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DMOG (Synonyms: Dimethyloxallyl Glycine)

Catalog No.GC16973

An HIF-PH inhibitor

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DMOG Chemical Structure

Cas No.: 89464-63-1

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10mM (in 1mL DMSO)
$61.00
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50mg
$46.00
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100mg
$68.00
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200mg
$127.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Cell experiment [1]:

Cell lines

B1 cells

Preparation Method

B1 cells were FACS sorted from total peritoneal cells. Cells were cultured in the presence of DMOG (1 mM) for 2 h followed by stimulation.

Reaction Conditions

1 mM DMOG for 2 hours

Applications

The hydroxylase inhibitor DMOG reduce susceptibility to endotoxemia by tolerating cells to LPS activation and promoting M2 polarization and subsequent up-regulation of IL-10 by peritoneal B1 cells.

Animal experiment [2]:

Animal models

BALB/c and C57BL/6 mice

Preparation Method

Intraperitoneal injection of DMOG

Dosage form

8 mg DMOG / mouse

Applications

DMOG significantly increased survival after LPS-induced shock. DMOG up-regulated the expression of IL-10 in peritoneal B-1 cells. Mice treated with DMOG before surgery developed severe worsening of disease symptoms and significantly increased mortality.

References:

[1]. Hams E, Saunders SP, et,al. The hydroxylase inhibitor dimethyloxallyl glycine attenuates endotoxic shock via alternative activation of macrophages and IL-10 production by B1 cells. Shock. 2011 Sep;36(3):295-302. doi: 10.1097/SHK.0b013e318225ad7e. PMID: 21844787; PMCID: PMC3157050.

Background

DMOG(dihydroxyalanine) is an antagonist of α-ketoglutarate cofactor and an inhibitor of HIF-proline hydroxylase, leading to the stability and accumulation of HIF-1α protein in the nucleus[4].

DMOG reduce susceptibility to endotoxemia by tolerating cells to LPS activation and promoting M2 polarization and subsequent up-regulation of IL-10 by peritoneal B1 cells[1]. DMOG inhibited hydroxyproline synthesis from chick embryo lung, with IC50 values of 9.3 μM and 3.7 μM corresponding to tissue and medium sources, respectively[2].The combination of DMOG and nSi exerted admirable effects on periodontal tissue regeneration. DMOG/nSi-PLGA fibrous membranes could enhance and orchestrate osteogenesis-angiogenesis[4].Inhibition of hydroxylase by oxygen sensing leads to upregulation of the transcription factors HIF-1α and NF-β under normal oxygen in vitro,0.1 to 1mM DMOG can stabilize the expression of HIF-1α[3].DMOG reduces FGF-2-induced proliferation and cyclin A expression by inhibiting prolyl hydroxylase activity in HPASMC[8]. DMOG acts as a pro-angiogenic agent and plays a protective role in experimental model of colitis and diarrhoea via HIF-1 related signal[5][6]. DMOG induces cell autophagy and protect cells from a subsequent OGD insult.[7].

DMOG inhibits endogenous HIF inactivation, and induces angiogenesis in ischaemic skeletal muscles of mice[5]. Up-regulation of hypoxia-inducible factor-1α by DMOG enhances the cardioprotective effects of ischemic postconditioning in hyperlipidemic rats[6].

References:
[1]: Hams E, Saunders SP, et,al. The hydroxylase inhibitor dimethyloxallyl glycine attenuates endotoxic shock via alternative activation of macrophages and IL-10 production by B1 cells. Shock. 2011 Sep;36(3):295-302. doi: 10.1097/SHK.0b013e318225ad7e. PMID: 21844787; PMCID: PMC3157050.
[2]: Baader E, Tschank G, et,al. Inhibition of prolyl 4-hydroxylase by oxalyl amino acid derivatives in vitro, in isolated microsomes and in embryonic chicken tissues. Biochem J. 1994 Jun 1;300 ( Pt 2)(Pt 2):525-30. doi: 10.1042/bj3000525. PMID: 8002959; PMCID: PMC1138193.
[3]: Jaakkola P, Mole DR, et,al. Targeting of HIF-alpha to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation. Science. 2001 Apr 20;292(5516):468-72. doi: 10.1126/science.1059796. Epub 2001 Apr 5. PMID: 11292861.
[4]: Shang L, Liu Z, Ma B, Shao J, Wang B, Ma C, Ge S. Dimethyloxallyl glycine/nanosilicates-loaded osteogenic/angiogenic difunctional fibrous structure for functional periodontal tissue regeneration. Bioact Mater. 2020 Oct 26;6(4):1175-1188. doi: 10.1016/j.bioactmat.2020.10.010. PMID: 33163699; PMCID: PMC7593348.
[5]: Milkiewicz M, Pugh CW, et,al. Inhibition of endogenous HIF inactivation induces angiogenesis in ischaemic skeletal muscles of mice. J Physiol. 2004 Oct 1;560(Pt 1):21-6. doi: 10.1113/jphysiol.2004.069757. Epub 2004 Aug 19. PMID: 15319416; PMCID: PMC1665195.
[6]: Li X, Zhao H, et,al. Up-regulation of hypoxia-inducible factor-1α enhanced the cardioprotective effects of ischemic postconditioning in hyperlipidemic rats. Acta Biochim Biophys Sin (Shanghai). 2014 Feb;46(2):112-8. doi: 10.1093/abbs/gmt132. Epub 2014 Jan 3. PMID: 24389644.
[7]: Singh A, Wilson JW, et,al. Hypoxia-inducible factor (HIF) prolyl hydroxylase inhibitors induce autophagy and have a protective effect in an in-vitro ischaemia model. Sci Rep. 2020 Jan 31;10(1):1597. doi: 10.1038/s41598-020-58482-w. Erratum in: Sci Rep. 2020 Apr 8;10(1):6041. PMID: 32005890; PMCID: PMC6994562.
[8]: Schultz K, Murthy V, et,al. Prolyl hydroxylase 2 deficiency limits proliferation of vascular smooth muscle cells by hypoxia-inducible factor-1{alpha}-dependent mechanisms. Am J Physiol Lung Cell Mol Physiol. 2009 Jun;296(6):L921-7. doi: 10.1152/ajplung.90393.2008. Epub 2009 Mar 20. PMID: 19304911; PMCID: PMC2692800.

Chemical Properties

Cas No. 89464-63-1 SDF
Synonyms Dimethyloxallyl Glycine
Chemical Name methyl 2-[(2-methoxy-2-oxoethyl)amino]-2-oxoacetate
Canonical SMILES COC(=O)CNC(=O)C(=O)OC
Formula C6H9NO5 M.Wt 175.14
Solubility DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 5.7097 mL 28.5486 mL 57.0972 mL
5 mM 1.1419 mL 5.7097 mL 11.4194 mL
10 mM 0.571 mL 2.8549 mL 5.7097 mL
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