title: New cross-linking quinoline and quinolone derivatives for sensitive fluorescent labeling.
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.
authors.affiliation: Department of Chemistry and Environmental Sciences, New Jersey Institute of Technology, 151 Tiernan Hall, University Heights, Newark, NJ 07102, USA.
authors.forename: Shyamala
authors.initials: S
authors.lastname: Pillai
authors.forename: Maxim
authors.initials: M
authors.lastname: Kozlov
authors.forename: Salvatore A E
authors.initials: SA
authors.lastname: Marras
authors.forename: Lev N
authors.initials: LN
authors.lastname: Krasnoperov
authors.forename: Arkady
authors.initials: A
authors.lastname: Mustaev
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D057230:Limit of Detection; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D005456:Fluorescent Dyes; D009838:Oligodeoxyribonucleotides; D011804:Quinolines; D015363:Quinolones; D004247:DNA; C037219:quinoline; D003545:Cysteine