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Nucleic Acids Symposium Series 2006 50(1):19-20; doi:10.1093/nass/nrl010
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© 2006 Oxford University Press

Synthesis of fluorescent cyclic cytosine nucleosides and their fluorescent properties upon incorporation into oligonucleotides

Masahiro Mizuta3, Kenichi Miyata1,3, Kohji Seio2,3, Tomofumi Santa4 and Mitsuo Sekine1,3

1 Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan, 2 Division of Collaborative Research for Bioscience and Biotechnology, Frontier Collaborative Research Center, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8503, Japan, 3 CREST, JST (Japan Science and Technology Agency), The University of Tokyo, Bunkyo-ku, Tokyo, Japan, 4 Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan

We report here the synthesis and spectroscopic characterization of a new fluorescent pyrimidopyrimidoindole nucleoside derivative (dCPPI) modified at the cytosine base. The photophysical properties of dCPPI were examined by fluorescent spectroscopy and quantum chemical calculations. It was found that dCPPI-labeled oligonucleotides gave almost the same thermal stability as that of the corresponding unmodified sequences. In addition, the quantum yield of dCPPI in the double-stranded state was significantly higher than that in the single-stranded state.


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