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D3695

Sigma-Aldrich

DMOG

≥98% (HPLC)

Synonym(s):
Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester
Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
Molecular Weight:
175.14
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

Dimethyloxalylglycine (DMOG) has been used as an inhibitor of ten-eleven translocation 3 (TET3) protein.
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

Packaging

10, 50 mg in glass bottle

Biochem/physiol Actions

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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More Documents

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Articles

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