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T7254

Sigma-Aldrich

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride

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
Beilstein:
7106867
EC Number:
224-266-4
MDL number:
MFCD00065395
UNSPSC Code:
12352202
PubChem Substance ID:
24278752
NACRES:
NA.77

product name

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

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)

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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Swaantje Peters et al.
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Erban T, et al.
Frontiers in Physiology, 7, 53-53 (2016)
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
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
Alan R Bassindale et al.
Journal of inorganic biochemistry, 96(2-3), 401-406 (2003-07-31)
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