Wang Yi, Guo Lei, Qi Suzhen, Zhang Hao, Liu Kechang, Liu Ruiquan, Liang Pei, Casida John E, Liu Shangzhong
Department of Applied Chemistry, College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China.
College of Agriculture and Biotechnology, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China.
Molecules. 2014 Apr 2;19(4):4105-14. doi: 10.3390/molecules19044105.
Diamide insecticides with high efficacy against pests and good environmental safety are broadly applied in crop protection. They act at a poorly-defined site in the very complex ryanodine (Ry) receptor (RyR) potentially accessible to a fluorescent probe. Two N-propynyl analogs of the major anthranilic diamide insecticides chlorantraniliprole (Chlo) and cyantraniliprole (Cyan) were accordingly synthesized and converted into two fluorescent ligands by click reaction coupling with 3-azido-7-hydroxy-2H-chromen-2-one. The new diamide analogs and fluorescent ligands were shown to be nearly as potent as Chlo and Cyan in inhibition of [3H]Chlo binding and stimulation of [3H]Ry binding in house fly thoracic muscle RyR. Although the newly synthesized compounds had only moderate activity in insect larvicidal activity assays, their high in vitro potency in a validated insect RyR binding assay encourages further development of fluorescent probes for insect RyRs.
对害虫高效且环境安全性良好的双酰胺类杀虫剂在作物保护中广泛应用。它们作用于非常复杂的鱼尼丁（Ry）受体中一个定义不明确的位点，该位点可能可被荧光探针接近。因此，合成了主要邻氨基苯甲酰胺类杀虫剂氯虫苯甲酰胺（Chlo）和氰虫苯甲酰胺（Cyan）的两种N-丙炔基类似物，并通过与3-叠氮基-7-羟基-2H-色烯-2-酮的点击反应偶联将其转化为两种荧光配体。新的双酰胺类似物和荧光配体在抑制家蝇胸肌RyR中[3H]Chlo结合以及刺激[3H]Ry结合方面显示出与Chlo和Cyan几乎相同的效力。尽管新合成的化合物在昆虫幼虫活性测定中仅具有中等活性，但它们在经过验证的昆虫RyR结合测定中的高体外效力鼓励进一步开发用于昆虫RyR的荧光探针。
