%0 Journal Article
%T Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and ¦Â-Cyclodextrins
%A Helmut Viernstein
%A Jintawee Kicuntod
%A Kanyani Sangpheak
%A Koichi Kato
%A Monika Mueller
%A Nawee Kungwan
%A Peter Wolschann
%A Piamsook Pongsawasdi
%A Saeko Yanaka
%A Thanyada Rungrotmongkol
%A Warinthorn Chavasiri
%J -
%D 2018
%R https://doi.org/10.3390/scipharm86010005
%X Abstract Pinostrobin (PNS) belongs to the flavanone subclass of flavonoids which shows several biological activities such as anti-inflammatory, anti-cancerogenic, anti-viral and anti-oxidative effects. Similar to other flavonoids, PNS has a quite low water solubility. The purpose of this work is to improve the solubility and the biological activities of PNS by forming inclusion complexes with ¦Â-cyclodextrin (¦ÂCD) and its derivatives, heptakis-(2,6-di- O-methyl)-¦Â-cyclodextrin (2,6-DM¦ÂCD) and (2-hydroxypropyl)-¦Â-cyclodextrin (HP¦ÂCD). The A L-type diagram of the phase solubility studies of PNS exhibited the formed inclusion complexes with the 1:1 molar ratio. Inclusion complexes were prepared by the freeze-drying method and were characterized by differential scanning calorimetry (DSC). Two-dimensional nuclear magnetic resonance (2D-NMR) and steered molecular dynamics (SMD) simulation revealed two different binding modes of PNS, i.e., its phenyl- ( P-PNS) and chromone- ( C-PNS) rings preferably inserted into the cavity of ¦ÂCD derivatives whilst only one orientation of PNS, where the C-PNS ring is inside the cavity, was detected in the case of the parental ¦ÂCD. All PNS/¦ÂCDs complexes had a higher dissolution rate than free PNS. Both PNS and its complexes significantly exerted a lowering effect on the IL-6 secretion in LPS-stimulated macrophages and showed a moderate cytotoxic effect against MCF-7 and HeLa cancer cell lines in vitro. View Full-Tex
%K pinostrobin
%K ¦Â-cyclodextrin
%K inclusion complexation
%K biological activity
%K steered molecular dynamics simulation
%U https://www.mdpi.com/2218-0532/86/1/5