Host-Guest Interactions of Plumbagin with β-Cyclodextrin, Dimethyl-β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin: Semi-Empirical Quantum Mechanical PM6 and PM7 Methods

Ornin Srihakulung; Ryo Maezono; Pisanu Toochinda; Waree Kongprawechnon; Apichart Intarapanich; And Luckhana Lawtrakul

doi:10.3390/scipharm86020020

Host-Guest Interactions of Plumbagin with β-Cyclodextrin, Dimethyl-β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin: Semi-Empirical Quantum Mechanical PM6 and PM7 Methods

Sci Pharm. 2018 May 15;86(2):20. doi: 10.3390/scipharm86020020.

Authors

Ornin Srihakulung^{1

2

3}, Ryo Maezono⁴, Pisanu Toochinda⁵, Waree Kongprawechnon⁶, Apichart Intarapanich⁷, And Luckhana Lawtrakul⁸

Affiliations

¹ School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand. [email protected].
² School of Information Science, Japan Advanced Institute of Science and Technology, Nomi, Ishikawa 923-1292, Japan. [email protected].
³ School of Information, Computer and Communication Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12000, Thailand. [email protected].
⁴ School of Information Science, Japan Advanced Institute of Science and Technology, Nomi, Ishikawa 923-1292, Japan. [email protected].
⁵ School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand. [email protected].
⁶ School of Information, Computer and Communication Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12000, Thailand. [email protected].
⁷ National Electronics and Computer Technology Center, National Science and Technology Development Agency, Pathumthani 12120, Thailand. [email protected].
⁸ School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand. [email protected].

Abstract

Molecular interactions of plumbagin inclusion complexes with β-cyclodextrin (BCD), dimethyl--cyclodextrin (MBCD), and hydroxypropyl-β-cyclodextrin (HPBCD) were investigated by semi-empirical, Parameterization Method 6 and 7 (PM6, and PM7) in the aqueous phase using polarizable continuum calculations. The results revealed two different binding modes of the plumbagin molecule inside the BCD cavity with a negative value of the complexation energy. In conformation-I, the hydroxyl phenolic group of plumbagin was placed in the BCD cavity near the narrow-side of the host molecule. In the other model, conformation-II, the methyl quinone group of plumbagin was placed in the cavity of BCD near the narrow-side of the host molecule. The higher the negative value of the complexation energy, the more favorable is the pathway of inclusion-complex formation.

Keywords: cyclodextrin; host–guest interaction; inclusion complex; plumbagin.