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A9891

Sigma-Aldrich

7-Amino-4-methylcoumarin

chromophore for enzyme substrates, fluorogenic, ≥98% (HPLC), powder

Synonyme(s) :

Coumarin 120

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About This Item

Formule empirique (notation de Hill):
C10H9NO2
Numéro CAS:
26093-31-2
Poids moléculaire :
175.18
Numéro Beilstein :
142231
Numéro CE :
247-454-8
Numéro MDL:
MFCD00006868
Code UNSPSC :
12352204
ID de substance PubChem :
24891406
Nomenclature NACRES :
NA.32

product name

7-Amino-4-methylcoumarin, Chromophore for substrates

Niveau de qualité

200

Description

chromophore for enzyme substrates

Pureté

≥98% (HPLC)

Forme

powder

Pf

223-226 °C (lit.)

Solubilité

acetone: 10 mg/mL, clear, colorless to yellow

Fluorescence

λex 365 nm; λem 440 nm in ethanol(lit.)

Température de stockage

2-8°C

Chaîne SMILES 

CC1=CC(=O)Oc2cc(N)ccc12

InChI

1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3

Clé InChI

GLNDAGDHSLMOKX-UHFFFAOYSA-N

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Application

7-Amino-4-methylcoumarin has been used:
  • to determine cathepsin B like- activity
  • as a substrate for leucine aminopeptidase (LAP)
  • in chymotryptic assay
  • as a standard to detect the activation of caspase-3 during
  • sanguinarine-induced damage
  • protection by human DEAD-box DDX3

Used as matrix for analysis of monosulfated disaccharides and as a co-matrix with 6-aza-2-thiothymidine for sulfated neutral and sialylated tri-and tetrasaccharides.

Actions biochimiques/physiologiques

7-Amino-4-methylcoumarin is a coumarin derivative, which serves as a fluorescence reference standard to screen protease inhibitors.

Notes préparatoires

Soluble in DMSO (10 mg/mL), DMF, and acetone (10 mg/mL).

Autres remarques

Reagent for preparing new fluorogenic AMC-based substrates for cystine aminopeptidase (and other hydrolases); used as reference compound in the enzyme assay.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Issues in Chemistry and General Chemical Research (2012)
Regulation of p21 expression for anti-apoptotic activity of DDX3 against sanguinarine-induced cell death on intrinsic pathway
Nguyen CN, et al.
Phytomedicine, 153096-153096 (2019)
Chymase uptake by cardiomyocytes results in myosin degradation in cardiac volume overload
Powell PC, et al.
Heliyon, 5(4), e01397-e01397 (2019)
Sander S van Berkel et al.
ChemMedChem, 7(4), 606-617 (2012-02-02)
The synthesis of a series of peptides containing C-terminal 7-amino-4-methylcoumarin (AMC) for use in the thrombin generation test (TGT) is described. The lead structure in this project was H-Gly-Gly-Arg-AMC, of which the water solubility and kinetic parameters (K(M) and k(cat))
Berberine-induced cardioprotection and Sirt3 modulation in doxorubicin-treated H9c2 cardiomyoblasts
Coelho AR, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1863(11), 2904-2923 (2017)
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Articles

Enzymatic Assay of Cathepsin B

Cathepsin B is a lysosomal cysteine proteinase with broad specificity. This protocol uses Nα–CBZ–Arg–Arg–7–amido–4–methylcoumarin as the substrate for fluorometric detection of Cathepsin B activity.

Enzymatic Assay of Cathepsin B

Cathepsin B is a lysosomal cysteine proteinase with broad specificity. This protocol uses Nα–CBZ–Arg–Arg–7–amido–4–methylcoumarin as the substrate for fluorometric detection of Cathepsin B activity.

Enzymatic Assay of Cathepsin B

Cathepsin B is a lysosomal cysteine proteinase with broad specificity. This protocol uses Nα–CBZ–Arg–Arg–7–amido–4–methylcoumarin as the substrate for fluorometric detection of Cathepsin B activity.

Enzymatic Assay of Cathepsin B

Cathepsin B is a lysosomal cysteine proteinase with broad specificity. This protocol uses Nα–CBZ–Arg–Arg–7–amido–4–methylcoumarin as the substrate for fluorometric detection of Cathepsin B activity.

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