Protein Information

Name acetylcholine receptor (protein family or complex)
Synonyms Acetylcholine receptor; Acetylcholine receptors

Compound Information

Name dinotefuran
CAS

Reference List

PubMed Abstract RScore(About this table)
16637697 Honda H, Tomizawa M, Casida JE: Insect nicotinic acetylcholine receptors: neonicotinoid binding site specificity is usually but not always conserved with varied substituents and species. J Agric Food Chem. 2006 May 3;54(9):3365-71.


The diversity of neonicotinoid insecticides acting as insect nicotinic acetylcholine (ACh) receptor (nAChR) agonists is illustrated by imidacloprid (IMI) with chloropyridinylmethyl (CPM) and N-nitroimine substituents, dinotefuran (DIN) with tetrahydrofurylmethyl (TFM) and N-nitroimine moieties, and acetamiprid (ACE) with CPM and N-cyanoimine groups.
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11852645 Mori K, Okumoto T, Kawahara N, Ozoe Y: Interaction of dinotefuran and its analogues with nicotinic acetylcholine receptors of cockroach nerve cords. Pest Manag Sci. 2002 Feb;58(2):190-6.
112(1,2,2,2) Details
16470540 Miyagi S, Komaki I, Ozoe Y: Identification of a high-affinity binding site for dinotefuran in the nerve cord of the American cockroach. Pest Manag Sci. 2006 Apr;62(4):293-8.

The binding of the neonicotinoid insecticide dinotefuran to insect nicotinic acetylcholine receptors (nAChRs) was examined by a centrifugation method using the nerve cord membranes of American cockroaches and [3H] dinotefuran (78 Ci mmol-1).
81(1,1,1,1) Details
17561262 Tan J, Galligan JJ, Hollingworth RM: Agonist actions of neonicotinoids on nicotinic acetylcholine receptors expressed by cockroach neurons. Neurotoxicology. 2007 Jul;28(4):829-42. Epub 2007 Apr 20.

Based on maximum inward currents, neonicotinoids could be divided into two subgroups: (1) those with a heterocyclic ring in their electronegative pharmacophore moiety (i.e. nicotine, imidacloprid and thiacloprid) were relatively weak partial agonists causing only 20-25% of the maximum ACh current and (2) open chain compounds (i.e. acetamiprid, dinotefuran, nitenpyram, and clothiandin) which were much more effective agonists producing 60-100% of the maximum ACh current.
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16981889 Liu Z, Williamson MS, Lansdell SJ, Han Z, Denholm I, Millar NS: A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. J Neurochem. 2006 Nov;99(4):1273-81. Epub 2006 Sep 18.

The agonist potency of several nicotinic agonists has been examined, including all of the neonicotinoid insecticides that are currently licensed for either crop protection or animal health applications (acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam).
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16153789 Honda H, Tomizawa M, Casida JE: Neo-nicotinoid metabolic activation and inactivation established with coupled nicotinic receptor-CYP3A4 and -aldehyde oxidase systems. Toxicol Lett. 2006 Feb 20;161(2):108-14. Epub 2005 Sep 8.

CYP3A4 oxidation at several molecular sites and AOX reduction at the nitro substituent result in either an increase (activation) or decrease (inactivation) of agonist potency at nicotinic acetylcholine receptors (nAChRs), both insect and vertebrate alpha 4beta 2.
The AOX system coupled with the Drosophila receptor strongly inactivates clothianidin, dinotefuran, imidacloprid, desmethyl-thiamethoxam, and thiamethoxam with some inactivation of nitenpyram and nithiazine, and little or no effect on four other compounds.
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14561066 Kiriyama K, Nishiwaki H, Nakagawa Y, Nishimura K: Insecticidal activity and nicotinic acetylcholine receptor binding of dinotefuran and its analogues in the housefly, Musca domestica. Pest Manag Sci. 2003 Oct;59(10):1093-100.
81(1,1,1,1) Details