Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations

Kerdpol, Khanittha; Kicuntod, Jintawee; Wolschann, Peter; Mori, Seiji; Rungnim, Chompoonut; Kunaseth, Manaschai; Okumura, Hisashi; Kungwan, Nawee; Rungrotmongkol, Thanyada

doi:10.3390/polym11010145

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Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations

¹,

²,

^2,3,4,

⁵,

⁶

⁶

⁷

^1,8,*

and

Thanyada Rungrotmongkol

^2,9,10,*

Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

Structural and Computational Biology Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand

Department of Pharmaceutical Chemistry, University of Vienna, Vienna 1090, Austria

⁴

Institute of Theoretical Chemistry, University of Vienna, Vienna 1090, Austria

⁵

Institute of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki 310-8512, Japan

⁶

National Nanotechnology Center (NANOTEC), National Science and Technology Development Agency (NSTDA), Pathum Thani 12120, Thailand

⁷

Research Center for Computational Science, Institute for Molecular Science, Okazaki, Aichi 444-8585, Japan

⁸

Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand

⁹

Ph.D. Program in Bioinformatics and Computational Biology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand

¹⁰

Molecular Sensory Science Center, Faculty of Science, Chulalongkorn University, 254 Phayathai Road, Patumwan, Bangkok 10330, Thailand

Authors to whom correspondence should be addressed.

Polymers 2019, 11(1), 145; https://doi.org/10.3390/polym11010145

Received: 13 December 2018 / Revised: 9 January 2019 / Accepted: 11 January 2019 / Published: 16 January 2019

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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Abstract

2-Hydroxypropyl-β-cyclodextrin (HPβCD) has unique properties to enhance the stability and the solubility of low water-soluble compounds by inclusion complexation. An understanding of the structural properties of HPβCD and its derivatives, based on the number of 2-hydroxypropyl (HP) substituents at the α-d-glucopyranose subunits is rather important. In this work, replica exchange molecular dynamics simulations were performed to investigate the conformational changes of single- and double-sided HP-substitution, called 6-HPβCDs and 2,6-HPβCDs, respectively. The results show that the glucose subunits in both 6-HPβCDs and 2,6-HPβCDs have a lower chance of flipping than in βCD. Also, HP groups occasionally block the hydrophobic cavity of HPβCDs, thus hindering drug inclusion. We found that HPβCDs with a high number of HP-substitutions are more likely to be blocked, while HPβCDs with double-sided HP-substitutions have an even higher probability of being blocked. Overall, 6-HPβCDs with three and four HP-substitutions are highlighted as the most suitable structures for guest encapsulation, based on our conformational analyses, such as structural distortion, the radius of gyration, circularity, and cavity self-closure of the HPβCDs. View Full-Text

Keywords: 2-hydroxypropyl-β-cyclodextrin (HPβCD); replica exchange molecular dynamics (REMD); conformational change; cavity self-closure

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Kerdpol, K.; Kicuntod, J.; Wolschann, P.; Mori, S.; Rungnim, C.; Kunaseth, M.; Okumura, H.; Kungwan, N.; Rungrotmongkol, T. Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations. Polymers 2019, 11, 145. https://doi.org/10.3390/polym11010145

AMA Style

Kerdpol K, Kicuntod J, Wolschann P, Mori S, Rungnim C, Kunaseth M, Okumura H, Kungwan N, Rungrotmongkol T. Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations. Polymers. 2019; 11(1):145. https://doi.org/10.3390/polym11010145

Chicago/Turabian Style

Kerdpol, Khanittha, Jintawee Kicuntod, Peter Wolschann, Seiji Mori, Chompoonut Rungnim, Manaschai Kunaseth, Hisashi Okumura, Nawee Kungwan, and Thanyada Rungrotmongkol. 2019. "Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations" Polymers 11, no. 1: 145. https://doi.org/10.3390/polym11010145

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Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations

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