2-Deoxy-D-glucose Chemical Properties

Melting point:

146-147 °C(lit.)

alpha 

45.5 º (c=2, H2O)

Boiling point:

211.61°C (rough estimate)

Density 

1.1738 (rough estimate)

refractive index 

46.5 ° (C=1, H2O)

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL, clear, colorless to faintly yellow

form 

crystalline

pka

pK1:12.52 (25°C)

color 

white

optical activity

+38.5 → +45.9

Water Solubility 

Soluble in water.

Merck 

14,2904

BRN 

1723331

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day.

InChIKey

PMMURAAUARKVCB-CEZCPVKQSA-N

LogP

-1.460 (est)

CAS DataBase Reference

154-17-6(CAS DataBase Reference)

EPA Substance Registry System

D-arabino-Hexose, 2-deoxy- (154-17-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-37/39-36-26

WGK Germany 

3

RTECS 

MQ3325000

F 

3-10

TSCA 

Yes

HS Code 

29400090

Hazardous Substances Data

154-17-6(Hazardous Substances Data)

MSDS

• Language:English Provider:D-Arabino-2-deoxyhexose
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Deoxy-D-glucose Usage And Synthesis

Description

2-Deoxy-D-glucose (154-17-6) is a synthetic glucose analog with extensive biological effects. It is commonly thought of as an inhibitor of glycolysis, but its metabolic effects are wide-ranging. 2-Deoxy-D-glucose competitively inhibits glucose uptake via its metabolite 2-Deoxy-D-glucose-6-phosphate, which inhibits hexokinase and phosphoglucose-isomerase leading to decreased ATP production, cell cycle blockage, decreased cell growth and ultimately cell death.1,2

Chemical Properties

white to light yellow crystal powde

Uses

2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical]

Uses

2-Deoxy-D-glucose is act as a culture media part in molecular genetics and as a targeted optical imaging agent for fluorescent in vivo imaging. It finds an application in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). It is utilized in the development of anti-cancer approaches like oxidative stress, radio and chemosensitization.

Uses

2-Deoxy-D-glucose (2-DG) is used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). 2-Deoxy-D-glucose is used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress.

Biochem/physiol Actions

2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which can not be further metabolized by phosphoglucose isomerase. This leads to the accumulation of 2-DG-P in the cell and the depletion in cellular ATP. In vitro, 2-Deoxyglucose has been shown to induce autophagy, increase ROS production, and activate AMPK.

Safety Profile

Poison by subcutaneous route. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

storage

Store at +4°C

Purification Methods

Crystallise 2-deoxy--D-glucose from MeOH/Me2CO, Me2CO or butanone to give a mixture of 
and 
anomers, m 142-144o, [] 18 +38o (35minutes) to +46o (c 0.5, H2O). Recrystallisation from isoPrOH gives mainly the -anomer m 134-136o , [ ] D +156o to +103o (c 0.9, pyridine). 1H NMR studies showed that at 44o in D2O the solution contained 36% of -pyranose and 64% of -pyranose sugar, but furanose structures were undetectable. [Snowden & Fischer J Am Chem Soc 69 1048 1947, derivatives: Bollinger & Schmidt Helv Chim Acta 34 989 1951; see Angyal & Pickles Aust J Chem 25 1711 1972 for ratio of isomers in solution, Beilstein 1 IV 4282.]

References

1) Ralser et al., (2008), A catabolic blockade does not sufficiently explain how 2-deoxy-D-glucose inhibits cell growth; Proc. Natl. Acad. Sci. USA 105 17807 2) Giammarioli et al. (2012), Differential effects of the glycolysis inhibitor 2-deoxy-D-glucose on the activity of pro-apoptotic agents in metastatic melanoma cells; Int. J. Cancer, 131 e337

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