7-Amino-4-methylcoumarinA fluorogenic reagent and antibacterial, antifungal agent

7-Amino-4-methylcoumarin (CAS 26093-31-2)

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Synonym: Coumarin 120; AMC
Application: A fluorogenic reagent and antibacterial, antifungal agent
CAS Number: 26093-31-2
Purity: ≥98%
Molecular Weight: 175.2
Molecular Formula: C10H9NO2
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7-Amino-4-methylcoumarin (AMC) is a well-known laboratory reagent employed in the preparation of fluorogenic AMC-based substrates for the detection of proteolytic enzyme activity. AMC has been utilized as a fluorescent probe to analyze glycoproteins' monosaccharides and N-linked oligosaccharides via chromatography and has been used as a laser dye. Recent research shows that AMC was extracted from an endophytic Xylaria fungal species and exhibited strong antibacterial and antifungal activities in vitro against Aspergillus, Candida, Escherichia, Staphylococcus, Salmonella and Vibrio species, among others. This product is also useful as a reference standard in enzymatic assays.


References

1. Zimmerman, M., et al. 1977. Anal. Biochem. 78: 47-51. PMID: 848756
2. Kanaoka, Y., et al. 1982. Chem. Pharm. Bull. 30: 1485-1487. PMID: 7105264
3. Liu, X et al. 2008. Appl. Microbiol. Biotechnol. 78: 241-247. PMID: 18092158
4. Yodoshi, M., et al. 2008. J Chromatogr A. 1203: 137-145. PMID: 18684461

Physical State :
Solid
Solubility :
Soluble in acetone (10 mg/ml), DMSO (10 mg/ml), and DMF.
Storage :
Store at 4° C
Melting Point :
223-226° C (lit.)
Boiling Point :
378.26° C at 760 mmHg (Predicted)
Density :
1.28 g/cm3 (Predicted)
Refractive Index :
n20D 1.63 (Predicted)
IC50 :
HIV-1(RF): IC50 = 5.21 µM (CEM); HIV-1(RF): EC5050 = >149 µM (CEM)
Ki Data :
Carbonic anhydrase XII: Ki= 9.13 µM (human); Carbonic anhydrase IX: Ki= 7.64 µM (human); Carbonic anhydrase I: Ki= 5.56 µM (human)
Fluoresence :
λex 365 nm, λem 440 nm in ethanol; λex 428 nm, λem 441 nm in methanol; λex 380 nm, λem 460 nm
pK Values :
pKb: 1.89
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
92249
MDL Number :
MFCD00006868
EC Number :
247-454-8
Beilstein Registry :
142231
SMILES :
CC1=CC(=O)OC2=C1C=CC(N)=C2

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7-Amino-4-methylcoumarin  Product Citations

See how others have used 7-Amino-4-methylcoumarin. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 22767595  Kakiya, N. et al. 2012. J. Biol. Chem. 287: 29362-29372.

PMID: # 22701711  Jung, YS. et al. 2012. PLoS ONE. 7: -.

PMID: # 22485137  Al-Mousa, F. et al. 2012. PLoS ONE. 7: -.

PMID: # 23558999  Geum-Hwa, L. et al. 2012. Biol. Res. 45: 403-410.

Citations 1 to 4 of 4 total
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