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A9891

Sigma-Aldrich

7-Amino-4-methylcumarin

Chromophore for substrates

Synonym(e):

Coumarin 120

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About This Item

Empirische Formel (Hill-System):
C10H9NO2
CAS-Nummer:
26093-31-2
Molekulargewicht:
175.18
Beilstein:
142231
EG-Nummer:
247-454-8
MDL-Nummer:
MFCD00006868
UNSPSC-Code:
12352204
PubChem Substanz-ID:
24891406
NACRES:
NA.32

Qualitätsniveau

200

Beschreibung

chromophore for enzyme substrates

Assay

≥98% (HPLC)

Form

powder

mp (Schmelzpunkt)

223-226 °C (lit.)

Löslichkeit

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

Fluoreszenz

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

Lagertemp.

2-8°C

SMILES String

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

InChIKey

GLNDAGDHSLMOKX-UHFFFAOYSA-N

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Anwendung

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.
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

Biochem./physiol. Wirkung

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

Angaben zur Herstellung

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

Sonstige Hinweise

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

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Issues in Chemistry and General Chemical Research (2012)
Significant activities of extracellular enzymes from a brown tide in the coastal waters of Qinhuangdao, China
Ou L, et al.
Harmful Algae, 74, 1-9 (2018)
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)
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)
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))
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This procedure applies to all products that have a specification for Cathepsin B activity determined by the liberation of 7-amino-4-methylcoumarin from Z-Arg-Arg 7-amido-4-methylcoumarin.

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