Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA
Overview of Dierckx A et al.
| Authors | Dierckx A Dinér P El-Sagheer AH Kumar JD Brown T Grøtli M Wilhelmsson LM |
|---|---|
| Affiliation | Department of Chemical and Biological Engineering/Physical Chemistry Chalmers University of Technology University of Gothenburg S-41296 Gothenburg Sweden. |
| Journal | Nucleic Acids Res |
| Year | 2011 |
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.