Title
Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins
Author
Jintawee Kicuntod
Structural and Computational Biology Research Group, Department of Biochemistry, Faculty of Science, Chulalongkorn University
Kanyani Sangpheak
Program in Biotechnology, Faculty of Science, Chulalongkorn University
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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 β-cyclodextrin (βCD) and its derivatives, heptakis-(2,6-di-O-methyl)-β-cyclodextrin (2,6-DMβCD) and (2-hydroxypropyl)-β-cyclodextrin (HPβCD). The AL-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 βCD derivatives whilst only one orientation of PNS, where the C-PNS ring is inside the cavity, was detected in the case of the parental βCD. All PNS/βCDs 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.
Keywords
pinostrobinβ-cyclodextrininclusion complexationbiological activitysteered molecular dynamics simulation
Object type
Language
English [eng]
Persistent identifier
Appeared in
Title
Scientia Pharmaceutica
Volume
86
Issue
1
Publication
MDPI AG
Version type
Date issued
2018
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© 2018 by the authors
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