Development of terpenoid repellents against Aedes albopictus: a combined study of biological activity evaluation and computational modelling.

IF 2.3 3区 环境科学与生态学 Q3 CHEMISTRY, MULTIDISCIPLINARY
J Wang, X Feng, W Yuan, J Zhang, S Zhu, L Xu, H Li, J Song, X Rao, S Liao, Z Wang, H Si
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引用次数: 0

Abstract

To explore novel terpenoid repellents, 22 candidate terpenoid derivatives were synthesized and tested for their electroantennogram (EAG) responses and repellent activities against Aedes albopictus. The results from the EAG experiments revealed that 5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-yl formate (compound 1) induced distinct EAG responses in female Aedes albopictus. At concentrations of 0.1, 1, 10, 100, and 1000 mg/L, the EAG response values for compound 1 were 179.59, 183.99, 190.38, 193.80, and 196.66 mV, demonstrating comparable or superior effectiveness to DEET. Repellent activity analysis indicated significant repellent activity for compound 1, closest to the positive control DEET. The in silico assessment of the ADMET profile of compound 1 indicates that it successfully passed the ADMET evaluation. Molecular docking studies exhibited favourable binding of compound 1 to the active site of the odorant binding protein (OBP) of Aedes albopictus, involving hydrophobic forces and hydrogen bond interactions with residues in the OBP pocket. The QSAR model highlighted the influential role of hydrogen-bonding receptors, positively charged surface area of weighted atoms, polarity parameters of molecules, and maximum nuclear-nuclear repulsion force of carbon-carbon bonds on the relative EAG response values of the tested compounds. This study holds substantial significance for the advancement of new terpenoid repellents.

开发针对白纹伊蚊的萜类驱虫剂:生物活性评估和计算模型的综合研究。
为了探索新型萜类驱虫剂,我们合成了 22 种候选萜类衍生物,并测试了它们对白纹伊蚊的电触觉图(EAG)反应和驱避活性。EAG 实验结果表明,5-(2-羟基丙-2-基)-2-甲基环己-2-烯-1-基甲酸酯(化合物 1)可诱导雌性白纹伊蚊产生不同的 EAG 反应。在浓度为 0.1、1、10、100 和 1000 mg/L 时,化合物 1 的 EAG 反应值分别为 179.59、183.99、190.38、193.80 和 196.66 mV,显示出与 DEET 相当或更高的有效性。驱避活性分析表明,化合物 1 具有明显的驱避活性,最接近阳性对照 DEET。对化合物 1 的 ADMET 特征进行的硅学评估表明,它成功通过了 ADMET 评估。分子对接研究表明,化合物 1 与白纹伊蚊气味结合蛋白 (OBP) 的活性位点结合良好,其中涉及与 OBP 口袋中残基的疏水作用力和氢键相互作用。QSAR 模型强调了氢键受体、加权原子的正电表面积、分子极性参数和碳-碳键的最大核-核排斥力对受试化合物相对 EAG 反应值的影响作用。这项研究对开发新的萜类驱虫剂具有重要意义。
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来源期刊
CiteScore
5.20
自引率
20.00%
发文量
78
审稿时长
>24 weeks
期刊介绍: SAR and QSAR in Environmental Research is an international journal welcoming papers on the fundamental and practical aspects of the structure-activity and structure-property relationships in the fields of environmental science, agrochemistry, toxicology, pharmacology and applied chemistry. A unique aspect of the journal is the focus on emerging techniques for the building of SAR and QSAR models in these widely varying fields. The scope of the journal includes, but is not limited to, the topics of topological and physicochemical descriptors, mathematical, statistical and graphical methods for data analysis, computer methods and programs, original applications and comparative studies. In addition to primary scientific papers, the journal contains reviews of books and software and news of conferences. Special issues on topics of current and widespread interest to the SAR and QSAR community will be published from time to time.
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