Abstract
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.
Highlights
IntroductionBy the late 1990s, two types of diamides were found to possess excellent insecticidal activity, producing poisoning signs similar to those of Ry. Radioligand binding and Ca2+ flux studies at Nihon
Natural ryanodine (Ry) from Ryania speciosa was used as a botanical insecticide in the 1940s [1].By the late 1990s, two types of diamides were found to possess excellent insecticidal activity, producing poisoning signs similar to those of Ry
Photoaffinity labeling revealed that Flu interacts in the insect transmembrane domain and that the N-terminus plays an important role in sensitivity [8]
Summary
By the late 1990s, two types of diamides were found to possess excellent insecticidal activity, producing poisoning signs similar to those of Ry. Radioligand binding and Ca2+ flux studies at Nihon. With commercialization of the anthranilic diamides chlorantraniliprole (Chlo) [11] and cyantraniliprole (Cyan) [14] (Figure 1) and phthalic diamide flubendiamide (Flu) [2], the insect RyR became one of the most important insecticide targets. Radioligand binding assays with [3H]Chlo and [3H]Ry established that anthranilic diamides and Ry act at the Musca domestica RyR [15,16]. Up to now, very little is known about the structure of the insect tetrameric transmembrane RyRs and their active binding site
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