Pharmacophoric search and 3D-QSAR comparative molecular field analysis studies on agonists of melatonin sheep receptors

J Med Chem. 1998 Nov 5;41(23):4453-65. doi: 10.1021/jm980026p.

Abstract

Conformational analysis was used to characterize the agonist pharmacophore for melatonin sheep brain receptor recognition and activation. The molecular geometry shared by all conformations of the selected active ligands was determined. Assuming that all the compounds interact at the same binding site at the receptor level, 2-iodomelatonin pharmacophoric conformation served as a template for the superimposition of 64 structurally heterogeneous agonists constituting the training set used to perform a three-dimensional quantitative structure-activity relationship study via the comparative molecular field analysis method. A statistically significant model was obtained for the totality of the compounds (n = 64, q2 = 0.62, N = 6, r2 = 0.96, s = 0.28, F = 249) with steric, electrostatic, and lipophilic relative contributions of 28%, 35%, and 37%, respectively. The predictive power of the proposed model was discerned by successfully testing the 78 agonist ligands constituting the test set. The model so obtained and validated brings important structural insights to aid the design of novel melatoninergic agonist ligands prior to their synthesis.

MeSH terms

  • Animals
  • Brain / metabolism
  • Ligands
  • Melatonin / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Receptors, Cell Surface / agonists*
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Melatonin
  • Reproducibility of Results
  • Sheep
  • Structure-Activity Relationship

Substances

  • Ligands
  • Receptors, Cell Surface
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, Melatonin
  • Melatonin