Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors

Luca Gabrielli, Ilaria Calloni, Giulia Donvito, Barbara Costa, Noemi Arrighetti, Paola Perego, Diego Colombo, Fiamma Ronchetti, Francesco Nicotra, Laura Cipolla

Research output: Contribution to journalArticle

Abstract

New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.

Original languageEnglish
Pages (from-to)5962-5967
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number27
DOIs
Publication statusPublished - 2014

Keywords

  • Antitumor agents
  • Carbohydrates
  • Enzymes
  • Inhibitors
  • Medicinal chemistry
  • Phospholipids

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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