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39145

Sigma-Aldrich

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

for fluorescence, ≥99.0% (HPLC)

Synonyme(s) :

DACM-3

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About This Item

Formule empirique (notation de Hill):
C16H14N2O4
Numéro CAS:
55145-14-7
Poids moléculaire :
298.29
Beilstein:
1545346
Numéro CE :
259-499-0
Numéro MDL:
MFCD00006863
Code UNSPSC :
12352200
ID de substance PubChem :
329755824

Qualité

for fluorescence

Essai

≥99.0% (HPLC)

Pf

218-220 °C (lit.)

Fluorescence

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

Chaîne SMILES 

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

Clé InChI

ADEORFBTPGKHRP-UHFFFAOYSA-N

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Autres remarques

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

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Y. Kanaoka
Angewandte Chemie (International Edition in English), 89, 141-141 (1977)
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
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)
G Pravatà et al.
Journal of dermatological science, 7(1), 14-23 (1994-02-01)
We have studied the distribution of SH groups and SS linkages in solar elastosis, in comparison with that in aged and juvenile sun-unexposed skin, using N-(7-dimethylamino-4-methyl-3-coumarinyl) maleimide (DACM) stain. In heavy solar elastosis we found increased fluorescence for SS bonds
B G Werneburg et al.
Archives of biochemistry and biophysics, 303(2), 214-221 (1993-06-01)
Inactivations of chicken liver pyruvate carboxylase with N-(7-dimethylamino-4-methyl-3-coumarinyl)maleimide (DACM) and o-phthalaldehyde (o-PA) have identified cysteine and lysine residues that are essential for catalytic activity. Protection experiments suggest that the modified residues are located in or near the first and second
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