2-Oxosuccinic acid
(Synonyms: 草酰乙酸; 2-Oxosuccinic acid) 目录号 : GC38276
2-Oxosuccinic acid（草酰乙酸）是一种α-酮酸，在柠檬酸循环的第一步中草酰乙酸与乙酰辅酶A和水反应形成柠檬酸盐，并在最后一步中通过L-苹果酸的氧化再生。
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.
2-Oxosuccinic acid（草酰乙酸）是一种α-酮酸，在柠檬酸循环的第一步中草酰乙酸与乙酰辅酶A和水反应形成柠檬酸盐，并在最后一步中通过L-苹果酸的氧化再生[1]。2-Oxosuccinic acid是线粒体内丙酮酸羧化形成的代谢中间体，随后脱羧和磷酸化形成磷酸烯醇丙酮酸[2]。2-Oxosuccinic acid可在5µM浓度下有效抑制琥珀酸脱氢酶（SDH）[3]。2-Oxosuccinic acid具有神经保护作用，通过激活血液驻留酶谷氨酸-草酰乙酸转氨酶而降低大脑和血液谷氨酸水平[4]。
在体外，2-Oxosuccinic acid（50mM）处理HepG2细胞12h和24h，显著降低了HIF1α和c-myc的mRNA和蛋白表达，减少了Akt磷酸化，抑制了细胞中的Akt/HIF通路[5]。2-Oxosuccinic acid（10mM）处理LO-2细胞24 h，能清除ROS，减轻了H2O2引起的氧化损伤，维持线粒体结构的完整性，增加了ATP的生产[6]。
在体内，2-Oxosuccinic acid（10mg/kg）通过腹腔注射治疗百草枯中毒小鼠3天，显著提高小鼠生存率，缓解中毒状态，降低小鼠肺脏湿重/干重比，减轻肺组织病理学损伤[7]。
| 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 | |
| 别名 | 草酰乙酸; 2-Oxosuccinic acid | ||
| Canonical SMILES | O=C(O)C(CC(O)=O)=O | ||
| 分子式 | C4H4O5 | 分子量 | 132.07 |
| 溶解度 | Water: ≥ 100 mg/mL (757.17 mM); DMSO: ≥ 100 mg/mL (757.17 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
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