2-Deoxy-D-glucose

Modify Date: 2024-01-02 08:49:33

2-Deoxy-D-glucose Structure
2-Deoxy-D-glucose structure
 Common Name 2-Deoxy-D-glucose
CAS Number 154-17-6 Molecular Weight 164.156
Density 1.4±0.1 g/cm3 Boiling Point 456.7±45.0 °C at 760 mmHg
Molecular Formula C6H12O5 Melting Point 146-147ºC
MSDS Chinese USA Flash Point 244.1±25.2 °C

 Use of 2-Deoxy-D-glucose


2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase.

 Names

Name 2-Deoxy-D-Glucose
Synonym More Synonyms

 2-Deoxy-D-glucose Biological Activity

Description 2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase.
Related Catalog
In Vitro 2-Deoxy-D-glucose (2-DG, 4, 8, or 16 mM) significantly reduces the level of ATP in MCF-7 cells in a dose- and time-dependent manner that paralleles the effects of 2-DG on cell growth. The levels of phosphorylated Akt are significantly decreased, whereas the levels of phosphorylated AMPK and Sirt-1 are significantly increased in MCF-7 cells exposed to 2-Deoxy-D-glucose at 4, 8, or 16 mM for 1, 3, or 5 days in a dose- and time-dependent manner[1]. 2-DG treatment increases the levels of pentose phosphate pathway (PPP) metabolites and augments the generation of NADPH by glucose-6-phosphate dehydrogenase. An increase in NADPH and upregulation of glutathione synthetase expression resultes in the increase in the reduced form of glutathione by 2-DG in NB4 cells[3].
In Vivo 2-Deoxy-D-glucose (0.03%, w/w) causes a 7% decrease in final weight that is statistically significant, and delayes the appearance of palpable mammary carcinomas[1]. 2-Deoxy-D-glucose (3 mmol/kg, i.v.) is decreased in a dose-dependent manner by insulin in rat muscle[2].
Cell Assay The effect of 2-DG on cell growth is determined by evaluating the number of adherent cells. Briefly, MCF-7 cells are plated at 3×104 cells per well in flat-bottomed 96-well plates in 100 μL of culture medium under the culture conditions. After 24 hours, cells are fed with fresh medium including 2-Deoxy-D-glucose at doses of 0, 4, 8, or 16 mM. At days 1, 3, and 5 after 2-Deoxy-D-glucose exposure, cells are fixed with 1% glutaraldehyde, replaced with PBS, and stored at 4°C. At the end of an experiment, all of the plates are stained with 0.02% aqueous crystal violet for 30 minutes and rinsed with deionized water. After redissolving the bound crystal violet in 70% ethanol, the absorbance is determined at 590 nm using a SPECTRA MAX PLUS Microplate Spectrophotometer System.
Animal Admin At 21 days of age, rats are injected with 50 mg 1-methyl-1-nitrosourea per kilogram of body weight (i.p.). Rats are housed two per cage in solid-bottomed polycarbonate cages equipped with a food cup. Six days following carcinogen injection, all rats are randomized into one of three groups, 30 rats per group, and are fed ad libitum AIN-93G diet containing 0.0%, 0.02%, or 0.03% (w/w) 2-Deoxy-D-glucose (2-DG) for 5 weeks. Animal rooms are maintained at 22±1°C with 50% relative humidity and a 12-hour light/12-hour dark cycle. Rats are weighed thrice per week and are palpated for detection of mammary tumors twice per week starting from 19 days postcarcinogen.
References

[1]. Zhu Z, et al. 2-Deoxyglucose as an energy restriction mimetic agent: effects on mammary carcinogenesis and on mammary tumor cell growth in vitro. Cancer Res. 2005 Aug 1;65(15):7023-30.

[2]. Ueyama A, et al. Nonradioisotope assay of glucose uptake activity in rat skeletal muscle using enzymatic measurement of 2-deoxyglucose 6-phosphate in vitro and in vivo. Biol Signals Recept. 2000 Sep-Oct;9(5):267-74.

[3]. Miwa H, et al. Leukemia cells demonstrate a different metabolic perturbation provoked by 2-deoxyglucose. Oncol Rep. 2013 May;29(5):2053-7.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 456.7±45.0 °C at 760 mmHg
Melting Point 146-147ºC
Molecular Formula C6H12O5
Molecular Weight 164.156
Flash Point 244.1±25.2 °C
Exact Mass 164.068466
PSA 97.99000
LogP -3.07
Vapour Pressure 0.0±2.5 mmHg at 25°C
Index of Refraction 1.534
Storage condition 2~8℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MQ3325000
CHEMICAL NAME :
D-arabino-Hexose, 2-deoxy-
CAS REGISTRY NUMBER :
154-17-6
BEILSTEIN REFERENCE NO. :
1723331
LAST UPDATED :
199701
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C6-H12-O5
MOLECULAR WEIGHT :
164.18
WISWESSER LINE NOTATION :
VH1YQYQYQ1Q -D-ARABINO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APFRAD Annales Pharmaceutiques Francaises. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1943- Volume(issue)/page/year: 39,327,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 17,814,1965 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2 gm/kg
SEX/DURATION :
female 7-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 gm/kg
SEX/DURATION :
female 7-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2 gm/kg
SEX/DURATION :
female 7-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 40,143,1989

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS MQ3325000
HS Code 2912491000

 Synthetic Route

 Customs

HS Code 2912491000
Summary 2912491000. other aldehyde-alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

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 Synonyms

2-DEOXY-D-ARABINOHEXOSE
D-arabino-Hexose, 2-deoxy-
2-Deoxy-D-arabino-hexose
2-Deoxy-D-glucose
2-deoxy-d-arabino-hexos
MFCD00151328
D-Arabino-2-deoxyhexose
EINECS 205-823-0
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