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Enhanced Solubility and Anticancer Potential of Mansonone G By ?-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study.

ABSTRACT: Mansonone G (MG), a plant-derived compound isolated from the heartwood of Mansonia gagei, possesses a potent antitumor effect on several kinds of malignancy. However, its poor solubility limits the use for practical applications. Beta-cyclodextrin (?CD), a cyclic oligosaccharide composed of seven (1?4)-linked ?-D-glucopyranose units, is capable of encapsulating a variety of poorly soluble compounds into its hydrophobic interior. In this work, we aimed to enhance the water solubility and the anticancer activity of MG by complexation with ?CD and its derivatives (2,6-di-O-methyl-?CD (DM?CD) and hydroxypropyl-?CD). The 90-ns molecular dynamics simulations and MM/GBSA-based binding free energy results suggested that DM?CD was the most preferential host molecule for MG inclusion complexation. The inclusion complex formation between MG and ?CD(s) was confirmed by DSC and SEM techniques. Notably, the MG/?CDs inclusion complexes exerted significantly higher cytotoxic effect (2-7 fold) on A549 lung cancer cells than the uncomplexed MG.

SUBMITTER: Mahalapbutr P

PROVIDER: S-EPMC6843486 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study.

Mahalapbutr Panupong P Wonganan Piyanuch P Charoenwongpaiboon Thanapon T Prousoontorn Manchumas M Chavasiri Warinthorn W Rungrotmongkol Thanyada T

Biomolecules 20190927 10

Mansonone G (MG), a plant-derived compound isolated from the heartwood of <i>Mansonia</i><i>gagei</i>, possesses a potent antitumor effect on several kinds of malignancy. However, its poor solubility limits the use for practical applications. Beta-cyclodextrin (βCD), a cyclic oligosaccharide composed of seven (1→4)-linked α-D-glucopyranose units, is capable of encapsulating a variety of poorly soluble compounds into its hydrophobic interior. In this work, we aimed to enhance the water solubility ...[more]

PMID: 31569832

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Project description:In this work, we aimed to improve the encapsulation efficiency of sepiapterin (SP), the natural precursor of the essential cofactor tetrahydrobiopterin (BH4) that displays mild water-solubility and a short biological half-life, within methoxy-poly(ethylene-glycol)-poly(epsilon-caprolactone)(mPEG-PCL) nanoparticles (NPs) by means of its complexation and hydrophobization with 2,3,6-triacetyl-β-cyclodextrin (TAβCD). For this, SP/TAβCD complexes were produced by spray-drying of SP/TAβCD binary solutions in ethanol using the Nano Spray Dryer B-90 HP. Dry powders were characterized by differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FTIR), and transmission and scanning electron microscopy (TEM and SEM, respectively) and compared to the pristine components and their physical mixtures (PMs). Next, SP was encapsulated within mPEG-PCL NPs by nano-precipitation of an SP/TAβCD complex/mPEG-PCL solution. In addition to the nano-encapsulation of a preformed complex within the polymeric NPs, we assessed an alternative encapsulation approach called drying with copolymer (DWC) in which pristine SP, TAβCD, and mPEG-PCL were co-dissolved in a mixture of acetone and methanol at the desired weight ratio, dried under vacuum, re-dissolved, and nano-precipitated in water. The dissolution-drying step was aimed to promote the formation of molecular hydrophobic interactions between SP, TAβCD, and the PCL blocks in the copolymer. SP-loaded mPEG-PCL NPs were characterized by dynamic light scattering (DLS) and SEM. NPs with a size of 74-75 nm and standard deviation (S.D., a measure of the peak width) of 21-22 nm were obtained when an SP:TAβCD (1:1 molar ratio) spray-dried complex was used for the nano-encapsulation and SEM analysis revealed the absence of free SP crystals. The encapsulation efficiency (%EE) and drug loading (%DL) were 85% and 2.6%, respectively, as opposed to the much lower values (14% and 0.6%, respectively) achieved with pristine SP. Moreover, the NPs sustained the SP release with relatively low burst effect of 20%. Overall, our results confirmed that spray-drying of SP/TAβCD solutions at the appropriate molar ratio leads to the hydrophobization of the relatively hydrophilic SP molecule, enabling its encapsulation within mPEG-PCL NPs and paves the way for the use of this strategy in the development of novel drug delivery systems of this vital biological precursor.

Dataset Information

Enhanced Solubility and Anticancer Potential of Mansonone G By ?-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study.

Publications

Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study.

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