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C1484

Sigma-Aldrich

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

≥95% purity (HPLC), solid

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Synonym(s):
1H-Pyrrole-2,5-dione, 1-(4-(7-(diethylamino)-4-methyl-2-oxo-2H-1-benzopyran-3-yl)phenyl)-, CPM
Empirical Formula (Hill Notation):
C24H22N2O4
CAS Number:
76877-33-3
Molecular Weight:
402.44
MDL number:
MFCD00077334
UNSPSC Code:
12171500
PubChem Substance ID:
24892413
NACRES:
NA.47

Quality Level

100

Assay

≥95% (HPLC)

form

solid

color

yellow

solubility

DMSO: soluble
methanol: soluble

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

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

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Victor Goncalves et al.
Analytical biochemistry, 421(1), 342-344 (2011-11-05)
N-myristoylation is the irreversible attachment of a C(14) fatty acid, myristic acid, to the N-terminal glycine of a protein via formation of an amide bond. This modification is catalyzed by myristoyl-coenzyme A (CoA):protein N-myristoyltransferase (NMT), an enzyme ubiquitous in eukaryotes
F C Ayers et al.
Analytical biochemistry, 154(1), 186-193 (1986-04-01)
A microfluorometric assay for thiols has been developed using the thiol-specific fluorochrome N-[4-(7-diethylamino-4-methyl-3-coumarinyl)phenyl]maleimide (CPM). The technique may be used to quantitate either cellular or plasma thiols over a range of 0.01 to 3.0 nmol and may be used with as
W Feng et al.
Molecular pharmacology, 55(5), 821-831 (1999-04-30)
Quinones undergo redox cycling and/or arylation reactions with key biomolecules involved with cellular Ca2+ regulation. The present study utilizes nanomolar quantities of the fluorogenic maleimide 7-diethylamino-3-(4'-maleimidylphenyl)-4-methylcoumarin (CPM) to measure the reactivity of hyperreactive sulfhydryl moieties on sarcoplasmic reticulum (SR) membranes
N T Lu et al.
Archives of biochemistry and biophysics, 375(1), 7-20 (2000-02-23)
The cystic fibrosis transmembrane conductance regulator (CFTR) is known to function as a regulated chloride channel and, when genetically impaired, to cause the disease cystic fibrosis. The novel studies reported here were undertaken to gain greater molecular insight into possible
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
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