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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

Excitation anisotropy spectrum (r0, solid line) of the AT nucleoside in a H2O/ethylene glycol glass (1:2 mixture) at −100°C. The isotropic absorption (Aiso, dashed line) is shown as a comparison and was measured in Milli-Q water.
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Figure 3: Excitation anisotropy spectrum (r0, solid line) of the AT nucleoside in a H2O/ethylene glycol glass (1:2 mixture) at −100°C. The isotropic absorption (Aiso, dashed line) is shown as a comparison and was measured in Milli-Q water.

Mentions: The fundamental fluorescence anisotropy of AT (r0, Figure 3) was measured in a H2O/ethylene glycol glass (1:2 mixture). A constant value of r0 = 0.38 can be observed between 280 and 320 nm, which approaches the theoretical maximum value of 0.4 and suggests that the emission and absorption transition moments are virtually parallel in this region. The constant r0 value in this region also indicates a single transition dipole moment in this absorption band.Figure 3.


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)

Excitation anisotropy spectrum (r0, solid line) of the AT nucleoside in a H2O/ethylene glycol glass (1:2 mixture) at −100°C. The isotropic absorption (Aiso, dashed line) is shown as a comparison and was measured in Milli-Q water.
© Copyright Policy - creative-commons
Related In: Results  -  Collection

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

Figure 3: Excitation anisotropy spectrum (r0, solid line) of the AT nucleoside in a H2O/ethylene glycol glass (1:2 mixture) at −100°C. The isotropic absorption (Aiso, dashed line) is shown as a comparison and was measured in Milli-Q water.
Mentions: The fundamental fluorescence anisotropy of AT (r0, Figure 3) was measured in a H2O/ethylene glycol glass (1:2 mixture). A constant value of r0 = 0.38 can be observed between 280 and 320 nm, which approaches the theoretical maximum value of 0.4 and suggests that the emission and absorption transition moments are virtually parallel in this region. The constant r0 value in this region also indicates a single transition dipole moment in this absorption band.Figure 3.

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