Eicar (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide). A novel potent inhibitor of inosinate dehydrogenase activity and guanylate biosynthesis

J Biol Chem. 1993 Nov 25;268(33):24591-8.

Abstract

EICAR (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide) is a cytostatic agent that inhibits murine leukemia L1210 and human lymphocyte CEM cells at a 50% inhibitory concentration of 0.80-1.4 microM, respectively. EICAR causes a rapid and marked inhibition of inosinate (IMP) dehydrogenase (EC 1.1.1.205) activity in intact L1210 and CEM cells reflected by a concentration-dependent accumulation of IMP and depletion of GTP and dGTP levels. EICAR 5'-monophosphate is a potent inhibitor of purified L1210 cell IMP dehydrogenase (Ki/Km 0.06). Inhibition of IMP dehydrogenase by EICAR 5'-monophosphate is competitive with respect to IMP. L1210 cells that were selected for resistance to the cytostatic action of EICAR proved to be adenosine kinase-deficient. Also, studies with other mutant L1210 and CEM cell lines revealed that adenosine kinase, as well as an alternative pathway, may be responsible for the conversion of EICAR to its 5'-monophosphate. Purified 2'-deoxycytidine kinase, 2'-deoxyguanosine kinase, cytosolic 5'-nucleotidase, and nicotinamide dinucleotide (NAD) pyrophosphorylase do not seem to be markedly involved in the metabolism of EICAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / pharmacology
  • Animals
  • Antineoplastic Agents / pharmacology*
  • Cell Division / drug effects
  • Deoxyguanine Nucleotides / antagonists & inhibitors
  • Deoxyguanine Nucleotides / biosynthesis*
  • Guanine / pharmacology
  • Guanosine / pharmacology
  • Guanosine Triphosphate / antagonists & inhibitors
  • Guanosine Triphosphate / biosynthesis*
  • Humans
  • IMP Dehydrogenase / antagonists & inhibitors*
  • Leukemia L1210 / enzymology
  • Leukemia L1210 / metabolism
  • Lymphocytes / metabolism
  • Mice
  • Mycophenolic Acid / pharmacology
  • Purine Nucleotides / metabolism
  • Ribavirin / analogs & derivatives
  • Ribavirin / pharmacology
  • Ribonucleosides / pharmacology*
  • Ribonucleotides / metabolism
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Deoxyguanine Nucleotides
  • Purine Nucleotides
  • Ribonucleosides
  • Ribonucleotides
  • 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide
  • Guanosine
  • Ribavirin
  • Guanine
  • Guanosine Triphosphate
  • deoxyguanosine triphosphate
  • IMP Dehydrogenase
  • Mycophenolic Acid
  • Adenosine
  • tiazofurin