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Interactions of Nabumetone with γ-Cyclodextrin Studied by Fluorescence Measurements

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Abstract

The inclusion of the anti-inflammatory drug, Nabumetone (NAB), in γ-cyclodextrin (γ-CD) was studied by fluorescence measurements. The emission fluorescence spectrum, of NAB reveals a maximum whose intensity increases with the different γ-CD’s growing concentrations. The stoichiometery (1:1) and binding constants of the complexes at 15, 25, 35, and 45 °C were extracted from the analysis of the emission spectra of NAB. The thermodynamic parameters ΔH ° and ΔS ° for the formation of the complex were calculated from the temperature dependence of the binding constants and compared with previous results for similar complexes of NAB with α- and β-CDs. The location of NAB in the complex was determined using the fluorescence quenching method. Our results indicate that NAB is completely penetrated into the cavity of γ-CD.

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References

  1. Bender M.L., Komiyama M. (eds) (1978) Cyclodextrin Chemistry. Springer-Verlag, Berlin

  2. J. Szejtli (1988) Cyclodextrin Technology Kluwer Dordrecht

    Google Scholar 

  3. J. Szejtli (1982) Cyclodextrins and their inclusion Complexes Akadémiai Kiadó Budapest

    Google Scholar 

  4. J. Szejtli (1991) Pharm Technol 3 15

    Google Scholar 

  5. D. Duchêne (1987) Cyclodextrins and Their Industrial Uses de Santé Paris

    Google Scholar 

  6. M.V. Rekharsky Y. Inoue (1998) Chem Rev 98 1875 Occurrence Handle11848952

    PubMed  Google Scholar 

  7. M.V. Rekharsky R.N. Goldberg F.P. Schwarz (1995) J Am Chem Soc 117 8830

    Google Scholar 

  8. L. Liu Q.-X. Guo (2002) J Incl Phenom 42 1

    Google Scholar 

  9. S.Z. Lin D. Wouessiidjewe D. Duchêne (1991) Int J Pharm 69 211

    Google Scholar 

  10. K. Uekama H. Otagiri A. Sakai T. Irie N. Matsuo Y. Matsmoka (1985) J Pharm Pharmacol 37 532 Occurrence Handle2864411

    PubMed  Google Scholar 

  11. F. Cramer W. Saenger H.-Ch. Spatz (1967) J Am Chem Soc 89 14

    Google Scholar 

  12. M. Matsui K. Mochida (1979) Bull Chem Soc Jpn 52 2808

    Google Scholar 

  13. T. Yorozu M. Hoshino M. Imamura H. Shizuka (1982) J Phys Chem 86 4422

    Google Scholar 

  14. A. Buvari J. Szejtli (1983) J Incl Phenom 1 151

    Google Scholar 

  15. S. Hamai (1988) J Phys Chem 93 2074

    Google Scholar 

  16. V.K. Smith T.T. Ndou A. Muñozdela Peña I.M. Warner (1991) J Incl Phenom 10 471

    Google Scholar 

  17. N. Kobayashi R. Saito H. Hino Y. Hino A. Ueno T. Osa (1983) J Chem Soc Perkin Trans 2 1031

    Google Scholar 

  18. T. Yorozu M. Hoshino M. Imamura (1982) J Phys Chem 86 4426

    Google Scholar 

  19. G. Patonay A. Shapira P. Diamond I.M. Warner (1986) J Phys Chem 90 1963

    Google Scholar 

  20. R.A. Agbaria B. Uzan D. Gill (1989) J Phys Chem 93 3855

    Google Scholar 

  21. S. Hamai (1989) J Phys Chem 93 6527

    Google Scholar 

  22. A. Muñozdela Peña T.T. Ndou J.B. Zung I.M. Warner (1991) J Phys Chem 95 3330

    Google Scholar 

  23. L. Flamigni (1993) J Phys Chem 97 9566

    Google Scholar 

  24. S. Monti G. Köhler G. Grabner (1993) J Phys Chem 97 13011

    Google Scholar 

  25. A. Nakamura K. Sato K. Hamasaki A. Ueno F. Toda (1995) J Phys Chem 99 10952

    Google Scholar 

  26. E. Mularz L.J. Cline-Love M. Petersheim (1988) Anal Chem 60 2751 Occurrence Handle3245599

    PubMed  Google Scholar 

  27. W.C. Cromwell K. Byström M.R. Eftink (1985) J Phys Chem 89 326

    Google Scholar 

  28. J.P. Diard E. Saint-Aman D. Serve (1985) J Electroanal Chem Interfacial Electrochem 189 113

    Google Scholar 

  29. D.C. Dong M.A. Winnik (1982) Photochem Photobiol 35 17

    Google Scholar 

  30. K. Fujimura T. Ueda K. Masashi H. Takayanagi T. Ando (1986) Anal Chem 58 2668

    Google Scholar 

  31. L.A. Blyshak K.Y. Dobson G. Patonay I.M. Warner N.E. May (1989) Anal Chem 61 955

    Google Scholar 

  32. R.M. Mohseni R.I. Hurtubise (1990) J Chromatogr 499 395

    Google Scholar 

  33. V.C. Anigbogu A. Muñozdela Peña T.T. Ndou I.M. Warner (1992) Anal Chem 64 484

    Google Scholar 

  34. J.A. Hamilton L.k. Steinranuf R.L. Van Etten (1968) Acta Crystallogr B 24 1560 Occurrence Handle5756996

    PubMed  Google Scholar 

  35. T. Yorozu M. Hoshino M. Imamura H. Shizuka (1982) J Phys Chem 86 4422

    Google Scholar 

  36. J.C. Márquez M. Hernandez F. Carcia Sánchez (1990) Analyst 115 1003 Occurrence Handle2221395

    PubMed  Google Scholar 

  37. D.A. Lerner B. Del Castillo S. Muñoz Botella (1989) Anal Chim Acta 227 297

    Google Scholar 

  38. O. Jules S. Scypinski L.J. Cline Love (1985) Anal Chim Acta 169 335

    Google Scholar 

  39. (a) Baeyens W., Lin B., Corbisier V. (1990) Analyst 115:359 (b) ibid, 234, 187 (1990)

  40. (a) Scypinski S., Cline Love L.J. (1984) Anal. Chem. 56, 322. (b) ibid, 56, 3331 (1984)

  41. H.J. Casal J.C. Netto-Perreira J.C. Scaiano (1985) J Incl Phenom 3 395

    Google Scholar 

  42. S. Hamai (1989) J Am Chem Soc 111 3954

    Google Scholar 

  43. F. Ginsberg J.D. Famaey (1982) J Int Med Res 10 209 Occurrence Handle7117677

    PubMed  Google Scholar 

  44. L.A. Verbruggen E. Cytryn H. Pintens (1982) J Int Med Res 10 214 Occurrence Handle7117678

    PubMed  Google Scholar 

  45. J.E. Ray R.O. Day (1984) J Chromatogr (Biomed Appl) 336 234

    Google Scholar 

  46. I.F. Almomani (1997) Analytical letters 30 2485

    Google Scholar 

  47. N.M. Davies (1997) Clinical Pharmacokinetics 33 IssueID6 403

    Google Scholar 

  48. N. Goyenechea M. Sánchez I. Vélaz C. Martín C.M. Martínez-Ohárriz G. González-Gaitano (2001) Luminescence 16 117 Occurrence Handle11312537

    PubMed  Google Scholar 

  49. M. Valero S.M.B. Costa J.R. Ascenso M. Velázquez L.J. Rodríguez (1999) J Incl Phenom 35 663

    Google Scholar 

  50. M. Valero S.M.B. Costa M.A. Santos (2000) J Photochem Photobiol A: Chem 132 67

    Google Scholar 

  51. N. Goyenechea M. Sanchez I. Velaz C. Martin C. Martinez-Oharriz A. Zornoza (2002) J Incl Phenom 44 283

    Google Scholar 

  52. J.R. Lakowicz (1986) Principles of Fluorescence Spectroscopy Plenum New York 126

    Google Scholar 

  53. K. Connors (1987) Binding Constants John Wiley & Sons New York

    Google Scholar 

Download references

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Correspondence to Nathir A. F. Al-Rawashdeh.

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Al-Rawashdeh, N.A.F. Interactions of Nabumetone with γ-Cyclodextrin Studied by Fluorescence Measurements. J Incl Phenom Macrocycl Chem 51, 27–32 (2005). https://doi.org/10.1007/s10847-004-1502-9

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  • DOI: https://doi.org/10.1007/s10847-004-1502-9

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