Naslov
Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences

Autori
Botti, Valentina ; Cesaretti, Alessio ; Ban, Željka ; Crnolatac, Ivo ; Consiglio, Giuseppe ; Elisei, Fausto ; Piantanida, Ivo

Izvornik
Organic & biomolecular chemistry (1477-0520) 17 (2019), 35; 8243-8258

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
DNA/RNA recognition ; styryl-based dyes ; fluorescence ; CD spectroscopy

Sažetak
A set of styryl- and bis- styryl dyes, varying in length, aromatic surface, net positive charge and steric positioning or bulkiness of substituents was tested for interactions with various ds-DNA or ds-RNA. The most of compounds showed strong affinity toward ds-DNA/RNA, directly correlated to the synergistic contribution of aromatic-conjugated surface and net positive charge. The volume or positioning of terminal aromatic substituents directly controlled binding mode of core structure, shifting between DNA/RNA groove binding or DNA/RNA intercalation. Consequently, the fluorimetric and induced CD (ICD) response varied, to the effect that particular compounds showed specific fluorescence increase for ATDNA or specific ICD response for AU-RNA. Preliminary screening on human tumour cell lines revealed efficient cellular uptake for all dyes. Only mono-styryl-quinoline derivatives showed strong antiproliferative activity combined with efficient fluorescent localisation, thus showing promising theragnostic potential, while other compounds were negligibly cytotoxic but still efficient fluorescent markers of cytoplasmic organelles.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA