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400091

Sigma-Aldrich

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

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.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark

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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