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T7254

N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride

Name: <I>N</I><SUB>&#945;</SUB>-Tosyl-<SC>L</SC>-lysine chloromethyl ketone hydrochloride
Brand: SIGMA

powder, ≥96% (TLC)

Synonyme(s) :

(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

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A propos de cet article

Formule empirique (notation de Hill) :

C₁₄H₂₁ClN₂O₃S · HCl

Numéro CAS:

4272-74-6

Poids moléculaire :

369.31

NACRES:

NA.77

PubChem Substance ID:

24278752

UNSPSC Code:

12352202

EC Number:

224-266-4

MDL number:

MFCD00065395

Beilstein/REAXYS Number:

7106867

eCl@ss:

32160406

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Propriétés

Nom du produit

N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride, ≥96% (TLC), powder

biological source

synthetic (organic)

Quality Level

200

assay

≥96% (TLC)

form

powder

potency

10-100 μM effective concentration

solubility

H₂O: 50 mg/mL

storage temp.

−20°C

SMILES string

Cl[H].Cc1ccc(cc1)S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl

InChI

1S/C14H21ClN2O3S.ClH/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16;/h5-8,13,17H,2-4,9-10,16H2,1H3;1H/t13-;/m0./s1

InChI key

YFCUZWYIPBUQBD-ZOWNYOTGSA-N

Gene Information

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

Description

Application

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride has been used:

in chymotrypsin purification to prevent binding of trypsins to the affinity support by inhibiting them in the crude extract
as a protease inhibitor in tissue and cell homogenization
as a trypsin inhibitor to determine the specific protease activity levels

Biochem/physiol Actions

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride (TLCK) blocks the lipopolysaccharide (LPS)- or cytokine-induced activation of nuclear factor κB (NF-κB), 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 in cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Disclaimer

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

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Classe de stockage

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

pictograms

GHS05,GHS07

signalword

Danger

hcodes

H302,H315,H317,H318

pcodes

P261 - P264 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1B

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Contenu apparenté

Product Information Sheet - T7254

Involvement of NF-kappaB in the regulation of cyclooxygenase-2 protein expression in LPS-stimulated J774 macrophages.

F D'Acquisto et al.

FEBS letters, 418(1-2), 175-178 (1997-12-31)

We investigated the involvement of NF-kappaB in the regulation of COX-2 protein expression and prostaglandin production in LPS-stimulated J774 macrophages. Incubation of J774 cells with LPS (1 microg/ml) for 24 h caused an increase of COX-2 protein expression and accumulation

Evidence for involvement of the proteasome complex (26S) and NFkappaB in IL-1beta-induced nitric oxide and prostaglandin production by rat islets and RINm5F cells.

G Kwon et al.

Diabetes, 47(4), 583-591 (1998-05-06)

Interleukin-1beta (IL-1beta) has been implicated as an effector molecule of beta-cell destruction in autoimmune diabetes. IL-1beta inhibits insulin secretion from pancreatic beta-cells by stimulating the expression of inducible nitric oxide synthase (iNOS) that generates the free radical nitric oxide. IL-1beta

Purification and characterization of a serine protease with fibrinolytic activity from the dung beetles, Catharsius molossus

Ahn MY, et al.

Thrombosis Research, 112(5-6), 339-347 (2003)

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