Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins
AbstractPinostrobin (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. View Full-Text
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Kicuntod, J.; Sangpheak, K.; Mueller, M.; Wolschann, P.; Viernstein, H.; Yanaka, S.; Kato, K.; Chavasiri, W.; Pongsawasdi, P.; Kungwan, N.; Rungrotmongkol, T. Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins. Sci. Pharm. 2018, 86, 5.
Kicuntod J, Sangpheak K, Mueller M, Wolschann P, Viernstein H, Yanaka S, Kato K, Chavasiri W, Pongsawasdi P, Kungwan N, Rungrotmongkol T. Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins. Scientia Pharmaceutica. 2018; 86(1):5.Chicago/Turabian Style
Kicuntod, Jintawee; Sangpheak, Kanyani; Mueller, Monika; Wolschann, Peter; Viernstein, Helmut; Yanaka, Saeko; Kato, Koichi; Chavasiri, Warinthorn; Pongsawasdi, Piamsook; Kungwan, Nawee; Rungrotmongkol, Thanyada. 2018. "Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins." Sci. Pharm. 86, no. 1: 5.