Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study
Mansonone G (MG), a plant-derived compound isolated from the heartwood of <i>Mansonia 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 oligosac...
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MDPI AG
2019-09-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/9/10/545 |
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| author | Panupong Mahalapbutr Piyanuch Wonganan Thanapon Charoenwongpaiboon Manchumas Prousoontorn Warinthorn Chavasiri Thanyada Rungrotmongkol |
| author_facet | Panupong Mahalapbutr Piyanuch Wonganan Thanapon Charoenwongpaiboon Manchumas Prousoontorn Warinthorn Chavasiri Thanyada Rungrotmongkol |
| author_sort | Panupong Mahalapbutr |
| collection | DOAJ |
| description | Mansonone G (MG), a plant-derived compound isolated from the heartwood of <i>Mansonia 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 and the anticancer activity of MG by complexation with βCD and its derivatives (2,6-di-<i>O</i>-methyl-βCD (DMβCD) and hydroxypropyl-βCD). The 90-ns molecular dynamics simulations and MM/GBSA-based binding free energy results suggested that DMβCD was the most preferential host molecule for MG inclusion complexation. The inclusion complex formation between MG and βCD(s) was confirmed by DSC and SEM techniques. Notably, the MG/βCDs inclusion complexes exerted significantly higher cytotoxic effect (~2−7 fold) on A549 lung cancer cells than the uncomplexed MG. |
| first_indexed | 2024-12-13T03:00:51Z |
| format | Article |
| id | doaj.art-d003e3f6a7474176ad9bde7c290a34b9 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-12-13T03:00:51Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-d003e3f6a7474176ad9bde7c290a34b92022-12-22T00:01:50ZengMDPI AGBiomolecules2218-273X2019-09-0191054510.3390/biom9100545biom9100545Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental StudyPanupong Mahalapbutr0Piyanuch Wonganan1Thanapon Charoenwongpaiboon2Manchumas Prousoontorn3Warinthorn Chavasiri4Thanyada Rungrotmongkol5Structural and Computational Biology Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandDepartment of Pharmacology, Faculty of Medicine, Chulalongkorn University, Bangkok 10330, ThailandStarch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandStarch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandCenter of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandStructural and Computational Biology Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandMansonone G (MG), a plant-derived compound isolated from the heartwood of <i>Mansonia 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 and the anticancer activity of MG by complexation with βCD and its derivatives (2,6-di-<i>O</i>-methyl-βCD (DMβCD) and hydroxypropyl-βCD). The 90-ns molecular dynamics simulations and MM/GBSA-based binding free energy results suggested that DMβCD was the most preferential host molecule for MG inclusion complexation. The inclusion complex formation between MG and βCD(s) was confirmed by DSC and SEM techniques. Notably, the MG/βCDs inclusion complexes exerted significantly higher cytotoxic effect (~2−7 fold) on A549 lung cancer cells than the uncomplexed MG.https://www.mdpi.com/2218-273X/9/10/545beta-cyclodextrinsinclusion complexmansonone gmolecular dynamics simulationlung cancer |
| spellingShingle | Panupong Mahalapbutr Piyanuch Wonganan Thanapon Charoenwongpaiboon Manchumas Prousoontorn Warinthorn Chavasiri Thanyada Rungrotmongkol Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study Biomolecules beta-cyclodextrins inclusion complex mansonone g molecular dynamics simulation lung cancer |
| title | Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study |
| title_full | Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study |
| title_fullStr | Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study |
| title_full_unstemmed | Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study |
| title_short | Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study |
| title_sort | enhanced solubility and anticancer potential of mansonone g by β cyclodextrin based host guest complexation a computational and experimental study |
| topic | beta-cyclodextrins inclusion complex mansonone g molecular dynamics simulation lung cancer |
| url | https://www.mdpi.com/2218-273X/9/10/545 |
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