Synthesis and DNA binding studies of bis-intercalators with a novel spiro-cyclic linker

Yongjun Chu, Vincent Lynch, Brent L. Iverson

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Threading polyintercalation has been demonstrated as a unique DNA binding mode in which a polyintercalating moiety threads back and forth through the DNA double helix. This binding topology necessitates linkers residing in both the minor and major grooves in an alternating fashion. In the present work, two novel, rigid, cis and trans oriented spiro-cyclic linkers were synthesized as potential groove binding elements in the context of threading bis-intercalation. Analysis of dissociation kinetics indicated that the cis oriented dimer has dramatically slower dissociation from poly(dGdC) and calf thymus (CT) DNA compared to the trans oriented dimer and a linear dimer control.

Original languageEnglish (US)
Pages (from-to)5536-5548
Number of pages13
JournalTetrahedron
Volume62
Issue number23
DOIs
StatePublished - Jun 5 2006

Keywords

  • Bis-intercalator
  • Dissociation kinetics
  • Polyintercalation
  • Rigid
  • Spiro-cyclic linker

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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