Cationic porphyrins bearing diazolium rings: Synthesis and their interaction with calf thymus DNA

Daryono H. Tjahjono, Takehiro Akutsu, Naoki Yoshioka, Hidenari Inoue

研究成果: Article

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Two novel cationic porphyrins bearing five-membered rings at the meso- positions, meso-tetrakis(1,3-dimethylimidazolium-2-yl)porphyrin (H2TDMImP) and meso-tetrakis(1,2-dimethylpyrazolium-4-yl)porphyrin (H2TDMPzP), have been synthesized. These two compounds interact with calf thymus DNA (CTDNA) in different binding modes from that of meso-tetrakis(N-methylpyridinium-4- yl)porphyrin (H2TMPyP). H2TDMImP outside binds to the minor groove of CTDNA while H2TDMPzP intercalates into CTDNA. These two novel cationic porphyrins strongly bind to CTDNA even at high ionic strength and the binding constant of H2TDMPzP to CTDNA is comparable to that of H2TMPyP. The binding of H2TDMImP to CTDNA is enthalpically driven. The favorable free energy changes in binding of H2TDMPzP to CTDNA come from the large negative enthalpy changes accompanied by small positive entropy changes.

元の言語English
ページ(範囲)333-343
ページ数11
ジャーナルBiochimica et Biophysica Acta - General Subjects
1472
発行部数1-2
DOI
出版物ステータスPublished - 1999 10 18

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology

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