Coumarin-Derived Fluorescent Chemosensors

Li, Hongqi; Cai, Li; Chen, Zhe

doi:10.5772/33157

Cited by 33 publications

(31 citation statements)

References 146 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is well known that addition of electron withdrawing substitutents at the 3-position of 7-aminocoumarins produce large bathochromic shifts in the absorption maximum 12 . For example, 3-nitro-DEAC ( 1 ) not only has a large absorption maximum at 470 nm, but an extremely low minimum in the 340-360 nm-range (Fig.…”

Section: Resultsmentioning

confidence: 99%

Spectral Evolution of a Photochemical Protecting Group for Orthogonal Two-Color Uncaging with Visible Light

et al. 2013

View full text Add to dashboard Cite

Caged compounds are molecules rendered functionally inert by derivatization with a photochemical protecting group. We describe the design logic behind the development of a diethylaminocoumarin (DEAC) caging chromophore, DEAC450, that absorbs blue light strongly (ε450 = 43,000 M-1 cm-1), and violet light 10-fold more weakly. The absorption minimum is in the wavelength range (340-360 nm) that is traditionally used for photolysis of many widely used nitroaromatic caged compounds (e.g. 4-carboxymethoxy-5,7-dinitroindolinyl(CDNI)-GABA). We used this chromophore to synthesize DEAC450-caged cAMP and found this probe was very stable towards aqueous hydrolysis in the electronic ground state but was photolyzed with a quantum efficiency of 0.76. When DEAC450-cAMP and CDNI-GABA where co-applied to striatal cholinergic interneurons, the caged compounds were photolyzed in an chromatically orthogonal manner using blue and violet light so as to modulate the neuronal firing rate in a bi-directional way.

show abstract

Section: Resultsmentioning

confidence: 99%

Spectral Evolution of a Photochemical Protecting Group for Orthogonal Two-Color Uncaging with Visible Light

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Another interesting phenomenon is the unaffected fluorescence spectra of 1e between pH 3.3 and 11.0. It is well known that the electron donating groups (such as amino-group) substituted on coumarin into electrondeficient positions (positions 4, 5 and 7) will increase the intramolecular electron transfer and thus enhance the fluorescence intensity of coumarin derivatives [12,27]. At the same time an electron-deficient 2-hydroxybenzyl substitution on the amino-group can decrease this effect.…”

Section: Proton Dissociation Processes and Calculated Lipophilicity Omentioning

confidence: 99%

“…Coumarin derivatives exhibit strong fluorescence in the visible wavelength region which is usually significantly influenced by the surrounding medium [27]. At the same time HSA contains a single tryptophan (Trp 214) residue near to site I that is responsible for the majority of the intrinsic fluorescence of the protein.…”

Section: Introductionmentioning

confidence: 99%

Interaction of anticancer reduced Schiff base coumarin derivatives with human serum albumin investigated by fluorescence quenching and molecular modeling

Dömötör

Tuccinardi

Karcz

et al. 2014

Bioorganic Chemistry

View full text Add to dashboard Cite

The specific binding of five reduced Schiff base derived 7-amino-coumarin compounds with antitumor activity to human serum albumin, the principal binding protein of blood, was studied by fluorescence spectroscopy. Their conditional binding constants were computed and the reversible binding at the Sudlow's site I was found to be strong (K D ~ 0.03-2.09 M).Based on the data albumin can provide a depot for the compounds and is responsible for their biodistribution and transport processes. The experimental data is complemented by proteinligand docking calculations for two representatives which support the observations. The proton dissociation constants of the compounds were also determined by UV-Vis spectrophotometric and fluorometric titrations to obtain the actual charges and distribution of the species in the various protonation states at physiological pH.

show abstract

“…The combined organic layers were dried over Na 2 SO 4 and concentrated under reduced pressure to afford a crude product, which was purified by column chromatography, using silica gel eluted with 30 % ethyl acetate in hexane, to give monomer 3, as a brown solid. ( 4 .5H 2 O (10 mol% of monomer 3) in a minimum amount of water were also added to the mixture. After stirring at room temperature for 24 h, the solvent was removed under reduced pressure and the residue stirred in water (50 mL) and isolated by vacuum filtration.…”

Section: Synthesis Of Monomermentioning

confidence: 99%

“…These features allow coumarin derivatives to have a wide range of applications in the photoelectronic, medicinal and biological fields, as well as in industry as fluorescent probes. [1][2][3][4] Furthermore, substituents manipulation on the coumarin backbone can lead to a fine-tuning of its emission properties. 5 One of the strategies that have been used to improve the emission properties of coumarin is to include a 1,2,3-triazole ring in the structure which is formed by means of a Cu(I)-catalyzed fluorogenic azide-alkyne 1,3-dipolar cycloaddition, a typical click reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorescent Poly(coumarin-triazoles) via a CuAAC 'click' reaction

2017

View full text Add to dashboard Cite

We describe a new fluorescent polymer system based on a coumarin-triazole functionality. The non-fluorescent 3-azidocoumarin-alkyne monomers are polymerized in a step-growth manner via a Cu (I)-catalyzed 1,3-dipolar cycloaddition (CuAAC) reaction. The process involves the conversion of a quenching azide group to 1,2,3-triazole in the monomer that leads to an increase in the intensity of fluorescence in the new polymer. The solubility and photophysical properties of the polymer were enhanced through co-polymerization with an aliphatic co-monomer. KEYWORDSCoumarin, poly(coumarin-triazole), click polymerization, solubility, photophysical properties.

show abstract

Coumarin-Derived Fluorescent Chemosensors

Cited by 33 publications

References 146 publications

Spectral Evolution of a Photochemical Protecting Group for Orthogonal Two-Color Uncaging with Visible Light

Spectral Evolution of a Photochemical Protecting Group for Orthogonal Two-Color Uncaging with Visible Light

Interaction of anticancer reduced Schiff base coumarin derivatives with human serum albumin investigated by fluorescence quenching and molecular modeling

Synthesis of Fluorescent Poly(coumarin-triazoles) via a CuAAC 'click' reaction

Contact Info

Product

Resources

About