N-fused porphyrin with pyridinium side-arms: a new class of aromatic ligand with DNA-binding ability |
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Authors: | Ikawa Yoshiya Touden Satoshi Furuta Hiroyuki |
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Institution: | Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan. |
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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. |
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