| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
The primary target of TPCK is chymotrypsin and other serine proteases that have a specificity for phenylalanine or other large hydrophobic amino acids. It acts as an irreversible inhibitor, forming a covalent bond with the active site histidine residue of the enzyme. This inactivates the enzyme, preventing it from cleaving its substrates. TPCK also inhibits the proteasome and other cysteine proteases at higher concentrations.
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|---|---|
| ln Vitro |
In vitro, TPCK has been shown to irreversibly inhibit chymotrypsin and other serine proteases. It inhibits proteasome activity and induces apoptosis in various cell types. The compound's effects on cell signaling pathways have been studied in various cell lines. TPCK has been shown to inhibit NF-κB activation and induce cell cycle arrest.
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| ln Vivo |
In vivo, TPCK has been studied for its effects on inflammation and immune responses. It has been shown to have anti-inflammatory effects in animal models. However, its use in vivo is limited due to its toxicity and lack of selectivity. The compound is primarily used as a research tool.
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| Enzyme Assay |
In vitro enzyme or receptor binding assays for TPCK involve measuring its inhibition of serine protease activity. The assay uses a purified serine protease enzyme, such as chymotrypsin, and a chromogenic or fluorogenic substrate. The cleavage of the substrate is measured spectrophotometrically or fluorometrically. The compound is incubated with the enzyme and substrate at varying concentrations, and the IC50 is determined. The irreversible nature of the inhibition is confirmed by pre-incubation studies.
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| Cell Assay |
In vitro cell-based assays for TPCK are performed using various cell lines. Cells are treated with the compound, and cell viability, apoptosis, and signaling pathways are assessed. The compound's effects on proteasome activity and NF-κB signaling are measured. Apoptosis is detected by measuring caspase activation or using Annexin V/PI staining.
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| Animal Protocol |
In vivo animal experiments for TPCK are limited due to its toxicity. The compound has been studied in models of inflammation and immune responses. However, its use is restricted due to its lack of selectivity and potential for off-target effects. The compound is primarily used as a research tool in vitro.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of TPCK indicate that it has a molecular weight of 351.85 and a molecular formula of C17H18ClNO3S. It is a solid at room temperature. The compound is soluble in DMSO and other organic solvents. It is typically stored at -20°C. The compound is reactive and should be handled with caution.
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| Toxicity/Toxicokinetics |
Toxicology (toxicology) data for TPCK indicate that it is toxic and should be handled with appropriate safety precautions. It is a reactive compound that can cause irritation to the skin, eyes, and respiratory tract. The compound is for research use only and not for human therapeutic use.
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| References | |
| Additional Infomation |
N-Toluenesulfonyl-L-phenylalanylchloromethyl ketone is an N-toluenesulfonyl derivative of L-phenylalanylchloromethyl ketone. It is an alkylating agent and a serine protease inhibitor. It is a sulfonamide compound and also an α-chloroketone. It contains an L-phenylalanyl group. Toluenesulfonylphenylalanylchloromethyl ketone has been reported in Streptomyces, Chaetoceros, and Aspergillus terreus, and relevant data are available. It is a serine endopeptidase inhibitor with alkylating activity and is known to interfere with the translation process.
Other information: TPCK is a serine protease inhibitor used in research. It is also known as N-tosyl-L-phenylalanine chloromethyl ketone. The compound irreversibly inhibits chymotrypsin and other serine proteases. It is used to study the role of serine proteases in various biological processes. Its CAS number is 402-71-1. |
| Molecular Formula |
C17H18CLNO3S
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|---|---|
| Molecular Weight |
351.84
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| Exact Mass |
351.069
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| CAS # |
402-71-1
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| PubChem CID |
439647
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
509.9±60.0 °C at 760 mmHg
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| Melting Point |
106-108ºC(lit.)
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| Flash Point |
262.2±32.9 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.583
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| LogP |
3.98
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
23
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| Complexity |
475
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)CCl
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| InChi Key |
MQUQNUAYKLCRME-INIZCTEOSA-N
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| InChi Code |
InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
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| Chemical Name |
N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
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| Synonyms |
Tos-Phe-CH2Cl; TPCK
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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 |
| 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) |
DMSO : ~100 mg/mL (~284.21 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8422 mL | 14.2110 mL | 28.4220 mL | |
| 5 mM | 0.5684 mL | 2.8422 mL | 5.6844 mL | |
| 10 mM | 0.2842 mL | 1.4211 mL | 2.8422 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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