Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, University of Gothenburg, S-41296 Gothenburg, Sweden.
Nucleic Acids Res. 2011 May;39(10):4513-24. doi: 10.1093/nar/gkr010. Epub 2011 Jan 29.
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.
为了增加具有改进性能的荧光碱基类似物的多样性，我们在此提出了一种新的基于点击化学的荧光腺嘌呤类似物三唑腺嘌呤（A(T)）的简便合成方法，并对其在 DNA 内的光物理特性进行了表征。与广泛使用的腺嘌呤类似物 2-氨基嘌呤相比，A(T)具有更有前景的特性。量子产率分别在单链和双链 DNA 中达到>20%和>5%，并依赖于相邻碱基。此外，A(T)对 DNA 双链的稳定性只有很小的破坏，与 2-氨基嘌呤相当，圆二色性研究表明 A(T)仅对正常 B-DNA 造成最小的结构扰动。此外，我们发现 A(T)与胸腺嘧啶具有良好的碱基配对性质，更令人惊讶的是，与正常腺嘌呤也具有良好的碱基配对性质。总之，A(T)作为一种新的荧光腺嘌呤类似物，具有很强的潜力，可以用于监测 DNA 中其微环境的变化。
