Abstract
A variety of contemporary analytical platforms, utilized in technical and biological applications, take advantage of labeling the objects of interest with fluorescent tracers—compounds that can be easily and sensitively detected. Here we describe the synthesis of new fluorescent quinoline and quinolone compounds, whose light emission can be conveniently tuned by simple structural modifications. Some of these compounds can be used as sensitizers for lanthanide emission in design of highly sensitive luminescent probes. In addition, we also describe simple efficient derivatization reactions that allow introduction of amine- or click-reactive cross-linking groups into the fluorophores. The reactivity of synthesized compounds was confirmed in reactions with low molecular weight nucleophiles, or alkynes, as well as with click-reactive DNA-oligonucleotide containing synthetically introduced alkyne groups. These reactive derivatives can be used for covalent attachment of the fluorophores to various biomolecules of interest including nucleic acids, proteins, living cells and small cellular metabolites. Obtained compounds are characterized using NMR, steady-state fluorescence spectroscopy as well as UV absorption spectroscopy.Electronic supplementary materialThe online version of this article (doi:10.1007/s10895-012-1039-z) contains supplementary material, which is available to authorized users.
Highlights
Fluorescent labels are used in numerous applications that relay on sensitive detection of biological macromolecules, as well as for specific labeling of cells and tissues
Detection sensitivity is proportional to the number of the light quanta emitted by the fluorophore, which in turn is a linear function of the intensity of the excitation light
We describe the synthesis and reaction mechanisms for new derivatives of these fluorophores that are suitable for attachment to
Summary
Fluorescent labels are used in numerous applications that relay on sensitive detection of biological macromolecules (proteins, nucleic acids, polycarbohydrates, etc.), as well as for specific labeling of cells and tissues In these applications, the fluorophore reporter groups are illuminated by visible or UV light, which leads to absorption of the light quantum and excitation of the molecule. The excited state is unstable and tends to relax either through dissipation of the absorbed energy by collision with other components in the medium or by emission of light For sensitive detection, high intensity light sources are employed This creates the problem of discrimination of excitation and emission light, since even a small fraction of the excitation light that reaches the detector can cause significant background and decreases the detection sensitivity. We describe the synthesis and reaction mechanisms for new derivatives of these fluorophores that are suitable for attachment to
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