2-Deoxy-D-Glucose , CAS:154-17-6

2-Deoxy-D-Glucose2-deoxy-D-Glucose is a glucose antimetabolite and an inhibitor of glycolysis. It inhibits hexokinase, the enzyme that converts glucose to glucose-6-phosphate, as well as phosphoglucose isomerase, the enzyme that converts glucose-6-phosphate to fructose-6-phosphate. 2-deoxy-D-glucose (16 mM) induces apoptosis in SK-BR-3 cells, as well as inhibits the growth of 143B osteosarcoma cells cultured under hypoxic conditions when used at a concentration of 2 mg/ml. In vivo, 2-deoxy-D-glucose (500 mg/kg) reduces tumor growth in 143B osteosarcoma and MV522 non-small cell lung cancer mouse xenograft models when used alone or in combination with doxorubicin or paclitaxel.2-Deoxyglucose, also known as 2-deoxy-D-mannose or D-2DGLC, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 2-Deoxyglucose has been primarily detected in urine. Within the cell, 2-deoxyglucose is primarily located in the cytoplasm. 2-Deoxyglucose exists in all eukaryotes, ranging from yeast to humans.2-deoxyglucose is predominantly used as a diagnostic agent in its radiolabelled form (fluorine-18 is used as the radiolabel). By using positron emission tomography (PET), radiolabelled 2-deoxyglucose can determine glucose metabolism, which is altered in diseases such as cardiovascular disease, tumors, and Alzheimer’s disease. Therapeutically, 2-deoxyglucose is an investigational drug that is being studied as an anticancer and antiviral agent. Concerning the former, 2- deoxyglucose was used as an adjunct to chemotherapy and radiotherapy in the treatment of solid tumors (lung, breast, pancreas, head, neck, and gastric tumors). The exact mechanisms of action of 2-deoxyglucose is still being investigated, but it is known that in hypoxic cancer cells, 2-deoxyglucose is a glycolysis inhibitor that prevents ATP production and, ultimately, cell survival. With respect to antiviral therapy, 2-deoxyglucose was shown to be effective against herpes simplex virus by affecting the virus’ ability to penetrate cells. As an experimental drug, 2-deoxyglucose was demonstrated to work as an anticonvulsant in temporal lobe epilepsy. In this condition, 2-deoxyglucose represses the expression of certain proteins that are at high levels after a seizure. Although there are several possible therapeutic indications for 2-deoxyglucose, presently there is no approved indication for 2-deoxyglucose as a therapeutic agent.2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.Title:?2-Deoxy-D-glucoseCAS Registry Number:?154-17-6CAS Name:?2-Deoxy-D-arabino-hexoseAdditional Names:?D-arabino-2-desoxyhexose; 2-deoxyglucose; 2-DGManufacturers’ Codes:?Ba-2758Molecular Formula:?C6H12O5Molecular Weight:?164.16Percent Composition:?C 43.90%, H 7.37%, O 48.73%Literature References:?Antimetabolite of glucose,?q.v.,?with antiviral activity. Synthesis: M. Bergmann?et al.,?Ber.?55,?158 (1922);?56,?1052 (1923); J. C. Sowden, H. O. L. Fischer,?J. Am. Chem. Soc.?69,?1048 (1947); H. R. Bolliger,?Helv. Chim. Acta?34,?989 (1954); H. R. Bolliger, M. D. Schmid,?ibid.?1597, 1671; H. R. Bolliger, “2-Deoxy-D-arabino-hexose (2-Deoxy-D-glucose)” in?Methods in Carbohydrate Chemistry?vol. I,?R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 186-189. Inhibition of influenza virus multiplication: E. D. Kilbourne,?Nature?183,?271 (1959). Effects on herpes simplex virus: R. J. Courtney?et al.,?Virology?52,?447 (1973). Mechanism of action studies: M. R. Steiner?et al.,?Biochem. Biophys. Res. Commun.?61,?745 (1974); E. K. Ray?et al.,?Virology?58,?118 (1978). Use in human genital herpes infections: H. A. Blough, R. L. Giuntoli,?J. Am. Med. Assoc.?241,?2798 (1979); L. Corey, K. K. Holmes,?ibid.?243,?29 (1980). Effect vs respiratory syncytial viral infections in calves: S. B. Mohanty?et al.,?Am. J. Vet. Res.?42,?336 (1981).Properties:?Cryst from acetone or butanone, mp 142-144?. [a]D17.5?+38.3? (35 min)??+45.9? (c = 0.52 in water); +22.8? (24 hrs)???+80.8? (c = 0.57 in pyridine).Melting point:?mp 142-144?Optical Rotation:?[a]D17.5?+38.3? (35 min)??+45.9? (c = 0.52 in water); +22.8? (24 hrs)???+80.8? (c = 0.57 in pyridine)?Derivative Type:?a-FormProperties:?Cryst from isopropanol, mp 134-136?. [a]D26?+156????+103? (c = 0.9 in pyridine).Melting point:?mp 134-136?Optical Rotation:?[a]D26?+156????+103? (c = 0.9 in pyridine)?Use:?Exptlly as an antiviral agent.CAS Number154-17-6Product NameDeoxyglucoseIUPAC Name(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanalMolecular FormulaC6H12O5Molecular Weight164.16 g/molInChIInChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1InChI KeyVRYALKFFQXWPIH-PBXRRBTRSA-NSMILESC(C=O)C(C(C(CO)O)O)OSolubilitySoluble in DMSOSynonyms2 Deoxy D glucose, 2 Deoxyglucose, 2 Desoxy D glucose, 2-Deoxy-D-glucose, 2-Deoxyglucose, 2-Desoxy-D-glucose, DeoxyglucoseCanonical SMILESC(C=O)C(C(C(CO)O)O)OIsomeric SMILESC(C=O)[C@@H]([C@H]([C@H](CO)O)O)O
CAS No: 154-17-6 MDL No: MFCD00151328 Chemical Formula: C6H12O5 Molecular Weight: 164.16In Stock, COA:Name:?2-Deoxy-D-Glucose? ? ? ? ? ? ? ? ??CAS:?154-17-6? ? ?M.F.:?C6H12O5M.W.:?164.16? ? ? ? ? ? ??Batch No:?20120203? ? ? ? ? ?Quantity: 26.22kgItemsStandardsResultsAppearanceWhite crystalline powderPositiveSolubilityReadily soluble in water andinsoluble in etherPositiveNMR and MSShould complyCompliesIdentificationIR and TLCPositiveM.P.145??~147?145??~147?[a]D?[c=1 inH2O].+44o?~ +47o+45.2oLoss Weight On DrynessMax. 1%CompliesHeavy MetalMax. 20ppmCompliesTLC?(15%H2SO4-C2H5OH)One spotCompliesAssay (HPLC)Min. 98%98.6%References:
1. Thakkar NS, Potten CS, Cancer Res. 1993, 53, 2057