Tos-Arg-OMe.HClUbiquitin ligase APC/C inhibitor; promotes Cdc20 autoubiquitination CAS# 1784-03-8 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1784-03-8 | SDF | Download SDF |
| PubChem ID | 2723792 | Appearance | Powder |
| Formula | C14H23ClN4O4S | M.Wt | 378.9 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 155 mg/mL (409.11 mM; Need ultrasonic) | ||
| Chemical Name | methyl (2S)-5-(diaminomethylideneamino)-2-[(4-methylphenyl)sulfonylamino]pentanoate;hydrochloride | ||
| SMILES | CC1=CC=C(C=C1)S(=O)(=O)NC(CCCN=C(N)N)C(=O)OC.Cl | ||
| Standard InChIKey | JIQFFACVQXXHMY-YDALLXLXSA-N | ||
| Standard InChI | InChI=1S/C14H22N4O4S.ClH/c1-10-5-7-11(8-6-10)23(20,21)18-12(13(19)22-2)4-3-9-17-14(15)16;/h5-8,12,18H,3-4,9H2,1-2H3,(H4,15,16,17);1H/t12-;/m0./s1 | ||
| 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 | Competitive inhibitor of the ubiquitin ligase anaphase-promoting complex/cyclosome (APC/C); promotes Cdc20 autoubiquitination. Inhibits cyclin proteolysis in mitotic Xenopus oocyte extracts (IC50 = 12 μM) and blocks cyclin degradation in interphase extract. |
Tos-Arg-OMe.HCl Dilution Calculator
Tos-Arg-OMe.HCl Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6392 mL | 13.1961 mL | 26.3922 mL | 52.7844 mL | 65.9805 mL |
| 5 mM | 0.5278 mL | 2.6392 mL | 5.2784 mL | 10.5569 mL | 13.1961 mL |
| 10 mM | 0.2639 mL | 1.3196 mL | 2.6392 mL | 5.2784 mL | 6.598 mL |
| 50 mM | 0.0528 mL | 0.2639 mL | 0.5278 mL | 1.0557 mL | 1.3196 mL |
| 100 mM | 0.0264 mL | 0.132 mL | 0.2639 mL | 0.5278 mL | 0.6598 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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An APC/C inhibitor stabilizes cyclin B1 by prematurely terminating ubiquitination.[Pubmed:22366722]
Nat Chem Biol. 2012 Feb 26;8(4):383-92.
The anaphase-promoting complex/cyclosome (APC) is a ubiquitin ligase that is required for exit from mitosis. We previously showed that tosyl arginine methyl ester (TAME) inhibits APC-dependent proteolysis by competing with the C-terminal isoleucine-arginine tail of the APC activator cell division cycle 20 (Cdc20) for APC binding. Here we show that in the absence of APC substrates, TAME ejects Cdc20 from the APC by promoting Cdc20 autoubiquitination in its N-terminal region. Cyclin B1 antagonizes TAME's effect by promoting binding of free Cdc20 to the APC and by suppressing Cdc20 autoubiquitination. Nevertheless, TAME stabilizes cyclin B1 in Xenopus extracts by two mechanisms. First, it reduces the k(cat) of the APC-Cdc20-cyclin B1 complex without affecting the K(m), slowing the initial ubiquitination of unmodified cyclin B1. Second, as cyclin B1 becomes ubiquitinated, it loses its ability to promote Cdc20 binding to the APC in the presence of TAME. As a result, cyclin B1 ubiquitination terminates before reaching the threshold necessary for proteolysis.
Pharmacologic inhibition of the anaphase-promoting complex induces a spindle checkpoint-dependent mitotic arrest in the absence of spindle damage.[Pubmed:20951947]
Cancer Cell. 2010 Oct 19;18(4):382-95.
Microtubule inhibitors are important cancer drugs that induce mitotic arrest by activating the spindle assembly checkpoint (SAC), which, in turn, inhibits the ubiquitin ligase activity of the anaphase-promoting complex (APC). Here, we report a small molecule, tosyl-L-arginine methyl ester (TAME), which binds to the APC and prevents its activation by Cdc20 and Cdh1. A prodrug of TAME arrests cells in metaphase without perturbing the spindle, but nonetheless the arrest is dependent on the SAC. Metaphase arrest induced by a proteasome inhibitor is also SAC dependent, suggesting that APC-dependent proteolysis is required to inactivate the SAC. We propose that mutual antagonism between the APC and the SAC yields a positive feedback loop that amplifies the ability of TAME to induce mitotic arrest.
