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C9521

Sigma-Aldrich

Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride

kallikrein substrate, ≥95% (HPLC), powder

Sinonimo/i:

Z-Phe-Arg-AMC

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CHF 514.00
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CHF 1’740.00

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25 MG
CHF 514.00
100 MG
CHF 1’740.00

About This Item

Formula empirica (notazione di Hill):
C33H36N6O6 · HCl
Numero CAS:
70382-26-2
Peso molecolare:
649.14
Numero MDL:
MFCD00077030
Codice UNSPSC:
12352204
ID PubChem:
24893165
NACRES:
NA.32

CHF 514.00

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Nome del prodotto

Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride, kallikrein substrate

Saggio

≥95% (HPLC)

Stato

powder

Concentrazione

≥95%

Solubilità

methanol: 20 mg/mL, clear, colorless

Temperatura di conservazione

−20°C

Stringa SMILE

O=C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](CCCNC(N)=N)C(NC2=CC=C(C(C)=CC(O3)=O)C3=C2)=O)=O)OCC4=CC=CC=C4.[Cl]

InChI

1S/C33H36N6O6/c1-21-17-29(40)45-28-19-24(14-15-25(21)28)37-30(41)26(13-8-16-36-32(34)35)38-31(42)27(18-22-9-4-2-5-10-22)39-33(43)44-20-23-11-6-3-7-12-23/h2-7,9-12,14-15,17,19,26-27H,8,13,16,18,20H2,1H3,(H,37,41)(H,38,42)(H,39,43)(H4,34,35,36)
ZZGDDBWFXDMARY-UHFFFAOYSA-N

Descrizione generale

Z-Phe-Arg 7-amido-4-methylcoumarin (Z-FR-AMC) is a peptidomimetic substrate for papain[1]and other enzymes such as cathepsin K.[2] It is also a fluorogenic synthetic peptide for the enzymes cathepsins L and B.[3]

Applicazioni

Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride has been used:
  • as a fluorogenic substrate in actinidin inhibition assay[4]
  • as a kallikrein substrate[5]
  • as a trypsin substrate for fluorometric assay[6]
  • as a cathepsin-L substrate[7]

Azioni biochim/fisiol

Z-Phe-Arg 7-amido-4-methylcoumarin (Z-FR-AMC) proteolytic lysis by proteases leads to the liberation of AMC resulting in increased fluorescence in the enzymatic reaction.[1]

Substrati

A fluorogenic substrate for plasma kallikrein.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
MKCV1775
MKCS0227
MKCP6580
MKCM1094
MKCJ7050

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P J Rosenthal
Experimental parasitology, 80(2), 272-281 (1995-03-01)
The effects of peptide proteinase inhibitors on globin hydrolysis by cultured malaria parasites were studied. All of the four cysteine proteinase inhibitors evaluated blocked globin hydrolysis, as documented by the development of a morphological abnormality in which parasite food vacuoles
C Illy et al.
The Journal of biological chemistry, 272(2), 1197-1202 (1997-01-10)
Within the lysosomal cysteine protease family, cathepsin B is unique due to its ability to act both as an endopeptidase and a peptidyldipeptidase. This latter capacity to remove C-terminal dipeptides has been attributed to the presence of a 20-residue insertion
R M C Deshapriya et al.
Journal of biochemistry, 147(3), 393-404 (2009-11-17)
To identify functionally essential sequences and residues of CTLA-2alpha, in vitro mutagenesis was carried out. The coefficient of inhibition (K(i)) was determined towards rabbit cathepsin L using Z-Phe-Arg-MCA as the substrate. Recombinant CTLA-2alpha inhibited the enzyme potently (K(i) = 15
H Ghoneim et al.
International journal for parasitology, 25(12), 1515-1519 (1995-12-01)
A previously described "major acidic proteinase" of adult Schistosoma mansoni, believed to play a key role in the parasite's metabolism, has been identified as a cathepsin B (Sm31). Purified Sm cathepsin B was not recognized by anti-Sm32 or anti-cathepsin L
Fabien Lecaille et al.
The Biochemical journal, 375(Pt 2), 307-312 (2003-07-03)
The limited availability of highly selective cathepsin substrates seriously impairs studies designed to monitor individual cathepsin activities in biological samples. Among mammalian cysteine proteases, cathepsin K has a unique preference for a proline residue at P2, the primary determinant of
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