Formation of a complex of 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)-21H, 23H-porphyrin with G-quadruplex DNA

Hajime Mita, Takako Ohyama, Yoshiyuki Tanaka, Yasuhiko Yamamoto

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

A water-soluble cationic porphyrin, 5,10,15,20-tetrakis(N-methylpyridinium- 4-yl)-21H,23H-porphyrin (TmPyP4), has been studied extensively because of its unique physicochemical properties that lead to interactions with nucleic acids, as well as its therapeutic application. Formation of a complex between TmPyP4 and parallel G-quadruplex DNA formed from a single repeat sequence of the human telomere, d(TTAGGG), has been characterized in an effort to elucidate the mode of molecular recognition between TmPyP4 and the DNA. The study demonstrated that TmPyP4 intercalates into the A3pG4 step of [d(TTAGGG)]4 with an association constant of 6.2 × 106 M-1 and a stoichiometric ratio of 1:1. The binding of TmPyP4 to the A3pG4 step of [d(TTAGGG)]4 was found to be stabilized by the π-π stacking interaction of the porphyrin ring of TmPyP4 with the G4 quartet as well as the A3 bases of the G-quadruplex DNA. These findings provide novel insights for the design of porphyrin derivatives that bind to DNA with high affinity and specificity.

Original languageEnglish
Pages (from-to)6765-6772
Number of pages8
JournalBiochemistry
Volume45
Issue number22
DOIs
Publication statusPublished - 2006 Jun 6

ASJC Scopus subject areas

  • Biochemistry

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