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, LUCAPrimo
;CALLONI, ILARIASecondo
;DONVITO, GIULIA;COSTA, BARBARA SIMONA;NICOTRA, FRANCESCOPenultimo
;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, WeinheimI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.