T7254
Sigma

N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride

≥96% (TLC), powder

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Synonym

(3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone hydrochloride

(3S)-7-Amino-1-chloro-3-tosylamino-2-heptanone hydrochloride

TLCK

Tosyl-L-lysyl-chloromethane hydrochloride

Molecular Formula

C₁₄H₂₁ClN₂O₃S · HCl

Molecular Weight

369.31

CAS Number

4272-74-6

Beilstein Registry Number

7106867

MDL number

MFCD00065395

PubChem Substance ID

24278752

EG/EC Number

224-266-4

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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 in cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli.

Caution

Stable at least two years when stored desiccated at −20°C.

Properties

assay

≥96% (TLC)

form

powder

potency

10-100 μM effective concentration

color

white to pink

solubility

H₂O: 50 mg/mL

Gene Information

human ... NFKB1(4790), NFKB2(4791)

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

Kwon, G., et al., Evidence for involvement of the proteasome complex (26S) and NFκB in IL-1β-induced nitric oxide and prostaglandin production by rat islets and RINm5F cells. Diabetes 47, 583-591, (1998) abstract

D'Acquisto, F., et al., Involvement of NF-κB in the regulation of cyclooxygenase-2 protein expression in LPS-stimulated J774 macrophages. FEBS Lett. 418, 175-178, (1997) abstract

Stefanis, L., et al., Inhibitors of trypsin-like serine proteases inhibit processing of the caspase Nedd-2 and protect PC12 cells and sympathetic neurons from death. J. Neurochem. 69, 1425-1437, (1997) abstract

Kwo, P., et al., Nuclear serine protease activity contributes to bile acid-induced apoptosis in hepatocytes. Am. J. Physiol. 268, G613-G621, (1995) 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

36/37/38

Safety Statements

26-36

WGK Germany

10-21

Related Categories

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... Plasma & Blood Proteins > Coagulation Proteins and Reagents

... Protease Inhibitor Specificity Index > Endoproteinase Arg-C

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... Enzyme Inhibitors > Papain

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... P to Q > Protein kinase C

... Protein Kinases and Phosphatases > Protein Kinase Inhibitors and Related Products

... Broad Spectrum Inhibitors of Proteolytic Enzyme Classes > Serine Protease Inhibitors

... Protease Inhibitor Specificity Index > Thrombin

... R to Z > Thrombin

... Enzyme Inhibitors > Thrombin

... R to Z > Trypsin Inhibitors

FT-IR Raman

FT-NMR

T7254 - Product Information Sheet (64kb)

MSDS

Specification Sheet

Certificate of Analysis

Certificate of Origin

More Information

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride

≥96% (TLC), powder

N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride