Issue 19, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
29 Nov 2011
Accepted
08 Mar 2012
First published
09 Mar 2012

Org. Biomol. Chem., 2012,10, 3830-3840

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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