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D3695

Sigma-Aldrich

DMOG

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

Sinónimos:

Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester

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About This Item

Fórmula empírica (notación de Hill):
C6H9NO5
Número de CAS:
89464-63-1
Peso molecular:
175.14
MDL number:
MFCD05865098
UNSPSC Code:
12352200
PubChem Substance ID:
329798774
NACRES:
NA.77

product name

DMOG, ≥98% (HPLC)

Quality Level

100

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). 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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Metabolic reprogramming by HIF-1 activation enhances survivability of human adipose-derived stem cells in ischaemic microenvironments
Chen C, et al.
Cell Proliferation, 50(5), e12363-e12363 (2017)
L Gómez-Maldonado et al.
Oncogene, 34(20), 2609-2620 (2014-07-16)
The presence of hypoxic regions in solid tumors is an adverse prognostic factor for patient outcome. Here, we show that hypoxia induces the expression of Ephrin-A3 through a novel hypoxia-inducible factor (HIF)-mediated mechanism. In response to hypoxia, the coding EFNA3
Jianping Peng et al.
PloS one, 12(5), e0178147-e0178147 (2017-05-26)
Acute kidney injury (AKI) leads to a worse prognosis in diabetic patients compared with prognoses in non-diabetic patients, but whether and how diabetes affects kidney repair after AKI remains unknown. Here, we used scratch-wound healing and transwell migration models to
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
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)
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