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Merck
CN

C1484

7-Diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin

≥95% purity (HPLC), solid

Synonym(s):

1H-Pyrrole-2,5-dione, 1-(4-(7-(diethylamino)-4-methyl-2-oxo-2H-1-benzopyran-3-yl)phenyl)-, CPM

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About This Item

Empirical Formula (Hill Notation):
C24H22N2O4
CAS Number:
76877-33-3
Molecular Weight:
402.44
UNSPSC Code:
12171500
PubChem Substance ID:
24892413
NACRES:
NA.47
MDL number:
MFCD00077334

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Product Name

7-Diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin, ≥95% (HPLC), solid

SMILES string

CCN(CC)c1ccc2C(C)=C(C(=O)Oc2c1)c3ccc(cc3)N4C(=O)C=CC4=O

InChI

1S/C24H22N2O4/c1-4-25(5-2)18-10-11-19-15(3)23(24(29)30-20(19)14-18)16-6-8-17(9-7-16)26-21(27)12-13-22(26)28/h6-14H,4-5H2,1-3H3

InChI key

YGIABALXNBVHBX-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

solid

technique(s)

titration: suitable

color

yellow

solubility

DMSO: soluble, methanol: soluble

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

Quality Level

100

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General description

7-Diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin (CPM), is a highly fluorescent, sulfhydryl (-SH) group containing coumarin derivative. It has excitation an emission wavelengths of 355 and 460 nm, respectively.

Application

7-Diethylamino-3-(4-maleimidophenyl)-4-methylcoumarin has been used:
  • as a nontoxic substitute for conjugation with antibody(93)
  • to aid fluorescent detection of Coenzyme A (CoA-SH) in human N-myristoyltransferases assay (94)
  • in thermostability shift assay of recombinant protein(95)

Biochem/physiol Actions

Used to monitor release of thiols, quantitate thiol in microplate reactions, and to distinguish proliferating cancer cells by nucleolar protein staining.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW8175
MKCV5953
MKCV1087
MKCR2045
MKCR7205

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Targeting Acyl-CoA: diacylglycerol acyltransferase 1 (DGAT1) with small molecule inhibitors for the treatment of metabolic diseases
Cao JS, et al.
The Journal of biological chemistry, 286(48), 41838-41851 (2011)
W Feng et al.
The Journal of biological chemistry, 275(46), 35902-35907 (2000-09-22)
Inositol 1,4,5-trisphosphate receptors (IP(3)R) and ryanodine receptors (RyR) mediate the release of endoplasmic and sarcoplasmic reticulum (ER/SR) Ca(2+) stores and regulate Ca(2+) entry through voltage-dependent or ligand-gated channels of the plasma membrane. A prominent property of ER/SR Ca(2+) channels is
D J Steenkamp
The Biochemical journal, 292 ( Pt 1), 295-301 (1993-05-15)
Methods for the qualitative and quantitative analysis of thiols by means of the fluorogenic reagent 7-diethylamino-3-(4'-maleimidylphenyl)-4-methylcoumarin are described, with particular reference to the trypanosomatid metabolites glutathionylspermidine (GSH-spermidine) and trypanothione. Second-order rate constants for the derivatization of seven different thiols under
Andrew A Voss et al.
The Journal of biological chemistry, 279(33), 34514-34520 (2004-06-16)
The skeletal-type ryanodine receptor (RyR1) undergoes covalent adduction by nitric oxide (NO), redox-induced shifts in cation regulation, and non-covalent interactions driven by the transmembrane redox potential that enable redox sensing. Tight redox regulation of RyR1 is thought to be primarily
Alice Talpin et al.
Arthritis research & therapy, 16(4), 417-417 (2014-08-22)
This study aimed to compare the functional capacity and gene expression profile of monocyte-derived dendritic cells (MD-DCs) in HLA-B27+ axial spondyloarthritis (SpA) patients and healthy controls. MD-DCs were differentiated with interleukin 4 (IL-4) and granulocyte-macrophage colony-stimulating factor (GM-CSF) for seven
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