Dataset Information

Delivery of Alpha-Mangostin Using Cyclodextrins through a Biological Membrane: Molecular Dynamics Simulation.

ABSTRACT: ?-Mangostin (MGS) exhibits various pharmacological activities, including antioxidant, anticancer, antibacterial, and anti-inflammatory properties. However, its low water solubility is the major obstacle for its use in pharmaceutical applications. To increase the water solubility of MGS, complex formation with beta-cyclodextrins (?CDs), particularly with the native ?CD and/or its derivative 2,6-dimethyl-?-CD (DM?CD) is a promising technique. Although there have been several reports on the adsorption of ?CDs on the lipid bilayer, the release of the MGS/?CDs inclusion complex through the biological membrane remains unclear. In this present study, the release the MGS from the two different ?CDs (?CD and DM?CD) across the lipid bilayer was investigated. Firstly, the adsorption of the free MGS, free ?CDs, and inclusion complex formation was studied by conventional molecular dynamics simulation. The MGS in complex with those two ?CDs was able to spontaneously release free MGS into the inner membrane. However, both MGS and DM?CD molecules potentially permeated into the deeper region of the interior membrane, whereas ?CD only adsorbed at the outer membrane surface. The interaction between secondary rim of ?CD and the 1-palmitoeyl-2-oleoyl-glycero-3-phosphocholine (POPC) phosphate groups showed the highest number of hydrogen bonds (up to 14) corresponding to the favorable location of ?CD on the POPC membrane. Additionally, the findings suggested that electrostatic energy was the main driving force for ?CD adsorption on the POPC membrane, while van der Waals interactions played a predominant role in DM?CD adsorption. The release profile of MGS from the ?CDs pocket across the lipid bilayer exhibited two energy minima along the reaction coordinate associated with the permeation of the MGS molecule into the deeper region of the POPC membrane.

SUBMITTER: Hotarat W

PROVIDER: S-EPMC7321106 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Delivery of Alpha-Mangostin Using Cyclodextrins through a Biological Membrane: Molecular Dynamics Simulation.

Hotarat Wiparat W Nutho Bodee B Wolschann Peter P Rungrotmongkol Thanyada T Hannongbua Supot S

Molecules (Basel, Switzerland) 20200529 11

α-Mangostin (MGS) exhibits various pharmacological activities, including antioxidant, anticancer, antibacterial, and anti-inflammatory properties. However, its low water solubility is the major obstacle for its use in pharmaceutical applications. To increase the water solubility of MGS, complex formation with beta-cyclodextrins (βCDs), particularly with the native βCD and/or its derivative 2,6-dimethyl-β-CD (DMβCD) is a promising technique. Although there have been several reports on the adsorpt ...[more]

PMID: 32485931

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Dataset Information

Delivery of Alpha-Mangostin Using Cyclodextrins through a Biological Membrane: Molecular Dynamics Simulation.

Publications

Delivery of Alpha-Mangostin Using Cyclodextrins through a Biological Membrane: Molecular Dynamics Simulation.

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