Azusa Suzuki

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

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.

Fluorometric detection of adenine in target DNA by exciplex formation with fluorescent 8-arylethynylated deoxyguanosine

We demonstrated an intriguing method to discriminate adenine by incident appearance of an intense new emission via exciplex formation in hybridization of target DNA with newly designed fluorescent 8-arylethynylated deoxyguanosine derivatives. We described the synthesis of such highly electron donating fluorescent guanosine derivatives and their incorporation into DNA oligomers which may be used for the structural study and the fluorometric analysis of nucleic acids.

Fluorescent Purine Nucleosides and Their Applications

Fluorescent nucleosides have been used in diverse fields as powerful reporter molecules for investigating structures, functions, and interactions of DNA and RNA, in addition to the conventional applications related to genomics such as gene detection, single nucleotide polymorphism (SNP) typing, and fluorescence imaging. In addition to the traditional fluorescent nucleosides such as 2-aminopurine (2AP), different types of fluorescent nucleosides possessing other functions such as the ability of sensing viscosity, polarity, and surrounding pH at local environments of nucleic acids have been developed. In this chapter, the design strategy of various fluorescent nucleosides, particularly purine derivatives, are described together with their photophysical characteristics. Fluorescent purine nucleosides are classified into several types depending upon their structural features. Design concept for environmentally sensitive fluorescent purine nucleosides and their applications to fluorescent DNA probes are described.