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Issue 12, 2015
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Interdependence of pyrene interactions and tetramolecular G4-DNA assembly

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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.

Graphical abstract: Interdependence of pyrene interactions and tetramolecular G4-DNA assembly

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The article was received on 28 Nov 2014, accepted on 02 Feb 2015 and first published on 02 Feb 2015

Article type: Paper
DOI: 10.1039/C4OB02499K
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Citation: Org. Biomol. Chem., 2015,13, 3742-3748
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    Interdependence of pyrene interactions and tetramolecular G4-DNA assembly

    O. Doluca, J. M. Withers, T. S. Loo, P. J. B. Edwards, C. González and V. V. Filichev, Org. Biomol. Chem., 2015, 13, 3742
    DOI: 10.1039/C4OB02499K

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