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Molecular Design of an Environmentally Sensitive Fluorescent Nucleoside, 3-Deaza-2′-Deoxyadenosine Derivative: Distinguishing Thymine by Probing the DNA Minor Groove

Authors

  • Azusa Suzuki,

    1. Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan)
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  • Takumi Yanaba,

    1. Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan)
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  • Prof. Isao Saito,

    1. NEWCAT Institute, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan)
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  • Prof. Yoshio Saito

    Corresponding author
    1. Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan)
    • Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan)===

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Abstract

An environmentally sensitive fluorescent nucleoside containing a 3-deazaadenine skeleton has been developed, and its photophysical properties were investigated. Newly developed C3-naphthylethynylated 3-deaza-2′-deoxyadenosine (3nzA, 1) exhibited dual fluorescence emission from an intramolecular charge-transfer state and a locally excited state, depending upon molecular coplanarity. DNA probes containing 1 clearly discriminated a perfectly matched thymine base on the complementary strand by a distinct change in emission wavelength.

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