Inclusion complexes of nabumetone with beta-cyclodextrins: thermodynamics and molecular modelling studies. Influence of sodium perchlorate

Luminescence : the Journal of Biological and Chemical Luminescence
N GoyenecheaG González-Gaitano

Abstract

Fluorescence, (1)H-NMR and molecular mechanics have been used to study the inclusion complexes of nabumetone (4,6-methoxy-2-naphthyl-butan-2-one; NAB) with beta-cyclodextrin (beta-CD), randomly methylated-beta (M beta-CD) and hydroxypropyl-beta-cyclodextrins (HP beta-CD). The emission spectrum of NAB shows a maximum whose fluorescence intensity increases with the different beta-CDs growing concentrations. This phenomenon allows calculation of the stability constants at 15, 25, 37 and 45 degrees C. The thermodynamic parameters Delta H degrees and Delta S degrees for the inclusion process were obtained from the temperature dependence of the stability constants. Molecular mechanics calculations, together with proton NMR measurements, for the complex with beta-CD prove that the complex can be formed by penetration through any of the rims, with the naphthalene nucleus included and the substituents outside the cavity. The influence of NaClO(4) in the aforementioned complexes has been analysed by spectrofluorimetric measurements. It has been found that the stability constants for the complexes decrease with the salt concentration; the causes are discussed.

References

Aug 1, 1985·The Journal of Pharmacy and Pharmacology·K UekamaY Matsuoka
Feb 19, 2002·Chemical Reviews·Mikhail V. Rekharsky, Yoshihisa Inoue

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Citations

May 14, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Lydie SéonFouzia Boulmedais
Jan 23, 2016·Journal of Controlled Release : Official Journal of the Controlled Release Society·Cezar-Doru RaduLacramioara Ochiuz
Mar 21, 2013·International Journal of Biological Macromolecules·Anastasia RomanovaIrina Terekhova
Oct 8, 2013·Journal of Chemical Theory and Computation·Haiyang ZhangDavid van der Spoel

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