title: Inclusion complexes of nabumetone with beta-cyclodextrins: thermodynamics and molecular modelling studies. Influence of sodium perchlorate.
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.
authors: Departamento de Química, Sección Química-Física, Facultad de Ciencias, Universidad de Navarra, 31080 Pamplona, Spain.
authors: N
authors: N
authors: Goyenechea
authors: M
authors: M
authors: Sánchez
authors: I
authors: I
authors: Vélaz
authors: C
authors: C
authors: Martín
authors: M C
authors: MC
authors: Martínez-Ohárriz
authors: G
authors: G
authors: González-Gaitano
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D000077430:Nabumetone; D010472:Perchlorates / Q000737:chemistry*; D017670:Sodium Compounds / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics; D047392:beta-Cyclodextrins
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D002074:Butanones; D003505:Cyclodextrins; D010472:Perchlorates; D017670:Sodium Compounds; D047392:beta-Cyclodextrins; C031068:sodium perchlorate; C031215:betadex; D000077430:Nabumetone