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

Shyamala Pillai, Maxim Kozlov, Salvatore A.E. Marras, Lev N. Krasnoperov, Arkady Mustaev

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1021-1032
Number of pages12
JournalJournal of Fluorescence
Volume22
Issue number4
DOIs
StatePublished - Jul 2012
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Clinical Psychology
  • Social Sciences (miscellaneous)
  • Sociology and Political Science
  • Spectroscopy
  • Clinical Biochemistry
  • Law

Keywords

  • Cross-linking probes
  • Fluorescence
  • Quinoline
  • Quinolone

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