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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)

Synonym(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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About This Item

Empirical Formula (Hill Notation):

C₁₄H₂₁ClN₂O₃S · HCl

CAS Number:

4272-74-6

Molecular Weight:

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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Properties

Product Name

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

Quality Level

200

biological source

synthetic (organic)

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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Storage Class

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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Protocols

Thrombin from Bovine Plasma

Thrombin is an endolytic serine protease that selectively cleaves the Arg–Gly bonds of fibrinogen to form fibrin and release fibrinopeptides A and B.

Nuclear serine protease activity contributes to bile acid-induced apoptosis in hepatocytes.

P Kwo et al.

The American journal of physiology, 268(4 Pt 1), G613-G621 (1995-04-01)

Glycodeoxycholate (GDC) induces apoptosis in hepatocytes by a mechanism associated with DNA cleavage by endonucleases. In many models of apoptosis, proteolysis is required prior to DNA cleavage. Our aims were to determine if enhanced proteolysis is a mechanism causing GDC-mediated

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)

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

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Global Trade Item Number

SKU	GTIN
T7254-100MG	04061837372452
T7254-1G	04061837372483
T7254-500MG	04061837372490