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About This Item
Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
Molecular Weight:
175.14
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
DMOG, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
H2O: >30 mg/mL
shipped in
wet ice
storage temp.
−20°C
SMILES string
COC(=O)CNC(=O)C(=O)OC
InChI
1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9)
InChI key
BNJOZDZCRHCODO-UHFFFAOYSA-N
Application
DMOG has been used:
- in hypoxia-inducible factor (HIF) activity assay
- to examine its effects on the degradation of HIF-1α and renal regeneration
- in DMOG preconditioning of adipose tissues
- as vehicle control for the primary liquid culture of CD34+ cells
- for endothelial cell stimulation
Dimethyloxalylglycine (DMOG) has been used as an inhibitor of ten-eleven translocation 3 (TET3) protein.
Biochem/physiol Actions
DMOG is a cell permeable prolyl-4-hydroxylase inhibitor, which upregulates HIF (hypoxia-inducible factor).
DMOG is a cell permeable prolyl-4-hydroxylase inhibitor, which upregulates HIF (hypoxia-inducible factor). The protein level of HIF-1α subunit is post-transcriptionally regulated by prolyl and asparaginyl hydroxylase (PAH). Suppression of PAH activity increases endogenous HIF-1α levels. DMOG is a cell permeable, competitive inhibitor of prolyl hydroxylase domain-containing proteins (PHDs and HIF-PHs). It has been discovered that the DMOG posseses neuroprotective effect on NFG deprived cell cultures through preservation of glucose metabolism. DMOG also attenuates myocardial injury in a rabbit ischemia reperfusion model. DMOG is more potent than the older inhibitor 4-Phenyl-pyridine-2,5-dicarboxylic acid (R395889; Sigma-Aldrich rare chemicals library). The IC50 is 5.18 μM.
Features and Benefits
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Articles
We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.
Fuhai Li et al.
American journal of translational research, 8(11), 4791-4801 (2016-12-03)
Background: Hypoxia has been reported to possess the ability to induce mature lipid-filled adipocytes to differentiate into fibroblast-like multipotent dedifferentiated fat (DFAT) cells and stem cells such as iPSCs (interstitial pluripotent stem cells) and ESCs (embryonic stem cells) and then
EPAS1/HIF-2 alpha-mediated downregulation of tissue factor pathway inhibitor leads to a pro-thrombotic potential in endothelial cells
Stavik B, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1862(4), 670-678 (2016)
Perparim Limani et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 22(23), 5887-5897 (2016-11-03)
Tumor hypoxia activates hypoxia-inducible factors (Hifs), which induce a range of malignant changes including vascular abnormalities. Here, we determine whether inhibition of the hypoxic tumor response through myo-inositol trispyrophosphate (ITPP), a compound with antihypoxic properties, is able to cause prolonged
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D3695-50MG | 04061833563526 |
| D3695-10MG | 04061833563519 |
