Synthesis and DNA-binding properties of water-soluble cationic pyropheophorbides derived from chlorophyll a/b

Hidetoshi Taima, Naoki Yoshioka, Hidenari Inoue

研究成果: Article査読

6 被引用数 (Scopus)

抄録

A series of mono-, di-, tetra- and hexacationic esters of pyropheophorbide a/b have been designed and synthesized to explore the intercalation of their phorbine ring between the base pairs of double-helical DNA and the influence of their peripheral substituents on the DNA interactions. Mono-(1), di-(2, 3) and tetra-(4, 5) cationic pyropheophorbides are soluble as an oligomeric aggregate in HEPES buffer, but hexa-(6) cationic pyropheophorbide is soluble as a monomer at lower concentrations. The interaction of these cationic pyropheophorbide derivatives with DNA has been investigated by DNA unwinding assay, fluorescence energy transfer, and measurements of the melting temperature of the double-helical DNA and visible absorption spectra. Dicationic 2 and 3 bind outside the double-helical DNA without and/or with self-aggregation and with self-aggregation, respectively, because they cannot intercalate between the base-pairs due to their aggregation. On the other hand, tetracationic 4 and 5 and hexacationic 6 intercalate between the base pairs of the double-helical DNA. The binding mode of the cationic pyropheophorbides a/b is strongly dependent on the number and position of the cationic peripheral substituents of the pyropheophorbides.

本文言語English
ページ(範囲)1176-1183
ページ数8
ジャーナルOrganic and Biomolecular Chemistry
7
6
DOI
出版ステータスPublished - 2009 3 19
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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