DMOG
- CAS No.
- 89464-63-1
- Chemical Name:
- DMOG
- Synonyms
- DIMETHYLOXALYLGLYCINE;OMOG;Dimethyloxaloylglycine;DIMETHYLOXALLYL GLYCINE;OMO;DMOG;DMOG, >=98%;DMOG USP/EP/BP;Dimethyloxalylglycine (Dmog);DiMethyloxaloylglycine (DMOG)
- CBNumber:
- CB8223849
- Molecular Formula:
- C6H9NO5
- Molecular Weight:
- 175.14
- MDL Number:
- MFCD05865098
- MOL File:
- 89464-63-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 46-48°C |
|---|---|
| Boiling point | 179-182 °C(Press: 12 Torr) |
| Density | 1.246±0.06 g/cm3(Predicted) |
| storage temp. | -20°C |
| solubility | H2O: >30mg/mL |
| pka | 10.55±0.46(Predicted) |
| form | Solid |
| color | white to off-white |
| Water Solubility | Soluble in water at 30mg/ml. |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions are not stable. Solutions must be made fresh and used within 1 working day. |
| InChI | InChI=1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9) |
| InChIKey | BNJOZDZCRHCODO-UHFFFAOYSA-N |
| SMILES | C(OC)(=O)CNC(C(OC)=O)=O |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P301+P312+P330 |
| Hazard Codes | Xi,Xn |
| Risk Statements | 22 |
| WGK Germany | 3 |
| HS Code | 2924.19.8000 |
| HazardClass | IRRITANT |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
DMOG price More Price(89)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | D3695 | DMOG ≥98% (HPLC) | 89464-63-1 | 10mg | $111 | 2026-04-30 | Buy |
| Sigma-Aldrich | 400091 | HIF-Hydroxylase Inhibitor, DMOG | 89464-63-1 | 50mg | $115 | 2026-04-30 | Buy |
| TCI Chemical | D5480 | Dimethyloxaloylglycine | 89464-63-1 | 50MG | $42 | 2026-04-30 | Buy |
| TCI Chemical | D5480 | Dimethyloxaloylglycine | 89464-63-1 | 250MG | $145 | 2026-04-30 | Buy |
| Cayman Chemical | 71210 | DMOG ≥98% | 89464-63-1 | 10mg | $28 | 2026-04-30 | Buy |
DMOG Chemical Properties, Uses, Production
Description
The pro-
Chemical Properties
Off-White to Pale Pink Solid
Uses
DMOG is a cell permeable prolyl-4-hydroxylase inhibitor which upregulates HIF activity. HIF activation stimulates angiogenesis in several different models (1nM). DMOG also inhibits FIH (factor inhibiting HIF), an asparaginyl hydroxylase, which enhances the HIF response. It is active in vivo and attenuates myocardial injury in a rabbit ischemia reperfusion model (20mg/Kg).
Uses
DMOG is a cell permeable prolyl-4-hydroxylase inhibitor that regulates hypoxia-inducible factor
Definition
ChEBI: Dimethyloxalylglycine is a glycine derivative that is the diester obtained by formal condensation of the carboxy groups of N-oxalylglycine with two molecules of methanol. It has a role as a neuroprotective agent and an EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor. It is a glycine derivative, a methyl ester and a secondary carboxamide. It is functionally related to a N-oxalylglycine.
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.
Synthesis
553-90-2
5680-79-5
89464-63-1
The general procedure for the synthesis of methyl 2-((2-methoxy-2-oxoethyl)amino)-2-oxoacetate from dimethyl oxalate and methyl glycinate hydrochloride was as follows: 1) Following the method of E. Menta et al. (J. Heterocyclic Chem., 1995, 32, 1693), methyl glycinate hydrochloride (12.59 g), dimethyl oxalate (23.65 g), triethylamine (14.0 mL) and methanol (110 mL) were mixed and reacted to prepare methyl N-methoxycarbonylmethoxyformate. The product was characterized by 1H-NMR (400 MHz, CDCl3), δ: 3.79 (3H, s), 3.92 (3H, s), 4.14 (2H, d, J = 5.6 Hz), 7.55 (1H, br).ESI-MS m/z: 176 (M + H)+.
in vitro
dmog acts to stabilize hif-1a expression under normal oxygen tension in cultured cells at concentrations from 0.1 to 1 mmol/l [2].
Enzyme inhibitor
This iron-binding a-ketoglutarate (2-oxoglutarate) analogue (FW = 147.09 g/mol; also named N-oxaloglycine) competitively inhibits prolyl-4- hydroxylase (Reaction: Procollagen (L-proline) + a-ketoglutarate + O2 → Procollagen ( (2S,4R) -4-hydroxyproline) + succinate + CO2). During catalysis, prolyl-4-hydroxylase forms Fe (III), and the latter most likely makes an extremely stable metal ion complex with N-oxaloglycine. Substitution on the glycine moiety alters inhibitor activity stereoselectively and that, if the w-carboxylate is homologated or replaced, either by acylsulfonamides or anilide, activity is likewise sharply reduced. Prolyl- 4-Hydroxylase Catalysis: Each catalytic round of this posttranslational modifying enzyme reaction occurs in two stages. O2 is bound end-on in an axial position, producing a dioxygen unit. Nucleophilic attack at C-2 generates a tetrahedral intermediate, with loss of the double bond in dioxygen and bonds to iron and the a-carbon of a-ketoglutarate. Elimination of CO2 coincides with formation of the Fe (IV) =O species. The second stage involves the abstraction of the pro-R hydrogen atom from C-4 of proline, followed by radical combination, yielding hydroxyproline. In the presence of a-ketoglutarate, enzyme-bound Fe2+ is rapidly converted to Fe3+, resulting in inactivation of the enzyme Ascorbate is utilized as a cofactor to reduce Fe (III) back to Fe (II). Cell-Permeable Analogue: Dimethyloxalylglycine (FW = 175.14 g/mol; CAS 89464-63-1; Symbol: DMOG, also named N- (methoxyoxoacetyl) -glycine methyl ester) is metabolicaly demethylated to form N-oxaloglycine upon entry to many cells.
in vivo
pre-treatment with dmog attenuates systemic lps-induced activation of the nf-κb pathway. furthermore, mice treated with dmog had significantly increased survival in lps-induced shock. in addition, in vivo dmog treatment upregulates the expression of il-10, specifically in the peritoneal b-1 cell population [3].
IC 50
9.3 and 3.7 μm for hydroxyproline synthesis inhibition of embryonic chicken lung extracted from tissue and culture medium [1].
storage
Store at -20°C
References
[1] TIINA M ASIKAINEN. Activation of hypoxia-inducible factors in hyperoxia through prolyl 4-hydroxylase blockade in cells and explants of primate lung.[J]. ACS Catalysis , 2005: 10212-10217. DOI:10.1073/pnas.0504520102
[2] PANU JAAKKOLA. Targeting of HIF-α to the von Hippel-Lindau Ubiquitylation Complex by O2-Regulated Prolyl Hydroxylation[J]. Science, 2001, 292 5516. DOI:10.1126/science.1059796
[3] SHOHEI HAMADA . Synthesis and activity of N-oxalylglycine and its derivatives as Jumonji C-domain-containing histone lysine demethylase inhibitors[J]. Bioorganic & Medicinal Chemistry Letters, 2009, 19 10: Pages 2852-2855. DOI:10.1016/j.bmcl.2009.03.098
[4] DAVID J LOMB. Prolyl hydroxylase inhibitors depend on extracellular glucose and hypoxia-inducible factor (HIF)-2alpha to inhibit cell death caused by nerve growth factor (NGF) deprivation: evidence that HIF-2alpha has a role in NGF-promoted survival of sympathetic neurons.[J]. Molecular Pharmacology, 2009, 75 5: 1198-1209. DOI:10.1124/mol.108.053157
[5] LIANG XIE. PHD3-dependent hydroxylation of HCLK2 promotes the DNA damage response.[J]. Journal of Clinical Investigation, 2012, 122 8: 2827-2836. DOI:10.1172/jci62374
DMOG Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai JiYi Biotechnology Co. Ltd. | 13621943973 | sales@shjiyipharmatech.com | China | 1166 | 55 |
| Shanghai Hengmao Biotechnology Co. , Ltd. | 18817538189 | hmbsales@163.com | China | 101 | 58 |
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Shanghai Longsheng chemical Co.,Ltd. | 58099637 13585536065 | sales@shlschem.com | China | 9880 | 59 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| Shandong Xiya Chemical Co., Ltd | 13355009207 13355009207 | 3007715519@qq.com | China | 18722 | 57 |
| China Langchem Inc. | 0086-21-58956006 | China | 7798 | 57 | |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
