Structural features of phenoxycarbonylimino neonicotinoids acting at the insect nicotinic receptor

Bioorg Med Chem Lett. 2010 Oct 1;20(19):5933-5. doi: 10.1016/j.bmcl.2010.07.049. Epub 2010 Jul 16.

Abstract

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.

MeSH terms

  • Animals
  • Binding Sites
  • Computer Simulation
  • Imidazoles / chemistry*
  • Insect Proteins / chemistry*
  • Insect Proteins / metabolism
  • Insecta
  • Insecticides / chemical synthesis
  • Insecticides / chemistry
  • Ligands
  • Neonicotinoids
  • Nitro Compounds / chemistry*
  • Pyridines / chemistry
  • Receptors, Nicotinic / chemistry*
  • Receptors, Nicotinic / metabolism
  • Structure-Activity Relationship

Substances

  • Imidazoles
  • Insect Proteins
  • Insecticides
  • Ligands
  • Neonicotinoids
  • Nitro Compounds
  • Pyridines
  • Receptors, Nicotinic
  • imidacloprid
  • pyridine