Mycobacterium tuberculosis dihydrofolate reductase is a target for isoniazid

Nat Struct Mol Biol. 2006 May;13(5):408-13. doi: 10.1038/nsmb1089. Epub 2006 Apr 30.

Abstract

Isoniazid is a key drug used in the treatment of tuberculosis. Isoniazid is a pro-drug, which, after activation by the katG-encoded catalase peroxidase, reacts nonenzymatically with NAD(+) and NADP(+) to generate several isonicotinoyl adducts of these pyridine nucleotides. One of these, the acyclic 4S isomer of isoniazid-NAD, targets the inhA-encoded enoyl-ACP reductase, an enzyme essential for mycolic acid biosynthesis in Mycobacterium tuberculosis. Here we show that the acyclic 4R isomer of isoniazid-NADP inhibits the M. tuberculosis dihydrofolate reductase (DHFR), an enzyme essential for nucleic acid synthesis. This biologically relevant form of the isoniazid adduct is a subnanomolar bisubstrate inhibitor of M. tuberculosis DHFR. Expression of M. tuberculosis DHFR in Mycobacterium smegmatis mc(2)155 protects cells against growth inhibition by isoniazid by sequestering the drug. Thus, M. tuberculosis DHFR is the first new target for isoniazid identified in the last decade.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cell Proliferation
  • Cloning, Molecular
  • Crystallography, X-Ray
  • Folic Acid Antagonists / chemistry
  • Folic Acid Antagonists / metabolism
  • Folic Acid Antagonists / pharmacology*
  • Gene Expression
  • Isoniazid / chemistry
  • Isoniazid / metabolism
  • Isoniazid / pharmacology*
  • Models, Molecular
  • Mycobacterium tuberculosis / cytology
  • Mycobacterium tuberculosis / drug effects*
  • Mycobacterium tuberculosis / enzymology*
  • Mycobacterium tuberculosis / genetics
  • NADP / chemistry
  • NADP / metabolism
  • Prodrugs / chemistry
  • Prodrugs / metabolism
  • Prodrugs / pharmacology
  • Protein Binding
  • Protein Structure, Tertiary
  • Tetrahydrofolate Dehydrogenase / genetics
  • Tetrahydrofolate Dehydrogenase / isolation & purification
  • Tetrahydrofolate Dehydrogenase / metabolism*

Substances

  • Folic Acid Antagonists
  • Prodrugs
  • NADP
  • Tetrahydrofolate Dehydrogenase
  • Isoniazid

Associated data

  • PDB/1DG8
  • PDB/2CIG