Interdependence of pyrene interactions and tetramolecular G4-DNA assembly

Osman Doluca, Jamie M. Withers, Trevor S. Loo, Patrick J. B. Edwards, Carlos Gonzalez, Vyacheslav V. Filichev

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Controlling the arrangement of organic chromophores in supramolecular architectures is of primary importance for the development of novel functional molecules. Insertion of a twisted intercalating nucleic acid (TINA) moiety, containing phenylethynylpyren-1-yl derivatives, into a G-rich DNA sequence alters G-quadruplex folding, resulting in supramolecular structures with defined pyrene arrangements. Based on CD, NMR and ESI-mass-spectra, as well as TINA excited dimer (excimer) fluorescence emission we propose that insertion of the TINA monomer in the middle of a dTG4T sequence (i.e. dTGGXGGT, where X is TINA) converts a parallel tetramolecular G-quadruplex into an assembly composed of two identical antiparallel G-quadruplex subunits stacked via TINA–TINA interface. Kinetic analysis showed that TINA–TINA association controls complex formation in the presence of Na+ but barely competes with guanine-mediated association in K+ or in the sequence with the longer G-run (dTGGGXGGGT). These results demonstrate new perspectives in the design of molecular entities that can kinetically control G-quadruplex formation and show how tetramolecular G-quadruplexes can be used as a tuneable scaffold to control the arrangement of organic chromophores.
Original languageEnglish
Pages (from-to)3742-3748
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number12
DOIs
Publication statusPublished - 2 Feb 2015

Keywords

  • G-quadruplex DNA
  • pyrene interactions
  • organic chromophores
  • supramolecular architectures

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