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Abstract:

A thermodynamic study of the inclusion process between 2-chlorobenzophenone (2ClBP) and cyclomaltoheptaose (β-cyclodextrin, β-CD) was performed using UV-vis spectroscopy, reversed-phase liquid chromatography (RP-HPLC), and molecular modeling (PM6). Spectrophotometric measurements in aqueous solutions were performed at different temperatures. The stoichiometry of the complex is 1:1 and its apparent formation constant (Kc) is 3846 M-1 at 30 °C. Temperature dependence of Kc values revealed that both enthalpy (δH° = -10.58 kJ/mol) and entropy changes (δS° = 33.76 J/K mol) are favorable for the inclusion process in an aqueous medium. Encapsulation was also investigated using RP-HPLC (C18 column) with different mobile-phase compositions, to which β-CD was added. The apparent formation constants in MeOH-H2O (KF) were dependent of the proportion of the mobile phase employed (50:50, 55:45, 60:40 and 65:35, v/v). The KF values were 419 M-1 (50% MeOH) and 166 M -1 (65% MeOH) at 30 °C. The thermodynamic parameters of the complex in an aqueous MeOH medium indicated that this process is largely driven by enthalpy change (δH° = -27.25 kJ/mol and δS° = -45.12 J/K mol). The results of the study carried out with the PM6 semiempirical method showed that the energetically most favorable structure for the formation of the complex is the 'head up' orientation. © 2011 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling
Autor:Sancho, M.I.; Gasull, E.; Blanco, S.E.; Castro, E.A.
Filiación:Área de Química Física, Facultad de Química Bioquímica y Farmacia, Universidad Nacional de San Luis, 5700 San Luis, Argentina
Instituto Multidisciplinario de Investigaciones Biológicas (IMIBIO-SL) CONICET, 5700 San Luis, Argentina
INIFTA, Dpto. de Química, Facultad de Ciencias Exactas, 1900 Buenos Aires, Argentina
Palabras clave:2-Chlorobenzophenone; Apparent formation constants; Molecular modeling; Reversed-phase liquid chromatography; Solubility; β-Cyclodextrin; Chromatography; Cyclodextrins; Enthalpy; Molecular modeling; Solubility; Solutions; Solvents; Temperature; Temperature distribution; Ultraviolet visible spectroscopy; 2-Chlorobenzophenone; Formation constants; Mobile-phase composition; Reversed phase liquid-chromatography; Semi-empirical methods; Spectrophotometric measurements; Temperature dependence; Thermodynamic parameter; Liquid chromatography; 2 chlorobenzophenone; benzophenone derivative; beta cyclodextrin; unclassified drug; article; controlled study; drug solubility; encapsulation; enthalpy; entropy; molecular model; priority journal; reversed phase high performance liquid chromatography; solvent effect; stoichiometry; temperature; thermodynamics; ultraviolet spectroscopy
Año:2011
Volumen:346
Número:13
Página de inicio:1978
Página de fin:1984
DOI: http://dx.doi.org/10.1016/j.carres.2011.05.002
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:beta cyclodextrin, 7585-39-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n13_p1978_Sancho

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Citas:

---------- APA ----------
Sancho, M.I., Gasull, E., Blanco, S.E. & Castro, E.A. (2011) . Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling. Carbohydrate Research, 346(13), 1978-1984.
http://dx.doi.org/10.1016/j.carres.2011.05.002
---------- CHICAGO ----------
Sancho, M.I., Gasull, E., Blanco, S.E., Castro, E.A. "Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling" . Carbohydrate Research 346, no. 13 (2011) : 1978-1984.
http://dx.doi.org/10.1016/j.carres.2011.05.002
---------- MLA ----------
Sancho, M.I., Gasull, E., Blanco, S.E., Castro, E.A. "Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling" . Carbohydrate Research, vol. 346, no. 13, 2011, pp. 1978-1984.
http://dx.doi.org/10.1016/j.carres.2011.05.002
---------- VANCOUVER ----------
Sancho, M.I., Gasull, E., Blanco, S.E., Castro, E.A. Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling. Carbohydr. Res. 2011;346(13):1978-1984.
http://dx.doi.org/10.1016/j.carres.2011.05.002