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Potency and Target Surface Interaction of Diazinoyl Nicotinic Insecticides.
Terajima, Takehito; Ayabe, Chihiro; Matsumoto, Yutsuki; Uehara, Kana; Horikoshi, Ryo; Suzuki, Tomonori; Shimomura, Kenji; Tomizawa, Motohiro.
Afiliación
  • Terajima T; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Ayabe C; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Matsumoto Y; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Uehara K; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Horikoshi R; Biological Solutions Research Center, Research and Development Division, Mitsui Chemicals Crop & Life Solutions, Inc., Mobara 297-0017, Chiba, Japan.
  • Suzuki T; Department of Molecular Microbiology, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Shimomura K; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
  • Tomizawa M; Department of Chemistry, Faculty of Life Sciences, Tokyo University of Agriculture, Setagaya, Tokyo 156-8502, Japan.
J Agric Food Chem ; 72(23): 12967-12974, 2024 Jun 12.
Article en En | MEDLINE | ID: mdl-38814790
ABSTRACT
Structure-activity relationships of diazinoyl nicotinic insecticides (diazinoyl isomers and 5- or 6-substituted pyrazin-2-oyl analogues) are considered in terms of affinity to the insect nicotinic acetylcholine receptor (nAChR) and insecticidal activity against the imidacloprid-resistant brown planthopper. Among the test compounds, 3-(6-chloropyridin-3-ylmethyl)-2-(pyrazinoyl)iminothiazoline shows the highest potency in nAChR affinity and insecticidal activity. Aplysia californica acetylcholine binding protein (AChBP) mutants (Y55W + Q57R and Y55W + Q57T) are utilized to compare molecular recognition of nicotinic insecticides with diverse pharmacophores. N-nitro- or N-cyanoimine imidacloprid or acetamiprid, respectively, exhibits a high affinity to these AChBP mutants at a similar potency level. Intriguingly, the pyrazin-2-oyl analogue has a higher affinity to AChBP Y55W + Q57R than that to Y55W + Q57T, thereby indicating that pyrazine nitrogen atoms contact Arg57 guanidinium and Trp55 indole NH. Furthermore, nicotine prefers AChBP Y55W + Q57T over Y55W + Q57R, conceivably suggesting that the protonated nicotine is repulsed by Arg57 guanidinium, consistent with its inferior potency to insect nAChR.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Receptores Nicotínicos / Proteínas de Insectos / Neonicotinoides / Hemípteros / Insecticidas Límite: Animals Idioma: En Revista: J Agric Food Chem Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Receptores Nicotínicos / Proteínas de Insectos / Neonicotinoides / Hemípteros / Insecticidas Límite: Animals Idioma: En Revista: J Agric Food Chem Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos