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Sci. Pharm. 2018, 86(1), 5; https://doi.org/10.3390/scipharm86010005

Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins

1
Structural and Computational Biology Research Group, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
2
Starch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
3
Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
4
Department of Pharmaceutical Technology and Biopharmaceutics, University of Vienna, 1090 Vienna, Austria
5
Institute of Theoretical Chemistry, University of Vienna, 1090 Vienna, Austria
6
Institute for Molecular Science and Okazaki Institute for Integrative Bioscience, National Institutes of Natural Science, 5-1 Higashiyama Myodaiji, Okazaki 444-8787, Japan
7
School of Physical Sciences, SOKENDAI (The Graduate University for Advanced Studies), 5-1 Higashiyama Myodaiji, Okazaki 444-8787, Japan
8
Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
9
Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
10
Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand
11
Program in Bioinformatics and Computational Biology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
12
Molecular Sensory Science Center, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
*
Author to whom correspondence should be addressed.
Received: 30 December 2017 / Revised: 20 January 2018 / Accepted: 22 January 2018 / Published: 30 January 2018
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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. View Full-Text
Keywords: pinostrobin; β-cyclodextrin; inclusion complexation; biological activity; steered molecular dynamics simulation pinostrobin; β-cyclodextrin; inclusion complexation; biological activity; steered molecular dynamics simulation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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