Prediction of the binding mode of imidacloprid and related compounds to house-fly head acetylcholine receptors using three-dimensional QSAR analysis

Abstract

The binding activity of imidacloprid and related compounds to nicotinic acetylcholine receptors (nAChR) of house flies was measured by use of radioactive α‐bungarotoxin as a ligand. Variations in the activity were examined three‐dimensionally using comparative molecular field analysis (CoMFA). The CoMFA results suggest that one conformer among the four stable ones is active and provide support for one of the proposed binding models for this class of compound, in which the nitrogen atom of the pyridine ring and the nitrogen atom at the 1‐position of the imidazolidine ring interact with the hydrogen‐donating and electron‐rich sites of nAChR, respectively. The CoMFA field map showed that the nitroimino moiety and a portion of the imidazolidine ring were mainly surrounded by a sterically and electrostatically sensitive region of nAChR. © 1998 Society of Chemical Industry

Initial stage of the degradation of three common neonicotinoids: theoretical prediction of charge transfer sites

“…For this case, we have used all basis sets considered in this work coupled with MP2, PBE, PBE0 and B3LYP, where it is impressive that there are no appreciable deviations from average values. [59][60][61] Comparing our results with those presented by Le Questel et al, we found that their results are in the ranges reported in Table 1, except for IMI-5, IMI-6, IMI-7 and IMI-8 (results reported in parenthesis in Table 1).…”

Agonists at the a4b2 Nicotinic Acetylcholine Receptors Relationships and Molecular Modelling

“…These studies are of insecticides structurally related to imidacloprid, which act at the α7 nAChRs (measured by α-bungarotoxin). As this receptor subtype has a low (micromolar) affinity for (S)-nicotine [4], the results are not likely to be comparable [84,85]. Dougherty and co-workers have published an elegant study showing strong correlation between the EC 50 value (measured for acetylcholine) and cation-π binding ability of differently substituted tryptophans incorporated in the α 149 position in the Torpedo nAChR [86].…”

Two‐ and three‐dimensional QSAR of carrier‐mediated transport of β‐lactam antibiotics in Caco‐2 cells

“…CoMFA is a QSAR technique that has been applied with considerable success in the areas of drug discovery and design, as well as enzyme and transporter kinetics including pest control agents 8,26–30. It explains the gradual changes in observed biological properties by evaluating the electrostatic (coulombic interactions) and steric (van der Waals interactions) fields at regularly spaced grid points surrounding a set of mutually aligned ligands.…”