Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane
BACKGROUND: Potato virus Y (PVY) is a prominent representative of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover new antiviral agents, a class of planar chiral thiourea molecules through the key step of...
| Main Authors: | , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Online Access: | https://hdl.handle.net/10356/179511 |
| _version_ | 1811687995342848000 |
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| author | Shu, Liangzhen Lv, Ya Chen, Zhongyin Huang, Yixian Zhang, Meng Jin, Zhichao Li, Tingting Chi, Robin Yonggui |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Shu, Liangzhen Lv, Ya Chen, Zhongyin Huang, Yixian Zhang, Meng Jin, Zhichao Li, Tingting Chi, Robin Yonggui |
| author_sort | Shu, Liangzhen |
| collection | NTU |
| description | BACKGROUND: Potato virus Y (PVY) is a prominent representative of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover new antiviral agents, a class of planar chiral thiourea molecules through the key step of N-heterocyclic carbene-catalyzed nitrile formation reaction was synthesized with excellent optical purities for antiviral evaluations against plant virus PVY. RESULTS: The absolute configurations of the planar chiral compounds exhibited obvious distinctions in the anti-PVY activities. Notability, compound (S)-4u exhibited remarkable curative activities against PVY, with a half maximal effective concentration (EC50) of 349.3 μg mL−1, which was lower than that of the ningnanmycin (NNM) (EC50 = 400.8 μg mL−1). Additionally, The EC50 value for the protective effects of (S)-4u was 146.2 μg mL−1, which was superior to that of NNM (276.4 μg mL−1). Furthermore, the mechanism-of-action of enantiomers of planar chiral compound 4u was investigated through molecular docking, defensive enzyme activity tests and chlorophyll content tests. CONCLUSION: Biological mechanism studies have demonstrated that the configuration of planar chiral target compounds plays a crucial role in the molecular interaction with PVY-CP, enhancing the activity of defense enzymes and affecting chlorophyll content. The current study has provided significant insights into the roles played by planar chiralities in plant protection against viruses. This paves the way for the development of novel green pesticides bearing planar chiralities with excellent optical purities. |
| first_indexed | 2024-10-01T05:25:10Z |
| format | Journal Article |
| id | ntu-10356/179511 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:25:10Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1795112024-08-06T05:04:35Z Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane Shu, Liangzhen Lv, Ya Chen, Zhongyin Huang, Yixian Zhang, Meng Jin, Zhichao Li, Tingting Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Engineering Potato virus Y Planar chirality BACKGROUND: Potato virus Y (PVY) is a prominent representative of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover new antiviral agents, a class of planar chiral thiourea molecules through the key step of N-heterocyclic carbene-catalyzed nitrile formation reaction was synthesized with excellent optical purities for antiviral evaluations against plant virus PVY. RESULTS: The absolute configurations of the planar chiral compounds exhibited obvious distinctions in the anti-PVY activities. Notability, compound (S)-4u exhibited remarkable curative activities against PVY, with a half maximal effective concentration (EC50) of 349.3 μg mL−1, which was lower than that of the ningnanmycin (NNM) (EC50 = 400.8 μg mL−1). Additionally, The EC50 value for the protective effects of (S)-4u was 146.2 μg mL−1, which was superior to that of NNM (276.4 μg mL−1). Furthermore, the mechanism-of-action of enantiomers of planar chiral compound 4u was investigated through molecular docking, defensive enzyme activity tests and chlorophyll content tests. CONCLUSION: Biological mechanism studies have demonstrated that the configuration of planar chiral target compounds plays a crucial role in the molecular interaction with PVY-CP, enhancing the activity of defense enzymes and affecting chlorophyll content. The current study has provided significant insights into the roles played by planar chiralities in plant protection against viruses. This paves the way for the development of novel green pesticides bearing planar chiralities with excellent optical purities. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) We acknowledge financial support from; the National Natural Science Foundation of China (U23A20201, 22071036, 22371057,32172459); the Science and Technology Department of Guizhou Province (Qiankehejichu-ZK[2021]Key033); Natural Science Foun-dation of Guizhou University [Guida Tegang Hezi (2023)23]; the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University; Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY(2020)004]; the Central Government Guides Local Science and Technology Development Fund Projects (Qiankehezhongyindi (2023) 001); Singapore National Research Foundation under its NRF Competitive Research Program (NRF-CRP22-2019-0002); Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award(RG84/22, RG70/21), MOE AcRF Tier 2 (MOE-T2EP10222-0006)and MOE AcRF Tier 3 Award (MOE2018-T3-1-003); and a Chair Professorship Grant, Nanyang Technological University. 2024-08-06T05:04:35Z 2024-08-06T05:04:35Z 2024 Journal Article Shu, L., Lv, Y., Chen, Z., Huang, Y., Zhang, M., Jin, Z., Li, T. & Chi, R. Y. (2024). Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane. Pest Management Science, 8149-. https://dx.doi.org/10.1002/ps.8149 1526-498X https://hdl.handle.net/10356/179511 10.1002/ps.8149 38662600 2-s2.0-85192386572 8149 en NRF-CRP22-2019-0002 RG84/22 RG70/21 MOE-T2EP10222-0006 MOE2018-T3-1- 003 Pest Management Science © 2024 Society of Chemical Industry. All rights reserved. |
| spellingShingle | Engineering Potato virus Y Planar chirality Shu, Liangzhen Lv, Ya Chen, Zhongyin Huang, Yixian Zhang, Meng Jin, Zhichao Li, Tingting Chi, Robin Yonggui Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title | Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title_full | Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title_fullStr | Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title_full_unstemmed | Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title_short | Design, synthesis and anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]paracyclophane |
| title_sort | design synthesis and anti pvy activity of planar chiral thiourea derivatives incorporated with 2 2 paracyclophane |
| topic | Engineering Potato virus Y Planar chirality |
| url | https://hdl.handle.net/10356/179511 |
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