2-Deoxy-D-glucose

2-Deoxy-d-glucose is a glucose molecule which has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. As such; it acts to competitively inhibit the production of glucose-6-phosphate from glucose at the phosphoglucoisomerase level (step 2 of glycolysis).^[2] 2-Deoxyglucose labeled with tritium or carbon-14 has been a popular ligand for laboratory research in animal models, where distribution is assessed by tissue-slicing followed by autoradiography, sometimes in tandem with either conventional or electron microscopy.

2-Deoxy-d-glucose^[1]

2-Deoxy-D-glucose
Names
IUPAC name 2-Deoxy-D-arabino-hexopyranose
Systematic IUPAC name (4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
Other names 2-Deoxyglucose 2-Deoxy-d-mannose 2-Deoxy-d-arabino-hexose 2-DG
Identifiers
CAS Number	154-17-6 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2074932
ChemSpider	388402 Y
ECHA InfoCard	100.005.295
EC Number	205-823-0
IUPHAR/BPS	4643
PubChem CID	108223
UNII	9G2MP84A8W Y
CompTox Dashboard (EPA)	DTXSID1037648
InChI InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1 Y Key: PMMURAAUARKVCB-CERMHHMHSA-N Y
SMILES O[C@H](C(CO)O[C@H](O)C1)[C@H]1O
Properties
Chemical formula	C6H12O5
Molar mass	164.16 g/mol
Melting point	142 to 144 °C (288 to 291 °F; 415 to 417 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

2-DG is up taken by the glucose transporters of the cell.^[3] Therefore, cells with higher glucose uptake, for example tumor cells, have also a higher uptake of 2-DG. Since 2-DG hampers cell growth, its use as a tumor therapeutic has been suggested, and in fact, 2-DG is in clinical trials.^[4] It is not completely clear how 2-DG inhibits cell growth. The fact that glycolysis is inhibited by 2-DG, seems not to be sufficient to explain why 2-DG treated cells stop growing.^[5] A synergistic effect between 2-DG and various other agents have been reported in the pursuit of anticancer strategies.^[6][7][8] Because of its structural similarity to mannose, 2DG has the potential to inhibit N-glycosylation in mammalian cells and other systems, and as such induces ER stress and the Unfolded Protein Response (UPR) pathway.^[9][10][11]

Use in optical imaging

2-DG has been used as a targeted optical imaging agent for fluorescent in vivo imaging.^[12][13] In clinical medical imaging (PET scanning), fluorodeoxyglucose is used, where one of the 2-hydrogens of 2-deoxy-D-glucose is replaced with the positron-emitting isotope fluorine-18, which emits paired gamma rays, allowing distribution of the tracer to be imaged by external gamma camera(s). This is increasingly done in tandem with a CT function which is part of the same PET/CT machine, to allow better localization of small-volume tissue glucose-uptake differences.^{[citation needed]}

Indian adoption for COVID-19 treatment

On May 8, 2021, the Drugs Controller General of India approved an oral formulation of 2-deoxy-D-glucose for emergency use as adjunct therapy in moderate to severe coronavirus patients.^[14][15] The drug was developed by the DRDO along with Dr. Reddy's Laboratories, who jointly claimed via a press release, that the drug "helps in faster recovery of hospitalised patients and reduces supplemental oxygen dependence".^[15][16][17] The Wire as well as The Hindu noted that the approval was based on poor evidence; no journal publication (or preprint) concerning efficacy and safety are yet available.^[16][17]

See also

• COVID-19 misinformation
• Fluorouracil