T4376

N-p-Tosyl-L-phenylalanine chloromethyl ketone

powder, ≥97% (TLC)

• Sinónimos: (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, TPCK, Tosyl-L-phenylalanyl-chloromethane
• Fórmula empírica (notación de Hill): C₁₇H₁₈ClNO₃S
• Número CAS: 402-71-1
• Peso molecular: 351.85
• NACRES: NA.77
• PubChem Substance ID: 24278737
• UNSPSC Code: 12352202
• EC Number: 206-954-6
• MDL number: MFCD00000935
• Beilstein/REAXYS Number: 2895215

Propiedades

• Nombre del producto: N-p-Tosyl-L-phenylalanine chloromethyl ketone, ≥97% (TLC), powder
• biological source: synthetic
• Quality Segment: 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
• 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)

Descripción

General description

stable for several months at 4°C. Stock solutions (10 mM in methanol or ethanol) are stable for several months at 4°C.

Application

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

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 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.

Disclaimer

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

Información de seguridad

• Pictogramas: GHS05,GHS07
• Palabra de advertencia: Danger
• Códigos de peligro: H315,H318,H335
• Indicaciones de precaución: P280 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• Órganos diana: Respiratory system
• Clase de almacenamiento: 11 - Combustible Solids
• ¿Qué está pasando?: WGK 3
• Punto de inflamación (°F): Not applicable
• Punto de inflamación (°C): Not applicable
• EPI (equipos de protección individual): dust mask type N95 (US), Eyeshields, Gloves