Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy

Carbohydr Res. 2005 Feb 7;340(2):181-9. doi: 10.1016/j.carres.2004.11.024.

Abstract

Tumor targeting of glycoconjugated antineoplastic agents is a strategy currently under investigation for cancer chemotherapy. We have synthesized the glucosides and galactosides of the clinically established drug hydroxyurea and of mesylglycol, the reactive moiety of the anticancer drug busulfan. Glycosides of hydroxyurea were obtained by carbamoylation of hydroxylamine glycosides. The glycosides of mesylglycol were synthesized by mesylation of protected glycol glycosides. All compounds were characterized by detailed 1H and 13C NMR analysis.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Drug Delivery Systems / methods*
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Hydroxyurea / analogs & derivatives*
  • Hydroxyurea / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mesylates / chemistry*
  • Molecular Structure
  • Neoplasms / drug therapy*

Substances

  • Antineoplastic Agents
  • Glycoconjugates
  • Mesylates
  • Hydroxyurea