Design of environmentally sensitive fluorescent 2'-deoxyguanosine containing arylethynyl moieties: distinction of thymine base by base-discriminating fluorescent (BDF) probe.
We have synthesized various substituted 8-arylethynylated 2'-deoxyguanosine derivatives. Among them, acetyl substituted deoxyguanosine analogue 4c showed a remarkable solvent dependent fluorescence property, that is, an intense fluorescence in non-polar solvents but extremely weak fluorescence in polar solvents like methanol. By using solvatofluorochromic deoxyguanosine analogue 4c, we have developed highly thymine (T) selective fluorescent DNA probes that can sense T opposite 4c in a target DNA regardless of the flanking sequences. We were able to demonstrate that 4c can be used as a T specific base-discriminating fluorescent (BDF) nucleoside in homogeneous fluorescence assay.
Shinohara
Yuta
Y
Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan.
Matsumoto
Katsuhiko
K
Kugenuma
Kenji
K
Morii
Takashi
T
Saito
Yoshio
Y
Saito
Isao
I
D001483:Base Sequence; D015342:DNA Probes / Q000737:chemistry; D003849:Deoxyguanosine / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013941:Thymine / Q000737:chemistry*
D015342:DNA Probes; D005456:Fluorescent Dyes; D009838:Oligodeoxyribonucleotides; D012997:Solvents; D003849:Deoxyguanosine; D013941:Thymine