Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus
An oxidising and substituting one-pot reaction strategy has been developed to synthesise dihydromyricetin derivatives with the aim of enhancing the inhibitory activity of dihydromyricetin against SARS-CoV-2. Different ω-methoxy-ω-oxeylkyl was introduced in C7-OH site and yielded eight analogs, all o...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2024-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2024.2390909 |
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| _version_ | 1846107515665776640 |
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| author | Cong Wu Qi Jiang Hui Zhong Xudong Zhou Leping Liu Tong Pan Chao Liu Wei Wang Wenbing Sheng |
| author_facet | Cong Wu Qi Jiang Hui Zhong Xudong Zhou Leping Liu Tong Pan Chao Liu Wei Wang Wenbing Sheng |
| author_sort | Cong Wu |
| collection | DOAJ |
| description | An oxidising and substituting one-pot reaction strategy has been developed to synthesise dihydromyricetin derivatives with the aim of enhancing the inhibitory activity of dihydromyricetin against SARS-CoV-2. Different ω-methoxy-ω-oxeylkyl was introduced in C7-OH site and yielded eight analogs, all of them showed good inhibitory activity against SARS-CoV-2 3CLpro with IC50 values ranging from 0.72 to 2.36 μM. In the Vero E6-cell, compound 3 has a good activity of anti-SARS-CoV-2 virus (Omicron virus BA.5) in the prevention model, with an EC50 of 15.84 μM, and so do compound 10 in the therapeutic model, with an EC50 of 11.52 μM. The results suggest that the introduction of long chain ω-oxeylkyl at C7-OH facilitate the inhibition of viral replication in the therapeutic model, which is consistent with the binding energies predicted from molecular docking conclusions. It implies that dihydromyricetin derivatives have the potential to become effective inhibitors of SARS-CoV-2 Omicron and other viruses. |
| format | Article |
| id | doaj-art-b8c4afc4f0714be49ec04784f514c329 |
| institution | Kabale University |
| issn | 1475-6366 1475-6374 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj-art-b8c4afc4f0714be49ec04784f514c3292024-12-26T09:30:44ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742024-12-0139110.1080/14756366.2024.2390909Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virusCong Wu0Qi Jiang1Hui Zhong2Xudong Zhou3Leping Liu4Tong Pan5Chao Liu6Wei Wang7Wenbing Sheng8School of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaTCM and Ethnomedicine Innovation and Development International Laboratory, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaZhangjiajie Meicha Technology Research Center Hunan Qiankun Biotechnology Co., Ltd, Zhangjiajie, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaSchool of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan, People’s Republic of ChinaAn oxidising and substituting one-pot reaction strategy has been developed to synthesise dihydromyricetin derivatives with the aim of enhancing the inhibitory activity of dihydromyricetin against SARS-CoV-2. Different ω-methoxy-ω-oxeylkyl was introduced in C7-OH site and yielded eight analogs, all of them showed good inhibitory activity against SARS-CoV-2 3CLpro with IC50 values ranging from 0.72 to 2.36 μM. In the Vero E6-cell, compound 3 has a good activity of anti-SARS-CoV-2 virus (Omicron virus BA.5) in the prevention model, with an EC50 of 15.84 μM, and so do compound 10 in the therapeutic model, with an EC50 of 11.52 μM. The results suggest that the introduction of long chain ω-oxeylkyl at C7-OH facilitate the inhibition of viral replication in the therapeutic model, which is consistent with the binding energies predicted from molecular docking conclusions. It implies that dihydromyricetin derivatives have the potential to become effective inhibitors of SARS-CoV-2 Omicron and other viruses.https://www.tandfonline.com/doi/10.1080/14756366.2024.2390909DihydromyricetinflavonesynthesisSARS-CoV-2 3CLproOmicron virus BA.5 |
| spellingShingle | Cong Wu Qi Jiang Hui Zhong Xudong Zhou Leping Liu Tong Pan Chao Liu Wei Wang Wenbing Sheng Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus Journal of Enzyme Inhibition and Medicinal Chemistry Dihydromyricetin flavone synthesis SARS-CoV-2 3CLpro Omicron virus BA.5 |
| title | Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus |
| title_full | Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus |
| title_fullStr | Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus |
| title_full_unstemmed | Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus |
| title_short | Design, synthesis, and biological activity evaluation of dihydromyricetin derivatives against SARS-CoV-2-Omicron virus |
| title_sort | design synthesis and biological activity evaluation of dihydromyricetin derivatives against sars cov 2 omicron virus |
| topic | Dihydromyricetin flavone synthesis SARS-CoV-2 3CLpro Omicron virus BA.5 |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2024.2390909 |
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