Nucleoside dimers analogues with a 1,2,3-triazole linkage: conjugation of floxuridine and thymidine provides novel tools for cancer treatment. Part II

Nucleosides Nucleotides Nucleic Acids. 2019;38(11):807-835. doi: 10.1080/15257770.2019.1610891. Epub 2019 Jun 8.

Abstract

The fluorinated nucleoside dimers with a 1,2,3-triazole linkage are novel compounds within the field of bioorganic chemistry. We report on the synthesis and properties of two groups of nucleoside dimers analogs possessing a different arrangement of the 1,4-disubstituted 1,2,3-triazole linkage. Based on analysis of the 3JHH, 3JH1'C2, and 3JH1'C6 we estimated conformational preferences of sugar part and orientation around glycosidic bond. These compounds show moderate anticancer activity, with cytostatic studies in three different cancer cell lines.

Keywords: 1,3-dipolar cycloaddition; Floxuridine; cancer therapy; nucleoside dimers derivatives.

Publication types

  • Video-Audio Media

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Click Chemistry
  • Cycloaddition Reaction
  • Dimerization
  • Floxuridine / analogs & derivatives
  • Floxuridine / pharmacology
  • Humans
  • Molecular Conformation
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Thymidine / analogs & derivatives
  • Thymidine / pharmacology
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Antineoplastic Agents
  • Nucleosides
  • Triazoles
  • Floxuridine
  • Thymidine