Aminooxyacetic acid hemihydrochloride (Carboxymethoxylamine Hemihydrochloride)
(Synonyms: 氨氧基乙酸半盐酸盐; Carboxymethoxylamine hemihydrochloride; Aminooxyacetate hemihydrochloride) 目录号 : GC34064
Aminooxyacetic acid hemihydrochloride (Carboxymethoxylamine Hemihydrochloride)是一种苹果酸-天冬氨酸穿梭(MAS)抑制剂和γ-氨基丁酸转氨酶(GABA-T)抑制剂。
Cas No.:2921-14-4
Sample solution is provided at 25 µL, 10mM.
Aminooxyacetic acid hemihydrochloride (Carboxymethoxylamine Hemihydrochloride) is an inhibitor of the malate-aspartate shuttle (MAS) and γ-aminobutyric acid transaminase (GABA-T). Aminooxyacetic acid hemihydrochloride blocks NADH transfer between mitochondria and the cytoplasm by interfering with malate-aspartate shuttle function. Aminooxyacetic acid hemihydrochloride can be used in studies related to energy metabolism, bioenergetic processes, GABA-related metabolic pathways in the nervous system, and cancer[1-4].
In vitro, Aminooxyacetic acid hemihydrochloride (5mM) treated rheumatoid arthritis fibroblast-like synoviocytes (RA-FLSs) for 36 hours. Aminooxyacetic acid hemihydrochloride significantly inhibited the malate-aspartate shuttle in RA-FLSs, thereby inhibiting ASIC1a-mediated migration and invasion of RA-FLSs[5]. Aminooxyacetic acid hemihydrochloride (0.5–2mM) treated RM-1 prostate cancer cells for 24 hours, significantly inhibiting cell proliferation, migration, and invasiveness, while reducing ATP levels and inducing apoptosis[6].
In vivo, Aminooxyacetic acid hemihydrochloride (5mg/kg; every 2 days) was administered intraperitoneally to ovariectomized C57BL/6J mice for 6 weeks. Aminooxyacetic acid hemihydrochloride effectively rescued bone loss[7]. After 16 weeks of N-nitrosodiethylamine/CCl4 treatment, Aminooxyacetic acid hemihydrochloride (5mg/kg; twice a week) was administered intraperitoneally to LKO mice for 16 weeks. Aminooxyacetic acid hemihydrochloride significantly inhibited tumor progression[8].
References:
[1] Wang C, Chen H, Zhang M, 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.
[2] Pagliusi SR, Gomes C, Leite JR, 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.
[3] Korangath P, Teo WW, Sadik H, et al. Targeting Glutamine Metabolism in Breast Cancer with Aminooxyacetate. Clin Cancer Res. 2015 Jul 15;21(14):3263-73.
[4] Katayama R, Nagata S, Iida H, et al. Possible role of cysteine-S-conjugate β-lyase in species differences in cisplatin nephrotoxicity. Food Chem Toxicol. 2011 Sep;49(9):2053-9.
[5] Hu W, Wang K, Dong Y, et al. RIPK3 promotes ASIC1a-mediated fibroblast-like synoviocyte migration and invasion via malate shuttle-driven mitochondrial respiration in rheumatoid arthritis. Theranostics. 2025 Aug 11;15(17):8719-8737.
[6] Teng H, Yang B, Su Y, et al. Aminooxyacetic acid hemihydrochloride leads to decreased intracellular ATP levels and altered cell cycle of prostate cancer cells by suppressing energy metabolism. Biomed Pharmacother. 2023 Nov;167:115605.
[7] Yang B, Su Y, Han S, et al. Aminooxyacetic acid hemihydrochloride inhibits osteoclast differentiation and bone resorption by attenuating oxidative phosphorylation. Front Pharmacol. 2022 Sep 30;13:980678.
[8] Xiang J, Chen C, Liu R, et al. Gluconeogenic enzyme PCK1 deficiency promotes CHK2 O-GlcNAcylation and hepatocellular carcinoma growth upon glucose deprivation. J Clin Invest. 2021 Apr 15;131(8):e144703.
Aminooxyacetic acid hemihydrochloride (Carboxymethoxylamine Hemihydrochloride)是一种苹果酸-天冬氨酸穿梭(MAS)抑制剂和γ-氨基丁酸转氨酶(GABA-T)抑制剂。Aminooxyacetic acid hemihydrochloride可通过干扰苹果酸-天冬氨酸穿梭功能阻断线粒体与胞质之间的NADH传递。Aminooxyacetic acid hemihydrochloride可用于能量代谢、生物能学过程、神经系统GABA相关代谢通路以及癌症的相关研究[1-4]。
在体外,Aminooxyacetic acid hemihydrochloride(5mM)处理类风湿性关节炎类纤维细胞样滑膜细胞(RA-FLSs)36小时。Aminooxyacetic acid hemihydrochloride显著抑制RA-FLSs的苹果酸-天冬氨酸穿梭,从而抑制ASIC1a介导的RA-FLSs迁移和侵袭[5]。Aminooxyacetic acid hemihydrochloride(0.5–2mM)处理RM-1前列腺癌细胞24小时,显著抑制细胞增殖、迁移和侵袭,同时降低ATP水平并诱导细胞凋亡[6]。
在体内,Aminooxyacetic acid hemihydrochloride(5mg/kg;每两天一次)腹腔注射于卵巢切除的C57BL/6J小鼠,持续6周。Aminooxyacetic acid hemihydrochloride有效挽回了骨丢失[7]。在N-nitrosodiethylamine/CCl4处理16周后,Aminooxyacetic acid hemihydrochloride(5mg/kg;每周两次)腹腔注射于LKO小鼠,持续16周。Aminooxyacetic acid hemihydrochloride显著抑制了肿瘤的进展[8]。
| Cell experiment [1]: | |
Cell lines | RM-1 cells (mouse prostate cancer cell line) |
Preparation Method | RM-1 cells were maintained in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% fetal bovine serum (FBS) and 1% penicillin/streptomycin (P/S) at 37°C, 5% CO₂, and 95% air humidity. RM-1 cells were treated with Aminooxyacetic acid hemihydrochloride (0.5-2mM). |
Reaction Conditions | 0.5–2mM; 24h |
Applications | Aminooxyacetic acid hemihydrochloride significantly inhibited cell proliferation, migration, and invasiveness, decreased ATP levels, increased reactive oxygen species (ROS), halted the cell cycle phase, and triggered apoptosis. Aminooxyacetic acid hemihydrochloride decreased mitochondrial membrane potential and the ability to uptake glucose. |
| Animal experiment [2]: | |
Animal models | C57BL/6J mice |
Preparation Method | Mice were ovariectomized (OVX) and, one week later, received intraperitoneal injections of Aminooxyacetic acid hemihydrochloride (5mg/kg) every 2 days for 6 weeks. |
Dosage form | 5mg/kg; i.p.; every 2 days for 6 weeks |
Applications | Aminooxyacetic acid hemihydrochloride treatment effectively rescued bone loss, improved bone parameters (BV/TV, Tb.N, Tb.Sp), decreased serum CTXI level, and inhibited excessive osteoclastogenesis in OVX mice. |
References: | |
| Cas No. | 2921-14-4 | SDF | |
| 别名 | 氨氧基乙酸半盐酸盐; Carboxymethoxylamine hemihydrochloride; Aminooxyacetate hemihydrochloride | ||
| Canonical SMILES | OC(CON)=O.[H]Cl.OC(CON)=O | ||
| 分子式 | NH2OCH2COOH · 0.5HCl | 分子量 | 109.3 |
| 溶解度 | DMSO : 42.9 mg/mL (392.50 mM) | 储存条件 | 4°C, protect from light |
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1 mg | 5 mg | 10 mg |
| 1 mM | 9.1491 mL | 45.7457 mL | 91.4913 mL |
| 5 mM | 1.8298 mL | 9.1491 mL | 18.2983 mL |
| 10 mM | 914.9 μL | 4.5746 mL | 9.1491 mL |
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