Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets. Issue 64 (24th October 2018)

• Record Type: Journal Article
• Authors: Mancuso, Aurora; Barattucci, Anna; Bonaccorsi, Paola; Giannetto, Antonino; La Ganga, Giuseppina; Musarra‐Pizzo, Maria; Salerno, Tania M. G.; Santoro, Antonio; Sciortino, Maria Teresa; Puntoriero, Fausto; Di Pietro, Maria Letizia
• Is Part Of: Chemistry. Volume 24:Issue 64(2018)
• Page Start: 16972
• Page End: 16976
• Publication Date: 2018-10-24
• Subjects: DNA -- drug design -- luminescence quenching -- OPEs -- sugar; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201803804
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐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. Abstract : Cooperation of biologically relevant sugar moieties, flat aromatic cores, and positive charges makes two new tetralkylammonium‐OPEs able to strongly interact with DNA, leading to the quenching of their luminescence due to guanine reduction (OPEs=oligo(phenylenethynylenes)). The new species are not cytotoxic on healthy cells (Vero), whereas the dicationic one is able to inhibit cancer cells (HEp‐2) proliferation.