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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

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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Yu-Chih Tsai et al.
Biochemistry, 45(32), 9675-9687 (2006-08-09)
We show that T7 DNA polymerase exists in three distinct structural states, as reported by a conformationally sensitive fluorophore attached to the recognition (fingers) domain. The conformational change induced by a correct nucleotide commits the substrate to the forward reaction
M Brune et al.
Biochemistry, 33(27), 8262-8271 (1994-07-12)
A probe has been developed that can rapidly measure micromolar concentrations of inorganic phosphate (Pi), in particular to follow the release of Pi in real time from enzymes such as phosphatases. Its application is described to investigate the mechanism of
A Vandecandelaere et al.
Biochemistry, 38(25), 8179-8188 (1999-07-01)
The molecular mechanism underlying microtubule dynamic instability depends on the relationship between the addition of tubulin-GTP to a growing microtubule and its hydrolysis in the microtubule lattice to tubulin-GDP, with release of inorganic phosphate (Pi). Since this relationship remains controversial
Jeremiah W Hanes et al.
Chemical communications (Cambridge, England), 47(8), 2273-2275 (2010-12-03)
This communication describes the development of a thiamin sensor based on the bacterial thiamin binding protein. A triple mutant (C48S, C50S, S62C) of TbpA was labeled on C62 with N-[2-(L-maleimidyl)ethyl]-7-(diethylamino)coumarin-3-carboxamide (MDCC). Thiamin binding to this protein reduced the coumarin fluorescence
Z H He et al.
The Journal of physiology, 501 ( Pt 1), 125-148 (1997-05-15)
1. The rate of appearance of inorganic phosphate (Pi) and hence the ATPase activity of rabbit psoas muscle in single permeabilized muscle fibres initially in rigor was measured following laser flash photolysis of the P3-1-(2-nitrophenyl)ethyl ester of ATP (NPE-caged ATP)
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