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首页> 外文期刊>Chemistry: A European journal >Furan-oxidation-triggered inducible DNA cross-linking: Acyclic versus cyclic furan-containing building blocks - On the benefit of restoring the cyclic sugar backbone
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Furan-oxidation-triggered inducible DNA cross-linking: Acyclic versus cyclic furan-containing building blocks - On the benefit of restoring the cyclic sugar backbone

机译：呋喃氧化触发的诱导型DNA交联：无环与含环呋喃的构建基块-恢复环状糖主链的益处

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摘要

Oligodeoxynucleotides incorporating a reactive functionality can cause irreversible cross-linking to the target sequence and have been widely studied for their potential in inhibition of gene expression or development of diagnostic probes for gene analysis. Reactive oligonucleotides further show potential in a supramolecular context for the construction of nanometer-sized DNA-based objects. Inspired by the cytochrome P450 catalyzed transformation of furan into a reactive enal species, we recently introduced a furan-oxidation- based methodology for crosslinking of nucleic acids. Previous experiments using a simple acyclic building block equipped with a furan moiety for incorporation into oligodeoxynucleotides have shown that cross-linking occurs in a very fast and efficient way and that substantial amounts of stable, site-selectively cross-linked species can be isolated. Given the destabilization of duplexes observed upon introduction of the initially designed furanmodified building block into DNA duplexes, we explore here the potential benefits of two new building blocks featuring an extended aromatic system and a restored cyclic backbone. Thorough experimental analysis of crosslinking reactions in a series of contexts, combined with theoretical calculations, permit structural characterization of the formed species and allow assessment of the origin of the enhanced cross-link selectivity. Our experiments clearly show that the modular nature of the furan-modified building blocks used in the current cross-linking strategy allow for fine tuning of both yield and selectivity of the interstrand crosslinking reaction.
机译：掺入反应性官能团的寡脱氧核苷酸可引起与靶序列的不可逆交联，并且已被广泛研究其抑制基因表达或开发用于基因分析的诊断探针的潜力。反应性寡核苷酸在超分子环境中进一步显示了构建纳米大小基于DNA的物体的潜力。受细胞色素P450催化的呋喃转化为反应性烯类物种的启发，我们最近引入了基于呋喃氧化的核酸交联方法。先前使用配备有呋喃部分并掺入寡脱氧核苷酸的简单无环结构块进行的实验表明，交联以非常快速有效的方式发生，并且可以分离出大量稳定的位点选择性交联物质。鉴于在将最初设计的呋喃修饰的结构单元引入DNA双链体后观察到的双链体不稳定，我们在这里探索了具有扩展的芳香族系统和还原的环状骨架的两个新的结构单元的潜在优势。在一系列情况下，对交联反应进行全面的实验分析，再结合理论计算，可以对所形成物质进行结构表征，并可以评估增强的交联选择性的起源。我们的实验清楚地表明，在当前的交联策略中使用的呋喃改性的结构单元的模块性质允许对链间交联反应的产率和选择性进行微调。

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