GLPBio

2-Oxosuccinic acid

Catalog No.: GC38276Purity:>98.00%Synonyms: NSC 284205, NSC 77688, OAA, Oxalacetic Acid
COASDSData Sheet
2-Oxosuccinic acid is an α-keto acid that reacts with acetyl-CoA and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the last step.

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2-Oxosuccinic acid
Cas No.: 328-42-7
10mM (in 1mL DMSO)In Stock
$24.00
1
100mgIn Stock
$22.00
1
500mgIn Stock
$32.00
1
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Description

2-Oxosuccinic acid is an α-keto acid that reacts with acetyl-CoA and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the last step[1]. 2-Oxosuccinic acid is a metabolic intermediate formed by the carboxylation of pyruvate in mitochondria, followed by decarboxylation and phosphorylation to form phosphoenolpyruvate[2]. 2-Oxosuccinic acid can effectively inhibit succinate dehydrogenase (SDH) at a concentration of 5µM[3]. 2-Oxosuccinic acid has a neuroprotective effect and reduces brain and blood glutamate levels by activating the blood-resident enzyme glutamate-oxaloacetate transaminase [4].

In vitro, 2-Oxosuccinic acid (50mM) treatment of HepG2 cells for 12h and 24h significantly reduced the mRNA and protein expression of HIF1α and c-myc, reduced Akt phosphorylation, and inhibited the Akt/HIF pathway in cells[5]. 2-Oxosuccinic acid (10 mM) treatment of LO-2 cells for 24 h can remove ROS, reduce oxidative damage caused by H2O2, maintain the integrity of mitochondrial structure, and increase ATP production[6].

In vivo, 2-Oxosuccinic acid (10 mg/kg) was used to treat paraquat-poisoned mice by intraperitoneal injection for 3 days, which significantly improved the survival rate of mice, alleviated the poisoning state, reduced the wet weight/dry weight ratio of the mouse lungs, and reduced the pathological damage of lung tissues[7].

References:
[1] Frizzell N. 10 CHAPTER The Tricarboxylic Acid Cycle[J]. Medical Biochemistry-E-Book: Medical Biochemistry-E-Book, 2022: 129.
[2] Jitrapakdee S, St Maurice M, Rayment I, et al. Structure, mechanism and regulation of pyruvate carboxylase[J]. Biochemical journal, 2008, 413(3): 369-387.
[3] Fink B D, Bai F, Yu L, et al. Oxaloacetic acid mediates ADP-dependent inhibition of mitochondrial complex II–driven respiration[J]. Journal of Biological Chemistry, 2018, 293(51): 19932-19941.
[4] Campos F, Sobrino T, Ramos-Cabrer P, et al. Oxaloacetate: a novel neuroprotective for acute ischemic stroke[J]. The international journal of biochemistry & cell biology, 2012, 44(2): 262-265.
[5] Kuang Y, Han X, Xu M, et al. Oxaloacetate induces apoptosis in HepG2 cells via inhibition of glycolysis[J]. Cancer medicine, 2018, 7(4): 1416-1429.
[6] Kuang Y, Han X, Xu M, et al. Oxaloacetate ameliorates chemical liver injury via oxidative stress reduction and enhancement of bioenergetic fluxes[J]. International journal of molecular sciences, 2018, 19(6): 1626.
[7] Li W, Li M, Chen K, et al. Oxaloacetate acid ameliorates paraquat-induced acute lung injury by alleviating oxidative stress and mitochondrial dysfunction[J]. Frontiers in Pharmacology, 2022, 13: 1029775.

Protocol

Cell experiment [1]:

Cell lines

HepG2 cells

Preparation Method

HepG2 cells were treated 50mM 2-Oxosuccinic acid for 1, 12, and 24 h. The mRNA expression and protein expression of HIF1α and c-myc were detected using qRT-PCR and Western blot. 

Reaction Conditions

50mM; 1, 12, and 24 h

Applications

The mRNA and protein expressions of HIF1α and c-myc were decreased in HepG2 cells treated with 2-Oxosuccinic acid for 12 and 24 h.

Animal experiment [2]:

Animal models

Male C57BL/6J mice

Preparation Method

Mice were randomly divided into four groups with six in each group: 1) control group, mice received saline solution; 2) Paraquat (PQ) group, mice received PQ (50mg/kg); 3) protection group, 2-Oxosuccinic acid (10mg/kg) was intraperitoneal injection into mice for three consecutive days, and PQ (50 mg/kg) was injected 1 h after the last day of 2-Oxosuccinic acid administration; 4) 2-Oxosuccinic acid group, mice received 2-Oxosuccinic acid (10mg/kg) for three consecutive days. The mice were killed at 48 h after PQ injection, and their serum, lung tissues, alveolar lavage fluid were collected for further analyses.

Dosage form

10mg/kg; i.p.

Applications

2-Oxosuccinic acid significantly improved survival and alleviated the state of mice following PQ poisoning, reduced the wet/dry weight ratio of mice lungs, reduced PQ-induced histopathological damage to lung tissues.

References:
[1]Kuang Y, Han X, Xu M, et al. Oxaloacetate induces apoptosis in HepG2 cells via inhibition of glycolysis[J]. Cancer medicine, 2018, 7(4): 1416-1429.
[2]Li W, Li M, Chen K, et al. Oxaloacetate acid ameliorates paraquat-induced acute lung injury by alleviating oxidative stress and mitochondrial dysfunction[J]. Frontiers in Pharmacology, 2022, 13: 1029775.

Product Documents

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
328-42-7
Synonyms
NSC 284205, NSC 77688, OAA, Oxalacetic Acid
SMILES
O=C(O)C(CC(O)=O)=O
Molecular Formula
C4H4O5
Molecular Weight
132.07
Solubility
Water: ≥ 100 mg/mL (757.17 mM); DMSO: ≥ 100 mg/mL (757.17 mM)
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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