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Issue 19, 2012
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Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands

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Abstract

Extended naphthalene diimides (NDIs) fused to 1,4-dihydropyrazine-2,3-dione, containing two solubilizing moieties, have been synthesized. Fluorescence spectra of the new NDIs were remarkably affected by pH, as the second deprotonation of the dihydropyrazinedione moiety (pKa 6.9) switched off the emission. Binding to a G-quadruplex folded oligonucleotide and stoichiometry were evaluated by FRET melting assay and CD analysis. G-quadruplex binding was strongly enhanced shifting from pH 7.4 to pH 6.0 as a consequence of the dihydropyrazinedione moiety protonation. Cytotoxicity studies using two human telomerase-positive cell lines (HT29 and A549) revealed that the best G-quadruplex ligand was very active against the colon cell line, with an EC50 of 300 nM.

Graphical abstract: Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands

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Publication details

The article was received on 29 Nov 2011, accepted on 08 Mar 2012 and first published on 09 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB07006E
Citation: Org. Biomol. Chem., 2012,10, 3830-3840
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    Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands

    F. Doria, M. Nadai, G. Sattin, L. Pasotti, S. N. Richter and M. Freccero, Org. Biomol. Chem., 2012, 10, 3830
    DOI: 10.1039/C2OB07006E

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