3-Aminopropionitrile fumarate 2:1 (Di-β-aminopropionitrile fumarate)
(Synonyms: β-丙炔腈) 目录号 : GC30510
3-Aminopropionitrile fumarate 2:1是一种不可逆赖氨酰氧化酶（LOX）抑制剂。
Cas No.:2079-89-2
Sample solution is provided at 25 µL, 10mM.
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3-Aminopropionitrile fumarate 2:1 is an irreversible lysyl oxidase (LOX) inhibitor [1]. 3-Aminopropionitrile fumarate 2:1 reduces the stability of the fibril network by inhibiting LOX-catalyzed collagen-elastin cross-linking [2]. 3-Aminopropionitrile fumarate 2:1 is used to study fibrosis, scar formation, metabolic disorders, and tumor invasion [3-4].
In MT6 cells, pretreatment with 3-Aminopropionitrile fumarate 2:1 (625μM; 48h) reduces the cytotoxicity of chemotherapeutic drugs. [5]. In Caco2 PLEKHA7 KO cells, 3-Aminopropionitrile fumarate 2:1 (150μM; 14d) treatment inhibits cell invasion [6].
In thoracic Alzheimer's disease (TAD) mice model, 3-Aminopropionitrile fumarate 2:1 (0.25% wt/vol; po; 28d) induced a significant upregulation of aortic gene expression and plasma MMP8 levels in mice [7]. In C56BL/6 mice, oral 3-Aminopropionitrile fumarate 2:1 (0.25% wt/vol; po; 100d) combined with periaortic elastase can induce chronic late abdominal aortic aneurysm [8].
References:
[1]. Wilk A, Grajkowski A, Phillips L R, et al. The 4-[N-methyl-N-(2, 2, 2-trifluoroacetyl) amino] butyl group as an alternative to the 2-cyanoethyl group for phosphate protection in the synthesis of oligodeoxyribonucleotides[J]. The Journal of Organic Chemistry, 1999, 64(20): 7515-7522.
[2]. Martínez-Martínez E, Rodríguez C, Galán M, et al. The lysyl oxidase inhibitor (β-aminopropionitrile) reduces leptin profibrotic effects and ameliorates cardiovascular remodeling in diet-induced obesity in rats[J]. Journal of molecular and cellular cardiology, 2016, 92: 96-104.
[3]. Lata A, Gowri C, Dhar S C, et al. Topical β-aminopropionitrile and biochemistry of granuloma tissue[J]. Journal of Surgical Research, 1988, 44(1): 67-72.
[4]. Halsey G. Cellular Mechanism of Pentagalloyl Gucose-Mediated Prevention and Reversal of Abdominal Aortic Aneurysms[D]. Clemson University, 2023.
[5]. Schütze F, Röhrig F, Vorlová S, et al. Inhibition of lysyl oxidases improves drug diffusion and increases efficacy of cytotoxic treatment in 3D tumor models[J]. Scientific reports, 2015, 5(1): 17576.
[6]. Daulagala A C, Cetin M, Nair-Menon J, et al. The epithelial adherens junction component PLEKHA7 regulates ECM remodeling and cell behavior through miRNA-mediated regulation of MMP1 and LOX[J]. bioRxiv, 2024.
[7]. Zhang C, Niu K, Ren M, et al. Targeted inhibition of matrix metalloproteinase-8 prevents aortic dissection in a murine model[J]. Cells, 2022, 11(20): 3218.
[8]. Lu G, Su G, Davis J P, et al. A novel chronic advanced stage abdominal aortic aneurysm murine model[J]. Journal of vascular surgery, 2017, 66(1): 232-242. e4.
3-Aminopropionitrile fumarate 2:1是一种不可逆赖氨酰氧化酶（LOX）抑制剂 [1]。3-Aminopropionitrile fumarate 2:1通过抑制LOX催化的胶原-弹性蛋白交联来降低纤维网络的稳定性 [2]。3-Aminopropionitrile fumarate 2:1用于研究纤维化、瘢痕形成、代谢紊乱和肿瘤侵袭 [3-4]。
在MT6细胞中，用3-Aminopropionitrile fumarate 2:1（625μM；48h）预处理可降低化疗药物的细胞毒性 [5]。在Caco2 PLEKHA7 KO细胞中，用3-Aminopropionitrile fumarate 2:1（150μM；14d）治疗抑制细胞的侵袭 [6]。
在胸腔阿尔茨海默病（TAD）小鼠模型中，3-Aminopropionitrile fumarate 2:1（0.25% wt/vol；po；28d）诱导小鼠主动脉基因表达和血浆MMP8水平显著上调 [7]。在C56BL/6小鼠中，口服3-Aminopropionitrile fumarate 2:1（0.25% wt/vol；po；100d）联合主动脉周围弹性蛋白酶可诱发慢性晚期腹主动脉瘤 [8]。
| Cell experiment [1]: | |
Cell lines | MT6 cells |
Preparation Method | Tumor cells were suspended at a density of 1.25 × 105 cells/mL in 60% (v/v) complete medium supplemented with 40% (v/v) bovine collagen I solution (3mg/mL). The pH was adjusted with 0.1M NaOH (10μL/mL suspension) and NaHCO3 (5μL/mL suspension). 40μL of the suspension per well was transferred to a 96-well culture plate and incubated at 37℃, 5% CO2 for 60 minutes to allow the collagen to solidify. 160μL of complete medium (supplemented with 625μM 3-Aminopropionitrile fumarate 2:1) was added, and the cells were incubated at 37℃, 5% CO2, 2% O2. After 48 hours, 50μL of DMEM containing cytotoxic chemotherapy drugs at 5x the indicated concentration was added to each well without removing the medium beforehand. Six replicates were performed for each concentration. After 60 minutes, the culture medium was removed, the cells were carefully washed, and the culture medium was changed three times, 30 minutes each time. Afterwards, the embedded cells were incubated for 72 hours. Relative remaining viable cells were determined using the resazurin assay. |
Reaction Conditions | 625μM; 48h |
Applications | Pretreatment with 3-Aminopropionitrile fumarate 2:1 reduces the cytotoxicity of chemotherapeutic drugs. |
| Animal experiment [2]: | |
Animal models | Thoracic Alzheimer's disease (TAD) mice model |
Preparation Method | For TAD model, three-week-old mice (WT: ApoE −/− /MMP8 +/+ or MMP8_KO: ApoE −/− /MMP8 −/−) were fed a normal diet and randomly administered vehicle (water) or freshly prepared 3-Aminopropionitrile fumarate 2:1 solution (0.25% wt/vol) in drinking water for up to 4 weeks. To determine the therapeutic potential of MMP8, mice were randomly divided into two groups, one of which received an intraperitoneal injection of vehicle (1% DMSO) or a specific MMP8i. Starting one day before 3-Aminopropionitrile fumarate 2:1 administration, vehicle or MMP8i were injected daily at a concentration of 5mg/kg for up to 28 days. At the end of the protocol, all mice were euthanized under deep anesthesia with 100% O2/5% isoflurane followed by decapitation. |
Dosage form | 0.25% wt/vol; po; 28d |
Applications | 3-Aminopropionitrile fumarate 2:1 induced a significant upregulation of aortic gene expression and plasma MMP8 levels in mice. |
References: | |
| Cas No. | 2079-89-2 | SDF | |
| 别名 | β-丙炔腈 | ||
| Canonical SMILES | OC(/C=C/C(O)=O)=O.NCCC#N | ||
| 分子式 | NH2CH2CH2CN · ½ (HO2CCH=CHCO2H) | 分子量 | 128.13 |
| 溶解度 | Water : 125 mg/mL (487.79 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 | 7.8046 mL | 39.0229 mL | 78.0457 mL |
| 5 mM | 1.5609 mL | 7.8046 mL | 15.6091 mL |
| 10 mM | 0.7805 mL | 3.9023 mL | 7.8046 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。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
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