Structural features of phenoxycarbonylimino neonicotinoids acting at the insect nicotinic receptor.
Substituted-phenoxycarbonylimino neonicotinoid ligands with an electron-donating group showed significantly higher affinity to the insect nicotinic receptor relative to that of the analogue with an electron-withdrawing substituent, thereby establishing in silico binding site interaction model featuring that the phenoxy ring of neonicotinoids and the receptor loop D tryptophan indole plane form a face-to-edge aromatic interaction.
Ohno
Ikuya
I
The United Graduate School of Agricultural Science, Gifu University, Gifu 501-1193, Japan.
Tomizawa
Motohiro
M
Miyazu
Nozomi
N
Kushibiki
Gohito
G
Noda
Kumiko
K
Hasebe
Yasunori
Y
Durkin
Kathleen A
KA
Miyake
Taiji
T
Kagabu
Shinzo
S
D000818:Animals; D001665:Binding Sites; D003198:Computer Simulation; D007093:Imidazoles / Q000737:chemistry*; D019476:Insect Proteins / Q000737:chemistry* / Q000378:metabolism; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D011978:Receptors, Nicotinic / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
D007093:Imidazoles; D019476:Insect Proteins; D007306:Insecticides; D008024:Ligands; D000073943:Neonicotinoids; D009574:Nitro Compounds; D011725:Pyridines; D011978:Receptors, Nicotinic; C082359:imidacloprid; C023666:pyridine