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96669

Sigma-Aldrich

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

suitable for fluorescence, BioReagent, ≥90% (HPCE)

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
MDL number:
MFCD00077334
UNSPSC Code:
12171500
PubChem Substance ID:
57653774
NACRES:
NA.32

product line

BioReagent

Assay

≥90% (HPCE)

form

solid

fluorescence

λex 391 nm; λem 472 nm in methanol: 2-mercaptoethanol

suitability

suitable for fluorescence

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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Application

Fluorescence probe for glutathione for intact cells; specific advantages: only thio derivative fluoresces, high quantum yield and good Stokes shift

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 Code

11 - Combustible Solids

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)

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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
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
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
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
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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