School of Chemistry, Centre of Synthesis and Chemical Biology, University of Dublin, Trinity College Dublin, Dublin2, Ireland.
Org Biomol Chem. 2012 Apr 21;10(15):3033-43. doi: 10.1039/c2ob06898b. Epub 2012 Mar 7.
The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1:1 complex with 5'-adenosine-monophosphate while it is partially quenched and red-shifted in its complex with 5'-guanosine-monophosphate. Linear and circular dichroism measurements show that 1 binds to double-stranded DNA by intercalation. Comparative UV-visible and fluorescence studies with double stranded synthetic polynucleotides poly(dA-dT)(2) and poly(dG-dC)(2) show that 1 binds much more strongly to the AT polymer; 1 also has a strong preference for A-T rich sequences in natural DNA. Thermal denaturation measurements also reveal a much greater stabilisation of the double-stranded poly(dA-dT)(2) than of natural DNA.
描述了一种阳离子 4-氨基-1,8-萘酰亚胺衍生物（1）的合成、表征和固态晶体结构。结果表明，1 的光物理性质随溶剂极性和氢键能力而变化。1 与 5'-单磷酸腺苷（5'-AMP）形成 1:1 配合物时，荧光增强且蓝移，而与 5'-鸟苷单磷酸（5'-GMP）形成配合物时，荧光部分猝灭且红移。线性和圆二色性测量表明，1 通过嵌入与双链 DNA 结合。与双链合成多核苷酸 poly(dA-dT)(2)和 poly(dG-dC)(2)的比较 UV-可见和荧光研究表明，1 与 AT 聚合物的结合更强；1 也强烈偏爱天然 DNA 中的富含 A-T 序列。热变性测量还揭示了双链 poly(dA-dT)(2)比天然 DNA 具有更大的稳定性。
