Identification of 2-amino-5-aryl-pyrazines as inhibitors of human lactate dehydrogenase

Bioorg Med Chem Lett. 2013 Oct 15;23(20):5533-9. doi: 10.1016/j.bmcl.2013.08.060. Epub 2013 Aug 22.

Abstract

A 2-amino-5-aryl-pyrazine was identified as an inhibitor of human lactate dehydrogenase A (LDHA) via a biochemical screening campaign. Biochemical and biophysical experiments demonstrated that the compound specifically interacted with human LDHA. Structural variation of the screening hit resulted in improvements in LDHA biochemical inhibition and pharmacokinetic properties. A crystal structure of an improved compound bound to human LDHA was also obtained and it explained many of the observed structure-activity relationships.

Keywords: Lactate dehydrogenase; Pyrazine; Tumor metabolism; X-ray crystal structure.

MeSH terms

  • Animals
  • Binding Sites
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Half-Life
  • Humans
  • L-Lactate Dehydrogenase / antagonists & inhibitors*
  • L-Lactate Dehydrogenase / metabolism
  • Male
  • Microsomes, Liver / metabolism
  • Protein Structure, Tertiary
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry*
  • Pyrazines / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Pyrazines
  • L-Lactate Dehydrogenase