Synthesis and in vitro investigation of potential antiproliferative monosaccharide–D-secoestrone bioconjugates

Brigitta Bodnár, E. Mernyák, Johanna Szabó, J. Wölfling, G. Schneider, I. Zupkó, Zoltán Kupihár, L. Kovács

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3 Citations (Scopus)

Abstract

The syntheses of monosaccharide–D-secoestrone conjugates are reported. They were prepared from 3-(prop-2-inyloxy)-D-secoestrone alcohol or oxime and monosaccharide azides via Cu(I)-catalyzed azide–alkyne cycloaddition reactions (CuAAC). The antiproliferative activities of the conjugates were investigated in vitro against a panel of human adherent cancer cell lines (HeLa, A2780 and MCF-7) by means of MTT assays. The protected D-glucose-containing D-secoestrone oxime bioconjugate (24b) proved to be the most effective with an IC50 value in the low micromolar range against A2780 cell line.

Original languageEnglish
Pages (from-to)1938-1942
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume27
Issue number9
DOIs
Publication statusPublished - May 1 2017

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Keywords

  • Bioconjugate
  • CuAAC
  • D-Secoestrone
  • Monosaccharide
  • Oxime

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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