| Size | Price | Stock | Qty |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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Purity: ≥98%
TAME (Tosyl-L-Arginine Methyl Ester) is a potent small molecule APC (anaphase-promoting complex/cyclosome) inhibitor, which can target proteins for degradation and cause chromatid separation.
| Targets |
Anaphase-promoting complex (APC)
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| ln Vitro |
TAME has an IC50 of 12 µM for inhibiting cyclin proteolysis in mitotic Xenopus egg extract. Interphase extract treated with recombinant cyclin B1/Cdc2 complex in mitosis is stopped by TAME at concentrations of 1-200 μM, leaving phosphorylated Cdc27 and stable cyclin B1. When TAME is added at a 200 μM concentration, it significantly reduces Cdh1's binding to the Anaphase-Promoting Complex (APC) and inhibits its ubiquitin ligase activity. The C-terminal isoleucine-arginine (IR) tail of APC is the contribution motif that TAME addition to interphase extract uses to reduce Cdc20 association with the APC in a dose-dependent manner. Trypsin hydrolyzes TAME, with a Km of 0.328 mM.[2] TAME causes an approximate 12-fold increase in ATP hydrolysis speed.[3] TAME interacts with ATP's β and γ phosphate as well as the adenine ring through the aromatic ring and guanidinium group.[4] TAME inhibits Bacillus subtilis nutrient-induced germination and pressure-induced germination at 600 MPa at a concentration of 50 mM.[5] On ileal strips, TAME causes a concentration-dependent contractile response with an EC50 of 4.3 x 103 M.[6]
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| ln Vivo |
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| Enzyme Assay |
TAME at concentrations ranging from 1 to 200 μM stops interphase extract treated with recombinant cyclin B1/Cdc2 complex in mitosis, resulting in phosphorylated Cdc27 and stable cyclin B1. At a 200 μM concentration, TAME significantly suppresses the ubiquitin ligase activity of the Anaphase-Promoting Complex (APC), which is accompanied by a decrease in Cdh1 binding to APC. By binding directly to APC, TAME addition to interphase extract reduces Cdc20 association with the APC in a dose-dependent manner. The C-terminal isoleucine-arginine (IR) tail on APC is the contribution motif. Trypsin hydrolyzes TAME, and its Km value is 0.328 mM. TAME speeds up the hydrolysis of ATP by a factor of twelve. Through the guanidinium group and the aromatic ring, TAME interacts with β and γ phosphate as well as the adenine ring of ATP. TAME inhibits both pressure-induced germination at 600 MPa and nutrient-induced germination in Bacillus subtilis at concentrations of 50 mM. On ileal strips, TAME causes a concentration-dependent contractile response with an EC50 of 4.3 x 103 M.
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| Cell Assay |
In order to prevent APC-dependent proteolysis in mitotic Xenopus oocytes, TAME competes with the Cdc20 C-terminal IR-tail for APC binding. Additionally, TAME stabilizes cyclin B1 by prematurely stopping ubiquitination. It inhibits the first round of ubiquitination of unmodified cyclin B1. Unubiquitinated cyclin B1 is unable to encourage Cdc20 binding to the APC when TAME is present.
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| References |
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| Additional Infomation |
TAMe is an L-arginine ester that is methyl L-argininate in which one of the hydrogens attached to the alpha-nitrogen is substituted by a tosyl group. It is a L-arginine ester, a sulfonamide, a methyl ester and a member of guanidines.
Arginine derivative which is a substrate for many proteolytic enzymes. As a substrate for the esterase from the first component of complement, it inhibits the action of C(l) on C(4). |
| Molecular Formula |
C14H22N4O4S
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| Molecular Weight |
342.41
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| Exact Mass |
342.136
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| CAS # |
901-47-3
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| Related CAS # |
1784-03-8
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| PubChem CID |
1550286
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| Appearance |
White to off-white solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
516.5±60.0 °C at 760 mmHg
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| Flash Point |
266.1±32.9 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.591
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| LogP |
0.77
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
23
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| Complexity |
503
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| Defined Atom Stereocenter Count |
1
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| SMILES |
S(C1C=CC(C)=CC=1)(=O)(=O)N[C@H](C(=O)OC)CCCNC(N)=N
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| InChi Key |
FKMJXALNHKIDOD-LBPRGKRZSA-N
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| InChi Code |
InChI=1S/C14H22N4O4S/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)/t12-/m0/s1
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| Chemical Name |
methyl (2S)-5-(diaminomethylideneamino)-2-[(4-methylphenyl)sulfonylamino]pentanoate
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9205 mL | 14.6024 mL | 29.2048 mL | |
| 5 mM | 0.5841 mL | 2.9205 mL | 5.8410 mL | |
| 10 mM | 0.2920 mL | 1.4602 mL | 2.9205 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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