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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/REAXYS Number:
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
339956/1
352505/1
1144958

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Y. Kanaoka
Angewandte Chemie (International Edition in English), 89, 141-141 (1977)
S Murase et al.
Biochemical and biophysical research communications, 195(3), 1159-1164 (1993-09-30)
Our previous studies suggested that in a tetrameric enzyme aspartase, Cys-140 and Trp-430 are located at or near the catalytic and activator sites, respectively. To estimate the distance between these two sites, fluorescence energy transfer between a single tryptophan (Trp-430)
M Kanamori et al.
The Journal of dermatology, 17(9), 559-563 (1990-09-01)
A case of infantile digital fibromatosis was studied with regard to the distribution of -SH groups and SS linkages, using N-(7-dimethylamino-4-methyl-3-coumarinyl) maleimide (DACM) stain. Tumor cells showed a strong fluorescence in the cytoplasm from the -SH stain. A brilliant -SH
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
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