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Merck

D3695

DMOG

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

Synonym(s):

Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester

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About This Item

Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
89464-63-1
Molecular Weight:
175.14
UNSPSC Code:
12352200
PubChem Substance ID:
329798774
NACRES:
NA.77
MDL number:
MFCD05865098

Product Name

DMOG, ≥98% (HPLC)

SMILES string

COC(=O)CNC(=O)C(=O)OC

InChI key

BNJOZDZCRHCODO-UHFFFAOYSA-N

InChI

1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9)

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

H2O: >30 mg/mL

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Related Categories

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
0000429809
0000428676
0000429810
0000428678
0000428678

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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
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)
Yaling Yu et al.
Biomaterials, 165, 48-55 (2018-03-05)
Although mammalian kidney regeneration has been reported to occur throughout life, mature kidneys in mammals are not thought to regenerate sufficiently, particularly glomeruli. In our previous work, we found that renal regeneration could be enhanced by decellularized renal scaffolds after
View All Related Papers

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