Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin

© 2018 Genistein is an isoflavone with promising pharmaceutical applications. However, its low water solubility interferes with its potency, and therefore cyclodextrins (CDs) have been considered as possible drug delivery system (DDS). To investigate the complexation mechanism of genistein in cyclod...

Full description

Saved in:
Bibliographic Details
Main Authors: Chonnikan Hanpaibool, Tipsuda Chakcharoensap, Arifin, Yuh Hijikata, Stephan Irle, Peter Wolschann, Nawee Kungwan, Piamsook Pongsawasdi, Puey Ounjai, Thanyada Rungrotmongkol
Format: Journal
Published: 2018
Subjects:
Online Access:https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85047790826&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/58438
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Chiang Mai University
id th-cmuir.6653943832-58438
record_format dspace
spelling th-cmuir.6653943832-584382018-09-05T04:38:36Z Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin Chonnikan Hanpaibool Tipsuda Chakcharoensap Arifin Yuh Hijikata Stephan Irle Peter Wolschann Nawee Kungwan Piamsook Pongsawasdi Puey Ounjai Thanyada Rungrotmongkol Chemistry Materials Science Physics and Astronomy © 2018 Genistein is an isoflavone with promising pharmaceutical applications. However, its low water solubility interferes with its potency, and therefore cyclodextrins (CDs) have been considered as possible drug delivery system (DDS). To investigate the complexation mechanism of genistein in cyclodextrin, we employed molecular dynamics (MD) simulations based on classical potentials and the density-functional tight-binding (DFTB) quantum chemical potential. Both classical and quantum chemical MD simulations predict that the phenol ring of genistein is preferentially complexed in the cavity of CD. The complexation process reduces the water-accessible solvation shell, and it is found that a hydrogen bond is formed between genistein and CD. The DFTB-based MD simulations reveal that spontaneous keto-enol tautomerization occurs even within a hundred picoseconds, which suggests that the encapsulated genistein is complexed in the ordinary enol form of the drug molecule. Analyses of the molecular charge distributions suggest that electrostatic interactions partially induce the complex formation, rather than extensive formation of hydrogen bonds. 2018-09-05T04:24:06Z 2018-09-05T04:24:06Z 2018-09-01 Journal 01677322 2-s2.0-85047790826 10.1016/j.molliq.2018.05.109 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85047790826&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/58438
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
topic Chemistry
Materials Science
Physics and Astronomy
spellingShingle Chemistry
Materials Science
Physics and Astronomy
Chonnikan Hanpaibool
Tipsuda Chakcharoensap
Arifin
Yuh Hijikata
Stephan Irle
Peter Wolschann
Nawee Kungwan
Piamsook Pongsawasdi
Puey Ounjai
Thanyada Rungrotmongkol
Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
description © 2018 Genistein is an isoflavone with promising pharmaceutical applications. However, its low water solubility interferes with its potency, and therefore cyclodextrins (CDs) have been considered as possible drug delivery system (DDS). To investigate the complexation mechanism of genistein in cyclodextrin, we employed molecular dynamics (MD) simulations based on classical potentials and the density-functional tight-binding (DFTB) quantum chemical potential. Both classical and quantum chemical MD simulations predict that the phenol ring of genistein is preferentially complexed in the cavity of CD. The complexation process reduces the water-accessible solvation shell, and it is found that a hydrogen bond is formed between genistein and CD. The DFTB-based MD simulations reveal that spontaneous keto-enol tautomerization occurs even within a hundred picoseconds, which suggests that the encapsulated genistein is complexed in the ordinary enol form of the drug molecule. Analyses of the molecular charge distributions suggest that electrostatic interactions partially induce the complex formation, rather than extensive formation of hydrogen bonds.
format Journal
author Chonnikan Hanpaibool
Tipsuda Chakcharoensap
Arifin
Yuh Hijikata
Stephan Irle
Peter Wolschann
Nawee Kungwan
Piamsook Pongsawasdi
Puey Ounjai
Thanyada Rungrotmongkol
author_facet Chonnikan Hanpaibool
Tipsuda Chakcharoensap
Arifin
Yuh Hijikata
Stephan Irle
Peter Wolschann
Nawee Kungwan
Piamsook Pongsawasdi
Puey Ounjai
Thanyada Rungrotmongkol
author_sort Chonnikan Hanpaibool
title Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
title_short Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
title_full Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
title_fullStr Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
title_full_unstemmed Theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
title_sort theoretical analysis of orientations and tautomerization of genistein in β-cyclodextrin
publishDate 2018
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85047790826&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/58438
_version_ 1681425065387753472