Computational study on the molecular inclusion of andrographolide by cyclodextrin

Due to the poor water solubility of andrographolide (andro), an inclusion technique has been developed to modify its physical and chemical properties so as to improve its bioavailability. In contrast with the immense experimental studies on the inclusion complexes of andro:cyclodextrin, no computati...

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Bibliographic Details
Published in:Journal of computer-aided molecular design 2009-03, Vol.23 (3), p.153-162
Main Authors: Zhou, Hongwei, Lai, Wai-Ping, Zhang, Zhiqiang, Li, Wai-Kee, Cheung, Hon-Yeung
Format: Article
Language:English
Subjects:
Animal Anatomy
Binding Sites
CAD
Chemistry
Chemistry and Materials Science
Computer aided design
Computer Applications in Chemistry
Computer Simulation
Cyclodextrins - chemistry
Cyclodextrins - metabolism
Diterpenes - chemistry
Diterpenes - metabolism
Histology
Hydrogen
Hydrogen Bonding
Models, Molecular
Molecular biology
Morphology
Physical Chemistry
Solubility
Studies
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Summary:Due to the poor water solubility of andrographolide (andro), an inclusion technique has been developed to modify its physical and chemical properties so as to improve its bioavailability. In contrast with the immense experimental studies on the inclusion complexes of andro:cyclodextrin, no computational study has so far been carried out on this system. In this work, preliminary docking experiments with AutoDock were performed. Density Functional Theory (DFT) and Austin Model 1 (AM1) calculations upon the docking instances were applied to investigate the two possible modes of molecular inclusions between andro and x -cyclodextrin ( x CD, where x is α , β or γ ). Atoms-in-Molecules (AIM) analysis based on the B3LYP/cc-pVDZ wavefunction was applied to verify the existence of the intermolecular hydrogen bonds. It was found that the most stable complex among the six possible inclusion complexes was the one formed between andro and β CD with andro’s decalin ring moiety wrapped by CD at a ratio of 1:1. The hydrogen bonds between andro and CD were responsible for the stability of the inclusion complexes. The calculated data were found to be consistent with the experimental results. Thus, the results of this study can aid new drug design processes.
ISSN:0920-654X
1573-4951
DOI:10.1007/s10822-008-9247-y