The application of molecular modelling in the safety assessment of chemicals: A case study on ligand-dependent PPARγ dysregulation

Toxicology. 2017 Dec 1:392:140-154. doi: 10.1016/j.tox.2016.01.009. Epub 2016 Feb 4.

Abstract

The aim of this paper was to provide a proof of concept demonstrating that molecular modelling methodologies can be employed as a part of an integrated strategy to support toxicity prediction consistent with the mode of action/adverse outcome pathway (MoA/AOP) framework. To illustrate the role of molecular modelling in predictive toxicology, a case study was undertaken in which molecular modelling methodologies were employed to predict the activation of the peroxisome proliferator-activated nuclear receptor γ (PPARγ) as a potential molecular initiating event (MIE) for liver steatosis. A stepwise procedure combining different in silico approaches (virtual screening based on docking and pharmacophore filtering, and molecular field analysis) was developed to screen for PPARγ full agonists and to predict their transactivation activity (EC50). The performance metrics of the classification model to predict PPARγ full agonists were balanced accuracy=81%, sensitivity=85% and specificity=76%. The 3D QSAR model developed to predict EC50 of PPARγ full agonists had the following statistical parameters: q2cv=0.610, Nopt=7, SEPcv=0.505, r2pr=0.552. To support the linkage of PPARγ agonism predictions to prosteatotic potential, molecular modelling was combined with independently performed mechanistic mining of available in vivo toxicity data followed by ToxPrint chemotypes analysis. The approaches investigated demonstrated a potential to predict the MIE, to facilitate the process of MoA/AOP elaboration, to increase the scientific confidence in AOP, and to become a basis for 3D chemotype development.

Keywords: Adverse outcome pathway; Liver steatosis; Molecular modelling; PPARγ; Receptor activation.

MeSH terms

  • Animals
  • Binding Sites
  • COS Cells
  • Cell Line, Tumor
  • Chlorocebus aethiops
  • Cricetinae
  • Databases, Protein
  • Fatty Liver / metabolism
  • Fatty Liver / pathology
  • Feasibility Studies
  • HEK293 Cells
  • Haplorhini
  • Hep G2 Cells
  • Humans
  • Ligands
  • Models, Molecular*
  • Molecular Docking Simulation
  • Molecular Structure
  • PPAR gamma / genetics
  • PPAR gamma / metabolism*
  • Protein Binding
  • Quantitative Structure-Activity Relationship
  • Reproducibility of Results
  • Risk Assessment
  • Sensitivity and Specificity
  • Toxicity Tests / methods*

Substances

  • Ligands
  • PPAR gamma