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

154-17-6 , 2-Deoxy-D-Glucose ,
CAS:154-17-6
C6H12O5 / 164.16
MFCD00151328

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.

CAS Number

154-17-6

Product Name

Deoxyglucose

IUPAC Name

(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal

Molecular Formula

C6H12O5

Molecular Weight

164.16 g/mol

InChI

InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1

InChI Key

VRYALKFFQXWPIH-PBXRRBTRSA-N

SMILES

C(C=O)C(C(C(CO)O)O)O

Solubility

Soluble in DMSO

Synonyms

2 Deoxy D glucose, 2 Deoxyglucose, 2 Desoxy D glucose, 2-Deoxy-D-glucose, 2-Deoxyglucose, 2-Desoxy-D-glucose, Deoxyglucose

Canonical SMILES

C(C=O)C(C(C(CO)O)O)O

Isomeric SMILES

C(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: 164.16

In Stock,

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COA:

Name: 2-Deoxy-D-Glucose                  CAS154-17-6     M.F.: C6H12O5

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

Items

Standards

Results

Appearance

White crystalline powder

Positive

Solubility

Readily soluble in water and

insoluble in ether

Positive

NMR and MS

Should comply

Complies

Identification

IR and TLC

Positive

M.P.

145 ~147

145 ~147

[a]D [c=1 inH2O].

+44o ~ +47o

+45.2o

Loss Weight On Dryness

Max. 1%

Complies

Heavy Metal

Max. 20ppm

Complies

TLC (15%H2SO4-C2H5OH)

One spot

Complies

Assay (HPLC)

Min. 98%

98.6%

References:

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


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