Structure via PubChem · Public domain (PubChem)
2-deoxy-D-glucose
Sign in to save2-Deoxy--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-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.
In the Vinony graph
Vinony's link graph records 23 inbound references to 2-deoxy-D-glucose, and connects out to molecule, glucose and digital object identifier.
Vinony files it under Aldohexoses, Deoxy sugars and ECHA InfoCard ID from Wikidata.
Vinony links it to 13 Wikipedia language editions.
Chemical data
- Formula
- C6H12O5
- Molecular weight
- 164.16 g/mol
- IUPAC name
- (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
- SMILES
- C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
- InChIKey
- VRYALKFFQXWPIH-PBXRRBTRSA-N
- XLogP
- -2.9
- Polar surface area
- 98 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- carbon
- Mass
- 164.068473484
Show 5 more facts
- chemical formula
- C₆H₁₂O₅
- isomeric SMILES
- OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
- subject has role
- antimetabolite
- canonical SMILES
- C(C=O)C(C(C(CO)O)O)O
- Commons category
- 2-Deoxy-D-glucose
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Use in optical imaging
- Indian adoption for COVID-19 treatment
- See also
- References
2-Deoxy--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-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-DG is up taken by the glucose transporters of the cell. 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. 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. A synergistic effect between 2-DG and various other agents have been reported in the pursuit of anticancer strategies. 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.
Excerpted from Wikipedia’s “2-deoxy-D-glucose” article, available under the CC BY-SA 4.0 licence.