| Size | Price | |
|---|---|---|
| 250mg | ||
| Other Sizes |
| Targets |
N-Oxalylglycine targets 2-oxoglutarate (2-OG)-dependent dioxygenases, a large family of enzymes that require 2-OG, iron, and oxygen as cofactors. Key targets include prolyl hydroxylases (PHD1, PHD2, PHD3) that regulate hypoxia-inducible factor (HIF) stability, and histone demethylases (e.g., JmjC domain-containing enzymes) that regulate gene expression. By inhibiting these enzymes, NOG stabilizes HIF-α subunits, activates hypoxic responses, and alters histone methylation patterns.
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|---|---|
| ln Vitro |
N-Oxalylglycine inhibits 2-OG-dependent dioxygenases including prolyl hydroxylases and histone demethylases. It stabilizes HIF-1α and HIF-2α under normoxic conditions by inhibiting PHD activity. The compound also inhibits JmjC domain-containing histone demethylases, leading to increased histone methylation. NOG has been shown to induce hypoxic responses in various cell types. The compound's inhibitory activity is competitive with 2-OG.
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| ln Vivo |
In vivo, N-oxalylglycine has been used to study the role of 2-OG-dependent dioxygenases in various physiological and pathological processes. By inhibiting PHDs, NOG stabilizes HIF and activates hypoxic responses, which may have effects on angiogenesis, metabolism, and inflammation. The compound has been used in animal models to study the role of HIF in cancer, ischemia, and other conditions. However, its broad-spectrum activity limits its specificity for individual targets.
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| Enzyme Assay |
2-OG-dependent dioxygenase activity assays are performed using recombinant enzymes and appropriate substrates. For PHD assays, the enzyme is incubated with HIF-α peptide substrate, 2-OG, iron, and ascorbate. Hydroxylation of the substrate is measured by mass spectrometry or using antibody-based detection. N-Oxalylglycine is added at varying concentrations, and inhibition is measured. IC50 values are calculated from concentration-response curves. Histone demethylase assays are performed using similar principles with histone peptide substrates.
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| Cell Assay |
Cellular assays for N-oxalylglycine employ various cell lines. Cells are treated with NOG (typically 0.1-1 mM) for 4-24 hours. HIF-1α and HIF-2α protein levels are assessed by Western blot. HIF target gene expression (e.g., VEGF, EPO, GLUT1) is analyzed by qPCR. Histone methylation levels (H3K4me3, H3K9me3, H3K27me3) are assessed by Western blot. Cell viability and proliferation are assessed using standard assays. The compound's effects on collagen synthesis can be assessed by measuring hydroxyproline levels.
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| Animal Protocol |
In vivo studies with N-oxalylglycine are typically performed in mouse models. The compound is administered via intraperitoneal or subcutaneous injection at various doses (typically 10-100 mg/kg). HIF stabilization is confirmed by measuring HIF-α protein levels in tissues. HIF target gene expression is analyzed by qPCR. The compound's effects on tumor growth, angiogenesis, or ischemia are assessed in appropriate models. However, NOG's broad-spectrum activity and rapid metabolism may limit its utility for in vivo studies.
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| ADME/Pharmacokinetics |
N-Oxalylglycine has molecular formula C4H5NO5 and molecular weight 147.09. It has CAS number 5262-39-5. The compound is soluble in water and DMSO. It should be stored at -20°C for long-term stability. N-Oxalylglycine is a research-use only compound for studying 2-OG-dependent dioxygenases. It is also known as N-oxalylglycine and NOG.
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| Toxicity/Toxicokinetics |
Toxicological data for N-oxalylglycine are limited as it is a research compound. As an inhibitor of 2-OG-dependent dioxygenases, it may have broad effects on cellular metabolism, hypoxia responses, and epigenetics. The compound should be handled with appropriate laboratory safety precautions. In cell culture, NOG is typically used at concentrations up to 1 mM, which are generally well-tolerated in short-term experiments.
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| Additional Infomation |
N-Oxaloylglycine is an aminodicarboxylic acid, specifically an iminodiacetic acid with an oxygen-substituted group. It functions as an inhibitor of α-ketoglutarate-dependent enzymes (EC 1.14.11.). It acts as an inhibitor of EC 1.14.11. (an oxidoreductase that acts on paired donors, where 2-ketoglutarate is one of the donors, and each donor introduces an oxygen atom). It is both an aminodicarboxylic acid and an N-acylglycine.
N-Oxalylglycine (NOG) is a competitive inhibitor of 2-oxoglutarate (2-OG)-dependent dioxygenases, including prolyl hydroxylases (PHDs) and histone demethylases. It is a structural analog of 2-oxoglutarate and acts as a broad-spectrum inhibitor. NOG is commonly used as a tool compound to study hypoxia signaling (HIF pathway), epigenetics (histone methylation), and collagen synthesis. The compound stabilizes HIF-α under normoxic conditions and alters histone methylation patterns. |
| Molecular Formula |
C4H5NO5
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|---|---|
| Molecular Weight |
147.0862
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| Exact Mass |
147.016
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| CAS # |
5262-39-5
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| PubChem CID |
3080614
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Index of Refraction |
1.521
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| LogP |
-1.61
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
10
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| Complexity |
175
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(C(=O)O)NC(=O)C(=O)O
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| InChi Key |
BIMZLRFONYSTPT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10)
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| Chemical Name |
2-(carboxymethylamino)-2-oxoacetic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~100 mg/mL (~679.86 mM)
DMSO :< 1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7986 mL | 33.9928 mL | 67.9856 mL | |
| 5 mM | 1.3597 mL | 6.7986 mL | 13.5971 mL | |
| 10 mM | 0.6799 mL | 3.3993 mL | 6.7986 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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