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

Abstract

Pyrene-labeled 3-deaza-2′-deoxyadenosine comprising a non-π-conjugated linker ^py3zA (1) was synthesized and its photophysical properties were investigated. Oligodeoxynucleotide (ODN) probes containing ^py3zA (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.