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Binding Properties of Photosynthetic Herbicides: Photosynthetic Activity and Molecular Docking Approach towards 1,4-Dihydropyridines Derivatives
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2022-11-16 , DOI: 10.1002/cbdv.202200586
Luís T X M G Soares 1 , Marcelo A F Basso 1 , Clarice M R Dos Santos 2 , Akbar Ali 3 , Leonardo G Vasconcelos 1 , Evandro L Dall'Oglio 1 , Olívia M Sampaio 1 , Lucas C C Vieira 1
Affiliation  

In the current work, we describe the synthesis of 1,4-dihydropyridine (1,4-DHP) derivatives via Hantzsch multicomponent reaction and their evaluation as photosystem II (PSII) inhibitors through chlorophyll a fluorescence bioassay. Among all the compounds tested, 1,1′-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(ethan-1-one) (4b) showed best results, reducing the parameters performance index on absorption basis (PIabs) and electron transport per reaction center by 61 % and 49 %, respectively, as compared to the control. These results indicate the inhibitory activity of PSII over the electron transport chain. Additionally, a molecular docking approach using the protein D1 (PDB code 4V82) was performed in order to assess the structure-activity relationship among the 1,4-DHP derivatives over the PSII, which revealed that both, size of the group at position 4 and the carbonyl groups at the dihydropyridine ring are important for the ligand's interaction, particularly for the hydrogen-bonding interaction with the residues His215, Ser264, and Phe265. Thus, the optimization of these molecular features is the aim of our research group to extend the knowledge of PSII electron chain inhibitors and the establishment of new potent bioactive molecular scaffolds.

中文翻译:

光合除草剂的结合特性:1,4-二氢吡啶衍生物的光合活性和分子对接方法

在目前的工作中,我们描述了通过 Hantzsch 多组分反应合成 1,4-二氢吡啶 (1,4-DHP) 衍生物,并通过叶绿素a荧光生物测定对其作为光系统 II (PSII) 抑制剂的评估。在所有测试的化合物中,1,1'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(ethan-1-one) ( 4b ) 显示出最佳结果,降低了参数基于吸收的性能指数(PI abs) 和电子传输每个反应中心分别为 61% 和 49%,与控制相比。这些结果表明 PSII 在电子传输链上的抑制活性。此外,还执行了使用蛋白质 D1(PDB 代码 4V82)的分子对接方法,以评估 PSII 上 1,4-DHP 衍生物之间的结构-活性关系,这表明 4 位组的大小二氢吡啶环上的羰基对配体的相互作用很重要,尤其是与残基 His215、Ser264 和 Phe265 的氢键相互作用。因此,优化这些分子特征是我们研究小组扩展 PSII 电子链抑制剂知识和建立新的有效生物活性分子支架的目标。
更新日期:2022-11-16
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