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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Gabrielli, L., Calloni, I., Donvito, G., Costa, B., Arrighetti, N., Perego, P., et al. (2014). Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(27), 5962-5967 [10.1002/ejoc.201402664].

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

GABRIELLI, LUCA
Primo
;
CALLONI, ILARIA
Secondo
;
DONVITO, GIULIA;COSTA, BARBARA SIMONA;NICOTRA, FRANCESCO
Penultimo
;
CIPOLLA, LAURA FRANCESCA
2014

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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Articolo in rivista - Articolo scientifico
Antitumor agents; Carbohydrates; Enzymes; Inhibitors; Medicinal chemistry; Phospholipids; Physical and Theoretical Chemistry; Organic Chemistry
English
5962
5967
6
Gabrielli, L., Calloni, I., Donvito, G., Costa, B., Arrighetti, N., Perego, P., et al. (2014). Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(27), 5962-5967 [10.1002/ejoc.201402664].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/98551
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