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Merck

C9521

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

kallikrein substrate, ≥95% (HPLC), powder

Synonym(s):

Z-Phe-Arg-AMC

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About This Item

Empirical Formula (Hill Notation):
C33H36N6O6 · HCl
CAS Number:
70382-26-2
Molecular Weight:
649.14
UNSPSC Code:
12352204
PubChem Substance ID:
24893165
NACRES:
NA.32
MDL number:
MFCD00077030

Product Name

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

SMILES string

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)

InChI key

ZZGDDBWFXDMARY-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

powder

concentration

≥95%

solubility

methanol: 20 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

100

Application

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

Biochem/physiol Actions

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.

General description

A fluorogenic substrate for plasma kallikrein.
Z-Phe-Arg 7-amido-4-methylcoumarin (Z-FR-AMC) is a peptidomimetic substrate for papainand other enzymes such as cathepsin K. It is also a fluorogenic synthetic peptide for the enzymes cathepsins L and B.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1775
MKCS0227
MKCP6580
MKCM1094
MKCJ7050

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Cinthia Bernardes Gomes et al.
Biochimie, 133, 28-36 (2016-12-07)
Leishmania (Viannia) braziliensis presents adaptive protease-dependent mechanisms, as cysteine proteinases B (CPB). This study investigates the expression of three cpb gene isoforms and CPB enzymatic activity during the parasite differentiation. Relative expression levels of LbrM.08.0810 gene were assessed, exhibiting a
Early ontogenetic development, digestive enzymatic activity and gene expression in red sea bream (Pagrus major)
Khoa TND, et al.
Aquaculture (Amsterdam, Netherlands), 512, 734283-734283 (2019)
Quantification of Functional Actinidin in Whole Kiwifruit Extract Using the Selective Cysteine Proteinase Inhibitor E-64
Martin H
Journal of Food & Nutrition Research, 4(4), 243-250 (2016)
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
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
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