T4376
Sigma

N-p-Tosyl-L-phenylalanine chloromethyl ketone

≥97% (TLC), powder

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Synonym

(S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone

(S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone

Tosyl-L-phenylalanyl-chloromethane

TPCK

Molecular Formula

C₁₇H₁₈ClNO₃S

Molecular Weight

351.85

CAS Number

402-71-1

Beilstein Registry Number

2895215

MDL number

MFCD00000935

PubChem Substance ID

24278737

EG/EC Number

206-954-6

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Descriptions

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.

Caution

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

Properties

assay

≥97% (TLC)

form

powder

potency

10-100 μM effective concentration

color

white

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.

Gene Information

human ... NFKB1(4790), NKAP(79576), NKRF(55922), NOS2A(4843), PTGS2(5743)

storage temp.

−20°C

References

Reference

Abate, A., and Schroder, H., Protease inhibitors protect macrophages from lipopolysaccharide-induced cytotoxicity: possible role for NF-κB. Life Sci. 62, 1081-1088, (1998) abstract

Kengatharan, M., et al., Analysis of the signal transduction in the induction of nitric oxide synthase by lipoteichoic acid in macrophages. Br. J. Pharmacol. 117, 1163-1170, (1996) abstract

Breithaupt, T.B., et al., The suppression of T cell function and NFκB expression by serine protease inhibitors is blocked by N-acetylcysteine. Cell. Immunol. 173, 124-130, (1996) abstract

Lo, C.J., et al., Regulation of macrophage eicosanoid generation is dependent on nuclear factor κB. J. Trauma 45, 19-24, (1998)

Jones, R.A., et al., Fas-mediated apoptosis in mouse hepatocytes involves the processing and activation of caspases. Hepatology 27, 1632-1642, (1998) abstract

Lotem, J., and Sachs, Differential suppression by protease inhibitors and cytokines of apoptosis induced by wild-type p53 and cytotoxic agents. L. Proc. Natl. Acad. Sci. USA 93, 12507-12512, (1996) abstract

Grammer, T.C., , and Blenis, J., The serine protease inhibitors tosylphenylalanine chloromethyl ketone and tosyllysine chloromethyl ketone potently inhibit pp^70s6k activation. J. Biol. Chem. 271, 23650, (1996) abstract

Safety

Hazard Codes

Risk Statements

37/38-41

Safety Statements

26-36

WGK Germany

RTECS

XT5613500

10-19-21