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Sci. Pharm.
Volume 86
Issue 1
10.3390/scipharm86010005
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Article

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

by
Jintawee Kicuntod
1,2,
Kanyani Sangpheak
3,
Monika Mueller
4,
Peter Wolschann
1,4,5,
Helmut Viernstein
4,
Saeko Yanaka
6,
Koichi Kato
6,7,
Warinthorn Chavasiri
8,
Piamsook Pongsawasdi
2,
Nawee Kungwan
9,10 and
Thanyada Rungrotmongkol
1,11,12,*
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
 
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Author to whom correspondence should be addressed.
Sci. Pharm. 2018, 86(1), 5; https://doi.org/10.3390/scipharm86010005
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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MDPI and ACS Style

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. https://doi.org/10.3390/scipharm86010005

AMA Style

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. https://doi.org/10.3390/scipharm86010005

Chicago/Turabian Style

Kicuntod, Jintawee, Kanyani Sangpheak, Monika Mueller, Peter Wolschann, Helmut Viernstein, Saeko Yanaka, Koichi Kato, Warinthorn Chavasiri, Piamsook Pongsawasdi, Nawee Kungwan, and Thanyada Rungrotmongkol. 2018. "Theoretical and Experimental Studies on Inclusion Complexes of Pinostrobin and β-Cyclodextrins" Scientia Pharmaceutica 86, no. 1: 5. https://doi.org/10.3390/scipharm86010005

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