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C1484

Sigma-Aldrich

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:
Molecular Weight:
402.44
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

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

Quality Level

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.

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

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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)
S Lutsenko et al.
Biochemistry, 32(26), 6737-6743 (1993-07-06)
The role of the Na,K-ATPase beta-subunit in stabilization of ion-binding sites has been investigated. Treatment of the purified renal Na,K-ATPase with 0.25 M DTT at 40 degrees C for 1 h resulted in 50% loss of Rb occlusion, which correlates
G Liu et al.
Molecular pharmacology, 45(2), 189-200 (1994-02-01)
The fluorogenic sulfhydryl probe 7-diethylamino-3-(4'-maleimidylphenyl)-4-methylcoumarin (CPM) (1-50 nM) is used to characterize the functional role and location of highly reactive thiol groups on the ryanodine-sensitive Ca2+ release channel complex [i.e., ryanodine receptors (RyRs)] of skeletal and cardiac junctional sarcoplasmic reticulum
Tamara N Tsalkova et al.
Biochemistry, 46(1), 106-119 (2007-01-03)
Design of a partially cysteine-depleted C98S/C239S/C377S/C468A cytochrome P450 3A4 mutant designated CYP3A4(C58,C64) allowed site-directed incorporation of thiol-reactive fluorescent probes into alpha-helix A. The site of modification was identified as Cys-64 with the help of CYP3A4(C58) and CYP3A4(C64), each bearing only
Simple Futarmal Kothari et al.
Pain, 156(12), 2545-2555 (2015-08-27)
The pathophysiology and underlying pain mechanisms of temporomandibular disorders (TMD) are poorly understood. The aims were to assess somatosensory function at the temporomandibular joints (TMJs) and to examine whether conditioned pain modulation (CPM) differs between TMD pain patients (n =

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