Pyrene-modified guanosine as fluorescent probe for DNA modulated by charge transfer.
8-(Pyren-1-yl)-2'-deoxyguanosine (Py-G) was incorporated synthetically as a modified DNA base and optical probe into oligonucleotides. A variety of Py-G-modified DNA duplexes have been investigated by methods of optical spectroscopy. The DNA duplex hybridization can be observed by both fluorescence and absorption spectroscopy since the Py-G group exhibits altered properties in single strands versus double strands for both spectroscopy methods. The fluorescence enhancement upon DNA hybridization can be improved significantly by the presence of 7-deazaguanin as an additional modification and charge acceptor three bases away from the Py-G modification site. Moreover, Py-G in DNA can be applied as a photoinducable donor for charge transfer processes when indol is present as an artificial DNA base and charge acceptor. Correctly base-paired duplexes can be discriminated from mismatched ones by comparison of their fluorescence quenching.
Wanninger-Weiss
Claudia
C
University of Regensburg, Institute for Organic Chemistry, Universitätstr. 31, D-93053 Regensburg, Germany.
Valis
Linda
L
Wagenknecht
Hans-Achim
HA
D020137:Base Pair Mismatch; D020029:Base Pairing; D004247:DNA / Q000032:analysis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D006151:Guanosine / Q000737:chemistry*; D009693:Nucleic Acid Hybridization; D015345:Oligonucleotide Probes / Q000138:chemical synthesis*; D011721:Pyrenes; D013057:Spectrum Analysis
D005456:Fluorescent Dyes; D015345:Oligonucleotide Probes; D011721:Pyrenes; D006151:Guanosine; D004247:DNA; C030984:pyrene