Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. 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...
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th-cmuir.6653943832-485222018-04-25T10:13:28Z Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins Jintawee Kicuntod Kanyani Sangpheak Monika Mueller Peter Wolschann Helmut Viernstein Saeko Yanaka Koichi Kato Warinthorn Chavasiri Piamsook Pongsawasdi Nawee Kungwan Thanyada Rungrotmongkol © 2018 by the authors. Licensee MDPI, Basel, Switzerland. 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 A L -typediagram 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. 2018-04-25T10:13:28Z 2018-04-25T10:13:28Z 2018-03-01 Journal 22180532 00368709 2-s2.0-85044082110 10.3390/scipharm86010005 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85044082110&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/48522 |
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© 2018 by the authors. Licensee MDPI, Basel, Switzerland. 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 A L -typediagram 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. |
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Jintawee Kicuntod Kanyani Sangpheak Monika Mueller Peter Wolschann Helmut Viernstein Saeko Yanaka Koichi Kato Warinthorn Chavasiri Piamsook Pongsawasdi Nawee Kungwan Thanyada Rungrotmongkol |
spellingShingle |
Jintawee Kicuntod Kanyani Sangpheak Monika Mueller Peter Wolschann Helmut Viernstein Saeko Yanaka Koichi Kato Warinthorn Chavasiri Piamsook Pongsawasdi Nawee Kungwan Thanyada Rungrotmongkol Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
author_facet |
Jintawee Kicuntod Kanyani Sangpheak Monika Mueller Peter Wolschann Helmut Viernstein Saeko Yanaka Koichi Kato Warinthorn Chavasiri Piamsook Pongsawasdi Nawee Kungwan Thanyada Rungrotmongkol |
author_sort |
Jintawee Kicuntod |
title |
Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
title_short |
Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
title_full |
Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
title_fullStr |
Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
title_full_unstemmed |
Theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
title_sort |
theoretical and experimental studies on inclusion complexes of pinostrobin and β-cyclodextrins |
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2018 |
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https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85044082110&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/48522 |
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