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Merck

D3695

DMOG

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

Synonyme(s) :

Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester

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A propos de cet article

Formule empirique (notation de Hill) :
C6H9NO5
Numéro CAS:
Poids moléculaire :
175.14
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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Nom du produit

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

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

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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Consulter la Bibliothèque de documents

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)
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)
Targeting the aryl hydrocarbon receptor nuclear translocator complex with DMOG and Stemregenin 1 improves primitive hematopoietic stem cell expansion
Jackson CS, et al.
Stem Cell Research, 21, 124-131 (2017)

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