Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin
In this paper, a modified Cyclotriveratrylene was synthesized and linked to a branched Polyethylenimine, and this unique polymeric material was subsequently examined as a potential supramolecular carrier for Doxorubicin. Spectroscopic analysis in different solvents had shown that Doxorubicin was coo...
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MDPI AG
2020-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/22/5455 |
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| author | Carmine Coluccini Yoke Mooi Ng Yves Ira A. Reyes Hsin-Yi Tiffany Chen Yit Lung Khung |
| author_facet | Carmine Coluccini Yoke Mooi Ng Yves Ira A. Reyes Hsin-Yi Tiffany Chen Yit Lung Khung |
| author_sort | Carmine Coluccini |
| collection | DOAJ |
| description | In this paper, a modified Cyclotriveratrylene was synthesized and linked to a branched Polyethylenimine, and this unique polymeric material was subsequently examined as a potential supramolecular carrier for Doxorubicin. Spectroscopic analysis in different solvents had shown that Doxorubicin was coordinated within the hollow-shaped unit of the armed Cyclotriveratrylene, and the nature of the host–guest complex revealed intrinsic Van der Waals interactions and hydrogen bonding between the host and guest. The strongest interaction was detected in water because of the hydrophobic effect shared between the aromatic groups of the Doxorubicin and Cyclotriveratrylene unit. Density functional theory calculations had also confirmed that in the most stable coordination of Doxorubicin with the cross-linked polymer, the aromatic rings of the Doxorubicin were localized toward the Cyclotriveratrylene core, while its aliphatic chains aligned closer with amino groups, thus forming a compact supramolecular assembly that may confer a shielding effect on Doxorubicin. These observations had emphasized the importance of supramolecular considerations when designing a novel drug delivery platform. |
| first_indexed | 2024-03-10T14:40:42Z |
| format | Article |
| id | doaj.art-32ac5fe9bab9479480e5941190fd355c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T14:40:42Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-32ac5fe9bab9479480e5941190fd355c2023-11-20T21:45:32ZengMDPI AGMolecules1420-30492020-11-012522545510.3390/molecules25225455Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with DoxorubicinCarmine Coluccini0Yoke Mooi Ng1Yves Ira A. Reyes2Hsin-Yi Tiffany Chen3Yit Lung Khung4Institute of New Drug Development, China Medical University, No. 91 Hsueh-Shih Road, Taichung 40402, TaiwanInstitute of New Drug Development, China Medical University, No. 91 Hsueh-Shih Road, Taichung 40402, TaiwanDepartment of Engineering and System Science, National Tsing Hua University, Hsinchu 30013, TaiwanDepartment of Engineering and System Science, National Tsing Hua University, Hsinchu 30013, TaiwanDepartment of Biological Science and Technology, No. 100, Jingmao 1st Rd, Beitun District, Taichung City 406, TaiwanIn this paper, a modified Cyclotriveratrylene was synthesized and linked to a branched Polyethylenimine, and this unique polymeric material was subsequently examined as a potential supramolecular carrier for Doxorubicin. Spectroscopic analysis in different solvents had shown that Doxorubicin was coordinated within the hollow-shaped unit of the armed Cyclotriveratrylene, and the nature of the host–guest complex revealed intrinsic Van der Waals interactions and hydrogen bonding between the host and guest. The strongest interaction was detected in water because of the hydrophobic effect shared between the aromatic groups of the Doxorubicin and Cyclotriveratrylene unit. Density functional theory calculations had also confirmed that in the most stable coordination of Doxorubicin with the cross-linked polymer, the aromatic rings of the Doxorubicin were localized toward the Cyclotriveratrylene core, while its aliphatic chains aligned closer with amino groups, thus forming a compact supramolecular assembly that may confer a shielding effect on Doxorubicin. These observations had emphasized the importance of supramolecular considerations when designing a novel drug delivery platform.https://www.mdpi.com/1420-3049/25/22/5455armed Cyclotriveratrylenesupramolecular interactionDoxorubicin loading |
| spellingShingle | Carmine Coluccini Yoke Mooi Ng Yves Ira A. Reyes Hsin-Yi Tiffany Chen Yit Lung Khung Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin Molecules armed Cyclotriveratrylene supramolecular interaction Doxorubicin loading |
| title | Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin |
| title_full | Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin |
| title_fullStr | Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin |
| title_full_unstemmed | Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin |
| title_short | Functionalization of Polyethyleneimine with Hollow Cyclotriveratrylene and Its Subsequent Supramolecular Interaction with Doxorubicin |
| title_sort | functionalization of polyethyleneimine with hollow cyclotriveratrylene and its subsequent supramolecular interaction with doxorubicin |
| topic | armed Cyclotriveratrylene supramolecular interaction Doxorubicin loading |
| url | https://www.mdpi.com/1420-3049/25/22/5455 |
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