Syntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential

HALAY E., Ay E., ŞALVA E., Ay K., KARAYILDIRIM T.

Nucleosides, Nucleotides and Nucleic Acids, vol.36, no.9, pp.598-619, 2017 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 36 Issue: 9
  • Publication Date: 2017
  • Doi Number: 10.1080/15257770.2017.1346258
  • Journal Name: Nucleosides, Nucleotides and Nucleic Acids
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.598-619
  • Keywords: 1,2,3-Triazoles, anticancer activity, azido sugars, Click chemistry, nucleobases, nucleosides
  • Uşak University Affiliated: Yes

Abstract

With the aim to create a library of compounds with potential bioactivities by combining special characteristics of two important groups such as nucleobases and carbohydrates, twenty 1,4-disubstituted-triazole nucleosides were synthesized in good yields (80-94%) using the copper catalyzed ‘Click’ reaction between azido-modified pento- or hexopyranoses and alkyne-bearing pyrimidine or purine nucleobases. Structural elucidation was made with the assistance of spectroscopic techniques such as FTIR, 1D-, 2D-NMR, and ESI-TOFMS. All the synthesized triazole nucleosides were evaluated for their cytotoxic activity against three human cancer cell lines (MDA-MB-231, Hep3B, PC-3) by using the MTT assay. Particularly, compounds 3a and 1b were identified as potential hits against Hep3B cell.