Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA
Journal article, 2011

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.

Author

Anke Dierckx

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Peter Dinér

University of Gothenburg

Afaf El-Sagheer

University of Southampton

Suez Canal University

Joshi Dhruval Kumar

Chalmers, Chemical and Biological Engineering, Physical Chemistry

T. Brown

University of Southampton

Morten Grötli

University of Gothenburg

Marcus Wilhelmsson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

Nucleic Acids Research

0305-1048 (ISSN) 1362-4962 (eISSN)

Vol. 39 10 4513-4524

Areas of Advance

Nanoscience and Nanotechnology (2010-2017)

Life Science Engineering (2010-2018)

Subject Categories

Physical Chemistry

Biochemistry and Molecular Biology

DOI

10.1093/nar/gkr010

More information

Latest update

4/18/2018