Zebularine: a unique molecule for an epigenetically based strategy in cancer chemotherapy. The magic of its chemistry and biology

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):305-18. doi: 10.1081/ncn-200059765.

Abstract

1-(beta-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (zebularine) is structurally 4-deamino cytidine. The increased electrophilic character of this simple aglycon endows the molecule with unique chemical and biological properties, making zebularine a versatile starting material for the synthesis of complex nucleosides and an effective inhibitor of cytidine deaminase and DNA cytosine methyltransferase. Zebularine is a stable, antitumor agent that preferentially targets cancer cells and shows activity both in vitro and in experimental animals, even after oral administration.

Publication types

  • Review

MeSH terms

  • Administration, Oral
  • Animals
  • Antineoplastic Agents / pharmacology*
  • Cytidine / analogs & derivatives*
  • Cytidine / pharmacology
  • Cytidine Deaminase / antagonists & inhibitors
  • DNA / chemistry
  • DNA / drug effects
  • Epigenesis, Genetic
  • Humans
  • Models, Chemical
  • Neoplasms / drug therapy*
  • Neoplasms / genetics

Substances

  • Antineoplastic Agents
  • Cytidine
  • pyrimidin-2-one beta-ribofuranoside
  • DNA
  • Cytidine Deaminase