%0 Journal Article %1 WOS:000296930000018 %A Cavalcanti, Isabella M F %A Mendonca, Elisangela A M %A Lira, Mariane C B %A Honrato, Sara B %A Camara, Celso A %A Amorim, Rosa V S %A Filho, Josue Mendes %A Rabello, Marcelo M %A Hernandes, Marcelo Z %A Ayala, Alejandro P %A Santos-Magalhaes, Nereide S %C RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS %D 2011 %I ELSEVIER %J EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES %K 2-Hydroxypropyl-beta-cyclodextrin; Inclusion Kinetics} Liposomes; Molecular complex; modeling; {beta-Lapachone; %N 3 %P 332-340 %R 10.1016/j.ejps.2011.08.011 %T The encapsulation of beta-lapachone in 2-hydroxypropyl-beta-cyclodextrin inclusion complex into liposomes: A physicochemical evaluation and molecular modeling approach %V 44 %X The aim of this study was to encapsulate lapachone (beta-lap) or inclusion complex (beta-lap:HP beta-CD) in liposomes and to evaluate their physicochemical characteristics. In addition, the investigation of the main aspects of the interaction between beta-lap and 2-hydroxypropyl-beta-cyclodextrin (HP beta-CD), using both experimental and molecular modeling approaches was discussed. Furthermore, the in vitro drug release kinetics was evaluated. First, a phase solubility study of beta-lap in HP beta-CD was performed and the beta-lap:HP beta-CD was prepared by the freeze-drying technique. A 302-fold increase of solubility was achieved for beta-lap in HP beta-CD solution with a constant of association K-1:1 of 961 M-1 and a complexation efficiency of beta-lap of 0.1538. H-1 NMR, TG, DSC, IR, Raman and SEM indicated a change in the molecular environment of beta-lap in the inclusion complex. Molecular modeling confirms these results suggesting that beta-lap was included in the cavity of HP beta-CD, with an intermolecular interaction energy of -23.67 kJ mol(-1). beta-lap:HP beta-CD and beta-lap-loaded liposomes presented encapsulation efficiencies of 93% and 97%, respectively. The kinetic rate constants of 183.95 +/- 1.82 mu g/h and 216.25 +/- 2.34 mu g/h were calculated for beta-lap and beta-lap:HP beta-CD-loaded liposomes, respectively. In conclusion, molecular modeling elucidates the formation of the inclusion complex, stabilized through hydrogen bonds, and the encapsulation of beta-lap and beta-lap:HP beta-CD into liposomes could provide an alternative means leading eventually to its use in cancer research. (C) 2011 Elsevier B.V. All rights reserved.

@article{WOS:000296930000018, abstract = {The aim of this study was to encapsulate lapachone (beta-lap) or inclusion complex (beta-lap:HP beta-CD) in liposomes and to evaluate their physicochemical characteristics. In addition, the investigation of the main aspects of the interaction between beta-lap and 2-hydroxypropyl-beta-cyclodextrin (HP beta-CD), using both experimental and molecular modeling approaches was discussed. Furthermore, the in vitro drug release kinetics was evaluated. First, a phase solubility study of beta-lap in HP beta-CD was performed and the beta-lap:HP beta-CD was prepared by the freeze-drying technique. A 302-fold increase of solubility was achieved for beta-lap in HP beta-CD solution with a constant of association K-1:1 of 961 M-1 and a complexation efficiency of beta-lap of 0.1538. H-1 NMR, TG, DSC, IR, Raman and SEM indicated a change in the molecular environment of beta-lap in the inclusion complex. Molecular modeling confirms these results suggesting that beta-lap was included in the cavity of HP beta-CD, with an intermolecular interaction energy of -23.67 kJ mol(-1). beta-lap:HP beta-CD and beta-lap-loaded liposomes presented encapsulation efficiencies of 93% and 97%, respectively. The kinetic rate constants of 183.95 +/- 1.82 mu g/h and 216.25 +/- 2.34 mu g/h were calculated for beta-lap and beta-lap:HP beta-CD-loaded liposomes, respectively. In conclusion, molecular modeling elucidates the formation of the inclusion complex, stabilized through hydrogen bonds, and the encapsulation of beta-lap and beta-lap:HP beta-CD into liposomes could provide an alternative means leading eventually to its use in cancer research. (C) 2011 Elsevier B.V. All rights reserved.}, added-at = {2022-05-23T20:00:14.000+0200}, address = {RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS}, author = {Cavalcanti, Isabella M F and Mendonca, Elisangela A M and Lira, Mariane C B and Honrato, Sara B and Camara, Celso A and Amorim, Rosa V S and Filho, Josue Mendes and Rabello, Marcelo M and Hernandes, Marcelo Z and Ayala, Alejandro P and Santos-Magalhaes, Nereide S}, biburl = {https://www.bibsonomy.org/bibtex/2aae168d106667d0543e573196f24042f/ppgfis_ufc_br}, doi = {10.1016/j.ejps.2011.08.011}, interhash = {0d73c87a992ac62ac842f8d991710965}, intrahash = {aae168d106667d0543e573196f24042f}, issn = {0928-0987}, journal = {EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES}, keywords = {2-Hydroxypropyl-beta-cyclodextrin; Inclusion Kinetics} Liposomes; Molecular complex; modeling; {beta-Lapachone;}, number = 3, pages = {332-340}, publisher = {ELSEVIER}, pubstate = {published}, timestamp = {2022-05-23T20:00:14.000+0200}, title = {The encapsulation of beta-lapachone in 2-hydroxypropyl-beta-cyclodextrin inclusion complex into liposomes: A physicochemical evaluation and molecular modeling approach}, tppubtype = {article}, volume = 44, year = 2011 }