Chiral recognition in the binding of helicenediamine to double strand DNA: Interactions between low molecular weight helical compounds and a helical polymer

Shinobu Honzawa, Hitoshi Okubo, Shuzo Anzai, Masahiko Yamaguchi, Kohei Tsumoto, Izumi Kumagai

Research output: Contribution to journalArticlepeer-review

71 Citations (Scopus)

Abstract

Binding of a helicene, 5,8-bis(aminomethyl)-1,12-dimethylbenzo[c]phenanthrene, to calf thymus DNA was studied using UV, CD, and fluorescence spectroscopy as well as calorimetry. The enantiomeric helicenes strongly bound to the double strand DNA possessing the right -handed helical structure. In addition, chiral recognition was observed in the binding, where the (P)-helicene with the right -handed helicity formed more stable complex than the (M)-helicene with the left-handed helicity. The binding studies of the helicenes and natural nucleosides by 1H NMR spectroscopy also revealed the higher affinity to the (P)-helicene. Both monomeric and polymeric nucleic acids thus turned out to favor the (P)-helicity.

Original languageEnglish
Pages (from-to)3213-3218
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume10
Issue number10
DOIs
Publication statusPublished - 2002 Aug 19

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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