The encapsulation of beta-lapachone in 2-hydroxypropyl-beta-cyclodextrin
inclusion complex into liposomes: A physicochemical evaluation and
molecular modeling approach
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.
%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
}