A new class of polyintercalating molecules

R. Scott Lokey, Yan Kwok, Vladimir Guelev, Christopher J. Pursell, Laurence H. Hurley, Brent L. Iverson

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

We have synthesized a series of polyintercalating compounds, including the first known tetraintercalator, based on the 1,4,5,8-naphthalenetetracarboxylic diimide chromophore. The chromophores are attached in a head-to-tail arrangement by peptide linkers and are synthesized by standard solid phase peptide synthesis methods. We report evidence, based on UV-visible spectroscopy and viscometry, that the compounds are fully intercalated upon binding to double-stranded DNA. Using DNAse I footprinting experiments, the bisintercalator 2 was found to bind to DNA in a cooperative manner. The footprinting results as well as association and dissociation kinetics data reveal that the compounds exhibit a tremendous preference for GC over AT sequences. A mode of binding is proposed in which the compounds intercalate completely from the major groove, and not in a threading manner as may be suggested by their structures. A kinetic scheme is proposed that takes into account the observed cooperativity and fits the data for the dissociations of the polyintercalators from poly(dAdT), although a similar scheme could not adequately model their dissociations from poly(dGdC) or from calf thymus DNA.

Original languageEnglish (US)
Pages (from-to)7202-7210
Number of pages9
JournalJournal of the American Chemical Society
Volume119
Issue number31
DOIs
StatePublished - Aug 6 1997
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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