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

Yoshiya Ikawa, Satoshi Touden, Hiroyuki Furuta

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8068-8078
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number23
DOIs
Publication statusPublished - Dec 7 2011

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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