Discovery of highly effective antiviral agents based on flavonoid-benzothiazole against TMV.

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-02-19 DOI:10.1007/s11030-025-11126-5

Jiao Tian, Chunmei Hu, Tianyu Deng, Qing Zhou, Xingping Luo, Jieyu Li, Haotao Pu, Ying Yang, Da Liu, Wei Xue

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引用次数: 0

Abstract

A series of flavonol derivatives containing benzothiazole were designed and synthesized. The structures of all the compounds were characterized by NMR and HRMS. The results of the activity assay showed that some of the target compounds possessed outstanding in vivo antiviral activity against the tobacco mosaic virus (TMV). Among them, the median effective concentration (EC₅₀) of L20 was 90.5 and 202.2 μg/mL for curative and protective activity against TMV, respectively, which was better than that of ningnanmycin (NNM: 252.0 and 204.2 μg/mL). The results of microcalorimetric thermophoresis (MST) and molecular docking experiments indicate that L20 binds TMV-CP more strongly than NNM; density functional theory (DFT) calculation the indicating that L20 is more chemical reactivity than NNM. In addition, malondialdehyde (MDA) and superoxide dismutase assay (SOD) activity measurements also fully confirmed that L20 stimulated the plant immune system and strengthened the plant's resistance to diseases by lowering the MDA content and increasing the SOD activity. Furthermore, the chlorophyll content test experiment found that L20 could reduce the destructive effect of viruses on chloroplasts, increase the content of chlorophyll, and promote photosynthesis. In conclusion, above experimental results suggested that flavonol derivatives containing benzothiazole could be further investigated as new plant virus antiviral drugs.

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基于类黄酮-苯并噻唑的高效抗病毒TMV药物的发现。

设计并合成了一系列含苯并噻唑的黄酮醇衍生物。所有化合物的结构都通过NMR和HRMS进行了表征。活性测定结果表明，部分靶化合物对烟草花叶病毒（TMV）具有较强的体内抗病毒活性。其中，L20对TMV的治疗和保护作用的中位有效浓度（EC50）分别为90.5和202.2 μg/mL，优于宁南霉素（NNM: 252.0和204.2 μg/mL）。微热电泳（MST）和分子对接实验结果表明，L20与TMV-CP的结合比NNM强；密度泛函理论（DFT）计算表明L20比NNM具有更强的化学反应性。此外，丙二醛（MDA）和超氧化物歧化酶（SOD）活性测定也充分证实了L20通过降低MDA含量和提高SOD活性来刺激植物免疫系统，增强植物抗病能力。叶绿素含量测试实验发现，L20能降低病毒对叶绿体的破坏作用，提高叶绿素含量，促进光合作用。综上所述，含苯并噻唑的黄酮醇衍生物可作为新型植物病毒抗病毒药物进行进一步研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;