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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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M Brune et al.
Biochemistry, 40(16), 5087-5094 (2001-04-18)
A sensor for purine nucleoside diphosphates in solution based on nucleoside diphosphate kinase (NDPK) has been developed. A single cysteine was introduced into the protein and labeled with the environmentally sensitive fluorophore, N-[2-(iodoacetamido)ethyl]-7-diethylaminocoumarin-3-carboxamide. The resultant molecule shows a 4-fold fluorescence
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
Z He et al.
Biophysical journal, 75(5), 2389-2401 (1998-10-28)
Inorganic phosphate (Pi) release was determined by means of a fluorescent Pi-probe in single permeabilized rabbit soleus and psoas muscle fibers. Measurements of Pi release followed photoliberation of approximately 1.5 mM ATP by flash photolysis of NPE-caged ATP in the
Adam Shutes et al.
Methods in enzymology, 407, 9-22 (2006-06-08)
Ras proteins are small GTPases that exhibit high-affinity binding to GDP and GTP and hydrolyze bound GTP to GDP. The intrinsic GTPase activity of Ras proteins is accelerated by GTPase activating proteins (GAPs), which act to attenuate GTPase signaling by
Simone Kunzelmann et al.
The Journal of biological chemistry, 284(48), 33130-33138 (2009-10-06)
Nearly every cellular process requires the presence of ATP. This is reflected in the vast number of enzymes like kinases or ATP hydrolases, both of which cleave the terminal phosphate from ATP, thereby releasing ADP. Despite the fact that ATP
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