Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands
Articolo
Data di Pubblicazione:
2012
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.
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.
Tipologia CRIS:
1.1 Articolo in rivista
Keywords:
ORGANIC SYNTHESIS; FLUORESCENT SENSORS; G-Quadruplex; Selective Ligands; Naphthalene Diimides
Elenco autori:
Doria, Filippo; Matteo, Nadai; Giovanna, Sattin; Pasotti, Luca; Sara N., Richter; Freccero, Mauro
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