DNA-binding properties and photocleavage activity of cationic water-soluble chlorophyll derivatives

Hidetoshi Taima, Akihiro Okubo, Naoki Yoshioka, Hidenari Inoue

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21 Citations (Scopus)

Abstract

Three cationic water-soluble chlorin e6 derivatives, that is, 6a-,γb-,7c-tris(2-trimethylammonioethyl)chlorin e6 (1), 6a-,γb-,7c-tris(3-methylpyridi-niummethyl)chlorin e6 (2), and 6a-,γb-, 7c-tris(2-trimethylammonioethyl)-2-(3trimethylammonioprop-1-enyl)chlorin e 6 (3), have been designed and synthesized to allow the study of their DNA-binding and -photocleavage activities. The DNA-unwinding assay, measurements of melting temperatures of double-stranded DNA, and the induced CD and visible absorption spectra have revealed that 1 and 3 are intercalated into the base pairs of the double-helical DNA, while 2 is bound to outside the minor groove of the double-helical DNA. The cationic water-soluble chlor-in e 6 derivatives effectively cleave the double-helical DNA under photoirradiation and the DNA-photocleavage activity increases in the order 3 > 1 > 2. The DNA-binding and -photocleavage characteristics of the three cationic water-soluble chlorin e6 derivatives are influenced by aspects of their molecular structure, such as the kind, number, and position of the cationic substituents.

Original languageEnglish
Pages (from-to)6331-6340
Number of pages10
JournalChemistry - A European Journal
Volume12
Issue number24
DOIs
Publication statusPublished - 2006 Aug 16

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Keywords

  • Bioorganic chemistry
  • Chlorins
  • DNA recognition
  • Photobiology
  • Porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

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