Structural basis for the potent and selective binding of LDN-212854 to the BMP receptor kinase ALK2

Bone. 2018 Apr:109:251-258. doi: 10.1016/j.bone.2017.09.004. Epub 2017 Sep 12.

Abstract

Individuals with the rare developmental disorder fibrodysplasia ossificans progressiva (FOP) experience disabling heterotopic ossification caused by a gain of function mutation in the intracellular region of the BMP type I receptor kinase ALK2, encoded by the gene ACVR1. Small molecule BMP type I receptor inhibitors that block this ossification in FOP mouse models have been derived from the pyrazolo[1,5-a]pyrimidine scaffold of dorsomorphin. While the first derivative LDN-193189 exhibited pan inhibition of BMP receptors, the more recent compound LDN-212854 has shown increased selectivity for ALK2. Here we solved the crystal structure of ALK2 in complex with LDN-212854 to define how its binding interactions compare to previously reported BMP and TGFβ receptor inhibitors. LDN-212854 bound to the kinase hinge region as a typical type I ATP-competitive inhibitor with a single hydrogen bond to ALK2 His286. Specificity arising from the 5-quinoline moiety was associated with a distinct pattern of water-mediated hydrogen bonds involving Lys235 and Glu248 in the inactive conformation favoured by ALK2. The structure of this complex provides a template for the design of future ALK2 inhibitors under development for the treatment of FOP and other related conditions of heterotopic ossification.

Keywords: BMP; Crystal structure; Drug; Fibrodysplasia ossificans progressiva; Heterotopic ossification; Kinase inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Activin Receptors, Type I / metabolism*
  • Animals
  • Bone Morphogenetic Protein Receptors / antagonists & inhibitors
  • Bone Morphogenetic Protein Receptors / metabolism
  • Myositis Ossificans / metabolism
  • Protein Binding
  • Pyrazoles / chemistry
  • Pyrazoles / metabolism*
  • Pyrimidines / chemistry
  • Pyrimidines / metabolism*
  • Quinolines / chemistry
  • Quinolines / metabolism*
  • Sf9 Cells

Substances

  • LDN-212854
  • Pyrazoles
  • Pyrimidines
  • Quinolines
  • Activin Receptors, Type I
  • Bone Morphogenetic Protein Receptors