Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins

© 2017 Elsevier Inc. The structural dynamics and stability of inclusion complexes of mansonone E (ME) and H (MH) including their stereoisomers with various βCDs (methylated- and hydroxypropylated-βCDs) were investigated by classical molecular dynamics (MD) simulations and binding free energy calcula...

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Main Authors: Panupong Mahalapbutr, Bodee Nutho, Peter Wolschann, Warinthorn Chavasiri, Nawee Kungwan, Thanyada Rungrotmongkol
Format: Journal
Published: 2018
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http://cmuir.cmu.ac.th/jspui/handle/6653943832/58478
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Institution: Chiang Mai University
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spelling th-cmuir.6653943832-584782018-09-05T04:32:13Z Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins Panupong Mahalapbutr Bodee Nutho Peter Wolschann Warinthorn Chavasiri Nawee Kungwan Thanyada Rungrotmongkol Chemistry Computer Science Materials Science © 2017 Elsevier Inc. The structural dynamics and stability of inclusion complexes of mansonone E (ME) and H (MH) including their stereoisomers with various βCDs (methylated- and hydroxypropylated-βCDs) were investigated by classical molecular dynamics (MD) simulations and binding free energy calculations. The simulation results revealed that mansonones are able to form inclusion complexes with βCDs. The guest molecules are not completely inserted into the host cavity, their preferably positions are nearby the secondary rim with the oxane ring dipping into the hydrophobic inner cavity. The encapsulation process leads to a higher rigidity of the βCDs enhancing the intramolecular hydrogen bond formation ability and decreasing the chance of glucopyranose rotation. According to the MM-PBSA binding free energy calculation, all considered inclusion complexes are stable and the binding energies are mainly caused by van der Waals interactions. Moreover, the free energy calculations showed significant differences in the complexation energies for the stereoisomers, which could enable the separation of the isomers by analytical techniques for further pharmaceutical applications. 2018-09-05T04:25:08Z 2018-09-05T04:25:08Z 2018-01-01 Journal 18734243 10933263 2-s2.0-85034089876 10.1016/j.jmgm.2017.11.006 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85034089876&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/58478
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
topic Chemistry
Computer Science
Materials Science
spellingShingle Chemistry
Computer Science
Materials Science
Panupong Mahalapbutr
Bodee Nutho
Peter Wolschann
Warinthorn Chavasiri
Nawee Kungwan
Thanyada Rungrotmongkol
Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
description © 2017 Elsevier Inc. The structural dynamics and stability of inclusion complexes of mansonone E (ME) and H (MH) including their stereoisomers with various βCDs (methylated- and hydroxypropylated-βCDs) were investigated by classical molecular dynamics (MD) simulations and binding free energy calculations. The simulation results revealed that mansonones are able to form inclusion complexes with βCDs. The guest molecules are not completely inserted into the host cavity, their preferably positions are nearby the secondary rim with the oxane ring dipping into the hydrophobic inner cavity. The encapsulation process leads to a higher rigidity of the βCDs enhancing the intramolecular hydrogen bond formation ability and decreasing the chance of glucopyranose rotation. According to the MM-PBSA binding free energy calculation, all considered inclusion complexes are stable and the binding energies are mainly caused by van der Waals interactions. Moreover, the free energy calculations showed significant differences in the complexation energies for the stereoisomers, which could enable the separation of the isomers by analytical techniques for further pharmaceutical applications.
format Journal
author Panupong Mahalapbutr
Bodee Nutho
Peter Wolschann
Warinthorn Chavasiri
Nawee Kungwan
Thanyada Rungrotmongkol
author_facet Panupong Mahalapbutr
Bodee Nutho
Peter Wolschann
Warinthorn Chavasiri
Nawee Kungwan
Thanyada Rungrotmongkol
author_sort Panupong Mahalapbutr
title Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
title_short Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
title_full Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
title_fullStr Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
title_full_unstemmed Molecular insights into inclusion complexes of mansonone E and H enantiomers with various β-cyclodextrins
title_sort molecular insights into inclusion complexes of mansonone e and h enantiomers with various β-cyclodextrins
publishDate 2018
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85034089876&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/58478
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