Preparation, spectroscopy and molecular modelling studies of the inclusion complex of cordycepin with cyclodextrins. (10th April 2015)

• Record Type: Journal Article
• 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
• Is Part Of: Carbohydrate research. Volume 406(2015)
• Page Start: 55
• Page End: 64
• Publication Date: 2015-04-10
• Subjects: Cordycepin -- Characterisation -- Cyclodextrins -- Inclusion complex -- Molecular modelling; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.01.005
• Languages: English
• ISSNs: 0008-6215

Abstract

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 (Δ E, Δ H, Δ G and Δ S ) 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. Graphical abstract: Highlights: 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.