%0 Journal Article %1 WOS:000412539400006 %A Xavier-Junior, Francisco H %A Rabello, Marcelo M %A Hernandes, Marcelo Z %A Dias, Marilia E S %A Andrada, Otoni H M S %A Bezerra, Beatriz P %A Ayala, Alejandro P %A Santos-Magalhaes, Nereide S %C 111 RIVER ST, HOBOKEN 07030-5774, NJ USA %D 2017 %I WILEY %J JOURNAL OF MOLECULAR RECOGNITION %K beta-lapachone} calorimetry; isothermal modeling; molecular phase solubility; titration {cyclodextrins; %N 11 %R 10.1002/jmr.2646 %T Supramolecular interactions between beta-lapachone with cyclodextrins studied using isothermal titration calorimetry and molecular modeling %V 30 %X Supramolecular interactions between beta-lapachone (beta-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 beta-, HP-beta-, SBE-beta, gamma-, and HP-gamma-CDs at 1.5% (w/w) allowed an increase in apparent solubility of beta-lap with enhancement factors of 12.0, 10.1, 11.8, 2.4, and 2.2, respectively. beta-lap has a weak interaction with gamma- and HP-gamma-CDs and tends to interact more favorably with beta-CD and its derivatives, especially SBE-beta-CD (K=4160M(-1); Delta G=-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 beta-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 beta-lap and SBE-beta-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-beta-CD is the most stable (average docking energy of --7.0 kcal/mol). In conclusion, beta-lap:SBE-beta-CD is proposed as an approach for use in drug delivery systems in cancer research.

@article{WOS:000412539400006, abstract = {Supramolecular interactions between beta-lapachone (beta-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 beta-, HP-beta-, SBE-beta, gamma-, and HP-gamma-CDs at 1.5% (w/w) allowed an increase in apparent solubility of beta-lap with enhancement factors of 12.0, 10.1, 11.8, 2.4, and 2.2, respectively. beta-lap has a weak interaction with gamma- and HP-gamma-CDs and tends to interact more favorably with beta-CD and its derivatives, especially SBE-beta-CD (K=4160M(-1); Delta G=-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 beta-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 beta-lap and SBE-beta-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-beta-CD is the most stable (average docking energy of --7.0 kcal/mol). In conclusion, beta-lap:SBE-beta-CD is proposed as an approach for use in drug delivery systems in cancer research.}, added-at = {2022-05-23T20:00:14.000+0200}, address = {111 RIVER ST, HOBOKEN 07030-5774, NJ USA}, author = {Xavier-Junior, Francisco H and Rabello, Marcelo M and Hernandes, Marcelo Z and Dias, Marilia E S and Andrada, Otoni H M S and Bezerra, Beatriz P and Ayala, Alejandro P and Santos-Magalhaes, Nereide S}, biburl = {https://www.bibsonomy.org/bibtex/29ba6e4ebc7f16a7d0e63b6b1a8d6fc2e/ppgfis_ufc_br}, doi = {10.1002/jmr.2646}, interhash = {f206deff66e19c19e52c945a3895f0d7}, intrahash = {9ba6e4ebc7f16a7d0e63b6b1a8d6fc2e}, issn = {0952-3499}, journal = {JOURNAL OF MOLECULAR RECOGNITION}, keywords = {beta-lapachone} calorimetry; isothermal modeling; molecular phase solubility; titration {cyclodextrins;}, number = 11, publisher = {WILEY}, pubstate = {published}, timestamp = {2022-05-23T20:00:14.000+0200}, title = {Supramolecular interactions between beta-lapachone with cyclodextrins studied using isothermal titration calorimetry and molecular modeling}, tppubtype = {article}, volume = 30, year = 2017 }