Unraveling the relationship between structure and stabilization of triarylpyridines as G-quadruplex binding ligands

N Smith, Gaelle Labrunie, Ben Corry, Phong Tran, Marck Norret, Mojgan Djavaheri-Mergny, Colin Raston, Jean-Louis Mergny

    Research output: Contribution to journalArticle

    33 Citations (Scopus)

    Abstract

    A series of novel 2,4,6-triarylpyridines have been synthesized and their interactions with intramolecular G-quadruplexes have been measured by Förster Resonance Energy Transfer (FRET) melting and Fluorescent Intercalator Displacement (FID) assays. A few of these compounds exhibit stabilization of G4-DNA that is comparable to other benchmark G4-DNA ligands with fair to excellent G4-DNA vs. duplex selectivity and significant cytotoxicity towards HeLa cells. The nature of the 4-aryl substituents along with side chain length governs the G4-DNA stabilization ability of the compounds. In addition, we demonstrate that there is a strong correlation between the ability of the compounds to stabilize the same G4-DNA sequence in K + and Na + conditions and a strong correlation between the ability of the compounds to stabilize different G4-DNA sequences in K + or Na + buffer.

    Original languageEnglish
    Pages (from-to)6154-6162
    Number of pages9
    JournalOrganic and Biomolecular Chemistry
    Volume9
    Issue number17
    DOIs
    Publication statusPublished - 7 Sep 2011

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