Please use this identifier to cite or link to this item: http://repositorio.ufc.br/handle/riufc/26554
Type: Artigo de Periódico
Title: Supramolecular interactions between β‐lapachone with cyclodextrins studied using isothermal titration calorimetry and molecular modeling
Authors: Xavier‐Junior, Francisco H.
Rabello, Marcelo M.
Hernandes, Marcelo Z.
Dias, Marília E.S.
Andrada, Otoni H.M.S.
Bezerra, Beatriz P.
Ayala, Alejandro P.
Santos‐Magalhães, Nereide S.
Keywords: Ciclodextrinas;Cyclodextrins;Calorimetria
Issue Date: Jul-2017
Publisher: Journal of molecular recognition
Citation: XAVIER-JUNIOR, F. H. et al. Supramolecular interactions between β-lapachone with cyclodextrins studied using isothermal titration calorimetry and molecular modeling. Journal of molecular recognition, London, v. 30, p. 1-10, jul. 2017.
Abstract: Supramolecular interactions between β-lapachone (β-lap) and cyclodextrins (CDs) were investigated by isothermal titration calorimetry. The most favorable host: guest interaction was characterized using X-ray powder diffraction (XRD), differential scanning calorimetry and thermogravimetry (DSC/TG), spectroscopy (FT-IR), spectroscopy (2D ROESY) nuclear magnetic resonance (NMR), and molecular modeling. Phase solubility diagrams showed β-, HP-β-, SBE-β-, γ-, and HP-γ-CDs at 1.5% (w/w) allowed an increase in apparent solubility of β-lap with enhancement factors of 12.0, 10.1, 11.8, 2.4, and 2.2, respectively. β-lap has a weak interaction with γ- and HP-γ-CDs and tends to interact more favorably with β-CD and its derivatives, especially SBE-β-CD (K = 4160 M−1; ΔG = −20.66 kJ·mol−1). Thermodynamic analysis suggests a hydrophobic interaction associated with the displacement of water from the cavity of the CD by the β-lap. In addition, van der Waals forces and hydrogen bonds were responsible for the formation of complexes. Taken together, the results showed intermolecular interactions between β-lap and SBE-β-CD, thereby confirming the formation of the inclusion complex. Molecular docking results showed 2 main orientations in which the interaction of benzene moiety at the wider rim of the SBE-β-CD is the most stable (average docking energy of −7.0 kcal/mol). In conclusion, β-lap:SBE-β-CD is proposed as an approach for use in drug delivery systems in cancer research
URI: http://www.repositorio.ufc.br/handle/riufc/26554
ISSN: 0952-3499
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