C9521

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

Name: Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride
Brand: SIGMA
Price: 595 USD
Availability: InStock

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

Key Documents

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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

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This Item	A3401	P9273	C5429
Sigma-Aldrich C9521 Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride	Sigma-Aldrich A3401 Ala-Ala-Phe-7-amido-4-methylcoumarin	Sigma-Aldrich P9273 Pro-Phe-Arg-7-amido-4-methylcoumarin	Sigma-Aldrich C5429 Z-Arg-Arg-7-amido-4-methylcoumarin hydrochloride
assay ≥95% (HPLC)	assay ≥98% (TLC)	assay ≥95%	assay -
solubility methanol: 20 mg/mL, clear, colorless	solubility ethanol: 20 mg/mL, clear, colorless to light yellow	solubility methanol: 50 mg/mL, clear, colorless to faintly yellow	solubility -
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form powder
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. −20°C
concentration ≥95%	concentration -	concentration -	concentration -

General description

A fluorogenic substrate for plasma kallikrein.

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]

Application

Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride has been used:

as a fluorogenic substrate in actinidin inhibition assay
as a kallikrein substrate[4]
as a trypsin substrate for fluorometric assay
as a cathepsin-L substrate[5]

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.[1]

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)

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

Biochemical properties of purified cathepsin B from Schistosoma mansoni.

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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Global Trade Item Number

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

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