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
Sign Into View Organizational & Contract Pricing
Select a Size
10 MG
₪665.00
50 MG
₪1,745.00
All Photos(3)
Select a Size
Change View
10 MG
₪665.00
50 MG
₪1,745.00
About This Item
Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
Molecular Weight:
175.14
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Product Name
DMOG, ≥98% (HPLC)
Quality Level
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[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). 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Choose from one of the most recent versions:
Certificates of Analysis (COA)
Lot/Batch Number
Don't see the Right Version?
If you require a particular version, you can look up a specific certificate by the Lot or Batch number.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
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)
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
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
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.
-
Is it suitable to use D3695 to induce hypoxia?
1 answer-
Helpful?
-
-
Bonjour, Quelle est la durée de conservation à -20°C de ce réactif ? Merci
1 answer-
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.
For more information you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/life-science/quality-and-regulatory-management/quality-services.
Helpful?
-
Active Filters
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service
