2-Oxosuccinic acid (Synonyms: NSC 284205, NSC 77688, OAA, Oxalacetic Acid) |
| Catalog No.GC38276 |
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.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 328-42-7
Sample solution is provided at 25 µL, 10mM.
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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.
| 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: | |
| Cas No. | 328-42-7 | SDF | |
| Synonyms | NSC 284205, NSC 77688, OAA, Oxalacetic Acid | ||
| Canonical SMILES | O=C(O)C(CC(O)=O)=O | ||
| Formula | C4H4O5 | M.Wt | 132.07 |
| Solubility | Water: ≥ 100 mg/mL (757.17 mM); DMSO: ≥ 100 mg/mL (757.17 mM) | 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. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.5717 mL | 37.8587 mL | 75.7174 mL |
| 5 mM | 1.5143 mL | 7.5717 mL | 15.1435 mL |
| 10 mM | 0.7572 mL | 3.7859 mL | 7.5717 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
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- Purity: >98.00%
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