ChemicalBook > CAS DataBase List > DMOG

DMOG

Product Name
DMOG
CAS No.
89464-63-1
Chemical Name
DMOG
Synonyms
DIMETHYLOXALYLGLYCINE;OMOG;Dimethyloxaloylglycine;OMO;DMOG;DMOG, >=98%;DMOG USP/EP/BP;DIMETHYLOXALLYL GLYCINE;Dimethyloxalylglycine (Dmog);DiMethyloxaloylglycine (DMOG)
CBNumber
CB8223849
Molecular Formula
C6H9NO5
Formula Weight
175.14
MOL File
89464-63-1.mol
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DMOG Property

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.
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
22
WGK Germany 
3
HS Code 
2924.19.8000
HazardClass 
IRRITANT
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D3695
Product name
DMOG
Purity
≥98% (HPLC)
Packaging
10mg
Price
$100
Updated
2024/03/01
Sigma-Aldrich
Product number
400091
Product name
HIF-Hydroxylase Inhibitor, DMOG
Packaging
50mg
Price
$99.4
Updated
2024/03/01
TCI Chemical
Product number
D5480
Product name
Dimethyloxaloylglycine
Packaging
50MG
Price
$50
Updated
2024/03/01
TCI Chemical
Product number
D5480
Product name
Dimethyloxaloylglycine
Packaging
250MG
Price
$171
Updated
2024/03/01
Alfa Aesar
Product number
J67077
Product name
Dimethyloxaloylglycine, 98%
Packaging
10mg
Price
$32.65
Updated
2024/03/01
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DMOG Chemical Properties,Usage,Production

Description

The pro-angiogenic factor HIF-1α is targeted for destruction in normoxic environments by the hydroxylation of a specific proline residue, P564, by the oxygen-sensing enzyme HIF-1α prolyl hydroxylase (HIF-PH). DMOG is a cell permeable, competitive inhibitor of HIF-PH. It acts to stabilize HIF-1α expression at normal oxygen tensions in cultured cells, at concentrations between 0.1 and 1 mM. DMOG is therefore expected to act as a pro-angiogenic compound, acting via the HIF-1α system.

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.

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].

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].

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.

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) Asikainen et al. (2005), Activation of hypoxia-inducible factors in hyperoxia through prolyl 4-hydroxylase blockade in cells and explants of primate lung; Proc. Natl. Acad. Sci. USA, 102 10212 2) Jaakkola et al. (2001), Targeting of HIF-alpha to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation; Science, 292 468 3) Hamada et al. (2009), Synthesis and activity of N-oxalylglycine and it’s derivatives as jumonji C-domain-containing histone lysine demethylase inhibitors; Bioorg. Med. Chem. Lett., 19 2852 4) Lomb et al. (2009), Prolyl hydroxylase inhibitors depend on extracellular glucose and hypoxia-inducible factor (HIF)-2alpha to inhibit cell death caused by nerve growth factor deprivation: evidence that HIF-2alpha has a role in NGF-promoted survival of sympathetic neurons; Mol. Pharmacol., 75 1198 5) Xie et al. (2012), PHD3-dependent hydroxylation of HCLK2 promotes the DNA damage response; J. Clin. Invest., 122 2827

DMOG Preparation Products And Raw materials

Raw materials

Preparation Products

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DMOG Suppliers

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Shanghai JiYi Biotechnology Co. Ltd.
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View Lastest Price from DMOG manufacturers

Career Henan Chemical Co
Product
DMOG 89464-63-1
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1ton
Release date
2019-09-03

89464-63-1, DMOGRelated Search:

8-OXO-2'-DEOXYGUANOSINE 4-Hydroxyquinazoline (+)-Camptothecin 2,3-Butanedione N-Methylformamide Selumetinib AGI6780 MG-132 IOX2 Avagacestat (BMS-708163) Olaparib N-OXALYL GLYCINE ETHYL 2-[(2-ETHOXY-2-OXOETHYL)AMINO]-2-OXOACETATE DMOG 2-(ETHOXYCARBONYL)-ALFA-OXO-1-PYRROLIDINE ACETIC ACID ETHYL ESTER ALFA-[(PHENYLMETHOXY)CARBONYL]OXY-1-PIPERIDINE ACETIC ACID METHYL ESTER

  • Dimethyloxaloylglycine
  • N-(METHOXYOXOACETYL)-GLYCINE METHYL ESTER
  • DIMETHYLOXALLYL GLYCINE
  • DIMETHYLOXALYLGLYCINE
  • DMOG
  • N-[(Methoxycarbonyl)Methyl]oxaMic Acid Methyl Ester
  • DiMethyloxaloylglycine (DMOG)
  • METHYL 2-(2-METHOXY-2-OXOETHYLAMINO)-2-OXOACETATE
  • N-(2-Methoxy-2-oxoacetyl)glycine methyl ester
  • DMOG Dimethyloxalylglycine N-[(Methoxycarbonyl)methyl]oxamic acid methyl ester
  • DMOG, >=98%
  • HIF-Hydroxylase Inhibitor, DMOG
  • Glycine,N-(2-methoxy-2-oxoacetyl)-, methyl ester
  • OMOG
  • HIF-Hydroxylase Inhibitor, DMOG - CAS 89464-63-1 - Calbiochem
  • DMOG; DIMETHYLOXALLYL GLYCINE; DIMETHYLOXALYLGLYCINE; 89464-63-1; METHYL N-[METHOXY(OXO)ACETYL]GLYCINATE
  • methyl n-[methoxy(oxo)acetyl]glycinate
  • Dimethyloxalylglycine (Dmog)
  • methyl 2-(2-methoxy-2-oxoacetamido)acetate
  • DMOG USP/EP/BP
  • DMOG (dimethyloxaloylglycine)
  • Dimethyloxalylglycine|||Dimethyloxallyl Glycine|||Dimethyloxaloylglycine
  • OMO
  • 89464-63-1
  • Other
  • Bio-material
  • NONE
  • Amino Acids 13C, 2H, 15N
  • Amino Acids & Derivatives
  • Inhibitors