Preparation, spectroscopy and molecular modelling studies of the inclusion complex of cordycepin with cyclodextrins

The inclusion complexes of cordycepin with cyclodextrins (CDs) were prepared, the resultant complexes were characterised by UV–vis, FTIR, DSC, SEM, XRD, ESI-MS and proton nuclear magnetic resonance spectroscopy (1H NMR). The stoichiometry was established using a Job plot and the inclusion mechanism...

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Bibliographic Details
Published in:Carbohydrate research 2015-04, Vol.406, p.55-64
Main Authors: Zhang, Jian-Qiang, Wu, Di, Jiang, Kun-Ming, Zhang, Da, Zheng, Xi, Wan, Chun-Ping, Zhu, Hong-You, Xie, Xiao-Guang, Jin, Yi, Lin, Jun
Format: Article
Language:English
Subjects:
Characterisation
Cordycepin
Cyclodextrins
Cyclodextrins - chemistry
Deoxyadenosines - chemistry
Inclusion complex
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Dynamics Simulation
Molecular modelling
Molecular Weight
Solubility
Spectroscopy, Fourier Transform Infrared
Surface Properties
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Summary:The inclusion complexes of cordycepin with cyclodextrins (CDs) were prepared, the resultant complexes were characterised by UV–vis, FTIR, DSC, SEM, XRD, ESI-MS and proton nuclear magnetic resonance spectroscopy (1H NMR). The stoichiometry was established using a Job plot and the inclusion mechanism was clarified using molecular dynamic simulations. Molecular modelling calculations have been carried out to rationalise the experimental findings and predict the stable molecular structure of the inclusion complex. The stability of the inclusion complexes were confirmed by energetic and thermodynamic properties (ΔE, ΔH, ΔG and ΔS) and HOMO, LUMO orbital. The 1:1 binding model of complexes were visually proved by ESI-MS experiment. Our results showed that the purine group of cordycepin molecule was deeply inserted into the cavity of CDs. [Display omitted] •The cordycepin/α-CD complex is more stable than others.•Purine ring of the cordycepin is included in the CD cavities.•ESI-MS examinations gave direct evidence for the 1:1 binding model.•Electrostatic force and hydrogen bond are the main interaction between CDs with cordycepin.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2015.01.005