Upon verification, D3695 is known to induce hypoxia. For further reference, you can refer the following citation: "Biomed Pharmacother. 2020 Jan;121:109606. doi: 10.1016/j.biopha.2019.109606. Epub 2019 Nov 25. Prodrug of epigallocatechin-3-gallate alleviates choroidal neovascularization via down-regulating HIF-1α/VEGF/VEGFR2 pathway and M1 type macrophage/microglia polarization."
D3695
DMOG
≥98% (HPLC), powder, HIF-hydroxylase inhibitor
Synonym(s):
Dimethyloxalylglycine, N-(Methoxyoxoacetyl)-glycine methyl ester
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50 MG
R 7,552.86
About This Item
Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
Molecular Weight:
175.14
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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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
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Related Categories
1 of 4
This Item | |||
|---|---|---|---|
| form powder | form powder | form solid | form powder |
| assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C |
| solubility H2O: >30 mg/mL | solubility DMSO: >20 mg/mL | solubility DMSO: >10 mg/mL | solubility DMSO: 20 mg/mL, clear |
| color white to off-white | color off-white to tan | color white to off-white | color white to beige |
Application
DMOG has been used:
- in hypoxia-inducible factor (HIF) activity assay[1]
- to examine its effects on the degradation of HIF-1α and renal regeneration[2]
- in DMOG preconditioning of adipose tissues[3]
- as vehicle control for the primary liquid culture of CD34+ cells[4]
- for endothelial cell stimulation[5]
Dimethyloxalylglycine (DMOG) has been used as an inhibitor of ten-eleven translocation 3 (TET3) protein.[6]
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.
signalword
Warning
hcodes
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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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
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)
Adipogenesis, lipogenesis and lipolysis is stimulated by mild but not severe hypoxia in 3T3-L1 cells
Weiszenstein M, et al.
Biochemical and biophysical research communications, 478(2), 727-732 (2016)
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)
Articles
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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Is it suitable to use D3695 to induce hypoxia?
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Bonjour, Quelle est la durée de conservation à -20°C de ce réactif ? Merci
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This product is not assigned an expiration date or recommended retest date. Products with no expiration date or recommended retest date should be routinely inspected by customers to ensure they perform as expected. These products are also subject to a one year warranty from the date of shipment.
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