Quantitative structure-activity relationship study on some azidopyridinyl neonicotinoid insecticides for their selective affinity towards the drosophila nicotinic receptor over mammalian alpha4beta2 receptor using electrotopological state atom index

Drug Des Discov. 2003;18(2-3):81-9. doi: 10.3109/10559610290249557.

Abstract

Neonicotinoids are the most important class of synthetic insecticides increasingly used in agriculture and veterinary medicine. Fundamental differences between the nicotinic acetylcholine receptors (nAChRs) of insects and mammals confer remarkable selectivity of the neonicotinoids at insect nAChR over mammalian nAChR. To identify pharmacophoric requirements of azidopyridinyl neonicotinoids for their efficacy and selectivity towards the insect nAChR over the mammalian one, quantitative structure-activity relationship (QSAR) study was performed using electrotopological state atom (ETSA) indices. This study clearly showed that nitroimines, nitromethylenes, and cyanoimines are more selective to Drosophila nAChR and safe for human being, whereas N-substituted imines have affinity to mammalian receptor. Pharmacophore mapping for both the activities was done.

MeSH terms

  • Anabasine / chemistry*
  • Animals
  • Binding Sites
  • Drosophila
  • Drosophila Proteins
  • Electricity
  • Imines / chemistry
  • Insecticides / chemistry*
  • Mammals
  • Molecular Structure
  • Quantitative Structure-Activity Relationship
  • Receptors, Nicotinic / chemistry*

Substances

  • Drosophila Proteins
  • Imines
  • Insecticides
  • Receptors, Nicotinic
  • nicotinic acetylcholine receptor alpha-subunits, Drosophila
  • nicotinic receptor alpha4beta2
  • Anabasine