Cytosine detection by a fluorescein-labeled probe containing base-discriminating fluorescent nucleobase

Chembiochem : a European Journal of Chemical Biology
Akimitsu OkamotoIsao Saito

Abstract

We report on a new method for the detection of a base at a specific site in a DNA sequence by monitoring the fluorescence emission of fluorescein. To achieve this goal, we developed a new base-discriminating fluorescent (BDF) nucleobase, naphthodeazaadenine ((ND)A). The fluorescence spectrum of the duplex possessing a cytosine base as a complementary base of (ND)A showed a fluorescence peak at 383 nm when using an excitation wavelength of 350 nm. When the complementary base of (ND)A was one of the other bases, the fluorescence intensity was very low. The fluorescence emission spectrum of (ND)A overlapped with the fluorescence excitation spectrum of fluorescein in the wavelength range of 400-500 nm. Thus, we designed FRET-BDF probes containing (ND)A as the FRET donor and fluorescein as the acceptor. The interaction of these two fluorophores, which are separated by defined base pairs, allowed an efficient energy transfer that resulted in a dominant fluorescence emission of fluorescein at 520 nm when using an excitation wavelength of 350 nm. Fluorescence emission from FRET-BDF probes was observed only when the complementary base of (ND)A is C, thus achieving a clear distinction of a C base on the complementary DNA strand. However,...Continue Reading

References

Jun 1, 1996·Current Opinion in Structural Biology·D P Millar
Feb 1, 1997·Current Opinion in Biotechnology·A N Glazer, R A Mathies
Apr 24, 2003·Journal of the American Chemical Society·Akimitsu OkamotoIsao Saito
Aug 2, 2003·Journal of the American Chemical Society·Akimitsu OkamotoIsao Saito

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Citations

May 19, 2010·Quarterly Reviews of Biophysics·L Marcus Wilhelmsson
Jul 13, 2006·Journal of the American Chemical Society·Alex H F Lee, Eric T Kool
Dec 17, 2005·Chemical Communications : Chem Comm·Rohan T Ranasinghe, Tom Brown
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Apr 27, 2005·Chembiochem : a European Journal of Chemical Biology·Chikara Dohno, Isao Saito
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Jul 28, 2005·Bioorganic & Medicinal Chemistry Letters·Akimitsu OkamotoIsao Saito
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Jan 24, 2017·Journal of the American Chemical Society·Vasyl KilinYves Mély
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May 7, 2021·Chemical Society Reviews·Dmytro DziubaYves Mély
Dec 30, 2006·The Journal of Organic Chemistry·Kenichi MiyataMitsuo Sekine

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