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

Bioorg Med Chem Lett. 2017 May 1;27(9):1938-1942. doi: 10.1016/j.bmcl.2017.03.029. Epub 2017 Mar 16.

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.

Keywords: Bioconjugate; CuAAC; Monosaccharide; Oxime; d-Secoestrone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Azides / chemistry
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cycloaddition Reaction
  • Estrone / analogs & derivatives*
  • Estrone / chemical synthesis
  • Estrone / chemistry
  • Estrone / pharmacology
  • Glucose / chemical synthesis
  • Glucose / chemistry*
  • Glucose / pharmacology*
  • Glycoconjugates / chemical synthesis
  • Glycoconjugates / chemistry*
  • Glycoconjugates / pharmacology*
  • HeLa Cells
  • Humans
  • MCF-7 Cells
  • Monosaccharides / chemical synthesis
  • Monosaccharides / chemistry
  • Monosaccharides / pharmacology
  • Neoplasms / drug therapy
  • Oximes / chemical synthesis
  • Oximes / chemistry
  • Oximes / pharmacology

Substances

  • Alkynes
  • Antineoplastic Agents
  • Azides
  • D-secoestrone
  • Glycoconjugates
  • Monosaccharides
  • Oximes
  • Estrone
  • Glucose