รหัสดีโอไอ 10.14457/TU.the.2019.753
Title The use of molecular modeling approaches to investigate molecular interactions in inclusion complexes of cyclodextrins
Creator Ornin Srihakulung
Contributor Luckhana Lawtrakul, Advisor
Publisher Thammasat University
Publication Year 2019
Keyword Cyclodextrin ,Hartree-fock ,Inclusion complex ,Interaction energy ,Molecular docking ,Molecular dynamics simulations ,Molecular interaction ,Nanoscience ,Plumbagin ,Semi-empirical ,Theoretical calculations
Abstract Nanoencapsulation of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) using β-cyclodextrin (BCD) and its two derivatives, including dimethyl-β-cyclodextrin (MBCD) and hydroxypropyl-β-cyclodextrin (HPBCD) to form inclusion complex was investigated to prevent the loss of plumbagin in pharmaceutical products, to increase its solubility in water, and reduce the cytotoxicity of the compound. To understand the properties of the complex geometries and the encapsulation process, this research used Molecular docking, Semi-empirical, and Hartree-Fock techniques to simulate the guest/host complexation system of plumbagin/BCD, plumbagin/MBCD, and plumbagin/HPBCD. All calculations were performed using AutoDock4.2.6, GaussView 6.0, and Gaussian 16 software packages. The complex energy, molecular interactions, and insertion pathway of plumbagin/BCDs were examined. The results revealed two different binding modes of the plumbagin molecule inside the BCDs cavity, with 1:1 molecular ratio. In conformation-I, the hydroxyl phenolic group of plumbagin was placed in the BCDs cavity near the narrow-side of the host molecule.(1)In the other model, conformation-II, the methyl quinone group of plumbagin was placed in the cavity of BCDs near the narrow-side of the host molecule. The intermolecular hydrogen bond, van der Waals, and hydrophobic interactions play an important role in complexation process of plumbagin with BCDs. The structures of plumbagin inclusion complexed with BCD, MBCD and HPBCD in aqueous solution have been investigated by using molecular dynamics simulations, Glycam06 force field run on AMBER18 program. The inclusion structures and the stability of the complexes were also analyzed and validated by thermodynamic properties. The results of molecular dynamics simulations indicate the conformation-II of HPBCD inclusion complex with plumbagin in aqueous solution has better stability than that of the others. Moreover, the releasing directions were also predicted.
ดิจิตอลไฟล์ Digital File #1

บรรณานุกรม

Ornin Srihakulung และผู้แต่งคนอื่นๆ. (2019) The use of molecular modeling approaches to investigate molecular interactions in inclusion complexes of cyclodextrins. Thammasat University:ม.ป.ท.
Ornin Srihakulung และผู้แต่งคนอื่นๆ. 2019. The use of molecular modeling approaches to investigate molecular interactions in inclusion complexes of cyclodextrins. ม.ป.ท.:Thammasat University;
Ornin Srihakulung และผู้แต่งคนอื่นๆ. The use of molecular modeling approaches to investigate molecular interactions in inclusion complexes of cyclodextrins. ม.ป.ท.:Thammasat University, 2019. Print.