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39145

Sigma-Aldrich

N-(7-Dimethylamino-4-methyl-3-coumarinyl)maleimide

for fluorescence, ≥99.0% (HPLC)

Synonym(s):

DACM-3

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About This Item

Empirical Formula (Hill Notation):
C16H14N2O4
CAS Number:
55145-14-7
Molecular Weight:
298.29
Beilstein:
1545346
EC Number:
259-499-0
MDL number:
MFCD00006863
UNSPSC Code:
12352200
PubChem Substance ID:
329755824

grade

for fluorescence

Assay

≥99.0% (HPLC)

mp

218-220 °C (lit.)

fluorescence

λex 398 nm; λem 482 nm in 0.1 M phosphate pH 7.0 (after derivatization with 2-mercaptoethanol)

SMILES string

CN(C)c1ccc2C(C)=C(N3C(=O)C=CC3=O)C(=O)Oc2c1

InChI

1S/C16H14N2O4/c1-9-11-5-4-10(17(2)3)8-12(11)22-16(21)15(9)18-13(19)6-7-14(18)20/h4-8H,1-3H3

InChI key

ADEORFBTPGKHRP-UHFFFAOYSA-N

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Other Notes

Fluorescent reagent with high selectivity for protein thiols and with superior fluorescence and water solubility properties than dansyl chloride

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Certificates of Analysis (COA)

Lot/Batch Number
352505/1
1144958
339956/1

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Y. Kanaoka
Angewandte Chemie (International Edition in English), 89, 141-141 (1977)
T Ohyashiki et al.
Journal of biochemistry, 115(2), 224-229 (1994-02-01)
The effects of lipid peroxidation on the SH reactivity of the proteins in porcine intestinal brush-border membranes were examined using a fluorogenic thiol reagent, N-[7-dimethyl-amino-4-methylcoumarinyl]maleimide (DACM) in relation to lipid organization. Changes in the lipid organization were assessed by measurement
L A Jurado et al.
Biochimica et biophysica acta, 1292(1), 188-196 (1996-01-04)
We studied the transition metal ion requirements for activity and sulfhydryl group reactivity in phospho enol pyruvate carboxykinase (PEP-carboxykinase; ATP:oxaloacetate carboxylase (transphosphorylating), EC 4.1.1.49), a key enzyme in the energy metabolism of the protozan parasite Trypanosoma (Schizotrypanum) cruzi. As for
Kuikui Wang et al.
Talanta, 84(2), 400-405 (2011-03-08)
A sensitive and selective method for the paraoxon detection based on enzyme inhibition and fluorescence quenching was presented in this study. Under the catalytic effect of acetylcholinesterase (AChE), acetylthiocholine (ATCh) hydrolysis released thiocholine (TCh) which could react with N-(7-dimethylamino-4-methylcoumarin-3-yl) maleimide
M Hatanaka et al.
Biochimica et biophysica acta, 1209(1), 117-122 (1994-11-16)
Purified C9 with expected hemolytic and polymerizing activities was found to contain approximately 0.2 mol of sulfhydryl groups/mol of C9. By proteolysis of C9 with labeled SH groups, the SH residues on intact C9 were mapped to Cys-359 and Cys-384
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