Synthesis and photophysical properties of pyrene-labeled 3-deaza-2'-deoxyadenosines comprising a non-π-conjugated linker: fluorescence quenching-based oligodeoxynucleotide probes for thymine identification.
Pyrene-labeled 3-deaza-2'-deoxyadenosine comprising a non-π-conjugated linker (py3z)A (1) was synthesized and its photophysical properties were investigated. Oligodeoxynucleotide (ODN) probes containing (py3z)A (1) exhibited remarkable fluorescence quenching only when the opposite base of the complementary strand was the perfectly matched thymine. Such fluorescence quenching-based ODN probes exhibited excellent on-off switching properties, making them useful tools for single nucleotide polymorphism (SNP) genotyping and for the identification of target genes and structural studies of nucleic acids.
Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan. saitoy@chem.ce.nihon-u.ac.jp.
Tatsuya
T
Aso
Koichiro
K
Saito
Azusa
A
Suzuki
Yoshio
Y
Saito
D002623:Chemistry Techniques, Analytical / Q000379:methods*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D010777:Photochemistry; D011721:Pyrenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013941:Thymine / Q000032:analysis* / Q000737:chemistry; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000737:chemistry
D005456:Fluorescent Dyes; D009838:Oligodeoxyribonucleotides; D011721:Pyrenes; C065642:3-deaza-2'-deoxyadenosine; C030984:pyrene; D014372:Tubercidin; D013941:Thymine