Cookies on this website
We use cookies to ensure that we give you the best experience on our website. If you click 'Continue' we'll assume that you are happy to receive all cookies and you won't see this message again. Click 'Find out more' for information on how to change your cookie settings.

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.

Original publication

DOI

10.1093/nar/gkr010

Type

Journal article

Journal

Nucleic Acids Res

Publication Date

05/2011

Volume

39

Pages

4513 - 4524

Keywords

Base Pairing, Circular Dichroism, DNA, DNA, Single-Stranded, Deoxyadenosines, Fluorescence, Fluorescent Dyes, Nucleic Acid Denaturation, Organophosphorus Compounds, Spectrometry, Fluorescence, Triazoles