New cross-linking quinoline and quinolone derivatives for sensitive fluorescent labeling

Document Type

Article

Publication Date

7-1-2012

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 al-kyne 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 UVabsorption spectroscopy. © The Author(s) 2012.

Identifier

84865220887 (Scopus)

Publication Title

Journal of Fluorescence

External Full Text Location

https://doi.org/10.1007/s10895-012-1039-z

ISSN

10530509

PubMed ID

22450725

First Page

1021

Last Page

1032

Issue

4

Volume

22

Grant

RO1 GM-30717-21

Fund Ref

National Institutes of Health

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