2-脱氧-D-葡萄糖, 2-Deoxy-D-Glucose

2-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-glucose

CAS Registry Number: 154-17-6

CAS Name: 2-Deoxy-D-arabino-hexose

Additional Names: D-arabino-2-desoxyhexose; 2-deoxyglucose; 2-DG

Manufacturers' Codes: Ba-2758

Molecular Formula: C6H12O5

Molecular Weight: 164.16

Percent 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-Form

Properties: 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.

COA:

Name: 2-Deoxy-D-Glucose                  CAS: 154-17-6     M.F.: C₆H₁₂O₅

M.W.: 164.16              Batch No: 20120203           Quantity: 26.22kg

References:

1. Thakkar NS, Potten CS, Cancer Res. 1993, 53, 2057