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A9891

Sigma-Aldrich

7-Amino-4-methylcoumarin

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

Synonym(s):

Coumarin 120

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
26093-31-2
Molecular Weight:
175.18
Beilstein/REAXYS Number:
142231
EC Number:
247-454-8
MDL number:
MFCD00006868
UNSPSC Code:
12352204
PubChem Substance ID:
24891406
NACRES:
NA.32

Key Documents

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Product Name

7-Amino-4-methylcoumarin, Chromophore for substrates

Quality Level

200

description

chromophore for enzyme substrates

assay

≥98% (HPLC)

form

powder

mp

223-226 °C (lit.)

solubility

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

fluorescence

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

storage temp.

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

InChI key

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.

Biochem/physiol Actions

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

Preparation Note

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

Other Notes

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000281995
0000281995
SLCL6256
SLCH3300
SLCD1283

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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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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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