T7254

N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride

Name: <I>N</I><SUB>α</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

Product Name

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

form

powder

InChI key

YFCUZWYIPBUQBD-ZOWNYOTGSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥96% (TLC)

potency

10-100 μM effective concentration

solubility

H₂O: 50 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

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

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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.

Disclaimer

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

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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Angiopoietin modulation of vascular endothelial growth factor: Effects on retinal endothelial cell permeability.

Swaantje Peters et al.

Cytokine, 40(2), 144-150 (2007-10-26)

Vascular permeability is important at many sites, but particularly so in diabetic retinopathy where macular oedema is the major cause of blindness. Angiopoietin-2 (Ang-2) and vascular endothelial growth factor (VEGF) are important factors involved in neovascularization and vascular leakage, but

Feces derived allergens of Tyrophagus putrescentiae reared on dried dog food and evidence of the strong nutritional interaction between the mite and Bacillus cereus producing protease bacillolysins and exo-chitinases

Erban T, et al.

Frontiers in Physiology, 7, 53-53 (2016)

Inhibitors of trypsin-like serine proteases inhibit processing of the caspase Nedd-2 and protect PC12 cells and sympathetic neurons from death evoked by withdrawal of trophic support.

L Stefanis et al.

Journal of neurochemistry, 69(4), 1425-1437 (1997-11-05)

Rat pheochromocytoma (PC12) cells and sympathetic neurons undergo apoptotic cell death upon withdrawal of trophic support. We have shown previously that selective cysteine aspartase (caspase) inhibitors protect PC12 cells and sympathetic neurons from such death, and that the caspase Nedd-2

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

Protease inhibitors protect macrophages from lipopolysaccharide-induced cytotoxicity: possible role for NF-kappaB.

A Abate et al.

Life sciences, 62(12), 1081-1088 (1998-03-31)

Recent studies suggest lipopolysaccharide (LPS) mediated cell death as underlying mechanism of hyporesponsiveness and dysfunction of macrophages in the late phase of septic shock. In the present study LPS (0.001 - 30 microg/ml) caused a concentration-dependent toxicity in the macrophage

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