%0 Journal Article %1 WOS:000457660000017 %A Xavier-Junior, F H %A Tavares, C T %A Rabello, M M %A Hernandes, M Z %A Bezerra, B P %A Ayala, A P %A Pessoa, O D L %A Ximenes, R M %A Santos-Magalhaes, N S %C PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS %D 2019 %I ELSEVIER SCIENCE BV %J JOURNAL OF MOLECULAR LIQUIDS %K Cyclodextrins; Isothermal Molecular Thermal a; analysis} calorimetry; modeling; titration {Oncocalyxone %P 165-172 %R 10.1016/j.molliq.2018.10.129 %T Elucidation of the mechanism of complexation between oncocalyxone A and cyclodextrins by isothermal titration calorimetry and molecular modeling %V 274 %X The physicochemical stability and bioavailability of oncocalyxone A (onco A), a quinone isolated from Auxemma oncocalyx tree, could be improved by supramotecular inclusion complexes with cyclodextrins (CDs). The aim of this study was thus to elucidate the complexation of onco A with different CDs using isothermal titration calorimetry (ITC) and molecular modeling. Data from the most favorable host:guest interaction made it possible to obtain onco A:HP-gamma-CD inclusion complex, which was characterized by FTIR, (HNMR)-H-1, DSC and TG. Experimental results showed that onco A tends to interact more favorably with HP-gamma-CD (K = 3175 M-1) with the most favorable Gibbs free energy (Delta G = -19.98 kj-mol(-1)). Thermodynamic analysis indicates that the formation of the inclusion complex was entropy-driven (-T Delta S = -19.54 kj.mol(-1)), associated mainly with the hydrophobic interactions and release of water molecules from the cavity of the CD. Taken together, physicochemical analysis showed host:guest intermolecular interactions between onco A and the cavity of the HP-gamma-CD, thereby confirming the formation of the inclusion complex. Moreover, molecular docking results showed two main orientations in which the interaction of the hydroxyl group and a hydroxymethyl group at the wider rim of the HP-gamma-CD was more stable (average docking energy of -7.3 kcal/mol) than the one involving the methoxy group with two carbonyl groups at the wider rim (-7.1 kcal/mol). In conclusion, onco A:HP-gamma-CD inclusion complex based on results of rational approaches was obtained for use in for further pharmaceutical application in drug delivery systems in cancer therapy. Published by Elsevier B.V.

@article{WOS:000457660000017, abstract = {The physicochemical stability and bioavailability of oncocalyxone A (onco A), a quinone isolated from Auxemma oncocalyx tree, could be improved by supramotecular inclusion complexes with cyclodextrins (CDs). The aim of this study was thus to elucidate the complexation of onco A with different CDs using isothermal titration calorimetry (ITC) and molecular modeling. Data from the most favorable host:guest interaction made it possible to obtain onco A:HP-gamma-CD inclusion complex, which was characterized by FTIR, (HNMR)-H-1, DSC and TG. Experimental results showed that onco A tends to interact more favorably with HP-gamma-CD (K = 3175 M-1) with the most favorable Gibbs free energy (Delta G = -19.98 kj-mol(-1)). Thermodynamic analysis indicates that the formation of the inclusion complex was entropy-driven (-T Delta S = -19.54 kj.mol(-1)), associated mainly with the hydrophobic interactions and release of water molecules from the cavity of the CD. Taken together, physicochemical analysis showed host:guest intermolecular interactions between onco A and the cavity of the HP-gamma-CD, thereby confirming the formation of the inclusion complex. Moreover, molecular docking results showed two main orientations in which the interaction of the hydroxyl group and a hydroxymethyl group at the wider rim of the HP-gamma-CD was more stable (average docking energy of -7.3 kcal/mol) than the one involving the methoxy group with two carbonyl groups at the wider rim (-7.1 kcal/mol). In conclusion, onco A:HP-gamma-CD inclusion complex based on results of rational approaches was obtained for use in for further pharmaceutical application in drug delivery systems in cancer therapy. Published by Elsevier B.V.}, added-at = {2022-05-23T20:00:14.000+0200}, address = {PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}, author = {Xavier-Junior, F H and Tavares, C T and Rabello, M M and Hernandes, M Z and Bezerra, B P and Ayala, A P and Pessoa, O D L and Ximenes, R M and Santos-Magalhaes, N S}, biburl = {https://www.bibsonomy.org/bibtex/2f41986bd061a874978a1178db4fe80b5/ppgfis_ufc_br}, doi = {10.1016/j.molliq.2018.10.129}, interhash = {d17c61a3b3e679a66d42793166f2c47d}, intrahash = {f41986bd061a874978a1178db4fe80b5}, issn = {0167-7322}, journal = {JOURNAL OF MOLECULAR LIQUIDS}, keywords = {Cyclodextrins; Isothermal Molecular Thermal a; analysis} calorimetry; modeling; titration {Oncocalyxone}, pages = {165-172}, publisher = {ELSEVIER SCIENCE BV}, pubstate = {published}, timestamp = {2022-05-23T20:00:14.000+0200}, title = {Elucidation of the mechanism of complexation between oncocalyxone A and cyclodextrins by isothermal titration calorimetry and molecular modeling}, tppubtype = {article}, volume = 274, year = 2019 }