Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and ?-Cyclodextrins.

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 ?-cyclodextrin (?CD) and its derivatives, heptakis-(2,6-di-O-methyl)-?-cyclodextrin (2,6-DM?CD) and (2-hydroxypropyl)-?-cyclodextrin (HP?CD). 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 ?CD derivatives whilst only one orientation of PNS, where the C-PNS ring is inside the cavity, was detected in the case of the parental ?CD. All PNS/?CDs 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.

SUBMITTER: Kicuntod J 

PROVIDER: S-EPMC5874535 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature