7-(Diethylamino)coumarin-3-carboxylic acid - CAS 50995-74-9
Molecular Formula:
C14H15NO4
Molecular Weight:
261.27
COA:
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Application\Fluorophore:
Other Fluorescent Probes
Description:
7-(Diethylamino)coumarin-3-carboxylic acid is an amine-reactive, non-activated fluorescent probe for bioconjugation.
Purity:
>98%
Synonyms:
Coumarin D 1421; D 1421
MSDS:
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Excitation:
430-440 nm
Emission:
470-480 nm
InChIKey:
WHCPTFFIERCDSB-UHFFFAOYSA-N
InChI:
InChI=1S/C14H15NO4/c1-3-15(4-2)10-6-5-9-7-11(13(16)17)14(18)19-12(9)8-10/h5-8H,3-4H2,1-2H3,(H,16,17)
Canonical SMILES:
CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)O
1.Interaction of bacteriochlorophyll with the LH1 and PufX polypeptides of photosynthetic bacteria: use of chemically synthesized analogs and covalently attached fluorescent probes.
Law CJ;Chen J;Parkes-Loach PS;Loach PA Photosynth Res. 2003;75(3):193-210.
The protein components of the reaction center (RC) and core light-harvesting (LH 1) complexes of photosynthetic bacteria have evolved to specifically, but non-covalently, bind bacteriochlorophyll (Bchl). The contribution to binding of specific structural elements in the protein and Bchl may be determined for the LH 1 complex because its subunit can be studied by reconstitution under equilibrium conditions. Important to the determination and utilization of such information is the characterization of the interacting molecular species. To aid in this characterization, a fluorescent probe molecule has been covalently attached to each of the LH 1 polypeptides. The fluorescent probes were selected for optimal absorption and emission properties in order to facilitate their unique excitation and to enable the detection of energy transfer to Bchl. Oregon Green 488 carboxylic acid and 7-diethylaminocoumarin-3-carboxylic acid seemed to fulfill these requirements. Each of these probes were utilized to derivatize the LH1 beta-polypeptide of Rhodobacter sphaeroides. It was demonstrated that the beta-polypeptides did not interact with each other in the absence of Bchl. When Bchl was present, the probe-labeled beta-polypeptides interacted with Bchl to form subunit-type complexes much as those formed with the native polypeptides.
2.Synthesis of a fluorescence resonance energy transfer-based probe containing a tricyclic nucleoside analog for single nucleotide polymorphism typing.
Hayai A;Maeda Y;Ueno Y Bioorg Med Chem Lett. 2016 Aug 1;26(15):3552-5. doi: 10.1016/j.bmcl.2016.06.024. Epub 2016 Jun 9.
Here, we report the synthesis of a fluorescence resonance energy transfer (FRET)-based probe for single nucleotide polymorphism (SNP) typing. The probe contains a fluorescent tricyclic base, 8-amino-3-(2,3-dihydroxypropyl)imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine, as a donor molecule and 7-diethylaminocoumarin-3-carboxylic acid as an acceptor molecule. FRET was observed between the donor and acceptor molecules on the probe. The identity of the target bases on DNA and RNA strands could be determined using the probe.
3.Interaction of fluorescently labeled triethyleneglycol and peptide derivatives with β-cyclodextrin.
Alouini MA;Moustoifa el-F;Rubio-Albenque S;Berthelot T;Fery-Forgues S;Déléris G Chemphyschem. 2014 Feb 24;15(3):444-57. doi: 10.1002/cphc.201301032. Epub 2014 Jan 8.
A triethyleneglycol (TEG) chain, a linear peptide, and a cyclic peptide labeled with 7-methoxycoumarin-3-carboxylic acid (MC) and 7-diethylaminocoumarin-3-carboxylic acid (DAC) were used to thoroughly study Förster resonance energy transfer (FRET) in inclusion complexes. (1) H NMR evidence was given for the formation of a 1:1 inclusion complex between β-cyclodextrin (β-CD) and the fluorophore moieties of model compounds. The binding constant was 20 times higher for DAC than for MC derivatives. Molecular modeling provided additional information. The UV/Vis absorption and fluorescence properties were studied and the energy transfer process was quantified. Fluorescence quenching was particularly strong for the peptide derivatives. The presence of β-CDs reduced the FRET efficiency slightly. Dye-labeled peptide derivatives can thus be used to form inclusion complexes with β-CDs and retain most of their FRET properties. This paves the way for their subsequent use in analytical devices that are designed to measure the activity of matrix metalloproteinases.
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CAS 50995-74-9 7-(Diethylamino)coumarin-3-carboxylic acid

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