Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences. Issue 35 (29th August 2019)

• Record Type: Journal Article
• Authors: Botti, Valentina; Cesaretti, Alessio; Ban, Željka; Crnolatac, Ivo; Consiglio, Giuseppe; Elisei, Fausto; Piantanida, Ivo
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 35(2019)
• Page Start: 8243
• Page End: 8258
• Publication Date: 2019-08-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01186b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A strong impact of fluorophores' charge and length on the binding mode, intracellular distribution and antiproliferative activity; intriguing theragnostic potential. Abstract : 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. Most of the compounds showed strong affinity toward ds-DNA/RNA, directly correlated to the synergistic contribution of the aromatic-conjugated surface and net positive charge. The volume or positioning of terminal aromatic substituents directly controlled the binding mode of the core structure, shifting between DNA/RNA groove binding or DNA/RNA intercalation. Consequently, upon binding to DNA/RNA the fluorimetric and induced CD (ICD) response varied for different compounds, for instance one derivative showed specific fluorescence increase with AT-DNA, while another derivative showed specific ICD response with AU-RNA. Preliminary screening on human tumour cell lines revealed an efficient cellular uptake for all dyes. Only mono-styryl-quinoline derivatives showed a 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.