Pierce Sarah E, Sherman Courtney L, Jayawickramarajah Janarthanan, Lawrence Candace M, Sessler Jonathan L, Brodbelt Jennifer S
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712-1167, United States.
Anal Chim Acta. 2008 Oct 3;627(1):129-35. doi: 10.1016/j.aca.2008.04.018. Epub 2008 Apr 15.
Based on binding studies undertaken by electrospray ionization-mass spectrometry, a synthetic pyrrole-inosine nucleoside, 1, capable of forming an extended three-point Hoogsteen-type hydrogen-bonding interaction with guanine, is shown to form specific complexes with two different quadruplex DNA structures dTG(4)T and d(T(2)G(4))(4) as well as guanine-rich duplex DNA. The binding interactions of two other analogs were evaluated in order to unravel the structural features that contribute to specific DNA recognition. The importance of the Hoogsteen interactions was confirmed through the absence of specific binding when the pyrrole NH hydrogen-bonding site was blocked or removed. While 2, with a large blocking group, was not found to interact with virtually any form of DNA, 3, with the pyrrole functionality missing, was found to interact non-specifically with several types of DNA. The specific binding of 1 to guanine-rich DNA emphasizes the necessity of careful ligand design for specific sequence recognition.
基于通过电喷雾电离质谱法进行的结合研究，一种能够与鸟嘌呤形成扩展的三点Hoogsteen型氢键相互作用的合成吡咯 - 肌苷核苷（1），被证明能与两种不同的四链体DNA结构dTG(4)T和d(T(2)G(4))(4)以及富含鸟嘌呤的双链DNA形成特异性复合物。为了阐明有助于特异性DNA识别的结构特征，对另外两种类似物的结合相互作用进行了评估。当吡咯NH氢键位点被阻断或去除时，由于缺乏特异性结合，证实了Hoogsteen相互作用的重要性。虽然带有大的阻断基团的2几乎未发现与任何形式的DNA相互作用，但缺少吡咯官能团的3被发现能与几种类型的DNA非特异性相互作用。1与富含鸟嘌呤的DNA的特异性结合强调了为特异性序列识别进行仔细配体设计的必要性。
