TAMEAPC (Anaphase-promoting complex/cyclosome) inhibitor CAS# 901-47-3 |
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Quality Control & MSDS
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| Cas No. | 901-47-3 | SDF | Download SDF |
| PubChem ID | 13481 | Appearance | Powder |
| Formula | C14H22N4O4S | M.Wt | 342.41 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble in DMSO > 10 mM | ||
| Chemical Name | methyl 2-amino-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]pentanoate | ||
| SMILES | CC1=CC=C(C=C1)S(=O)(=O)NC(=NCCCC(C(=O)OC)N)N | ||
| Standard InChIKey | GIGVCLWIEMFWBF-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C14H22N4O4S/c1-10-5-7-11(8-6-10)23(20,21)18-14(16)17-9-3-4-12(15)13(19)22-2/h5-8,12H,3-4,9,15H2,1-2H3,(H3,16,17,18) | ||
| 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 | TAME is an inhibitor of anaphase-promoting complex (APC), which prevents its activation by Cdc20 and Cdh1; TAME is also an inhibitor of cyclin proteolysis in mitotic Xenopus egg extract, with an IC50 of 12 µM.In Vitro:TAME (tosyl-L-arginine methyl ester, 200 μM) shows inhibitory effect on APC activation when added to mitotic Xenopus extract. TAME (1-200 μM) inhibits Cdc20 association with mitotic APC and also inhibits Cdh1 association with interphase APC. TAME significantly inhibits crosslinking of the IR peptide to Cdc27 and Cdc16 but only slightly reduces crosslinking to Cdc23 and Apc7 at 20 µM; TAME strongly inhibits crosslinking to all APC subunits at 200 µM. TAME (200 µM) also inhibits binding of wild type Cdc20 to the APC, but not binding of a ΔIR mutant[1]. TAME (200 μM) induces Cdc20 dissociation from the APC in mitotic Xenopus extract calls for APC-dependent ubiquitination. TAME induces Cdc20 dissociation from the APC by promoting Cdc20 ubiquitination, but the dissociation can be suppresses by Cyclin B1. TAME terminates cyclin B1 ubiquitination prematurely[2]. TAME interacts with ATP by β and γ phosphate and the adenine ring of ATP. TAME in combination with the Mg(II) ion accelerates the ATP hydrolysis process[3]. References: | |||||
TAME Dilution Calculator
TAME Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9205 mL | 14.6024 mL | 29.2048 mL | 58.4095 mL | 73.0119 mL |
| 5 mM | 0.5841 mL | 2.9205 mL | 5.841 mL | 11.6819 mL | 14.6024 mL |
| 10 mM | 0.292 mL | 1.4602 mL | 2.9205 mL | 5.841 mL | 7.3012 mL |
| 50 mM | 0.0584 mL | 0.292 mL | 0.5841 mL | 1.1682 mL | 1.4602 mL |
| 100 mM | 0.0292 mL | 0.146 mL | 0.292 mL | 0.5841 mL | 0.7301 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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TAME (Tosyl-L-Arginine Methyl Ester) is a small molecule APC (Anaphase-promoting complex/cyclosome) inhibitor with IC50 of 12 μM in Xenopus oocytes. [1]
APC is an ubiquitin ligase with multi subunits. It ubiquitinates substrates (e.g. cyclin B1 and secrin) and make them the targets for degradation with 26s proteasome, resulting in initiation of anaphase and mitotic exit. [2]
In mitotic Xenopus oocytes, TAME competes with the Cdc20 C-terminal IR-tail for APC binding to inhibit APC-dependent proteolysis. [3] TAME also stabilizes cyclin B1via terminating ubiquitination prenaturally. It slows the unmodified cyclin B1 initial ubiquitination. In the presence of TAME, ubiquitinated cyclin B1 is not able to promote Cdc20 binding to the APC. [4]
References:
1．Verma R, Oania R, Graumann J, Deshaies RJ. Multiubiquitin chain receptors define a layer of substrate selectivity in the ubiquitin-proteasome system. Cell. 2004 Jul 9;118(1):99-110.
2．Peters JM. The anaphase promoting complex/cyclosome: a machine designed to destroy. Nat Rev Mol Cell Biol. 2006; 7:644–656.
3．Zeng X, Sigoillot F, Gaur S, Choi S, Pfaff KL, Oh DC, Hathaway N, Dimova N, Cuny GD, King RW. Pharmacologic inhibition of the anaphase-promoting complex induces a spindle checkpoint-dependent mitotic arrest in the absence of spindle damage. Cancer Cell. 2010 Oct 19;18(4):382-95.
4. Zeng X, King RW. An APC/C inhibitor stabilizes cyclin B1 by prematurely terminating ubiquitination. Nat Chem Biol. 2012 Feb 26;8(4):383-92.
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Facial shape differences between rats selected for tame and aggressive behaviors.[Pubmed:28369080]
PLoS One. 2017 Apr 3;12(4):e0175043.
Domestication has been consistently accompanied by a suite of traits called the domestication syndrome. These include increased docility, changes in coat coloration, prolonged juvenile behaviors, modified function of adrenal glands and reduced craniofacial dimensions. Wilkins et al recently proposed that the mechanistic factor underlying traits that encompass the domestication syndrome was altered neural crest cell (NCC) development. NCC form the precursors to a large number of tissue types including pigment cells, adrenal glands, teeth and the bones of the face. The hypothesis that deficits in NCC development can account for the domestication syndrome was partly based on the outcomes of Dmitri Belyaev's domestication experiments initially conducted on silver foxes. After generations of selecting for TAMEness, the foxes displayed phenotypes observed in domesticated species. Belyaev also had a colony of rats selected over 64 generations for either TAMEness or defensive aggression towards humans. Here we focus on the facial morphology of Belyaev's TAME, 'domesticated' rats to test whether: 1) TAMEness in rats causes craniofacial changes similar to those observed in the foxes; 2) facial shape, i.e. NCC-derived region, is distinct in the TAME and aggressive rats. We used computed-tomography scans of rat skulls and landmark-based geometric morphometrics to quantify and analyze the facial skeleton. We found facial shape differences between the TAME and aggressive rats that were independent of size and which mirrored changes seen in domesticated animals compared to their wild counterparts. However, there was no evidence of reduced sexual dimorphism in the face of the TAME rats. This indicates that not all morphological changes in NCC-derived regions in the rats follow the pattern of shape change reported in domesticated animals or the silver foxes. Thus, certain phenotypic trends that are part of the domestication syndrome might not be consistently present in all experimental animal models.
Plans Favor Product Preferencing To Tame Spending on Biologics.[Pubmed:28121527]
Manag Care. 2016 Jul;25(7):21.
Historically, it's rare for commercial payers to have drug formularies for medical benefits, but that's changing. In effect, health plans are, in some ways, choosing drugs they prefer, based on their judgments about safety and efficacy, as well as availability, lowest net cost, and how a drug is administered.
Vapor intrusion risk of fuel ether oxygenates methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME) and ethyl tert-butyl ether (ETBE): A modeling study.[Pubmed:28279869]
J Hazard Mater. 2017 Jun 15;332:10-18.
Vapor intrusion of synthetic fuel additives represents a critical yet still neglected problem at sites contaminated by petroleum fuel releases. This study used an advanced numerical model to investigate the vapor intrusion potential of fuel ether oxygenates methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME), and ethyl tert-butyl ether (ETBE). Simulated indoor air concentration of these compounds can exceed USEPA indoor air screening level for MTBE (110mug/m(3)). Our results also reveal that MTBE has much higher chance to cause vapor intrusion problems than TAME and ETBE. This study supports the statements made by USEPA in the Petroleum Vapor Intrusion (PVI) Guidance that the vertical screening criteria for petroleum hydrocarbons may not provide sufficient protectiveness for fuel additives, and ether oxygenates in particular. In addition to adverse impacts on human health, ether oxygenate vapor intrusion may also cause aesthetic problems (i.e., odour and flavour). Overall, this study points out that ether oxygenates can cause vapor intrusion problems. We recommend that USEPA consider including the field measurement data of synthetic fuel additives in the existing PVI database and possibly revising the PVI Guidance as necessary.
Taming a Vinyl Cation with a Simple Al(OTf)3 Catalyst To Promote C-C Bond Cleavage.[Pubmed:28370437]
Chemistry. 2017 Sep 7;23(50):12184-12189.
A detailed mechanistic investigation identified the stepwise nature of the 1,3-aryl shift, which enables our recently disclosed Al(3+) -catalyzed insertion of unactivated alkynes into the sp(2) -sp(3) C-C bond of benzyl alcohols. The selectivity for the rearranged product was found to be induced by the continued coordination of the aluminum catalyst to the rearranging species, which is encouraged by a reversible background reaction. This participation of the catalyst beyond the ionization step is unique in the realm of carbocation driven reactions and opens up the possibility of a catalyst-induced chiral induction in the future. Furthermore, the study represents a rare example of detailed mechanistic analysis of a reaction with a product selectivity that changes with increasing conversion.
