Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants
Potato virus Y (PVY) is an important plant virus that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized and their anti-PVY activities...
| Main Authors: | , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Online Access: | https://hdl.handle.net/10356/178207 |
| _version_ | 1826112961011253248 |
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| author | Huang, Yixian Peng, Xiaolin Chen, Jinli Shu, Liangzhen Zhang, Meng Jin, Jiamiao Jin, Zhichao Chi, Robin Yonggui |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Huang, Yixian Peng, Xiaolin Chen, Jinli Shu, Liangzhen Zhang, Meng Jin, Jiamiao Jin, Zhichao Chi, Robin Yonggui |
| author_sort | Huang, Yixian |
| collection | NTU |
| description | Potato virus Y (PVY) is an important plant virus that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized and their anti-PVY activities were evaluated. Biological activity tests demonstrated that many chiral compounds exhibited promising anti-PVY activities and that their absolute configurations exhibited obvious distinctions in antiviral bioactivities. Notably, compound (S)-4v displayed excellent curative and protective efficacy against PVY, with EC50 values of 328.6 and 256.1 μg/mL, respectively, which were superior to those of commercial virucide ningnanmycin (NNM, 437.4 and 397.4 μg/mL, respectively). The preliminary antiviral mechanism was investigated to determine the difference in antiviral activity between the two enantiomers of 4v chiral compounds. Molecular docking indicated a stronger binding affinity between the coating proteins of PVY (PVY-CP) and (S)-4v (-6.5 kcal/mol) compared to (R)-4v (-6.2 kcal/mol). Additionally, compound (S)-4v can increase the chlorophyll content and defense-related enzyme activities more effectively than its enantiomer. Therefore, this study provides an important basis for the development of chiral indole derivatives containing oxazoline moieties as novel agricultural chemicals. |
| first_indexed | 2024-10-01T03:15:23Z |
| format | Journal Article |
| id | ntu-10356/178207 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:15:23Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1782072024-06-05T06:59:40Z Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants Huang, Yixian Peng, Xiaolin Chen, Jinli Shu, Liangzhen Zhang, Meng Jin, Jiamiao Jin, Zhichao Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Chemistry Indole derivatives Potato virus Y Potato virus Y (PVY) is an important plant virus that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized and their anti-PVY activities were evaluated. Biological activity tests demonstrated that many chiral compounds exhibited promising anti-PVY activities and that their absolute configurations exhibited obvious distinctions in antiviral bioactivities. Notably, compound (S)-4v displayed excellent curative and protective efficacy against PVY, with EC50 values of 328.6 and 256.1 μg/mL, respectively, which were superior to those of commercial virucide ningnanmycin (NNM, 437.4 and 397.4 μg/mL, respectively). The preliminary antiviral mechanism was investigated to determine the difference in antiviral activity between the two enantiomers of 4v chiral compounds. Molecular docking indicated a stronger binding affinity between the coating proteins of PVY (PVY-CP) and (S)-4v (-6.5 kcal/mol) compared to (R)-4v (-6.2 kcal/mol). Additionally, compound (S)-4v can increase the chlorophyll content and defense-related enzyme activities more effectively than its enantiomer. Therefore, this study provides an important basis for the development of chiral indole derivatives containing oxazoline moieties as novel agricultural chemicals. We acknowledge financial support from the National Natural Science Foundation of China (32172459, 21961006, 22371057, 22071036, U23A20201), the 10 Talent Plan (Shicengci) of Guizhou Province ([2016] 5649), the Science and Technology Department of Guizhou Province ([2019] 1020, Qiankehejichu-ZK [2021] Key 033), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, the Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020) 004], and Guizhou University (China). 2024-06-05T06:59:40Z 2024-06-05T06:59:40Z 2024 Journal Article Huang, Y., Peng, X., Chen, J., Shu, L., Zhang, M., Jin, J., Jin, Z. & Chi, R. Y. (2024). Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants. Journal of Agricultural and Food Chemistry, 72(13), 6979-6987. https://dx.doi.org/10.1021/acs.jafc.4c00119 0021-8561 https://hdl.handle.net/10356/178207 10.1021/acs.jafc.4c00119 38520352 2-s2.0-85188806208 13 72 6979 6987 en Journal of Agricultural and Food Chemistry © 2024 American Chemical Society. All rights reserved. |
| spellingShingle | Chemistry Indole derivatives Potato virus Y Huang, Yixian Peng, Xiaolin Chen, Jinli Shu, Liangzhen Zhang, Meng Jin, Jiamiao Jin, Zhichao Chi, Robin Yonggui Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title | Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title_full | Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title_fullStr | Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title_full_unstemmed | Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title_short | Discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| title_sort | discovery of novel chiral indole derivatives containing the oxazoline moiety as potential antiviral agents for plants |
| topic | Chemistry Indole derivatives Potato virus Y |
| url | https://hdl.handle.net/10356/178207 |
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