400091
DMOG
≥98% (HPLC), solid, HIF-hydroxylase inhibitor, Calbiochem
Synonym(s):
HIF-Hydroxylase Inhibitor, DMOG, N-(Methoxyoxoacetyl)-glycine methyl ester, Dimethyloxalylglycine, HIF Prolyl Hydroxylase Inhibitor I, HIF Aspartyl β-Hydroxylase Inhibitor, HIF Asparanginyl β-Hydroxylase Inhibitor
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About This Item
Empirical Formula (Hill Notation):
C6H9NO5
CAS Number:
Molecular Weight:
175.14
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
product name
HIF-Hydroxylase Inhibitor, DMOG, The HIF-Hydroxylase Inhibitor, DMOG, also referenced under CAS 89464-63-1, controls the biological activity of HIF-Hydroxylase. This small molecule/inhibitor is primarily used for Cell Structure applications.
Quality Level
Assay
≥98% (HPLC)
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
desiccated (hygroscopic)
color
pink-white to peach-white
solubility
DMSO: 50 mg/mL
shipped in
ambient
storage temp.
2-8°C
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
General description
A cell-permeable 2-OG (2-oxoglutarate) analog that is expected to act as a competitive inhibitor against all 2-OG-dependent dioxygenases. Effectively upregulates normoxia HIF-α transcription activity (effective conc. = 1 mM in cultures) by inhibiting HIF-PH- (HIF-α-prolyl hydroxylase) catalyzed ODD (oxygen-dependent degradation domain) Prolyl hydroxylation (Pro564 and Pro530 in HIF-1α and HIF-2α, respectively) and aspartyl/asparanginyl β-hydroxylase-catalyzed CAD Asp hydroxylation (Asn803 and Asn851 in HIF-1α and HIF-2α, respectively), resulting in a blockage of pVHL (von Hippel-Lindau) ubiquitin ligase complex-mediated HIF-α degradation and a simultaneous promotion of HIF CAD (COOH-terminal activation domain) p300/CBP association. DMOG is also demonstrated to augment artery ligation-induced up-regulation of HIF-1α and FLK (by 100% and 40%, respectively, in 11 days; 8 mg/0.5 ml/animal/i.p.; q.o.d.) in muscle tissues in a murine ischaemic model in vivo.
A cell-permeable 2-OG (2-oxoglutarate) analog that is expected to act as a competitive inhibitor against all 2-OG-dependent dioxygenases. Effectively upregulates normoxia HIF-α transcription activity (effective conc. = 1 mM in cultures) by inhibiting HIF-PH- (HIF-α-prolyl hydroxylase) catalyzed ODD (oxygen-dependent degradation domain) Prolyl hydroxylation (Pro564 and Pro530 in HIF-1α and HIF-2α, respectively) and aspartyl/asparanginyl β-hydroxylase-catalyzed CAD Asp hydroxylation (Asn803 and Asn851 in HIF-1α and HIF-2α, respectively), resulting in a blockage of pVHL (von Hippel-Lindau) ubiquitin ligase complex-mediated HIF-α degradation and a simultaneous promotion of HIF CAD (COOH-terminal activation domain) p300/CBP association. DMOG is also demonstrated to augment artery ligation-induced up-regulation of HIF-1α and FLK (by 100% and 40%, respectively, in 11 days; 8 mg/0.5 ml/animal/i.p.; q.o.d.) in muscle tissues in a murine ischaemic model in vivo.
Warning
Toxicity: Standard Handling (A)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Pollard, P.J., et al. 2008. Biochem. J.416, 387.
Chen, H., et al. 2006. Cancer Res.66, 9009.
Milkiewicz, M., et al. 2004. J. Physiol.560, 21.
Lando, D., et al. 2002. Science295, 858.
Jaakkola, P., et al. 2001. Science292, 468.
Chen, H., et al. 2006. Cancer Res.66, 9009.
Milkiewicz, M., et al. 2004. J. Physiol.560, 21.
Lando, D., et al. 2002. Science295, 858.
Jaakkola, P., et al. 2001. Science292, 468.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
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
Certificates of Analysis (COA)
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