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

Hidetoshi Taima, Naoki Yoshioka, Hidenari Inoue

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1176-1183
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number6
DOIs
Publication statusPublished - 2009 Mar 19
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and DNA-binding properties of water-soluble cationic pyropheophorbides derived from chlorophyll a/b'. Together they form a unique fingerprint.

Cite this