Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone
Plant bacteria and viruses have a huge negative impact on food crops in the world. Therefore, it is important to create new and efficient green pesticides. In this paper, a series of myricetin derivatives containing quinazolinone sulfide were introduced. Good antibacterial and antiviral activities o...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-08-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535222003355 |
| _version_ | 1811240436939882496 |
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| author | Tingting Liu Feng Peng Yunying Zhu Xiao Cao Qifan Wang Fang Liu Liwei Liu Wei Xue |
| author_facet | Tingting Liu Feng Peng Yunying Zhu Xiao Cao Qifan Wang Fang Liu Liwei Liu Wei Xue |
| author_sort | Tingting Liu |
| collection | DOAJ |
| description | Plant bacteria and viruses have a huge negative impact on food crops in the world. Therefore, it is important to create new and efficient green pesticides. In this paper, a series of myricetin derivatives containing quinazolinone sulfide were introduced. Good antibacterial and antiviral activities of the drug molecules 2-((3-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)propyl)thio)-6-fluoro-3-phenylquinazolin-4(3H)-one (T5) and 2-((4-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)butyl)thio)-6-methyl-3-phenylquinazolin-4(3H)-one (T15) respectively were found by biological activity screening. The value of dissociation constant (Kd) of compound T15 to TMV CP was 0.024 ± 0.006 μM, determined by Microscale thermophoresis (MST), which was far less than the value of 8.491 ± 2.027 μM of commercial drug ningnanmycin (NNM). The interaction between compound T15 and TMV CP was further verified by molecular docking. Compound T15 formed strong hydrogen bonds with residues SER:49 and SER:15 (1.92 Å, 2.20 Å, respectively), which were superior to the traditional hydrogen bonds formed by NNM with residue SER:215 (3.64 Å). In addition, the effects of compound T15 on the contents of chlorophyll and peroxidase (POD) in tobacco were studied, and the results indicated that compound T15 could enhance the disease resistance of tobacco plants to a certain extent. |
| first_indexed | 2024-04-12T13:20:17Z |
| format | Article |
| id | doaj.art-0248b0be284f405cb6997284abb924ba |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-12T13:20:17Z |
| publishDate | 2022-08-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-0248b0be284f405cb6997284abb924ba2022-12-22T03:31:31ZengElsevierArabian Journal of Chemistry1878-53522022-08-01158104019Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinoneTingting Liu0Feng Peng1Yunying Zhu2Xiao Cao3Qifan Wang4Fang Liu5Liwei Liu6Wei Xue7State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaSchool of Chemical Engineering, Guizhou Institute of Technology, Guiyang 550001, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China; Corresponding author.Plant bacteria and viruses have a huge negative impact on food crops in the world. Therefore, it is important to create new and efficient green pesticides. In this paper, a series of myricetin derivatives containing quinazolinone sulfide were introduced. Good antibacterial and antiviral activities of the drug molecules 2-((3-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)propyl)thio)-6-fluoro-3-phenylquinazolin-4(3H)-one (T5) and 2-((4-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)butyl)thio)-6-methyl-3-phenylquinazolin-4(3H)-one (T15) respectively were found by biological activity screening. The value of dissociation constant (Kd) of compound T15 to TMV CP was 0.024 ± 0.006 μM, determined by Microscale thermophoresis (MST), which was far less than the value of 8.491 ± 2.027 μM of commercial drug ningnanmycin (NNM). The interaction between compound T15 and TMV CP was further verified by molecular docking. Compound T15 formed strong hydrogen bonds with residues SER:49 and SER:15 (1.92 Å, 2.20 Å, respectively), which were superior to the traditional hydrogen bonds formed by NNM with residue SER:215 (3.64 Å). In addition, the effects of compound T15 on the contents of chlorophyll and peroxidase (POD) in tobacco were studied, and the results indicated that compound T15 could enhance the disease resistance of tobacco plants to a certain extent.http://www.sciencedirect.com/science/article/pii/S1878535222003355MyricetinQuinazolinoneAntibacterialAntiviralTMV CPChlorophyll content |
| spellingShingle | Tingting Liu Feng Peng Yunying Zhu Xiao Cao Qifan Wang Fang Liu Liwei Liu Wei Xue Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone Arabian Journal of Chemistry Myricetin Quinazolinone Antibacterial Antiviral TMV CP Chlorophyll content |
| title | Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| title_full | Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| title_fullStr | Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| title_full_unstemmed | Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| title_short | Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| title_sort | design synthesis biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone |
| topic | Myricetin Quinazolinone Antibacterial Antiviral TMV CP Chlorophyll content |
| url | http://www.sciencedirect.com/science/article/pii/S1878535222003355 |
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