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D3695

Sigma-Aldrich

DMOG

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

Synonyme(s) :

Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester

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About This Item

Formule empirique (notation de Hill):
C6H9NO5
Numéro CAS:
89464-63-1
Poids moléculaire :
175.14
Numéro MDL:
MFCD05865098
Code UNSPSC :
12352200
ID de substance PubChem :
329798774
Nomenclature NACRES :
NA.77

product name

DMOG, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

H2O: >30 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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)
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
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
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
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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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.

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