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Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets
Author(s) -
Mancuso Aurora,
Barattucci Anna,
Bonaccorsi Paola,
Giannetto Antonino,
La Ganga Giuseppina,
MusarraPizzo Maria,
Salerno Tania M. G.,
Santoro Antonio,
Sciortino Maria Teresa,
Puntoriero Fausto,
Di Pietro Maria Letizia
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803804
Subject(s) - chemistry , guanine , luminescence , titration , biocompatibility , quenching (fluorescence) , dna , aqueous solution , combinatorial chemistry , photochemistry , organic chemistry , biochemistry , materials science , fluorescence , optoelectronics , physics , gene , nucleotide , quantum mechanics
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.