N-fused porphyrin with pyridinium side-arms: A new class of aromatic ligand with DNA-binding ability

Yoshiya Ikawa, Satoshi Touden, Hiroyuki Furuta

    研究成果: Contribution to journalArticle査読

    12 被引用数 (Scopus)

    抄録

    N-fused porphyrin (NFP) is a porphyrin analogue with an 18π tetrapyrrolic macrocycle, in which a unique tripentacyclic ring is embedded. While the optical properties of NFP of absorbing and emitting near-infrared (NIR) light around 1000 nm are promising for its application to NIR technology, its unique structure is also attractive as a platform to construct a novel class of DNA-binding ligands. Herein, we have synthesized a water-soluble derivative of NFP (pPyNFP) possessing four cationic pyridinium substituents and examined its acid/base behaviors and interactions with various forms of DNAs in aqueous solution. pPyNFP interacts with ssDNA and dsDNA electrostatically. pPyNFP also interacts with a G-quadruplex DNA derived from the human telomeric sequence and causes a characteristic spectral change of the G-quadruplex DNA, which suggests that pPyNFP modulates the Na +-induced (2 + 2) antiparallel G-quadruplex to the all-parallel structure.

    本文言語英語
    ページ(範囲)8068-8078
    ページ数11
    ジャーナルOrganic and Biomolecular Chemistry
    9
    23
    DOI
    出版ステータス出版済み - 12 7 2011

    All Science Journal Classification (ASJC) codes

    • 生化学
    • 物理化学および理論化学
    • 有機化学

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