Preparation of Dinotefuran Related Compounds and Agonistic Action on SADβ2 Hybrid Nicotinic Acetylcholine Receptors Expressed in <i>Xenopus laevis</i> Oocytes

Journal of Pesticide Science
2002.0

Abstract

We tested dinotefuran on hybrid SADβ2 nicotinic acetylcholine receptors (nAChRs) expressed in Xenopus laevis oocytes by electrophysiology to investigate how its unique structure influences agonist actions. Three structural variations (3-5) of dinotefuran were prepared by combining acyclic/cyclic nitroguanidine and tetrahydrofuran/acyclic ether to elucidate isosterism around the dinotefuran structure. Dinotefuran evoked dose-dependent inward currents in the hybrid nAChR with a pEC50 (–log EC50) of 3.65 ± 0.02 and an Imax (normalized maximum response) of 1.04 ± 0.03 (full agonist), while imidacloprid had a higher pEC50 (5.55 ± 0.06) but lower Imax (0.50 ± 0.02, partial agonist). Compound 3 (1-(3-tetrahydrofuranylmethyl)-2-nitroiminoimidazolidine) had a similar pEC50 (3.83 ± 0.06) to dinotefuran but much lower Imax (0.12 ± 0.01), and compounds 4 (1-(3-ethoxy-2-methyl)propyl-3-methyl-2-nitroguanidine) and 5 (1-(3-ethoxy-2-methyl)propyl-2-nitroiminoimidazolidine) showed no agonistic effects. The study demonstrated that dinotefuran has lower affinity but stronger channel-opening ability than imidacloprid for the SADβ2 hybrid nAChR, and it remains to be clarified how these electrophysiological features relate to its insecticidal potency and unique spectra in practice.

Knowledge Graph

Similar Paper

Preparation of Dinotefuran Related Compounds and Agonistic Action on SADβ2 Hybrid Nicotinic Acetylcholine Receptors Expressed in &lt;i&gt;Xenopus laevis&lt;/i&gt; Oocytes
Journal of Pesticide Science 2002.0
Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part
Journal of Pesticide Science 2004.0
Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Tetrahydro-3-furylmethyl Part
Journal of Pesticide Science 2004.0
Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency
Journal of Pesticide Science 2006.0
Molecular Design of Dinotefuran with Unique Insecticidal Properties
Journal of Agricultural and Food Chemistry 2011.0
Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the &lt;i&gt;Torpedo&lt;/i&gt; Electric Organ
Journal of Pesticide Science 1995.0
Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor
Journal of Pesticide Science 1992.0
Potency and Selectivity of Trifluoroacetylimino and Pyrazinoylimino Nicotinic Insecticides and Their Fit at a Unique Binding Site Niche
Journal of Medicinal Chemistry 2008.0
Furan-2,5-dimethylene-Tethered Bis-imidacloprid Insecticide Conferring High Potency
Journal of Agricultural and Food Chemistry 2010.0
Chiral 1,5-disubstituted 1,3,5-hexahydrotriazine-2-N-nitroimine analogues as novel potent neonicotinoids: Synthesis, insecticidal evaluation and molecular docking studies
European Journal of Medicinal Chemistry 2011.0