Hybridization-dependent fluorescence of oligodeoxynucleotides incorporating new pyrene-modified adenosine residues.
We report the synthesis and properties of oligonucleotides incorporating N(6)-[N-(pyren-1-ylmethyl)carbamoyl]-deoxyadenosine (dA(pymcm)). We designed the ODN which incorporated two consecutive dA(pymcm) residues. It was revealed that on hybridization with the target DNA and RNA oligomers, the fluorescence spectra of ODNs having two consecutive dA(pymcm) molecules near the 5'-terminal position can change from the pyrene monomer emission to the excimer, depending on the chain length of the target DNA and RNA. These results indicated that dA(pymcm)-modified ODNs can be used as interesting hybridization sensors that are sensitive to the size of the target strand.
Seio
Kohji
K
Department of Life Science, Tokyo Institute of Technology and CREST, JST Nagatsuda, Midoriku, Yokohama 226-8501, Japan.
Mizuta
Masanhiro
M
Tasaki
Kaori
K
Tamaki
Keigo
K
Ohkubo
Akihiro
A
Sekine
Mitsuo
M
D001483:Base Sequence; D015374:Biosensing Techniques; D004247:DNA / Q000737:chemistry; D003839:Deoxyadenosines / Q000737:chemistry*; D004563:Electrochemistry / Q000379:methods; D004566:Electrodes; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D012313:RNA / Q000737:chemistry; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence / Q000379:methods
D003839:Deoxyadenosines; D009838:Oligodeoxyribonucleotides; D011721:Pyrenes; D012313:RNA; D004247:DNA