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

Hidetoshi Taima, Akihiro Okubo, Naoki Yoshioka, Hidenari Inoue

Research output: Contribution to journalArticle

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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Chlorophyll
DNA
Derivatives
Water
Molecular structure
Melting point
Absorption spectra
Assays
chlorin e6

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

DNA-binding properties and photocleavage activity of cationic water-soluble chlorophyll derivatives. / Taima, Hidetoshi; Okubo, Akihiro; Yoshioka, Naoki; Inoue, Hidenari.

In: Chemistry - A European Journal, Vol. 12, No. 24, 16.08.2006, p. 6331-6340.

Research output: Contribution to journalArticle

Taima, Hidetoshi ; Okubo, Akihiro ; Yoshioka, Naoki ; Inoue, Hidenari. / DNA-binding properties and photocleavage activity of cationic water-soluble chlorophyll derivatives. In: Chemistry - A European Journal. 2006 ; Vol. 12, No. 24. pp. 6331-6340.
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