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C9521

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

Name: Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride
Brand: SIGMA

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

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Product Name

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

Quality Level

100

assay

≥95% (HPLC)

form

powder

concentration

≥95%

solubility

methanol: 20 mg/mL, clear, colorless

storage temp.

−20°C

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

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.

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.

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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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)

Increasing in cysteine proteinase B expression and enzymatic activity during in vitro differentiation of Leishmania (Viannia) braziliensis: First evidence of modulation during morphological transition.

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

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)

Plasmodium falciparum: effects of proteinase inhibitors on globin hydrolysis by cultured malaria parasites.

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

Role of the occluding loop in cathepsin B activity.

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

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Global Trade Item Number

SKU	GTIN
C9521-100MG	04061832908281
C9521-25MG	04061833530801

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