1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose - CAS 69515-91-9
Category: Carbohydrates
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1.Inhibitory action of the anomers of 2-deoxy-D-glucose tetraacetate on the metabolism of D-glucose in rat pancreatic islets.
Bakkali-Nadi A1, Kadiata MM, Malaisse WJ. Int J Pancreatol. 2000 Feb;27(1):59-63.
BACKGROUND: The tetra-acetate ester of 2-deoxy-D-glucose was recently found to either inhibit or augment insulin secretion, depending on the concentration of the ester. Both the positive and negative insulinotropic actions of the ester display anomeric specificity.
2.Potentiation by 2-deoxy-D-glucose tetraacetate of the cytostatic action of alpha-difluoromethylornithine in tumoral insulin-producing cells.
Olivares E1, Malaisse WJ. Oncol Rep. 1998 Nov-Dec;5(6):1395-7.
Insulin-producing tumoral cells of the RINm5F line were cultured for 8 to 96 h in the absence or presence of 2-deoxy-D-glucose tetraacetate (0.01 mM to 1.0 mM) and/or á-difluoromethylornithine (also 0.01 mM to 1.0 mM). The ester of the glucose analog potentiated the inhibitory action of the ornithine decarboxylase inhibitor. For instance, when both agents were tested in combination at a concentration of 0.01 mM each, the generation of formazan from 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium was decreased, within 2 days, to 23.2+/- 6.1% of its paired control value, whilst neither the ester of 2-deoxy-D-glucose nor the ornithine analog exerted any significant effect upon cell growth when used separately at the same low concentration and over the same length of culture. These findings suggest that 2-deoxy-D-glucose tetraacetate could be used to sensitize tumoral cells to the cytostatic action of established chemotherapeutic agents in the treatment of neoplastic diseases.
3.Dual effect of 2-deoxy-D-glucose tetraacetate upon glucose-induced insulin release.
Malaisse WJ1, Flores LE, Kadiata MM. Biochem Mol Biol Int. 1998 Jul;45(3):429-34.
The effect of 2-deoxy-D-glucose tetraacetate upon glucose-stimulated insulin release was explored in pancreatic islets from either normal or hereditary diabetic rats. At a high concentration (10 mM), it decreased the secretory response to D-glucose, such an inhibitory effect being more marked in the case of the alpha- than beta-anomer of the ester. At lower concentrations (0.19 to 1.7 mM), however, 2-deoxy-D-glucose tetraacetate augmented insulin secretion evoked by 8.3 mM D-glucose, with again a preference for the alpha-anomer of the ester. In relative terms, such an enhancing action was more marked in Goto-Kakizaki than normal rats. Hence, it is proposed that selected esters of non-nutrient carbohydrates could be used as insulinotropic tools in the treatment of non-insulin-dependent diabetes mellitus.
4.Cytotoxic action of 2-deoxy-D-glucose tetraacetate upon human lymphocytes, fibroblasts and melanoma cells.
Reinhold U1, Malaisse WJ. Int J Mol Med. 1998 Feb;1(2):427-30.
The tetraacetate ester of 2-deoxy-D-glucose was found to cause a concentration-related (10 microM to 1.0 mM) inhibition of activated T cell proliferation and decrease in viability of both unstimulated and anti-CD3 monoclonal antibody-stimulated peripheral blood mononuclear cells. Comparable findings were made in primary fibroblast cultures initiated from human skin explants. Likewise, 2-deoxy-D-glucose tetraacetate exerted a time-related (4-72 h) and concentration-related (0.1-1.0 mM) cytotoxic action upon human melanoma cells of the Colo 38 line. In this cell line, multiparameter flow cytometric analysis of cells stained with annexin V and propidium iodide revealed a necrotic, rather than apoptotic, form of cell death after exposure to 2-deoxy-D-glucose tetraacetate.
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CAS 69515-91-9 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose

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