Two new tetralkylammonium-OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two b-d-glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H-bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp-2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.

Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets

Mancuso, Aurora
Primo
;
Barattucci, Anna
Secondo
;
Bonaccorsi, Paola;Giannetto, Antonino;La Ganga, Giuseppina;Musarra-Pizzo, Maria;Salerno, Tania M. G.;Santoro, Antonio;Sciortino, Maria Teresa;Puntoriero, Fausto
Penultimo
;
Di Pietro, Maria Letizia
Ultimo
2018-01-01

Abstract

Two new tetralkylammonium-OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two b-d-glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H-bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp-2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.
2018
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/3131727
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