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Sigma-Aldrich

7-Amino-4-methyl-3-coumarinacetic acid N-succinimidyl ester

BioReagent, suitable for fluorescence, ≥90% (HPLC)

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Synonym(s):
7-(Dimethylamino)coumarin-4-acetic acid-NHS, 7-Amino-4-methyl-3coumarinylacetyl, N-Succinimidyl 7-amino-4-methyl-3-coumarinylacetate, AMCA-NHS, Succinimidyl-7-amino-4-methylcoumarin-3-acetate
Empirical Formula (Hill Notation):
C16H14N2O6
CAS Number:
Molecular Weight:
330.29
Beilstein/REAXYS Number:
9007679
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

assay

≥90% (HPLC)

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 354 nm; λem 440 nm in methanol

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CC1=C(CC(=O)ON2C(=O)CCC2=O)C(=O)Oc3cc(N)ccc13

InChI

1S/C16H14N2O6/c1-8-10-3-2-9(17)6-12(10)23-16(22)11(8)7-15(21)24-18-13(19)4-5-14(18)20/h2-3,6H,4-5,7,17H2,1H3

InChI key

ILKQVTIMOGNSAS-UHFFFAOYSA-N

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666548

7-Methyladenine

assay

≥90% (HPLC)

assay

≥96.0% (HPLC)

assay

97%

assay

-

solubility

DMF: soluble, DMSO: soluble

solubility

DMF: soluble, DMSO: soluble, acetonitrile: soluble

solubility

-

solubility

-

fluorescence

λex 354 nm; λem 440 nm in methanol

fluorescence

λex 445 nm; λem 482 nm in 0.1 M phosphate pH 7.0

fluorescence

-

fluorescence

-

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

Application

AMCA-NHS has been utilized in the development of a donor europium chelate fluorochrome for use in LRET based analyses by first reacting with an amino group and then with DTPA anhydride . Utilized in FRET based studies, acting as the donor dye and can be paired with fluorescein-5-isothiocyanate as the acceptor dye . A blue fluorescent dye reactive towards primary amine groups on proteins, peptides, antibodies, and other biomolecules (at pH 7.0-9.0).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Labeling of lysyl residues in proteins

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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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H I Stefanova et al.
Biochemistry, 32(1), 356-362 (1993-01-12)
The (Ca(2+)-Mg2+)-ATPase of sarcoplasmic reticulum was labeled with the succinimidyl ester of 7-amino-4-methylcoumarin-3-acetic (AMCA). Although a large number of residues were labeled, it was found that Lys-492 was labeled preferentially at pH values between 6 and 8, consistent with an

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