T4376

N-p-Tosyl-L-phenylalanine chloromethyl ketone

≥97% (TLC), powder

• Synonym(s): (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, TPCK, Tosyl-L-phenylalanyl-chloromethane
• Empirical Formula (Hill Notation): C₁₇H₁₈ClNO₃S
• CAS Number: 402-71-1
• Molecular Weight: 351.85
• Beilstein: 2895215
• EC Number: 206-954-6
• MDL number: MFCD00000935
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278737
• NACRES: NA.77

Properties

• biological source: synthetic
• Quality Level: 200
• Assay: ≥97% (TLC)
• form: powder
• potency: 10-100 μM effective concentration
• color: white
• mp: 106-108 °C (lit.)
• 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
• SMILES string: Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc2ccccc2)C(=O)CCl
• 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
• InChI key: MQUQNUAYKLCRME-INIZCTEOSA-N
• Gene Information: human ... NFKB1(4790) , NKAP(79576) , NKRF(55922) , NOS2(4843) , PTGS2(5743)

Description

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

Irreversible inhibitor of certain serine proteases; used to inhibit chymotrypsin in preparations of trypsin.

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 pp70^s6k 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).

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Shelf-life is at least two years when stored desiccated at -20 °C.

Safety Information

• Pictograms: GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H315 - H318 - H335
• Precautionary Statements: P280 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves