Thonzonium Bromidesurface active agent and inhibitor of V-ATPase proton transport CAS# 553-08-2 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 553-08-2 | SDF | Download SDF |
| PubChem ID | 11102 | Appearance | Powder |
| Formula | C32H55BrN4O | M.Wt | 591.71 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 30 mg/mL (50.70 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | hexadecyl-[2-[(4-methoxyphenyl)methyl-pyrimidin-2-ylamino]ethyl]-dimethylazanium;bromide | ||
| SMILES | CCCCCCCCCCCCCCCC[N+](C)(C)CCN(CC1=CC=C(C=C1)OC)C2=NC=CC=N2.[Br-] | ||
| Standard InChIKey | WBWDWFZTSDZAIG-UHFFFAOYSA-M | ||
| Standard InChI | InChI=1S/C32H55N4O.BrH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-27-36(2,3)28-26-35(32-33-24-19-25-34-32)29-30-20-22-31(37-4)23-21-30;/h19-25H,5-18,26-29H2,1-4H3;1H/q+1;/p-1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Thonzonium bromide is a monocationic detergent. Target: Antibacterial A solution of Thonzonium bromide is a surfactant and a detergent that promotes tissue contact by dispersion and penetration of the cellular debris and exudate of the containing solution. Thonzonium bromide is used in cortisporin-TC ear drops to help penetration of active ingredients through cellular debris for its antibacterial action. | |||||
| Kinase experiment [1]: | |
| ATP-dependent proton transport assay | Purified vacuolar membrane vesicles (10 μg of protein) were incubated with alexidine dihydrochloride or thonzonium bromide at the indicated concentrations for 10 min on ice. ATP-dependent proton transport was measured as follows: Fluorescence quenching of ACMA was monitored (ex 410 nm, em 490 nm) upon the addition of 0.5mM ATP and 1mM MgSO4. Initial velocities were calculated for 15 s following addition of MgATP (n=2). The apparently enhanced rate measured with benzbromarone and tolazamide was not dose-dependent and was sustained in the controls, when the drugs were added to the reaction mixture prior to the membrane vesicles. |
| Cell experiment [1]: | |
| Cell lines | In wild-type yeast cells |
| Preparation method | Limited solubility. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
| Reacting condition | Yeast cells expressing pHluorin were grown overnight to mid-log phase (0.4–0.6 A600/ml) and pre-incubated with 100 μM drug in 0.2% DMSO. |
| Applications | Treatment of yeast cells with thonzonium bromide significantly lowers the pH to (pHcyt 6.22±0.02), 10 μM thonzonium bromide reduces cell growth, with the cells developing a mild vma phenotype at 37 °C. Moreover, thonzonium bromide completely prevents yeast growth at 50 and 100 μM concentrations. |
| References: 1. Chan CY, Prudom C, Raines SM, et al. Inhibitors of V-ATPase proton transport reveal uncoupling functions of tether linking cytosolic and membrane domains of V0 subunit a (Vph1p). J Biol Chem, 2012, 287(13): 10236-10250. | |
Thonzonium Bromide Dilution Calculator
Thonzonium Bromide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.69 mL | 8.4501 mL | 16.9002 mL | 33.8003 mL | 42.2504 mL |
| 5 mM | 0.338 mL | 1.69 mL | 3.38 mL | 6.7601 mL | 8.4501 mL |
| 10 mM | 0.169 mL | 0.845 mL | 1.69 mL | 3.38 mL | 4.225 mL |
| 50 mM | 0.0338 mL | 0.169 mL | 0.338 mL | 0.676 mL | 0.845 mL |
| 100 mM | 0.0169 mL | 0.0845 mL | 0.169 mL | 0.338 mL | 0.4225 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Thonzonium Bromide is a surface active agent and an inhibitor of V-ATPase proton transport with EC50 value of 69 µM [1] [2].
Vacuolar ATPases (V-ATPases) are proton pumps that maintain pH homeostasis. V-ATPases couple the energy of ATP hydrolysis to proton transport across intracellular membranes [2].
Thonzonium Bromide is a surface active agent and an inhibitor of V-ATPase proton transport. In wild-type yeast cells, thonzonium bromide significantly decreased the cytosolic pH to 6.22. In vacuolar membrane vesicles, thonzonium bromide inhibited proton transport with EC50 value of 69 µM in a dose-dependent way. However, thonzonium bromide didn’t inhibit ATP hydrolysis, which suggested that thonzonium bromide uncoupled V-ATPase proton pumps. In wild-type yeast cells, thonzonium bromide (1 µM) didn’t inhibit cell growth. However, thonzonium bromide inhibited cell growth at 10 µM and caused a mild vma (vacuolar membrane ATPase) mutant growth phenotype. At concentrations up to 50 and 100 µM, thonzonium bromide completely inhibited yeast growth [2].
References:
[1]. Chafetz L, Greenough RC, Frank J. Thermal decomposition of thonzonium bromide. Pharm Res, 1986, 3(5): 298-301.
[2]. Chan CY, Prudom C, Raines SM, et al. Inhibitors of V-ATPase proton transport reveal uncoupling functions of tether linking cytosolic and membrane domains of V0 subunit a (Vph1p). J Biol Chem, 2012, 287(13): 10236-10250.
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Thermal decomposition of thonzonium bromide.[Pubmed:24271714]
Pharm Res. 1986 Oct;3(5):298-301.
Thonzonium Bromide, a quaternary ammonium compound used as a surface active agent in a phenylephrine nasal solution, gave a gas chromatographic peak which was proportional in height and area to its concentration. Quaternary ammonium salts are nonvolatile and polar, thus the peak was attributed to a thermal decomposition product. It was identified as hexadecyldimethylamine by spectroscopic analysis and comparison with an authentic sample. A second product was identified by mass spectroscopy as 2[(2-hexadecylmethylaminoethyl)(4-methoxybenzylamino)] pyrimidine, the desmethyl bromide product. These decomposition products were detected in stability samples of formulations.
Thonzonium bromide inhibits RANKL-induced osteoclast formation and bone resorption in vitro and prevents LPS-induced bone loss in vivo.[Pubmed:26906912]
Biochem Pharmacol. 2016 Mar 15;104:118-30.
Osteoclasts (OCs) play a pivotal role in a variety of lytic bone diseases including osteoporosis, arthritis, bone tumors, Paget's disease and the aseptic loosening of orthopedic implants. The primary focus for the development of bone-protective therapies in these diseases has centered on the suppression of OC formation and function. In this study we report that Thonzonium Bromide (TB), a monocationic surface-active agent, inhibited RANKL-induced OC formation, the appearance of OC-specific marker genes and bone-resorbing activity in vitro. Mechanistically, TB blocked the RANKL-induced activation of NF-kappaB, ERK and c-Fos as well as the induction of NFATc1 which is essential for OC formation. TB disrupted F-actin ring formation resulting in disturbances in cytoskeletal structure in mature OCs during bone resorption. Furthermore, TB exhibited protective effects in an in vivo murine model of LPS-induced calvarial osteolysis. Collectively, these data suggest that TB might be a useful alternative therapy in preventing or treating osteolytic diseases.
