Acid-base properties and DNA-binding of water soluble N-confused porphyrins with cationic side-arms

Yoshiya Ikawa, Shoji Moriyama, Hiroyuki Harada, Hiroyuki Furuta

    Research output: Contribution to journalArticlepeer-review

    31 Citations (Scopus)

    Abstract

    Water soluble N-confused porphyrins, 5,10,15,20-tetrakis(α-pyridinio- p-tolyl)-2-aza-21-carbaporphyrin (pPyNCP) and its N-methyl derivative, 2-N-methyl-5,10,15,20-tetrakis(α-pyridinio-p-tolyl)-2-aza-21- carbaporphyrin (NMe-pPyNCP), have been synthesized by introducing cationic side-arms at the meso-positions of N-confused porphyrin. Their acid-base properties (pK 1-4 ) and DNA-binding ability in aqueous solutions were elucidated in comparison with the corresponding porphyrin derivative. Photophysical behaviors of pPyNCP were largely influenced by buffer compositions and DNA structures, whereas NMe-pPyNCP is considerably robust against these factors. In addition, significant enhancement of the fluorescence was observed with NMe-pPyNCP by the addition of DNA. The unique properties of pPyNCP and NMe-pPyNCP stem from the confused pyrrole rings in the macrocycle.

    Original languageEnglish
    Pages (from-to)4157-4166
    Number of pages10
    JournalOrganic and Biomolecular Chemistry
    Volume6
    Issue number22
    DOIs
    Publication statusPublished - Nov 12 2008

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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