154-17-6 Usage
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
Different sources of media describe the Uses of 154-17-6 differently. You can refer to the following data:
1. 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]
2. 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.
3. 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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 154-17-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 4 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 154-17:
(5*1)+(4*5)+(3*4)+(2*1)+(1*7)=46
46 % 10 = 6
So 154-17-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5-,6+/m1/s1
154-17-6Relevant articles and documents
SYNTHESIS OF 2-DEOXY-D-arabino-HEXITOL AND ITS OXIDATION TO 5-DEOXY-D-threo-HEXULOSE ("5-DEOXY-D-FRUCTOSE") USING IMMOBILIZED CELLS OF Gluconobacter oxydans
Tiwari, Kamal N.,Dhawale, Motiram R.,Szarek, Walter A.,Hay, George W.,Kropinski, Andrew M. B.
, p. 19 - 24 (1986)
2-Deoxy-D-arabino-hexitol (6) was obtained by borohydride reduction of 2-deoxy-D-arabino-hexose (5).The synthesis of 5, starting from 2,3:4,5-di-O-isopropylidene-D-arabinitol (1), was achieved by one-carbon chain-elongation involving formylation of the Grignard reagent derived from 1-bromo-1-deoxy-2,3:4,5-di-O-isopropylidene-D-arabinitol (2), using lithium formate, followed by hydrolytic removal of the isopropylidene groups.Immobilized cells of Gluconobacter oxydans (ATCC) 15178) selectively oxidized 6 to give 5-deoxy-D-threo-hexulose (7) in 65percent yield (-9percent overall yield from 1).
-
Bolliger
, p. 989 (1951)
-
Solvolyses of 2-Deoxy-α- and β-D-Glucopyranosyl 4′-Bromoisoquinolinium Tetrafluoroborates
Zhu, Jiang,Bennet, Andrew J.
, p. 4423 - 4430 (2007/10/03)
The solvolyses of 2-deoxy-α- and β-D-glucopyranosyl 4′-bromoisoquinolinium tetrafluoroborates (1 and 2) were monitored in aqueous methanol, ethanol, trifluoroethanol, and binary mixtures of ethanol and trifluoroethanol. The observed rate constants are consistent with the solvolyses of 1 and 2 proceeding via dissociative (DN * AN) transition states. In comparison to the α-anomer, solvolysis of the β-compound gives a greater transition state charge delocalization onto the ring oxygen atom. Analysis of the solvolysis product ratios indicates that the 2-deoxyglucosyl oxacarbenium ion is not solvent-equilibrated in the solvent mixtures studied. In the solvolysis of compound 1, the solvent trifluoroethanol facilitates diffusional separation of the leaving group and, in so doing, promotes the formation of the retained trifluoroethyl glycoside.
