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首页> 美国卫生研究院文献>PLoS Clinical Trials >A New Cationic Porphyrin Derivative (TMPipEOPP) with Large Side Arm Substituents: A Highly Selective G-Quadruplex Optical Probe
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A New Cationic Porphyrin Derivative (TMPipEOPP) with Large Side Arm Substituents: A Highly Selective G-Quadruplex Optical Probe

机译：具有大侧臂取代基的新型阳离子卟啉衍生物（TMPipEOPP）：高选择性G-四链体光学探针

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The discovery of uncommon DNA structures and speculation about their potential functions in genes has brought attention to specific DNA structure recognition. G-quadruplexes are four-stranded nucleic acid structures formed by G-rich DNA (or RNA) sequences. G-rich sequences with a high potential to form G-quadruplexes have been found in many important genomic regions. Porphyrin derivatives with cationic side arm substituents are important G-quadruplex-binding ligands. For example, 5,10,15,20-Tetrakis(N-methylpyridinium-4-yl)-21H,23H-porphyrin (TMPyP4), interacts strongly with G-quadruplexes, but has poor selectivity for G-quadruplex versus duplex DNA. To increase the G-quadruplex recognition specificity, a new cationic porphyrin derivative, 5,10,15,20-tetra-{4-[2-(1-methyl-1- piperidinyl)ethoxy]phenyl} porphyrin (TMPipEOPP), with large side arm substituents was synthesized, and the interactions between TMPipEOPP and different DNA structures were compared. The results show that G-quadruplexes cause large changes in the UV-Vis absorption and fluorescence spectra of TMPipEOPP, but duplex and single-stranded DNAs do not, indicating that TMPipEOPP can be developed as a highly specific optical probe for discriminating G-quadruplex from duplex and single-stranded DNA. Visual discrimination is also possible. Job plot and Scatchard analysis suggest that a complicated binding interaction occurs between TMPipEOPP and G-quadruplexes. At a low [G-quadruplex]/[TMPipEOPP] ratio, one G-quadruplex binds two TMPipEOPP molecules by end-stacking and outside binding modes. At a high [G-quadruplex]/[TMPipEOPP] ratio, two G-quadruplexes bind to one TMPipEOPP molecule in a sandwich-like end-stacking mode.
机译：对不常见的DNA结构的发现以及对它们在基因中潜在功能的推测引起了人们对特定DNA结构识别的关注。 G-四链体是由富含G的DNA（或RNA）序列形成的四链核酸结构。在许多重要的基因组区域中发现了具有高潜力形成G-四链体的富G序列。具有阳离子侧臂取代基的卟啉衍生物是重要的G-四链体结合配体。例如，5,10,15,20-四（N-甲基吡啶-4-基）-21H，23H-卟啉（TMPyP4）与G-四链体强烈相互作用，但对G-四链体与双链体DNA的选择性差。为了增加G-四链体识别的特异性，一种新的阳离子卟啉衍生物5,10,15,20-四-{4- [2-（2-（1-甲基-1-哌啶基）乙氧基]苯基]苯基}卟啉（TMPipEOPP）合成了较大的侧臂取代基，并比较了TMPipEOPP与不同DNA结构之间的相互作用。结果表明，G-四链体会导致TMPipEOPP的UV-Vis吸收和荧光光谱发生较大变化，但是双链和单链DNA却不会，这表明TMPipEOPP可作为区分G-四链体的高特异性光学探针而开发。双链和单链DNA。视觉辨别也是可能的。作业图和Scatchard分析表明，TMPipEOPP和G-四链体之间发生复杂的结合相互作用。在低的[G-四链体] / [TMPipEOPP]比下，一个G-四链体通过末端堆积和外部结合模式结合两个TMPipEOPP分子。在[G-四链体] / [TMPipEOPP]高比率下，两个G-四链体以三明治状的末端堆积模式结合到一个TMPipEOPP分子上。

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