3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation

Bioorg Chem. 2019 Mar:84:276-284. doi: 10.1016/j.bioorg.2018.11.045. Epub 2018 Nov 29.

Abstract

Following on the recent publication of pharmacologically relevant effects, small molecule inhibitors of adipocyte fatty-acid binding protein 4 (FABP4) have attracted high interest. FABP4 is mainly expressed in macrophages and adipose tissue, where it regulates fatty acid storage and lipolysis, being also an important mediator of inflammation. In this regard, FABP4 recently demonstrated an interesting molecular target for the treatment of type 2 diabetes, other metabolic diseases and some type of cancers. In the past years, hundreds of effective FABP4 inhibitors have been synthesized. In this paper, a quantitative structure-activity relationship (QSAR) model has been produced, in order to predict the bioactivity of FABP4 inhibitors. The methodology has been combined with a scaffold-hopping approach, allowing to identify three new molecules that act as effective inhibitors of this protein. These molecules, synthesized and tested for their FABP4 inhibitor activity, showed IC50 values between 3.70 and 5.59 μM, with a high level of agreement with the predicted values.

Keywords: 3D-QSAR; A-FABP; BMS309403 analogs; FABP4 inhibitors; Forge and Spark software; Scaffold-hopping; Thiazole; Triazole; aP2.

MeSH terms

  • Fatty Acid-Binding Proteins / antagonists & inhibitors*
  • Fatty Acid-Binding Proteins / metabolism
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / metabolism
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Imidazoles / metabolism
  • Models, Molecular
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / metabolism
  • Quantitative Structure-Activity Relationship*
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry
  • Thiophenes / metabolism

Substances

  • FABP4 protein, human
  • Fatty Acid-Binding Proteins
  • Hypoglycemic Agents
  • Imidazoles
  • Pyrazoles
  • Thiophenes