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COO/COA

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39145

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

Name: <I>N</I>-(7-Dimethylamino-4-methyl-3-coumarinyl)maleimide
Brand: SIAL

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

λ_ex 398 nm; λ_em 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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Y. Kanaoka

Angewandte Chemie (International Edition in English), 89, 141-141 (1977)

SH abundant body in infantile digital fibromatosis--a histochemical study on distribution of sulfhydryl groups.

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

Use of hybridization for distance measurement by fluorescence energy transfer in oligomeric proteins: distance between two functional sites in aspartase.

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)

Increased SS bonds in chronic solar elastosis: a study with N-(7-dimethylamino-4-methyl-3-coumarinyl) maleimide (DACM) stain.

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

Chemical modifications of chicken liver pyruvate carboxylase: evidence for essential cysteine-lysine pairs and a reactive sulfhydryl group.

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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