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Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA.

Dierckx A, Dinér P, El-Sagheer AH, Kumar JD, Brown T, Grøtli M, Wilhelmsson LM - Nucleic Acids Res. (2011)

Bottom Line: To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA.A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine.In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, University of Gothenburg, S-41296 Gothenburg, Sweden.

ABSTRACT
To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

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Related in: MedlinePlus

Absorption (dashed line) and emission (solid line) spectrum of the AT monomer in water.
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Figure 2: Absorption (dashed line) and emission (solid line) spectrum of the AT monomer in water.

Mentions: The absorption and emission spectra of AT, where the triazole-modified A-nucleobase constitutes the chromophoric/fluorophoric unit of the nucleoside, in Milli-Q water are shown in Figure 2. Their shapes are virtually identical to the corresponding spectra recorded for AT in methanol (data not shown). In water, the lowest energy absorption band is centred at 282 nm with an extinction coefficient of 16 500 M−1cm−1 and the emission maximum is located at 353 nm. The absorption spectrum recorded for AT in methanol shows a redshift of 4 nm compared to in water whereas a blueshift of 7 nm was observed for the corresponding emission spectrum of AT. Moreover, AT shows a very high quantum yield both in water (0.61) and in methanol (0.49). Furthermore, a lifetime of 1.8 ns was recorded for the AT monomer in water. A small residual could be observed, which is most probably a result of small deviations in the instrument response function.Figure 2.


Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA.

Dierckx A, Dinér P, El-Sagheer AH, Kumar JD, Brown T, Grøtli M, Wilhelmsson LM - Nucleic Acids Res. (2011)

Absorption (dashed line) and emission (solid line) spectrum of the AT monomer in water.
© Copyright Policy - creative-commons
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3105426&req=5

Figure 2: Absorption (dashed line) and emission (solid line) spectrum of the AT monomer in water.
Mentions: The absorption and emission spectra of AT, where the triazole-modified A-nucleobase constitutes the chromophoric/fluorophoric unit of the nucleoside, in Milli-Q water are shown in Figure 2. Their shapes are virtually identical to the corresponding spectra recorded for AT in methanol (data not shown). In water, the lowest energy absorption band is centred at 282 nm with an extinction coefficient of 16 500 M−1cm−1 and the emission maximum is located at 353 nm. The absorption spectrum recorded for AT in methanol shows a redshift of 4 nm compared to in water whereas a blueshift of 7 nm was observed for the corresponding emission spectrum of AT. Moreover, AT shows a very high quantum yield both in water (0.61) and in methanol (0.49). Furthermore, a lifetime of 1.8 ns was recorded for the AT monomer in water. A small residual could be observed, which is most probably a result of small deviations in the instrument response function.Figure 2.

Bottom Line: To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA.A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine.In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, University of Gothenburg, S-41296 Gothenburg, Sweden.

ABSTRACT
To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

Show MeSH
Related in: MedlinePlus