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

Jian-Qiang Zhang; Di Wu; Kun-Ming Jiang; Da Zhang; Xi Zheng; Chun-Ping Wan; Hong-You Zhu; Xiao-Guang Xie; Yi Jin; Jun Lin

doi:10.1016/j.carres.2015.01.005

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

Carbohydr Res. 2015 Apr 10:406:55-64. doi: 10.1016/j.carres.2015.01.005. Epub 2015 Jan 26.

Authors

Jian-Qiang Zhang¹, Di Wu¹, Kun-Ming Jiang¹, Da Zhang¹, Xi Zheng², Chun-Ping Wan², Hong-You Zhu¹, Xiao-Guang Xie¹, Yi Jin³, Jun Lin⁴

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
² Central Laboratory, The First Hospital Affiliated Yunnan University of Traditional Chinese Medicine, Kunming 650021, PR China.
³ Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: jinyi@ynu.edu.cn.
⁴ Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: linjun@ynu.edu.cn.

PMID: 25679304
DOI: 10.1016/j.carres.2015.01.005

Abstract

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 ((1)H 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.

Keywords: Characterisation; Cordycepin; Cyclodextrins; Inclusion complex; Molecular modelling.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclodextrins / chemistry*
Deoxyadenosines / chemistry*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Dynamics Simulation
Molecular Weight
Solubility
Spectroscopy, Fourier Transform Infrared
Surface Properties

Substances

Cyclodextrins
Deoxyadenosines
cordycepin