5-(N,N-Hexamethylene)-amiloride (Synonyms: HMA) |
Catalog No.GC35147
One-Click Copy Product Info
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5-(N,N-Hexamethylene)-amiloride is a potent inhibitor of the Na+/H+ exchanger and is toxic to tumor cells.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 1428-95-1
Sample solution is provided at 25 µL, 10mM.
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.
| 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 | |
| Synonyms | HMA | ||
| Canonical SMILES | O=C(C1=NC(Cl)=C(N2CCCCCC2)N=C1N)NC(N)=N | ||
| Formula | C12H18ClN7O | M.Wt | 311.77 |
| Solubility | DMSO: 100 mg/mL (320.75 mM) | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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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 |
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Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 40 reference(s) in Google Scholar.)