T4376

N-p-Tosyl-L-phenylalanine chloromethyl ketone

powder, ≥97% (TLC)

• Synonim(y): (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, TPCK, Tosyl-L-phenylalanyl-chloromethane
• Wzór empiryczny (zapis Hilla): C₁₇H₁₈ClNO₃S
• Numer CAS: 402-71-1
• Masa cząsteczkowa: 351.85
• NACRES: NA.77
• PubChem Substance ID: 24278737
• UNSPSC Code: 12352202
• EC Number: 206-954-6
• MDL number: MFCD00000935
• Beilstein/REAXYS Number: 2895215

Właściwości

• Nazwa produktu: 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)

Opis

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).[1]

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.

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Informacja o środkach bezpieczeństwa

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H315,H318,H335
• pcodes: P280 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Klasa składowania: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves