Near-membrane iminocoumarin-based low affinity fluorescent Ca2+ indicators

Liepouri, Fotini; Deligeorgiev, Todor; Veneti, Zoe; Savakis, Charalambos; Katerinopoulos, Haralambos E.

doi:10.1016/s0143-4160(02)00035-0

Cited by 22 publications

(8 citation statements)

References 15 publications

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“…Fluorescence spectra studies indicated a clear shift in their excitation wavelength maxima upon Ca 2+ binding (469 to 401 nm and 471 to 421 nm, respectively, Fig. 3) as well as changes in fluorescence intensity that make the compounds potential ratiometric near-membrane, low Ca 2+ affinity probes [28]. …”

Section: Aptra-btcmentioning

confidence: 99%

The Coumarin Moiety as Chromophore of Fluorescent Ion Indicators in Biological Systems

Katerinopoulos

2004

CPD

120

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Fluorescent probes have evolved into an extremely useful tool for the detection of ions in biological systems. The design of ion indicators is based in the proper choice of the ion chelating group as well as the chromophore moiety. The chromophores of choice should fulfill a number of requirements concerning the photostability of the group, the range of the excitation and emission wavelengths of the indicators, the Stokes shift, the fluorescence quantum yield, the excitation and/or emission wavelength shift upon coordination of the probe with its target ion, the lipophilicity of the indicators, and their possible cell toxicity. Coumarin and its analogues have been extensively used in ion detection by incorporation of the coumarin chromophore in the larger indicator framework. Coumarins fulfill all the aforementioned requirements since they are relatively photostable and their excitation and emission maxima, in many cases, are long enough to minimise "background" fluorescence of cellular components, tissues and biological fluids. They exhibit Stokes shifts large enough to avoid significant overlap of the excitation and emission spectra, their fluorescence quantum yields allow for ion detection at low indicator concentrations, and they can be introduced to cells either by microinjection or as membrane permeable derivatives without causing cell death. Synthetic approaches, aiming at the optimisation of indicator properties, have extended the conjugated coumarin system either by introduction of substituents or by expansion of the heterocyclic system. In this review, the basic rationale for the selection of the particular coumarin analogues is analysed, synthetic pathways leading to the desired structures are presented, and properties and relative advantages in the use of these probes are described.

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Section: Aptra-btcmentioning

confidence: 99%

The Coumarin Moiety as Chromophore of Fluorescent Ion Indicators in Biological Systems

Katerinopoulos

2004

CPD

120

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“…Other types of enzyme substrates containing coumarin or an iminocoumarin moiety are used in various biological or medicinal analyses. Some iminocoumarin derivatives are utilised as low‐affinity fluorescent Ca 2+ indicators [15,16]. The presence of 2H‐chromene moieties in a number of biologically active substances makes the synthesis of their new analogues of great importance for further study and clarification of the chemotherapeutic properties and reactivity of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and electronic spectra of 3‐hetaryl substituted coumarin derivatives 7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on

Deligeorgiev

Tsvetkova

Ivanova

et al. 2008

Coloration Technology

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The synthesis of 3‐hetaryl substituted coumarin derivatives [7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on] containing a hydroxyl group by reacting 2,4‐dihydroxybenzaldehyde and 2,4‐dihydroxynaphtaldehydes with 2‐cyanomethylbenzothiazole, 2‐cyanomethylbenzimidazole, 1‐methyl‐2‐cyanomethylbenzimidazole and 2‐cyanomethyl‐4‐phenylthiazole is presented. The absorption and steady‐state fluorescence characteristics of the synthesised 3‐hetaryl substituted 7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on in a solution of ethanol and at different pH values are studied to assess their possible application as fluorescent probes for use in molecular biology and medicine.

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“…Regarding their high fluorescence ability, they are widely used as fluorescent probes [8] in biology and medicine [9] and also as optical whitening agents, brighteners [10], laser dyes [11] and new types of probes for optical oxygen sensing [12]. Some of the iminocoumarin derivatives are used as low‐affinity fluorescent Ca 2+ indicators [13,14]. There has been a long‐standing interest in the interaction between oil and water [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel water‐soluble fluorescent coumarins bearing sulphonic and hydroxyl groups

Deligeorgiev

Tsvetkova

Stanimirov

2011

Coloration Technology

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Two dihydroxynaphtaldehydes (2,5-dihydroxynaphtaldehyde and 2,7-dihydroxynaphtaldehyde) and 2,4dyhydroxybenzaldehyde were sulphonated. These intermediates were used in subsequent reactions with 2-cyanomethylbenzothiazole, 2-cyanomethylbenzoimidazole and 1-methyl-2-cyanomethylbenzoimidazole to synthesise sulphonated coumarin derivatives. The absorption and steady-state fluorescence characteristics of the prepared coumarins were studied in ethanol and in water.

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Near-membrane iminocoumarin-based low affinity fluorescent Ca2+ indicators

Cited by 22 publications

References 15 publications

The Coumarin Moiety as Chromophore of Fluorescent Ion Indicators in Biological Systems

The Coumarin Moiety as Chromophore of Fluorescent Ion Indicators in Biological Systems

Synthesis and electronic spectra of 3‐hetaryl substituted coumarin derivatives 7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on

Synthesis of novel water‐soluble fluorescent coumarins bearing sulphonic and hydroxyl groups

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