu, S., Bao, F.: Crystal structure of cyclomaltoheptaose (β-cyclodextrin) complexes with p-aminobenzoic acid and o-aminobenzoic acid. Carbohydr. Res. 343, 2504–2508 (2008)

    Article  CAS  Google Scholar 

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Correspondence to Nadiia V. Roik.

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Roik, N.V., Belyakova, L.A. Thermodynamic, IR spectral and X-ray diffraction studies of the “β-cyclodextrin-para-aminobenzoic acid” inclusion complex. J Incl Phenom Macrocycl Chem 69, 315–319 (2011). https://doi.org/10.1007/s10847-010-9737-0

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  • DOI: https://doi.org/10.1007/s10847-010-9737-0

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