Host–guest interactions between dapsone and β-cyclodextrin (part I): study of the inclusion compound by nuclear magnetic resonance techniques

• Published in: Journal of Inclusion Phenomena and Macrocyclic Chemistry 2013-02, Vol.75 (1-2), p.77-86
• Main Authors: Calderini, Adriana, Martins, Milene H., Pessine, Francisco B. T.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Food Science; Organic Chemistry; Original Article
• ISSN: 0923-0750; 1573-1111
• DOI: 10.1007/s10847-012-0148-2

Dapsone (4,4′diaminodiphenylsulfone) is a very effective drug to treat leprosy and a broad range of infectious conditions such as Pneumocystis carinii pneumonia, toxoplasmosis and tuberculosis. However, the oral administration of this drug generally is related to serious side effects and treatment failures. It is believed that the inclusion compound of this drug and cyclodextrins would increase the wettability and the solubility of the encapsulated drug for a supported and gradual release, maximizing its biodisponibility over time. The encapsulation of dapsone in β-cyclodextrin was investigated by five nuclear magnetic resonance spectroscopy techniques. The data obtained for the complex in aqueous solution and in solid-state revealed a strong interaction between host and guest, showing that the drug molecule is deeply inserted in the CD cavity. The diffusion experiments (diffusion ordered spectroscopy) showed a high percentage of complexation (86 %) and that the drug molecule is preferentially interacting with the large side of the β-cyclodextrin cavity.