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Fabrication of Host–Guest Complexes between Adamantane-Functionalized 1,3,4-Oxadiazoles and β-Cyclodextrin with Improved Control Efficiency against Intractable Plant Bacterial Diseases
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2022-01-04 , DOI: 10.1021/acsami.1c19758
Qing-Tian Ji 1 , Xian-Fu Mu 1 , De-Kun Hu 1 , Li-Jun Fan 1 , Shu-Zhen Xiang 1 , Hao-Jie Ye 1 , Xiu-Hui Gao 1 , Pei-Yi Wang 1
Affiliation  

Supramolecular chemistry provides huge potentials and opportunities in agricultural pest management. In an attempt to develop highly bioactive, eco-friendly, and biocompatible supramolecular complexes for managing intractable plant bacterial diseases, herein, a type of interesting adamantane-functionalized 1,3,4-oxadiazole was rationally prepared to facilitate the formation of supramolecular complexes via β-cyclodextrin–adamantane host–guest interactions. Initial antibacterial screening revealed that most of these adamantane-decorated 1,3,4-oxadiazoles were obviously bioactive against three typically destructive phytopathogens. The lowest EC50 values could reach 0.936 (III18), 0.889 (III18), and 2.10 (III19) μg/mL against the corresponding Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and Pseudomonas syringae pv. actinidiae (Psa). Next, the representative supramolecular binary complex III18@β-CD (binding mode 1:1) was successfully fabricated and characterized by 1H nuclear magnetic resonance (NMR), isothermal titration calorimetry (ITC), high-resolution mass spectrometry (HRMS), dynamic light scattering (DLS), and transmission electron microscopy (TEM). Eventually, correlative water solubility and foliar surface wettability were significantly improved after the formation of host–guest assemblies. In vivo antibacterial evaluation found that the achieved supramolecular complex could distinctly alleviate the disease symptoms and promote the control efficiencies against rice bacterial blight (from 34.6–35.7% (III18) to 40.3–43.6% (III18@β-CD)) and kiwi canker diseases (from 41.0–42.3% (III18) to 53.9–68.0% (III18@β-CD)) at 200 μg/mL (active ingredient). The current study can provide a feasible platform and insight for constructing biocompatible supramolecular assemblies for managing destructive bacterial infections in agriculture.

中文翻译:

金刚烷功能化 1,3,4-恶二唑和 β-环糊精之间的主客体复合物的制备,提高了对难治性植物细菌病害的控制效率

超分子化学为农业害虫防治提供了巨大的潜力和机遇。为了开发具有高生物活性、生态友好和生物相容性的超分子复合物来治疗难治性植物细菌病害,本文合理制备了一种有趣的金刚烷功能化 1,3,4-恶二唑,以促进超分子复合物的形成。 β-环糊精-金刚烷主客体相互作用。最初的抗菌筛选表明,这些金刚烷修饰的 1,3,4-恶二唑中的大多数对三种典型的破坏性植物病原体具有明显的生物活性。最低 EC 50值可达到 0.936 ( III 18 )、0.889 ( III 18 ) 和 2.10 ( III 19 )) μg/mL 针对相应的Xanthomonas oryzae pv。oryzae ( Xoo ), Xanthomonas axonopodis pv. 柑橘( Xac ) 和Pseudomonas syringae pv。猕猴桃Psa)。接下来,成功制备了具有代表性的超分子二元复合物III 18 @β-CD(结合模式 1:1),并通过1H 核磁共振 (NMR)、等温滴定量热法 (ITC)、高分辨率质谱 (HRMS)、动态光散射 (DLS) 和透射电子显微镜 (TEM)。最终,在主客体组装形成后,相关的水溶性和叶面润湿性显着提高。体内抗菌评估发现,所获得的超分子复合物可以明显减轻病害症状,提高对水稻白叶枯病的防治效率(从 34.6-35.7% ( III 18 ) 到 40.3-43.6% ( III 18 @β-CD))和猕猴桃溃疡病(从 41.0–42.3% ( III 18 ) 到 53.9–68.0% ( III 18 )@β-CD)) 200 μg/mL(活性成分)。目前的研究可以为构建生物相容性超分子组件以管理农业中的破坏性细菌感染提供一个可行的平台和见解。
更新日期:2022-01-19
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