5-(N,N-Hexamethylene)-amiloride
Based on 3 publication(s) in Google Scholar
5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) derives from an amiloride and is a potent Na+/H+ exchanger inhibitor, which decreases the intracellular pH (pHi) and induces apoptosis in leukemic cells. 5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) is also an inhibitor of the HIV-1 Vpu virus ion channel and inhibits mouse hepatitis virus (MHV) replication and human coronavirus 229E (HCoV229E) replication in cultured L929 cells with EC50s of 3.91 μM and 1.34 μM, respectively.
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- Pureté : 99.14%
- CAS No.: 1428-95-1
- Formule: C12H18ClN7O
- Masse moléculaire:311.77
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Stockage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Protocole
- Pureté et documentation
- Références
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Help & FAQs
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Publications Citing Use of MedChemExpress (MCE) 5-(N,N-Hexamethylene)-amiloride
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Activité biologique
Description
IC50 & Target
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HIV-1 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HEK293 | IC50 |
0.27 μM
Compound: 2; HMA
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Displacement of [3H]ZM-241,385 from human N-terminal FLAG-tagged adenosine A2A receptor W246A 6.48 mutant expressed in HEK293 cell membrane by microbeta scintillation counting method
Displacement of [3H]ZM-241,385 from human N-terminal FLAG-tagged adenosine A2A receptor W246A 6.48 mutant expressed in HEK293 cell membrane by microbeta scintillation counting method
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[PMID: 27124340] |
| HEK293 | IC50 |
2.8 μM
Compound: 5; HMA
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Cytotoxicity against HEK293 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
Cytotoxicity against HEK293 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
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[PMID: 30130401] |
| HEK293 | IC50 |
5.1 μM
Compound: 2; HMA
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Displacement of [3H]ZM-241,385 from human N-terminal FLAG-tagged adenosine A2A receptor expressed in HEK293 cell membrane by microbeta scintillation counting method
Displacement of [3H]ZM-241,385 from human N-terminal FLAG-tagged adenosine A2A receptor expressed in HEK293 cell membrane by microbeta scintillation counting method
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[PMID: 27124340] |
| HepG2 | IC50 |
20.2 μM
Compound: 5; HMA
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Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
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[PMID: 30130401] |
| HT-1080 | IC50 |
13.8 μM
Compound: HMA
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Cytotoxicity against human HT-1080 cells assessed as inhibition of cell growth incubated for 48 hrs by WST-8 assay
Cytotoxicity against human HT-1080 cells assessed as inhibition of cell growth incubated for 48 hrs by WST-8 assay
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[PMID: 38246115] |
| HT-1080 | IC50 |
6.6 μM
Compound: 5; HMA
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Cytotoxicity against human HT1080 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
Cytotoxicity against human HT1080 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
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[PMID: 30130401] |
| MDA-MB-231 | IC50 |
27.3 μM
Compound: 5; HMA
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Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by CellTiter 96 Aqueous One solution cell proliferation assay
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[PMID: 30130401] |
| NHDF | IC50 |
23.7 μM
Compound: HMA
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Cytotoxicity against HDF cells assessed as inhibition of cell growth incubated for 48 hrs by WST-8 assay
Cytotoxicity against HDF cells assessed as inhibition of cell growth incubated for 48 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-1 | IC50 |
10.6 μM
Compound: HMA
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Cytotoxicity against human TE-1 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-1 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-10 | IC50 |
11.8 μM
Compound: HMA
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Cytotoxicity against human TE-10 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-10 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-11 | IC50 |
5.6 μM
Compound: HMA
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Cytotoxicity against human TE-11 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-11 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-15 | IC50 |
17.9 μM
Compound: HMA
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Cytotoxicity against human TE-15 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-15 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-5 | IC50 |
4.7 μM
Compound: HMA
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Cytotoxicity against human TE-5 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-5 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-6 | IC50 |
13.6 μM
Compound: HMA
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Cytotoxicity against human TE-6 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-6 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TE-9 | IC50 |
9.6 μM
Compound: HMA
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Cytotoxicity against human TE-9 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TE-9 cells expressing NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
| TMK-1 | IC50 |
42.8 μM
Compound: HMA
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Cytotoxicity against human TMK-1 cells expressing HA-tagged full length human NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
Cytotoxicity against human TMK-1 cells expressing HA-tagged full length human NHE5 assessed as inhibition of cell growth incubated for 72 hrs by WST-8 assay
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[PMID: 38246115] |
In Vitro
5-(N,N-Hexamethylene)-amiloride inhibits human cardiac ion channels hERG (in CHO cells), Nav1.5 and Cav1.2 (in EHK293 cells) with of 3.3 μM, 30 μM, 8.3 μM, respectively, inelectrophysiology assays[3].
5-(N,N-Hexamethylene)-amiloride (1 μM; 0-60 min; 37 °C) exhibits microsomal stability, (1 μg/mL; 4.2 h; 37 °C) shows mouse plasma stability and plasma protein binding, (20 μM; 4 h) displays Caco-2 cell permeability, cardiac ion channel activity[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:In vitro pharmacokinetics properties
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Concentration:1 μM
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Incubation Time:0-60 min
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Result:
t1/2 (min) CLint (μL/min/mg protein) CLint (μL/min/mg protein) Human liver microsomers in vitro 73 24 74 Mouse liver microsomers in vitro 2.4 726 2243
In Vivo
In vivo pharmacokinetics in mice or rat model[3]
Dosage: 2.5 mg/kg Administration: Intravenous injection; single does; collected 10 min and 60 min after treatment.
| t1/2 (h) | Plasma CLint (mL/min/kg) | Plasma Vss (L/kg) | Plasma AUC0-inf (h·μM) | B/P ratio | Blood CL (mL/min/kg) | Blood Vss (L/kg) | |
| Female Balb/c mice | 0.62 | 86 | 2.0 | 1.5 | 1.5 | 59 | 1.4 |
| Sprague Dawley rats | 3.2 | 83.5 | 5.3 | 1.6 | 1.8 | 46.2 | 2.9 |
| % IV dose excreted in urine (0-24 h) | Renal Blood CL (mL/min/kg) | Non-Renal Blood CL (mL/min/kg) | |||||
| Sprague Dawley rats | 0.5 | 0.2 | 46.0 |
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 1428-95-1
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Appearance Solid
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Masse moléculaire 311.77
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Formule C12H18ClN7O
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Color Light yellow to yellow
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SMILES
O=C(C1=NC(Cl)=C(N2CCCCCC2)N=C1N)NC(N)=N
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Synonyms
Hexamethylene amiloride; HMA
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Publications (3)
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Journal Impact Factor
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Most Recent
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Sci Adv
Anti-phagocytosis-blocking repolarization-resistant membrane-fusogenic liposome (ARMFUL) for adoptive cell immunotherapy. [Abstract]2023 Aug 9;9(32):eadh2413. PMID: 37556535 -
STAR Protoc
Protocol for detecting lysosome quantity and membrane permeability in acute myeloid leukemia cell lines. [Abstract]2024 Sep 12;5(3):103309. PMID: 39269898 -
Solvant et solubilité
In Vitro:
DMSO : 100 mg/mL (320.75 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: 2.08 mg/mL (6.67 mM); Clear solution; Need ultrasonic
This protocol yields a clear solution of 2.08 mg/mL.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.08 mg/mL (6.67 mM); Clear solution
This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocole
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Two-electrode voltage clamp in Xenopus oocytes
Two-electrode voltage clamp measures whole-oocyte membrane current from Xenopus oocytes expressing exogenous ion channels, receptors, or transporters; one intracellular microelectrode senses membrane voltage, and the second injects current so the amplifier can hold the membrane at command voltages while recording the compensating current as the functional readout. The method is suited to Xenopus oocytes because their large size supports microinjection and intracellular electrode impalement, but the large membrane area can limit voltage-clamp speed and accuracy, especially for large or fast currents.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
Pureté et documentation
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Fiche technique (280 KB)
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SDS (480 KB)
- English - EN (480 KB)
- Français - FR (480 KB)
- Deutsch - DE (480 KB)
- Norwegian - NO (480 KB)
- Español - ES (480 KB)
- Swedish - SV (480 KB)
- Italian - IT (480 KB)
- Korean - KR (480 KB)
- Portuguese - PT (480 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Rich IN, et al. Apoptosis of leukemic cells accompanies reduction in intracellular pH after targeted inhibition of the Na(+)/H(+) exchanger. Blood. 2000 Feb 15;95(4):1427-34. [Content Brief]
[2]. Wilson L, et al. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication. Virology. 2006 Sep 30;353(2):294-306. Epub 2006 Jul 3. [Content Brief]
[3]. Buckley BJ, et al. Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride. Bioorg Med Chem. 2021 May 1;37:116116. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.2075 mL | 16.0375 mL | 32.0749 mL | 80.1873 mL |
| 5 mM | 0.6415 mL | 3.2075 mL | 6.4150 mL | 16.0375 mL | |
| 10 mM | 0.3207 mL | 1.6037 mL | 3.2075 mL | 8.0187 mL | |
| 15 mM | 0.2138 mL | 1.0692 mL | 2.1383 mL | 5.3458 mL | |
| 20 mM | 0.1604 mL | 0.8019 mL | 1.6037 mL | 4.0094 mL | |
| 25 mM | 0.1283 mL | 0.6415 mL | 1.2830 mL | 3.2075 mL | |
| 30 mM | 0.1069 mL | 0.5346 mL | 1.0692 mL | 2.6729 mL | |
| 40 mM | 0.0802 mL | 0.4009 mL | 0.8019 mL | 2.0047 mL | |
| 50 mM | 0.0641 mL | 0.3207 mL | 0.6415 mL | 1.6037 mL | |
| 60 mM | 0.0535 mL | 0.2673 mL | 0.5346 mL | 1.3365 mL | |
| 80 mM | 0.0401 mL | 0.2005 mL | 0.4009 mL | 1.0023 mL | |
| 100 mM | 0.0321 mL | 0.1604 mL | 0.3207 mL | 0.8019 mL |
5-(N,N-Hexamethylene)-amiloride Related Classifications
HY-128067 Related Classifications
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