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05019

Sigma-Aldrich

7-Diethylamino-3-[N-(2-maleimidoethyl)carbamoyl]coumarin

suitable for fluorescence, BioReagent, ≥97.0% (HPLC)

Synonym(s):

MDCC

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About This Item

Empirical Formula (Hill Notation):
C20H21N3O5
CAS Number:
156571-46-9
Molecular Weight:
383.40
MDL number:
MFCD07366642
UNSPSC Code:
12352116
PubChem Substance ID:
329748005
NACRES:
NA.32

product line

BioReagent

Quality Level

100

Assay

≥97.0% (HPLC)

suitability

suitable for fluorescence

SMILES string

CCN(CC)c1ccc2C=C(C(=O)NCCN3C(=O)C=CC3=O)C(=O)Oc2c1

InChI

1S/C20H21N3O5/c1-3-22(4-2)14-6-5-13-11-15(20(27)28-16(13)12-14)19(26)21-9-10-23-17(24)7-8-18(23)25/h5-8,11-12H,3-4,9-10H2,1-2H3,(H,21,26)

InChI key

IXQPRUQVJIJUEB-UHFFFAOYSA-N

Application

7-Diethylamino-3-[N-(2-maleimidoethyl)carbamoyl]coumarin is utilized as a fluoresencent biological sensing device . Used for real-time measurements for the release of inorganic phosphates during enzymatic reaction when MDCC is conjugated to a mutant phosphate-binding protein . Also, utilized for intramolecular fluorescence energy transfer (FRET) experiments .
Thiol-reactive probe for protein labelling

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

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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Lyndon L E Salins et al.
Sensors and actuators. B, Chemical, 97(1), 81-89 (2004-03-06)
This work explores the potential use of a member of the periplasmic family of binding proteins, the phosphate binding protein (PBP), as the biorecognition element in a sensing scheme for the detection of inorganic phosphate (Pi). The selectivity of this
Maria M Martinez-Senac et al.
Biochemistry, 44(51), 16967-16976 (2005-12-21)
RecG is a DNA helicase involved in the repair of damage at a replication fork and catalyzes the reversal of the fork to a point beyond the damage in the template strand. It unwinds duplex DNA in reactions that are
M A Ferenczi et al.
Biophysical journal, 68(4 Suppl), 191S-192S (1995-04-01)
A new method for the measurement of phosphate release in contracting and relaxed permeabilized muscle fibers is described. The assay is based on a genetically engineered phosphate-binding protein labeled with a coumarin fluorescent probe, which binds inorganic phosphate tightly and
M Hirshberg et al.
Biochemistry, 37(29), 10381-10385 (1998-07-22)
Crystal structures are presented for the A197C mutant of Escherichia coli phosphate binding protein (PBP) and the same mutant labeled at Cys197 with N-[2-(1-maleimidyl)ethyl]-7-(diethylamino)coumarin-3-carboxamide (MDCC). Both proteins are complexed with inorganic phosphate. The latter molecule, MDCC-PBP, exhibits a large increase
Martin R Webb
Molecular bioSystems, 3(4), 249-256 (2007-03-21)
Biosensors are becoming widely used both in basic research and in screening assays and reagentless sensors with fluorescent reporter groups attached to proteins form one class. This article describes the development of sensors for two small molecules, driven in particular
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