Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA

Akihiko Hatano, Kentaro Tanaka, Motoo Shiro, Mitsuhiko Shionoya

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

This paper describes design and syntheses of a new class of chelator-type nucleic acid mimics. Four nucleic acid mimics 7, 11, 15, 17 possess a nucleobase and two ethylenediamine moieties for intermolecular metal coordination. We expected that chelator-type nucleic acid mimics formed a strand in the presence of metal ion and then interacted with a single-stranded DNA. Efficient synthetic routes leading to the four nucleic acid analogues have been achieved via the key intermediate compound 5 which was derived from 3,5-dimethylphenol in five steps. Compound 7 was treated with zinc nitrate and Zn complex 8 was isolated as crystals. 1H NMR study of Zn complex 8 in D2O showed the single-strand formation. Job plots showed that mixture of (dT)70 with Zn complex 8 at 5°C reached a minimum absorbance at a mole ratio of 2:1, and the hypochromic effect showed the π-π stacking interaction between the nucleobases. Thermal denaturation study at 2:1 mole ratio of complexes between (dT)70 and Zn complex 8 showed melting point at 27°C.

Original languageEnglish
Pages (from-to)2965-2972
Number of pages8
JournalTetrahedron
Volume58
Issue number15
DOIs
Publication statusPublished - 2002 Apr 8
Externally publishedYes

Keywords

  • Chelator-type nucleic acid mimics
  • DNA
  • Intermolecular metal coordination

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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