D3695

DMOG

≥98% (HPLC), powder, HIF-hydroxylase inhibitor

• Synonym(s): Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester
• Empirical Formula (Hill Notation): C₆H₉NO₅
• CAS Number: 89464-63-1
• Molecular Weight: 175.14
• MDL number: MFCD05865098
• UNSPSC Code: 12352200
• PubChem Substance ID: 329798774
• NACRES: NA.77

Properties

• product name: DMOG, ≥98% (HPLC)
• 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

Description

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). 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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable