Free-Wilson Analysis of Comprehensive Data on Phosphoinositide-3-kinase (PI3K) Inhibitors Reveals Importance of N-Methylation for PI3Kδ Activity

J Med Chem. 2019 Nov 27;62(22):10402-10422. doi: 10.1021/acs.jmedchem.9b01499. Epub 2019 Nov 6.

Abstract

Phosphoinositide-3-kinase δ (PI3Kδ) is a critical regulator of cell growth and transformation and has been explored as a therapeutic target for a range of diseases. Through the exploration of the thienopyrimidine scaffold, we have identified a ligand-efficient methylation that leads to remarkable selectivity for PI3Kδ over the closely related isoforms. Interrogation through the Free-Wilson analysis highlights the innate selectivity the thienopyrimidine scaffold has for PI3Kδ and provides a predictive model for the activity against the PI3K isoforms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Humans
  • Isoenzymes / chemistry
  • Isoenzymes / metabolism
  • Methylation
  • Nitrogen / chemistry
  • Phosphatidylinositol 3-Kinases / chemistry
  • Phosphatidylinositol 3-Kinases / metabolism*
  • Phosphoinositide-3 Kinase Inhibitors / chemical synthesis
  • Phosphoinositide-3 Kinase Inhibitors / chemistry*
  • Phosphoinositide-3 Kinase Inhibitors / pharmacology*
  • Pyrimidines / chemistry
  • Serum Albumin, Human / metabolism
  • Structure-Activity Relationship*

Substances

  • Amines
  • Isoenzymes
  • Phosphoinositide-3 Kinase Inhibitors
  • Pyrimidines
  • 2-aminopyrimidine
  • Nitrogen
  • Serum Albumin, Human