title: Anthraquinone as a redox label for DNA: synthesis, enzymatic incorporation, and electrochemistry of anthraquinone-modified nucleosides, nucleotides, and DNA.
abstract: Modified 2'-deoxynucleosides and deoxynucleoside triphosphates (dNTPs) bearing anthraquinone (AQ) attached through an acetylene or propargylcarbamoyl linker at the 5-position of pyrimidine (C) or at the 7-position of 7-deazaadenine were prepared by Sonogashira cross-coupling of halogenated dNTPs with 2-ethynylanthraquinone or 2-(2-propynylcarbamoyl)anthraquinone. Polymerase incorporations of the AQ-labeled dNTPs into DNA by primer extension with KOD XL polymerase have been successfully developed. The electrochemical properties of the AQ-labeled nucleosides, nucleotides, and DNA were studied by cyclic and square-wave voltammetry, which show a distinct reversible couple of peaks around -0.4 V that make the AQ a suitable redox label for DNA.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences and IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic.
authors.forename: Jana
authors.initials: J
authors.lastname: Balintová
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Petra
authors.initials: P
authors.lastname: Horáková
authors.forename: Pavlína
authors.initials: P
authors.lastname: Vidláková
authors.forename: Luděk
authors.initials: L
authors.lastname: Havran
authors.forename: Miroslav
authors.initials: M
authors.lastname: Fojta
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D000880:Anthraquinones / Q000737:chemistry*; D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D004259:DNA-Directed DNA Polymerase / Q000737:chemistry* / Q000378:metabolism; D004563:Electrochemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism; D009711:Nucleotides / Q000737:chemistry* / Q000378:metabolism; D009841:Oligonucleotides / Q000737:chemistry* / Q000378:metabolism; D010084:Oxidation-Reduction; D013194:Staining and Labeling / Q000379:methods
chemical_list: D000880:Anthraquinones; D009705:Nucleosides; D009711:Nucleotides; D009841:Oligonucleotides; D004247:DNA; D004259:DNA-Directed DNA Polymerase