Aminooxyacetic Acid
(Synonyms: 2-(氨基氧基)乙酸,Aminooxyacetate) 目录号 : GC45380氨基氧乙酸是 GABA-t 的抑制剂，也可抑制 CBS 和 CSE，IC50 分别为 8.5 和 1.1 μM。
Cas No.:645-88-5
Sample solution is provided at 25 µL, 10mM.
Aminooxyacetic Acid, an inhibitor of GABA-t, is also inhibited CBS and CSE with an IC50s of 8.5 and 1.1 μM.
The CCK-8 assay indicated that Aminooxyacetic Acid inhibited the viability of colon cancer cells in a concentration-dependent manner. Aminooxyacetic Acid (100 and 200 mol/L) had no effect on the survival of HCT116 and HT29 cells, respectively [1]. Aminooxyacetic Acid also decreased the glycolytic rate and the levels of extracellular lactate and pyruvate, without affecting the mitochondrial membrane potential of C6 cells[2]. Aminooxyacetic acid inhibits the malate-aspartate shuttle in isolated nerve terminals and prevents the mitochondria from utilizing glycolytic substrates[3].
Aminooxyacetic acid can improve learning and memory in a chronic alcoholism rat model, which may be associated with reduction of hippocampal H2S level and mitochondrial ATPase activity, and up-regulation of myelin basic protein levels in the hippocampus [4]. TCE decreased fetal weight, and this was prevented by Aminooxyacetic Acid but not NAC pre/co-treatment to TCE. Although Aminooxyacetic Acid inhibited CCBL activity in maternal kidney, it did not inhibit CCBL activity in maternal liver and placenta, suggesting that Aminooxyacetic Acid prevention of TCE-induced decreased fetal weight was due to CCBL activity inhibition in the kidneys but not liver or placenta [5]. Tumor (HCT116 cells) growth was significantly reduced by 9 mg/kg/day Aminooxyacetic Acid [6]. Aminooxyacetic acid induced accumulation of GABA in the rat brain [7]. Both H2S biosynthesis inhibition (using Aminooxyacetic Acid) and H2S donation (using AP39) suppresses inflammatory mediator production and reduces multi-organ injury in a murine model of burn injury, both at an early time point and at a later time point [8]. Aminooxyacetic Acid inhibited growth of SUM159, SUM149, and MCF-7 xenografts and c-myc-overexpressing transgenic mouse mammary tumors [9].
References:
[1]. Yue T, Zuo S, et,al. Aminooxyacetic acid (AOAA) sensitizes colon cancer cells to oxaliplatin via exaggerating apoptosis induced by ROS. J Cancer. 2020 Jan 20;11(7):1828-1838. doi: 10.7150/jca.35375. PMID: 32194794; PMCID: PMC7052847.
[2]. Wang C, Chen H, et,al. Malate-aspartate shuttle inhibitor aminooxyacetic acid leads to decreased intracellular ATP levels and altered cell cycle of C6 glioma cells by inhibiting glycolysis. Cancer Lett. 2016 Aug 1;378(1):1-7. doi: 10.1016/j.canlet.2016.05.001. Epub 2016 May 6. PMID: 27157912.
[3]. Kauppinen RA, Sihra TS, et,al. Aminooxyacetic acid inhibits the malate-aspartate shuttle in isolated nerve terminals and prevents the mitochondria from utilizing glycolytic substrates. Biochim Biophys Acta. 1987 Sep 14;930(2):173-8. doi: 10.1016/0167-4889(87)90029-2. PMID: 3620514.
[4]. Du AL, Qin HZ, et,al. Aminooxyacetic acid improves learning and memory in a rat model of chronic alcoholism. Neural Regen Res. 2018 Sep;13(9):1568-1574. doi: 10.4103/1673-5374.237120. PMID: 30127117; PMCID: PMC6126113.
[5]. Su AL, Lash LH, et,al. N-Acetyl-L-cysteine and aminooxyacetic acid differentially modulate trichloroethylene reproductive toxicity via metabolism in Wistar rats. Arch Toxicol. 2021 Apr;95(4):1303-1321. doi: 10.1007/s00204-021-02991-8. Epub 2021 Feb 18. PMID: 33599830; PMCID: PMC8035313.
[6]. Chao C, Zatarain JR,et,al. Cystathionine-beta-synthase inhibition for colon cancer: Enhancement of the efficacy of aminooxyacetic acid via the prodrug approach. Mol Med. 2016 Sep;22:361-379. doi: 10.2119/molmed.2016.00102. Epub 2016 May 16. PMID: 27257787; PMCID: PMC5072412.
[7]. Pagliusi SR, Gomes C, et,al. Aminooxyacetic acid induced accumulation of GABA in the rat brain. Interaction with GABA receptors and distribution in compartments. Naunyn Schmiedebergs Arch Pharmacol. 1983 Apr;322(3):210-5. doi: 10.1007/BF00500767. PMID: 6306485.
[8]. Ahmad A, Szabo C. Both the H2S biosynthesis inhibitor aminooxyacetic acid and the mitochondrially targeted H2S donor AP39 exert protective effects in a mouse model of burn injury. Pharmacol Res. 2016 Nov;113(Pt A):348-355. doi: 10.1016/j.phrs.2016.09.013. Epub 2016 Sep 14. PMID: 27639598.
[9]. Korangath P, Teo WW, et,al.Targeting Glutamine Metabolism in Breast Cancer with Aminooxyacetate. Clin Cancer Res. 2015 Jul 15;21(14):3263-73. doi: 10.1158/1078-0432.CCR-14-1200. Epub 2015 Mar 26. PMID: 25813021; PMCID: PMC4696069.
氨基氧乙酸是 GABA-t 的抑制剂,也可抑制 CBS 和 CSE,IC50 分别为 8.5 和 1.1 μM。
CCK-8 测定表明氨基氧乙酸以浓度依赖性方式抑制结肠癌细胞的活力。氨基氧乙酸(100和200 mol/L)分别对HCT116和HT29细胞的存活没有影响[1]。 Aminoxyacetic Acid 还可以降低糖酵解速率以及细胞外乳酸和丙酮酸的水平,而不影响 C6 细胞的线粒体膜电位[2]。氨氧乙酸抑制孤立神经末梢的苹果酸-天冬氨酸穿梭,并阻止线粒体利用糖酵解底物[3]。
氨基氧乙酸可以改善慢性酒精中毒大鼠模型的学习和记忆,这可能与海马 H2S 水平和线粒体 ATP 酶活性降低以及海马髓鞘碱性蛋白水平上调有关 [4] 。 TCE 降低了胎儿体重,氨氧乙酸可以防止这种情况发生,但 NAC 对 TCE 进行预处理/联合处理则不能。虽然氨基氧乙酸抑制母体肾脏中的 CCBL 活性,但它不抑制母体肝脏和胎盘中的 CCBL 活性,这表明氨基氧乙酸预防 TCE 引起的胎儿体重下降是由于肾脏中的 CCBL 活性抑制,而不是肝脏或胎盘 <sup >[5]。 9 毫克/千克/天的氨基氧乙酸 [6] 显着降低了肿瘤（HCT116 细胞）的生长。氨氧乙酸诱导大鼠脑内 GABA 积累[7]。 H2S 生物合成抑制（使用氨基氧乙酸）和 H2S 捐赠（使用 AP39）均抑制炎症介质的产生并减少小鼠烧伤模型中的多器官损伤,无论是在早期时间点还是在稍后时间点[ 8]。氨基氧乙酸抑制 SUM159、SUM149 和 MCF-7 异种移植物和 c-myc 过表达转基因小鼠乳腺肿瘤的生长[9]。
| Kinase experiment [1]: | |
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Preparation Method |
Each reaction was performed in the presence of 100 μL sodium phosphate buffer containing 5 μg of CSE, 10 μM PLP and 1 mM of L-cys as substrates. Inhibitors( Aminooxyacetic Acid) were added 15 min before the L-cys at the indicated concentration and reactions allowed to proceed for 60 min. |
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Reaction Conditions |
10-7M - 10-4M Aminooxyacetic Acid at 37℃ for 60 min |
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Applications |
Aminooxyacetic Acid , a frequently used selective CBS inhibitor, also inhibited CSE with an IC50 of 1.1 μM. |
| Cell experiment [2]: | |
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Cell lines |
HCT116 and HT29 cells |
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Preparation Method |
To obtain a concentration of Aminooxyacetic Acid that inhibited cellular H2S synthesis but was noncytotoxic to cell survival, cells were treated with gradient concentrations of Aminooxyacetic Acid for 48 hours. After determining the Aminooxyacetic Acid concentrations, cells were treated with gradient concentrations of OXA in the presence or absence of this specific concentration of Aminooxyacetic Acid for 48 hours, and the IC50 values of OXA were measured. |
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Reaction Conditions |
100 and 200 µmol/L Aminooxyacetic Acid for 48 hours |
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Applications |
Aminooxyacetic Acid inhibited survival of colon cancer cell lines in a concentration-dependent manner, Aminooxyacetic Acid significantly decreased the IC50 values of OXA in HCT116 and HT29 cells. |
| Animal experiment [3]: | |
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Animal models |
Sixty 2-month-old, male, Sprague-Dawley rats weighing 120–160 g |
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Preparation Method |
To establish a model of chronic alcoholism, the model and Aminooxyacetic Acid remedy groups were given free access to 6% (v/v) alcohol solution for 28 days, with the alcohol solution being changed at 9:00 a.m. every day. From day 15 to day 28, rats in the Aminooxyacetic Acid remedy group were intraperitoneally injected once a day with 5 mg/kg Aminooxyacetic Acid dissolved in 1 mL of saline |
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Dosage form |
5 mg/kg Aminooxyacetic Acid from day 15 to day 28 |
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Applications |
Aminooxyacetic acid can improve learning and memory in a chronic alcoholism rat model. |
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References: [1]. Asimakopoulou A, Panopoulos P, Chasapis CT, Coletta C, Zhou Z, Cirino G, Giannis A, Szabo C, Spyroulias GA, Papapetropoulos A. Selectivity of commonly used pharmacological inhibitors for cystathionine β synthase (CBS) and cystathionine γ lyase (CSE). Br J Pharmacol. 2013 Jun;169(4):922-32. doi: 10.1111/bph.12171. PMID: 23488457; PMCID: PMC3687671. [2].Yue T, Zuo S, et,al. Aminooxyacetic acid (AOAA) sensitizes colon cancer cells to oxaliplatin via exaggerating apoptosis induced by ROS. J Cancer. 2020 Jan 20;11(7):1828-1838. doi: 10.7150/jca.35375. PMID: 32194794; PMCID: PMC7052847. [3].Du AL, Qin HZ, et,al. Aminooxyacetic acid improves learning and memory in a rat model of chronic alcoholism. Neural Regen Res. 2018 Sep;13(9):1568-1574. doi: 10.4103/1673-5374.237120. PMID: 30127117; PMCID: PMC6126113. |
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| Cas No. | 645-88-5 | SDF | |
| 别名 | 2-(氨基氧基)乙酸,Aminooxyacetate | ||
| 化学名 | 2-(aminooxy)-acetic acid | ||
| Canonical SMILES | OC(CON)=O | ||
| 分子式 | C2H5NO3 | 分子量 | 91.1 |
| 溶解度 | 5mg/mL in DMSO, 2mg/mL in DMF | 储存条件 | Store at -20°C, protect from light |
| 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 | 10.9769 mL | 54.8847 mL | 109.7695 mL |
| 5 mM | 2.1954 mL | 10.9769 mL | 21.9539 mL |
| 10 mM | 1.0977 mL | 5.4885 mL | 10.9769 mL |
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动物平均体重 | g | |
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动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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2.
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Quality Control & SDS
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- Purity: >98.00%
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