Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA |
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| Authors: | Dierckx Anke Dinér Peter El-Sagheer Afaf H Kumar Joshi Dhruval Brown Tom Grøtli Morten Wilhelmsson L Marcus |
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| Affiliation: | 1Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, 2Department of Chemistry, Medicinal Chemistry, University of Gothenburg, S-41296 Gothenburg, Sweden, 3School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK and 4Department of Science and Mathematics, Chemistry Branch, Faculty of Petroleum and Mining Engineering, Suez Canal University, Suez 43721, Egypt |
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| 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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