Promising applications in drug delivery systems of a novel b-cyclodextrin derivative obtained by green synthesis

GARCÍA, A.; LAMAS, M.C.; LEONARDI, D.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2016 vol. 26 p. 602 - 608

0960-894X

An efficient and green method has been developed for the synthesis of succinyl-b-cyclodextrin in aqueous media obtaining very good yield. Acidic groups have been introduced in the synthesized carrier molecule to improve the guest?host affinity. To evaluate the suitability of the novel excipient focused to develop oral dosage forms, albendazole, a BSC class II compound, was chosen as a model drug. The b-cyclodextrin derivative and the inclusion complex were thoroughly characterized in solution and solid state by phase solubility studies, FT-IR spectroscopy, SEM, XRD, ESI-MS, DSC, 1D 1H NMR, 1D 13C NMR, selective 1D TOCSY, 2D COSY, 2D HSQC, 2D HMBC and ROESY NMR spectroscopy. Phase solubility studies indicated that both of them b-cyclodextrin and succinyl-b-cyclodextrin formed 1:1 inclusion complexes with albendazole, and the stability constants were 68 M_1 (b-cyclodextrin), 437 M_1 (succinyl- b-cyclodextrin), respectively. Water solubility and dissolution rate of albendazole were significantly improved in complex forms. Thus, the succinyl-b-cyclodextrin derivative could be a promising excipient to design oral dosage forms.