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Merck

616382

Nα-Tosyl-Lys Chloromethyl Ketone, Hydrochloride

≥95% (elemental analysis), trypsin like proteases inhibitor, solid

Synonym(s):

Nα-Tosyl-Lys Chloromethyl Ketone, Hydrochloride, TLCK

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About This Item

Empirical Formula (Hill Notation):
C14H21ClN2O3S · xHCl
CAS Number:
4238-41-9
Molecular Weight:
332.85 (free base basis)
MDL number:
MFCD00065395
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (elemental analysis)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, desiccated (hygroscopic)

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Product Name

Nα-Tosyl-Lys Chloromethyl Ketone, Hydrochloride, Inhibits trypsin-like serine proteinases.

SMILES string

[S](=O)(=O)(N[C@@H](CCCC[N+H3])C(=O)CCl)c1ccc(cc1)C.[Cl-]

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

description

RTECS - XT5160000

assay

≥95% (elemental analysis)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, desiccated (hygroscopic)

color

off-white

solubility

aqueous solution, pH <6.0: 1 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

General description

Inhibits trypsin-like serine proteases. Inactivates trypsin irreversibly without affecting chymotrypsin. Prevents nitric oxide production by activated macrophages by interfering with transcription of the iNOS gene. Blocks cell-cell adhesion and binding of HIV-1 virus to target cells. In macrophages, blocks nitric oxide synthase induced by interferon-γ and lipopolysaccharides (EC50 = 80 µM). Prevents endonucleolysis accompanying apoptotic death of HL-60 leukemic cells and normal thymocytes. Suggesting working concentration is 10-100 µM.
Inhibits trypsin-like serine proteinases. Irreversibly inactivates trypsin without affecting chymotrypsin. Prevents nitric oxide production by activated macrophages by interfering with transcription of the iNOS gene. Blocks cell-cell adhesion and binding of HIV-1 virus to the target cells. In macrophages, blocks nitric oxide synthase induced by interferon-γ and lipopolysaccharides (EC50 = 80 µM). Prevents endonucleolysis accompanying apoptotic death of HL-60 leukemia cells and normal thymocytes.

Biochem/physiol Actions

Cell permeable: no
EC50 = 80 µM blocking nitric oxide synthase induced by interferon-γ and lipopolysaccharides in macrophages
Primary Target
trypsin like proteases
Product does not compete with ATP.
Reversible: no

Preparation Note

Unstable in solution; reconstitute just prior to use.

Other Notes

Griscavage, J.M., et al. 1995. Biochem. Biophys. Res. Commun.215, 721.
Kim, H., et al. 1995. J. Immunol.154, 4741.
Bourinbaiar, A.S. and Nagorny, R. 1994. Cell Immunol. 155, 230.
Biro, A., et al. 1992. Eur. J. Immunol.22, 2547.
Bruno, S., et al. 1992. Leukemia6, 1113.
Lee, S.F. 1992. Infect. Immun. 60, 4032.
Schmidt, H.H., et al. 1992. Mol. Pharmacol.41, 615.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Shota Yamauchi et al.
Bio-protocol, 7(24), e2653-e2653 (2017-12-20)
The opening of stomata in plants in response to blue light is driven by the plasma membrane H+-ATPase in guard cells. To evaluate the activation of the H+-ATPase in vivo, we can use H+-pumping by guard cells in response to

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