Design, synthesis and anti-TMV activity of novel α-aminophosphonate derivatives containing a chalcone moiety that induce resistance against plant disease and target the TMV coat protein

Zhou, Xiang; Ye, Yiqiang; Li, Shasha; Shao, Wu-Bin; Liu, Liwei; Yang, Song; Wu, Zhibing

doi:10.1016/j.pestbp.2020.104749

Cited by 29 publications

(23 citation statements)

References 32 publications

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“…Meanwhile, the ligands were prepared, subsequently energy minimised using the Tripos force field and atomic charges were assigned using Gasteiger-Huckel method. Finally, the docking results were performed by PyMol software and Discovery Studio (DS) 2020 41 , 53 , 54 .…”

Section: Methodsmentioning

confidence: 99%

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Discovery of facile amides-functionalized rhodanine-3-acetic acid derivatives as potential anticancer agents by disrupting microtubule dynamics

Zhou

Liu

Meng³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Microtubule dynamics are crucial for multiple cell functions, and cancer cells are particularly sensitive to microtubule-modulating agents. Here, we describe the design and synthesis of a series of ( Z )-2-(5-benzylidene-4-oxo-2-thioxothiazolidin-3-yl)- N -phenylacetamide derivatives and evaluation of their microtubule-modulating and anticancer activities in vitro . Proliferation assays identified I 20 as the most potent of the antiproliferative compounds, with 50% inhibitory concentrations ranging from 7.0 to 20.3 µM with A549, PC-3, and HepG2 human cancer cell lines. Compound I 20 also disrupted cancer A549 cell migration in a concentration-dependent manner. Immunofluorescence microscopy, transmission electron microscopy, and tubulin polymerisation assays suggested that compound I 20 promoted protofilament assembly. In support of this possibility, computational docking studies revealed a strong interaction between compound I 20 and tubulin Arg β 369, which is also the binding site for the anticancer drug Taxol. Our results suggest that ( Z )-2-(5-benzylidene-4-oxo-2-thioxothiazolidin-3-yl)- N -phenylacetamide derivatives could have utility for the development of microtubule-stabilising therapeutic agents.

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Section: Methodsmentioning

confidence: 99%

“…Briefly, rhodanine-3-acetic acid and corresponding amines were dissolved in acetonitrile solution 41 , 56 . Subsequently, EDCI and HOBt were added in the reaction mixture at room temperature to produce the corresponding intermediates.…”

Section: Methodsmentioning

confidence: 99%

Discovery of facile amides-functionalized rhodanine-3-acetic acid derivatives as potential anticancer agents by disrupting microtubule dynamics

Zhou

Liu

Meng³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Compounds 8 and 9 not only have good passivation activities (EC 50 , 51.65 and 30.57 mg/L) for TMV, but also have a strong binding ability to TMV-CP ( Gan et al, 2017b ; Zhou et al, 2018 ). Compound 10 has good curative and protective activities against TMV (57.6 and 59.9%), which may trigger the breakdown of TMV by directly interacting with TMV, while also inducing plant resistance ( Zhou et al, 2021 ). The derivatization direction of chalcone is mainly two benzene rings.…”

Section: Antiviral Active Compoundsmentioning

confidence: 99%

Recent Research Progress: Discovery of Anti-Plant Virus Agents Based on Natural Scaffold

et al. 2022

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Plant virus diseases, also known as “plant cancers”, cause serious harm to the agriculture of the world and huge economic losses every year. Antiviral agents are one of the most effective ways to control plant virus diseases. Ningnanmycin is currently the most successful anti-plant virus agent, but its field control effect is not ideal due to its instability. In recent years, great progress has been made in the research and development of antiviral agents, the mainstream research direction is to obtain antiviral agents or lead compounds based on structural modification of natural products. However, no antiviral agent has been able to completely inhibit plant viruses. Therefore, the development of highly effective antiviral agents still faces enormous challenges. Therefore, we reviewed the recent research progress of anti-plant virus agents based on natural products in the past decade, and discussed their structure-activity relationship (SAR) and mechanism of action. It is hoped that this review can provide new inspiration for the discovery and mechanism of action of novel antiviral agents.

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“…TSWV belongs to the genus Orthotospovirus in the family Tospoviridae . The genome of TSWV contains three RNA segments named small (S), medium (M), and large (L). ,, TSWV coat protein (CP), named the N protein, is a multifunctional protein encoded by S. , TSWV CP interacts with genomic RNA, TSWV Gn, Gc glycoproteins, and NSm and has multiple functions, including viral mRNA transcription, viral RNA replication, the formation of virions, and viral RNA movement. − In the research of pesticide discovery, the CP of plant viruses has always been considered as a potential target of antiviral drugs. , The combination of antiviral drugs and viral CP can inhibit virus replication and assembly, thereby inhibiting virus infection . There have been a large number of reports on the study of plant CPs as potential targets, and there are also some related reports in our previous work. ,, In addition, transgenic plants expressing the TSWV CP gene exhibited post-transcriptional gene silencing and resistance to TSWV .…”

Section: Introductionmentioning

confidence: 99%

First Report on Anti-TSWV Activities of Quinazolinone Derivatives Containing a Dithioacetal Moiety

Liu

Chen

Xie

et al. 2021

J. Agric. Food Chem.

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Tomato spotted wilt virus (TSWV) is a plant virus with strong infectivity and destructive power. Given the lack of effective control agents, TSWV causes significant economic damage to several vegetables and ornamental plants worldwide. In this study, we designed and synthesized a series of novel quinazolinone derivatives containing a dithioacetal moiety and evaluated their antiviral activity in vitro and in vivo against TSWV. Some candidate compounds showed good anti-TSWV activity. Compound 6n shows excellent anti-TSWV activity in vivo, and the EC50 value is 188 mg/L, which is notably better than that observed for ribavirin (642 mg/L), xiangcaoliusuobingmi (420 mg/L), and ningnanmycin (257 mg/L). In addition, compound 6n interacts with TSWV coat protein at sites ARG94 and ARG95 forming four π-alkyl interactions. Compound 6n (9.4 μM) shows a better binding affinity with TSWV coat protein than ribavirin (67.8 μM), xiangcaoliusuobingmi (33.8 μM), and ningnanmycin (24.3 μM). Therefore, compound 6n can serve as a lead compound for the discovery of new antiviral agents for the management of TSWV.

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Design, synthesis and anti-TMV activity of novel α-aminophosphonate derivatives containing a chalcone moiety that induce resistance against plant disease and target the TMV coat protein

Cited by 29 publications

References 32 publications

Discovery of facile amides-functionalized rhodanine-3-acetic acid derivatives as potential anticancer agents by disrupting microtubule dynamics

Discovery of facile amides-functionalized rhodanine-3-acetic acid derivatives as potential anticancer agents by disrupting microtubule dynamics

Recent Research Progress: Discovery of Anti-Plant Virus Agents Based on Natural Scaffold

First Report on Anti-TSWV Activities of Quinazolinone Derivatives Containing a Dithioacetal Moiety

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