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Merck

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

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About This Item

Fórmula empírica (notación de Hill):
C17H18ClNO3S
Número CAS:
Peso molecular:
351.85
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
206-954-6
MDL number:
Beilstein/REAXYS Number:
2895215

Nombre del producto

N-p-Tosyl-L-phenylalanine chloromethyl ketone, ≥97% (TLC), powder

InChI key

MQUQNUAYKLCRME-INIZCTEOSA-N

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

SMILES string

Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc2ccccc2)C(=O)CCl

biological source

synthetic

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

Quality Level

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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 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).
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.

Disclaimer

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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Y Huang et al.
Oncogene, 18(23), 3431-3439 (1999-06-22)
The mechanism of Taxol-induced apoptosis was investigated in MCF-7 human breast carcinoma cells. Taxol-induced apoptosis was associated with phosphorylation of both c-Raf-1 and Bcl-2 and activation of ERK and JNK MAP kinases. The serine protease inhibitor N-tosyl-L-phenylalanine chloromethyl ketone (TPCK)
Christopher S Anderson et al.
Scientific reports, 7(1), 14614-14614 (2017-11-04)
The induction of antibodies specific for the influenza HA protein stalk domain is being pursued as a universal strategy against influenza virus infections. However, little work has been done looking at natural or induced antigenic variability in this domain and
c-myc is required for osteoclast differentiation
Battaglin R, et al.
Journal of Bone and Mineral Research, 17(5), 763-773 (2002)
David Scheibner et al.
Scientific reports, 9(1), 11556-11556 (2019-08-11)
Avian influenza viruses (AIV) are classified into 16 hemagglutinin (HA; H1-H16) and 9 neuraminidase (NA; N1-N9) subtypes. All AIV are low pathogenic (LP) in birds, but subtypes H5 and H7 AIV can evolve into highly pathogenic (HP) forms. In the
Ryo Nagao et al.
Nature plants, 5(8), 890-901 (2019-07-31)
Light-harvesting antenna systems in photosynthetic organisms harvest solar energy and transfer it to the photosynthetic reaction centres to initiate charge-separation and electron-transfer reactions. Diatoms are one of the important groups of oxyphototrophs and possess fucoxanthin chlorophyll a/c-binding proteins (FCPs) as

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