Structural basis of inhibitor specificity of the human protooncogene proviral insertion site in moloney murine leukemia virus (PIM-1) kinase

J Med Chem. 2005 Dec 1;48(24):7604-14. doi: 10.1021/jm0504858.

Abstract

The kinase PIM-1 plays a pivotal role in cytokine signaling and is implicated in the development of a number of tumors. The three-dimensional structure of PIM-1 is characterized by an unique hinge region which lacks a second hydrogen bond donor and makes it particularly important to determine how inhibitors bind to this kinase. We determined the structures of PIM-1 in complex with bisindolylmaleimide (BIM-1) and established the structure-activity relationship (SAR) for this inhibitor class. In addition, we screened a kinase targeted library and identified a number of high affinity inhibitors of PIM-1 such as imidazo[1,2-b]pyridazines, pyrazolo[1,5-a]pyrimidines, and members of the flavonoid family. In this paper we present an initial SAR of the identified scaffolds determined on the basis of a thermostability shift assay, calorimetric binding data, and biochemical assays which may find applications for the treatment of PIM-1 dependent cancer types.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Crystallization
  • Crystallography, X-Ray
  • Flavonoids / chemical synthesis
  • Flavonoids / chemistry
  • Humans
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Maleimides / chemical synthesis*
  • Maleimides / chemistry
  • Models, Molecular
  • Molecular Structure
  • Moloney murine leukemia virus / enzymology
  • Moloney murine leukemia virus / physiology*
  • Phosphorylation
  • Protein Binding
  • Proto-Oncogene Proteins c-pim-1 / antagonists & inhibitors*
  • Proto-Oncogene Proteins c-pim-1 / chemistry*
  • Proviruses / physiology*
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyridazines / chemical synthesis
  • Pyridazines / chemistry
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Flavonoids
  • Imidazoles
  • Indoles
  • Maleimides
  • Pyrazoles
  • Pyridazines
  • Pyrimidines
  • Proto-Oncogene Proteins c-pim-1
  • bisindolylmaleimide