Furan-2,5-dimethylene-Tethered Bis-imidacloprid Insecticide Conferring High Potency

Bis-imidacloprid (bis-IMI) analogues with suitable alkylene spacers have plant-systemic insecticidal properties. The alkylene-tethered bis-IMI binds in a unique mode to the insect nicotinic acetylcholine receptor (nAChR) wherein the chloropyridine moieties are embraced by two distinct and distant do...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2010-11, Vol.58 (22), p.11832-11836
Main Authors: Kagabu, Shinzo, Ohno, Ikuya, Tomizawa, Motohiro, Durkin, Kathleen A, Matsuura, Ryota, Uchiyama, Daiki, Nagae, Nozomi, Kumazawa, Satoru
Format: Article
Language:English
Subjects:
Animals
Binding Sites
Biological and medical sciences
chemical analysis
chemical composition
cholinergic receptors
Crop and Animal Protection Chemistry
Female
Food industries
Fundamental and applied biological sciences. Psychology
furan-2,5-dimethylene-tethered Bis-imidacloprid insecticide
furans
Houseflies - chemistry
Houseflies - drug effects
imidacloprid
Imidazoles - chemistry
Imidazoles - pharmacology
Insect Proteins - antagonists & inhibitors
Insect Proteins - chemistry
insecticidal properties
Insecticides - chemistry
Insecticides - pharmacology
Molecular Conformation
Neonicotinoids
Nicotinic Antagonists
Nitro Compounds - chemistry
Nitro Compounds - pharmacology
Protein Binding
Receptors, Nicotinic - chemistry
Structure-Activity Relationship
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Summary:Bis-imidacloprid (bis-IMI) analogues with suitable alkylene spacers have plant-systemic insecticidal properties. The alkylene-tethered bis-IMI binds in a unique mode to the insect nicotinic acetylcholine receptor (nAChR) wherein the chloropyridine moieties are embraced by two distinct and distant domains. The heptamethylene spacer optimally bridges these two subsites, yet the linker itself binds in a relatively nonspecific manner. This investigation examines the hypothesis that a bis-IMI analogue with a heteroaromatic tether, which undergoes specific interaction(s) with the newly recognized receptor cavity, may enhance the potency relative to those of the alkylene-tethered derivatives. Remarkably, a novel bis-IMI with a furan-2,5-dimethylene fulcrum showed highest receptor potency and insecticidal activity among the analogues with various chemotype spacers. The nAChR structural model, simulating the binding site interactions of the furan-2,5-dimethylene-tethered bis-IMI, reveals that the furan ring is nestled in a hydrophobic pocket, consisting of three aromatic amino acids, and is stabilized via hydrogen bonding.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf102819n