5-(N,N-Hexamethylene)-amiloride
(Synonyms: 阿米洛利,Hexamethylene amiloride; HMA) 目录号 : GC35147
一键复制产品信息
5-(N,N-Hexamethylene)-amiloride是一种强效的Na+/H+交换体抑制剂，对肿瘤细胞具有毒性。
Cas No.:1428-95-1
Sample solution is provided at 25 µL, 10mM.
_1-3.$$$39978408@51.jpg');)
_1-9.$$$38538795@65.jpg');)
_1-9.$$$39112701@51.jpg');)
_1-7.$$$37316672@70.jpg');)
_366-372.$$$36198801@70.jpg');)
.$$$38565142@65.jpg');)
_1867-1883.$$$33248023@67.jpg');)
_eads6055.$$$39977546@45.jpg');)
_eadm9805.$$$40080571@45.jpg');)
_eadj3020.$$$39666821@45.jpg');)
_1-20.$$$39757301@28.jpg');)
_1-24.$$$38898113@28.jpg');)
_273-287.$$$36806353@46.jpg');)
_1-16.$$$37156877@44.jpg');)
_1-19.$$$37460805@44.jpg');)
_1291-1307.$$$34518654@46.jpg');)
5-(N,N-Hexamethylene)-amiloride is a potent inhibitor of the Na+/H+ exchanger and is toxic to tumor cells [1]. 5-(N,N-Hexamethylene)-amiloride can inhibit DNA synthesis in regenerating liver and induce cell apoptosis, while activating the activity of Jun N-terminal kinase (JNK)[2]. 5-(N,N-Hexamethylene)-amiloride has been widely used to inhibit the growth of Cryptococcus strains and as a starting point for antifungal drug development to develop new analogues with high antifungal activity[3]. 5-(N,N-Hexamethylene)-amiloride has fluorescent properties and can regulate intracellular acidity, which can be used as a self-biomarker of pH changes in cellular studies[4].
In vitro, 5-(N,N-hexamethylene)-amiloride treatment for 48 hours inhibited the replication of mouse hepatitis virus (MHV) and human coronavirus 229E (HCoV-229E) in L929 cells, with EC50 values of 3.91μM and 1.34μM, respectively[5]. Treatment of RPMI-8226 cells with 20μM 5-(N,N-hexamethylene)-amiloride for 48 hours led to cell proliferation inhibition, and caused intracellular acidification[6]. 80µM of 5-(N,N-hexamethylene)-amiloride was applied for 24 hours to induce programmed necrosis in the cultured MCF7 cells through lysosomal and reactive oxygen species (ROS)-dependent mechanisms[7].
In vivo, 5-(N,N-hexamethylene)-amiloride treatment via intraperitoneal injection at a dose of 10mg/kg/day for 14 days suppressed tumor growth in the RPMI-8226 cell xenograft mouse models without affecting body weight[5].
References:
[1] Luo J, Tannock I F. Inhibition of the regulation of intracellular pH: potential of 5-(N, N-hexamethylene) amiloride in tumour-selective therapy[J]. British journal of cancer, 1994, 70(4): 617-624.
[2] Suzuki T, Tsukamoto I. Apoptosis induced by 5-(N, N-hexamethylene)-amiloride in regenerating liver after partial hepatectomy[J]. European journal of pharmacology, 2004, 503(1-3): 1-7.
[3] Vu K, Buckley B J, Bujaroski R S, et al. Antifungal activity of 6-substituted amiloride and hexamethylene amiloride (HMA) analogs[J]. Frontiers in Cellular and Infection Microbiology, 2023, 13: 1101568.
[4] Giansanti V, Santamaria G, Torriglia A, et al. Fluorescence properties of the Na+/H+ exchanger inhibitor HMA (5-(N, N-hexamethylene) amiloride) are modulated by intracellular pH[J]. European Journal of Histochemistry: EJH, 2012, 56(1): e3.
[5] Wilson L, Gage P, Ewart G. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication[J]. Virology, 2006, 353(2): 294-306.
[6] Yang N, Dong Z, Xiao W, et al. Hexamethylene amiloride induces lysosome-mediated cell death in multiple myeloma through transcription factor E3[J]. Cell Death Discovery, 2024, 10(1): 505.
[7] Rowson-Hodel A R, Berg A L, Wald J H, et al. Hexamethylene amiloride engages a novel reactive oxygen species-and lysosome-dependent programmed necrotic mechanism to selectively target breast cancer cells[J]. Cancer letters, 2016, 375(1): 62-72.
5-(N,N-Hexamethylene)-amiloride是一种强效的Na+/H+交换体抑制剂，对肿瘤细胞具有毒性[1]。5-(N,N-Hexamethylene)-amiloride可抑制再生肝中的DNA合成并诱导细胞凋亡，同时激活Jun N末端激酶（JNK）的活性[2]。5-(N,N-Hexamethylene)-amiloride已被广泛用于抑制隐球菌菌株的生长，并作为抗真菌药物开发的起点，以开发具有高抗真菌活性的新型类似物[3]。5-(N,N-Hexamethylene)-amiloride具有荧光特性，可调节细胞内酸度，在细胞研究中可用作pH变化的自身生物标志物[4]。
在体外，5-(N,N-Hexamethylene)-amiloride处理48小时抑制了小鼠肝炎病毒（MHV）和人冠状病毒229E（HCoV-229E）在L929细胞中的复制，EC50值分别为3.91µM和1.34µM[5]。使用20µM的5-(N,N-Hexamethylene)-amiloride处理RPMI-8226细胞48小时，导致细胞增殖受抑制，并引起细胞内酸化[6]。使用80µM的5-(N,N-Hexamethylene)-amiloride处理24小时，通过溶酶体和活性氧（ROS）依赖的机制诱导培养的MCF7细胞发生程序性坏死[7]。
在体内，每日腹腔注射10mg/kg的5-(N,N-Hexamethylene)-amiloride，持续14天，抑制了RPMI-8226细胞异种移植小鼠模型中的肿瘤生长，且未影响体重[5]。
| Cell experiment [1]: | |
Cell lines | MCF-7 cells |
Preparation Method | MCF-7 cells were cultured in high-glucose DMEM medium, supplemented with 10% fetal bovine serum, 100U/ml penicillin and 100μg/ml streptomycin, in a 37°C humidified environment with 5% CO2. MCF-7 cells were seeded at a density of 5×104/ml in 96-well plates. The cells were treated with different concentrations of 5-(N,N-hexamethylene)-amiloride (0, 10, 20, 40, and 80μM). After 24 hours, the cell viability was analyzed. |
Reaction Conditions | 0, 1, 2, 5, 10, and 20μM; 24h |
Applications | 5-(N,N-hexamethylene)-amiloride treatment reduced the cell viability of MCF-7 cells in a dose-dependent manner. |
| Animal experiment [2]: | |
Animal models | Female BALB/c Nude mice |
Preparation Method | Female BALB/c Nude mice, 4-6 weeks old and weighing 20g, were housed in a specific pathogen-free (SPF) animal house at 24±2°C temperature and 55±5% humidity and maintained on a 12h light/12h dark circadian rhythm. Mice received a standard diet and water ad libitum. RPMI-8226 cells (1×107 cells) were injected subcutaneously into the right abdomen of mice. When the tumors were palpable, the mice were randomly divided into two groups: the experimental group received 5-(N,N-hexamethylene)-amiloride (10mg/kg; i.p.) once a day for 14 consecutive days; Mice in the control group were intraperitoneally injected with normal saline. Tumor volume and body weight of mice were analyzed. |
Dosage form | 10mg/kg/day for 14 days; i.p. |
Applications | 5-(N,N-hexamethylene)-amiloride treatment suppressed tumor growth in the RPMI-8226 cell xenograft mouse model without affecting body weight. |
References: | |
| Cas No. | 1428-95-1 | SDF | |
| 别名 | 阿米洛利,Hexamethylene amiloride; HMA | ||
| Canonical SMILES | O=C(C1=NC(Cl)=C(N2CCCCCC2)N=C1N)NC(N)=N | ||
| 分子式 | C12H18ClN7O | 分子量 | 311.77 |
| 溶解度 | DMSO: 100 mg/mL (320.75 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.2075 mL | 16.0375 mL | 32.0749 mL |
| 5 mM | 641.5 μL | 3.2075 mL | 6.415 mL |
| 10 mM | 320.7 μL | 1.6037 mL | 3.2075 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。
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet