N-p-Tosyl-L-phenylalanine chloromethyl ketone
SIGMA/T4376 - ≥97% (TLC), powder
Synonym: (S)
CAS Number: 402-71-1
Empirical Formula (Hill Notation): C17H18ClNO3S
Molecular Weight: 351.85
EC Number: 206-954-6
MDL Number: MFCD00000935
Linear Formula: C17H18ClNO3S
Product Type: Chemical
| assay | ≥97% (TLC) |
| biological source | synthetic |
| color | white |
| form | powder |
| InChI | 1S/C17H18ClNO3S/c1-13-7-9 |
| InChI key | MQUQNUAYKLCRME-INIZCTEOSA |
| mp | 106-108 °C (lit.) |
| potency | 10-100 μM effective concentration |
| Quality Level | 200  |
| SMILES string | Cc1ccc(cc1)S(=O)(=O)N[C@@ |
| solubility | DMSO: >10 mg/mL (stable for several months at 4°C.) |
| ethanol: 20 mg/mL (stable for several months at 4°C. Stock solutions (10 mM in methanol or ethanol) are stable for several months at 4°C.) | |
| storage temp. | −20°C |
| Application: | Irreversible inhibitor of certain serine proteases; used to inhibit chymotrypsin in preparations of trypsin. |
| Application: | N-p-Tosyl-L-phenylalanine chloromethyl ketone has been used: • to investigate whether transcription factor NFκB is involved in renalase expression • to test the role of NF-κB activation • to study its inhibitory effect on chymotrypsin |
| Biochem/physiol Actions: | Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells). |
| Biochem/physiol Actions: | N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK) blocks the lipopolysaccharide (LPS)- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells). TPCK recognises the phenylalanine residue in chymotrypsin′s and prevents its function. |
| Caution: | Shelf-life is at least two years when stored desiccated at -20 °C. |
| Packaging: | Bottomless glass bottle. Contents are inside inserted fused cone. |
| Symbol |   GHS05,GHS07 |
| Signal word | Danger |
| Hazard statements | H315 - H318 - H335 |
| Precautionary statements | P280 - P302 + P352 - P305 + P351 + P338 + P310 |
| Hazard Codes | Xi |
| Risk Statements | 37/38-41 |
| Safety Statements | 26-36 |
| RIDADR | UN 3335 |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥97% (TLC) |
| mp | 106-108 °C (lit.) |
| Storage Temp. | −20°C |
| UNSPSC | 12352202 |