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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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Properties

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

Description

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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Production of anti-peptide antibodies against trypanopain-Tb from Trypanosoma brucei brucei: effects of antibodies on enzyme activity against Z-Phe-Arg-AMC.

L Troeberg et al.

Immunopharmacology, 36(2-3), 295-303 (1997-06-01)

Anti-peptide antibodies were produced against the cysteine proteinase trypanopain-Tb from Trypanosoma brucei brucei and the effects of these antibodies on enzyme activity against carboxybenzoyl (Z)-Phe-Arg-aminomethylcoumarin (AMC) investigated. A peptide was synthesised corresponding to a region of the trypanopain-Tb active site

Modulation of the catalytic activity of cruzipain, the major cysteine proteinase from Trypanosoma cruzi, by temperature and pH.

L Salvati et al.

European journal of biochemistry, 268(11), 3253-3258 (2001-06-08)

Cysteine proteinases are relevant to several aspects of the parasite life cycle and of parasite-host relationships. Here, a quantitative investigation of the effect of temperature and pH on the total substrate inhibition of cruzipain, the major papain-like cysteine proteinase from

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)

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Global Trade Item Number

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