GLPBio

5-(N,N-Hexamethylene)-amiloride

Catalog No.: GC35147Purity:>98.00%Synonyms: HMA
COASDSData Sheet
5-(N,N-Hexamethylene)-amiloride is a potent inhibitor of the Na+/H+ exchanger and is toxic to tumor cells.

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5-(N,N-Hexamethylene)-amiloride
Cas No.: 1428-95-1
10mM (in 1mL DMSO)In Stock
$62.00
1
1mgIn Stock
$28.00
1
5mgIn Stock
$56.00
1
10mgIn Stock
$90.00
1
50mgIn Stock
$224.00
1
100mgIn Stock
$375.00
1
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Citations

1 publicationsPublications from researchers using this product

Description

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.

Protocol

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:
[1] 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.
[2] 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.

Product Documents

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
1428-95-1
Synonyms
HMA
SMILES
O=C(C1=NC(Cl)=C(N2CCCCCC2)N=C1N)NC(N)=N
Molecular Formula
C12H18ClN7O
Molecular Weight
311.77
Solubility
DMSO: 100 mg/mL (320.75 mM)
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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