Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin
Isorhapontigenin has been proposed as a better alternative for oral administration than the famous resveratrol, as it shares many biological activities, but with a structure that could make its delivery easier. Although this hydrophobic structure could enhance bioavailability, it could also be a dis...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-11-01
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| Series: | Biomedicines |
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| Online Access: | https://www.mdpi.com/2227-9059/11/11/3023 |
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| author | Silvia Navarro-Orcajada Francisco José Vidal-Sánchez Irene Conesa Francisco Escribano-Naharro Adrián Matencio José Manuel López-Nicolás |
| author_facet | Silvia Navarro-Orcajada Francisco José Vidal-Sánchez Irene Conesa Francisco Escribano-Naharro Adrián Matencio José Manuel López-Nicolás |
| author_sort | Silvia Navarro-Orcajada |
| collection | DOAJ |
| description | Isorhapontigenin has been proposed as a better alternative for oral administration than the famous resveratrol, as it shares many biological activities, but with a structure that could make its delivery easier. Although this hydrophobic structure could enhance bioavailability, it could also be a disadvantage in the development of products. In this research, we study the antiproliferative activity of this stilbene against colorectal cancer and overcome its limitations through molecular encapsulation in cyclodextrins. The cytotoxic activity against human colorectal cancer cells of isorhapontigenin was similar to that of resveratrol or piceatannol, supporting its use as a bioactive alternative. The study of the encapsulation through fluorescence spectroscopy and molecular docking revealed that the complexation satisfies a 1:1 stoichiometry and that HP-β-CD is the most suitable CD to encapsulate this stilbene. Through a spectrophotometric assay, it was observed that this CD could double the basal water solubility, exceeding the solubility of other hydroxylated stilbenes. The stability of these inclusion complexes was higher at a pH below 9 and refrigeration temperatures. Moreover, the use of CDs retained more than 78% of isorhapontigenin after storage for 12 weeks, compared to 15% in free form. Overall, these findings could help design novel formulations to better deliver isorhapontigenin. |
| first_indexed | 2024-03-09T16:59:58Z |
| format | Article |
| id | doaj.art-7004523590344946b275a774be726e71 |
| institution | Directory Open Access Journal |
| issn | 2227-9059 |
| language | English |
| last_indexed | 2024-03-09T16:59:58Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomedicines |
| spelling | doaj.art-7004523590344946b275a774be726e712023-11-24T14:31:12ZengMDPI AGBiomedicines2227-90592023-11-011111302310.3390/biomedicines11113023Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin IsorhapontigeninSilvia Navarro-Orcajada0Francisco José Vidal-Sánchez1Irene Conesa2Francisco Escribano-Naharro3Adrián Matencio4José Manuel López-Nicolás5Department of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia—Regional Campus of International Excellence “Campus Mare Nostrum”, E-30100 Murcia, SpainDepartment of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia—Regional Campus of International Excellence “Campus Mare Nostrum”, E-30100 Murcia, SpainDepartment of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia—Regional Campus of International Excellence “Campus Mare Nostrum”, E-30100 Murcia, SpainDepartment of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia—Regional Campus of International Excellence “Campus Mare Nostrum”, E-30100 Murcia, SpainDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDepartment of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia—Regional Campus of International Excellence “Campus Mare Nostrum”, E-30100 Murcia, SpainIsorhapontigenin has been proposed as a better alternative for oral administration than the famous resveratrol, as it shares many biological activities, but with a structure that could make its delivery easier. Although this hydrophobic structure could enhance bioavailability, it could also be a disadvantage in the development of products. In this research, we study the antiproliferative activity of this stilbene against colorectal cancer and overcome its limitations through molecular encapsulation in cyclodextrins. The cytotoxic activity against human colorectal cancer cells of isorhapontigenin was similar to that of resveratrol or piceatannol, supporting its use as a bioactive alternative. The study of the encapsulation through fluorescence spectroscopy and molecular docking revealed that the complexation satisfies a 1:1 stoichiometry and that HP-β-CD is the most suitable CD to encapsulate this stilbene. Through a spectrophotometric assay, it was observed that this CD could double the basal water solubility, exceeding the solubility of other hydroxylated stilbenes. The stability of these inclusion complexes was higher at a pH below 9 and refrigeration temperatures. Moreover, the use of CDs retained more than 78% of isorhapontigenin after storage for 12 weeks, compared to 15% in free form. Overall, these findings could help design novel formulations to better deliver isorhapontigenin.https://www.mdpi.com/2227-9059/11/11/3023isorhapontigeninstilbenecancerencapsulationsolubilitystability |
| spellingShingle | Silvia Navarro-Orcajada Francisco José Vidal-Sánchez Irene Conesa Francisco Escribano-Naharro Adrián Matencio José Manuel López-Nicolás Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin Biomedicines isorhapontigenin stilbene cancer encapsulation solubility stability |
| title | Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin |
| title_full | Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin |
| title_fullStr | Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin |
| title_full_unstemmed | Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin |
| title_short | Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin |
| title_sort | antiproliferative effects in colorectal cancer and stabilisation in cyclodextrins of the phytoalexin isorhapontigenin |
| topic | isorhapontigenin stilbene cancer encapsulation solubility stability |
| url | https://www.mdpi.com/2227-9059/11/11/3023 |
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