Discovery and binding mode of small molecule inhibitors of the apo form of human TDO2

Sci Rep. 2024 Nov 14;14(1):27937. doi: 10.1038/s41598-024-78981-4.

Abstract

Tryptophan-2,3-dioxygenase (TDO2) and indoleamine-2,3-dioxygenase (IDO1) are structurally distinct heme enzymes that catalyze the conversion of L-tryptophan to N-formyl-kynurenine, and play important roles in metabolism, inflammation, and tumor immune surveillance. The enzymes can adopt an inactive, heme-free (apo) state or an active, heme-containing (holo) state, with the balance between them varying dynamically according to biological conditions. Inhibitors of holo-TDO2 are known but, despite several advantages of the heme-free state as a drug target, no inhibitors of apo-TDO2 have been reported. We describe the discovery of the first apo-TDO2 binding inhibitors, to our knowledge, and their inhibition of cellular TDO2 activity at low nanomolar concentrations. The crystal structure of a potent, small molecule inhibitor bound to apo-TDO2 reveals its detailed binding interactions within the large, hydrophobic heme binding pocket of the active site.

MeSH terms

  • Binding Sites
  • Catalytic Domain
  • Crystallography, X-Ray
  • Drug Discovery
  • Enzyme Inhibitors* / chemistry
  • Enzyme Inhibitors* / pharmacology
  • Heme / chemistry
  • Heme / metabolism
  • Humans
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / antagonists & inhibitors
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / chemistry
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / metabolism
  • Models, Molecular
  • Protein Binding*
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology
  • Tryptophan Oxygenase* / antagonists & inhibitors
  • Tryptophan Oxygenase* / chemistry
  • Tryptophan Oxygenase* / metabolism

Substances

  • Tryptophan Oxygenase
  • Enzyme Inhibitors
  • Heme
  • Small Molecule Libraries
  • Indoleamine-Pyrrole 2,3,-Dioxygenase