Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes
In the present study, our aim is to investigate the preferential binding mode and encapsulation of the flavonoid fisetin in the nano-pore of β-cyclodextrin (β-CD) at the molecular level using various theoretical approaches: molecular docking, molecular dynamics (MD) simulations and binding free ener...
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doaj-471870d075734888b5e4a3690a1ea2532021-02-02T01:06:59ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-11-011012789279910.3762/bjoc.10.2961860-5397-10-296Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexesBodee Nutho0Wasinee Khuntawee1Chompoonut Rungnim2Piamsook Pongsawasdi3Peter Wolschann4Alfred Karpfen5Nawee Kungwan6Thanyada Rungrotmongkol7Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandNanoscience and Technology Program, Graduate School, Chulalongkorn University, Bangkok, 10330, ThailandNational Nanotechnology Center (NANOTEC), National Science and Technology Development Agency (NSTDA), 111 Thailand Science Park, Thanon Phahonyothin Tambon Khlong Nueng, Amphoe Khlong Luang, Pathum Thani 12120, ThailandDepartment of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandDepartment of Pharmaceutical Technology and Biopharmaceutics, University of Vienna, Vienna 1090, AustriaInstitute of Theoretical Chemistry, University of Vienna, Vienna 1090, AustriaDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, ThailandDepartment of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandIn the present study, our aim is to investigate the preferential binding mode and encapsulation of the flavonoid fisetin in the nano-pore of β-cyclodextrin (β-CD) at the molecular level using various theoretical approaches: molecular docking, molecular dynamics (MD) simulations and binding free energy calculations. The molecular docking suggested four possible fisetin orientations in the cavity through its chromone or phenyl ring with two different geometries of fisetin due to the rotatable bond between the two rings. From the multiple MD results, the phenyl ring of fisetin favours its inclusion into the β-CD cavity, whilst less binding or even unbinding preference was observed in the complexes where the larger chromone ring is located in the cavity. All MM- and QM-PBSA/GBSA free energy predictions supported the more stable fisetin/β-CD complex of the bound phenyl ring. Van der Waals interaction is the key force in forming the complexes. In addition, the quantum mechanics calculations with M06-2X/6-31G(d,p) clearly showed that both solvation effect and BSSE correction cannot be neglected for the energy determination of the chosen system.https://doi.org/10.3762/bjoc.10.296cyclodextrinfisetinflavonoidMM-PBSAmolecular dynamics simulationQM-PBSA |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Bodee Nutho Wasinee Khuntawee Chompoonut Rungnim Piamsook Pongsawasdi Peter Wolschann Alfred Karpfen Nawee Kungwan Thanyada Rungrotmongkol |
spellingShingle |
Bodee Nutho Wasinee Khuntawee Chompoonut Rungnim Piamsook Pongsawasdi Peter Wolschann Alfred Karpfen Nawee Kungwan Thanyada Rungrotmongkol Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes Beilstein Journal of Organic Chemistry cyclodextrin fisetin flavonoid MM-PBSA molecular dynamics simulation QM-PBSA |
author_facet |
Bodee Nutho Wasinee Khuntawee Chompoonut Rungnim Piamsook Pongsawasdi Peter Wolschann Alfred Karpfen Nawee Kungwan Thanyada Rungrotmongkol |
author_sort |
Bodee Nutho |
title |
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
title_short |
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
title_full |
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
title_fullStr |
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
title_full_unstemmed |
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
title_sort |
binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2014-11-01 |
description |
In the present study, our aim is to investigate the preferential binding mode and encapsulation of the flavonoid fisetin in the nano-pore of β-cyclodextrin (β-CD) at the molecular level using various theoretical approaches: molecular docking, molecular dynamics (MD) simulations and binding free energy calculations. The molecular docking suggested four possible fisetin orientations in the cavity through its chromone or phenyl ring with two different geometries of fisetin due to the rotatable bond between the two rings. From the multiple MD results, the phenyl ring of fisetin favours its inclusion into the β-CD cavity, whilst less binding or even unbinding preference was observed in the complexes where the larger chromone ring is located in the cavity. All MM- and QM-PBSA/GBSA free energy predictions supported the more stable fisetin/β-CD complex of the bound phenyl ring. Van der Waals interaction is the key force in forming the complexes. In addition, the quantum mechanics calculations with M06-2X/6-31G(d,p) clearly showed that both solvation effect and BSSE correction cannot be neglected for the energy determination of the chosen system. |
topic |
cyclodextrin fisetin flavonoid MM-PBSA molecular dynamics simulation QM-PBSA |
url |
https://doi.org/10.3762/bjoc.10.296 |
work_keys_str_mv |
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