title: N-fused porphyrin with pyridinium side-arms: a new class of aromatic ligand with DNA-binding ability.
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.
authors: Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
authors: Yoshiya
authors: Y
authors: Ikawa
authors: Satoshi
authors: S
authors: Touden
authors: Hiroyuki
authors: H
authors: Furuta
mesh_terms: D004247:DNA / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D011166:Porphyrins / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: D008024:Ligands; D011166:Porphyrins; D011725:Pyridines; D004247:DNA