Formation of triplex rA/dA-containing nucleic acid helices induced by new thiazole orange analogues and their biological evaluation. H-aggregate formation conditioned by rA sequence

Zonjić, Iva; Kurutos, Atanas; Mihovilović, Petra; Crnolatac, Ivo; Tumir, Lidija-Marija; Tomašić Paić, Ana; Kralj, Juran; Horvat, Lucija; Brozovic, Anamaria; Stojković, Ranko; Radić Stojković, Marijana

doi:10.1016/j.dyepig.2022.110715

Pregled bibliografske jedinice broj: 1213529

Formation of triplex rA/dA-containing nucleic acid helices induced by new thiazole orange analogues and their biological evaluation. H-aggregate formation conditioned by rA sequence

Zonjić, Iva; Kurutos, Atanas; Mihovilović, Petra; Crnolatac, Ivo; Tumir, Lidija-Marija; Tomašić Paić, Ana; Kralj, Juran; Horvat, Lucija; Brozovic, Anamaria; Stojković, Ranko; Radić Stojković, Marijana

Formation of triplex rA/dA-containing nucleic acid helices induced by new thiazole orange analogues and their biological evaluation. H-aggregate formation conditioned by rA sequence // Dyes and pigments, 207 (2022), 110715, 14 doi:10.1016/j.dyepig.2022.110715 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 1213529 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Formation of triplex rA/dA-containing nucleic acid helices induced by new thiazole orange analogues and their biological evaluation. H-aggregate formation conditioned by rA sequence

Autori
Zonjić, Iva ; Kurutos, Atanas ; Mihovilović, Petra ; Crnolatac, Ivo ; Tumir, Lidija-Marija ; Tomašić Paić, Ana ; Kralj, Juran ; Horvat, Lucija ; Brozovic, Anamaria ; Stojković, Ranko ; Radić Stojković, Marijana

Izvornik
Dyes and pigments (0143-7208) 207 (2022); 110715, 14

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

Ključne riječi
Thiazole orange dyes ; DNA/RNA recognition ; Triplex helix formation ; H-aggregate ; Mitochondrial dyes ; Cell viability

Sažetak
A series of 3 dicationic monomethine cyanine dyes was synthesized in moderate yields, applying structural alternations with respect to both the peripheral carrier of additional possitive charge - cyclic amine (pyrrolidine or pyridine) and the introduction of a halogen atom (fluorine or chlorine) at position 6 of the benzothiazole moiety. Structural elucidation of the target fluorophores was achieved employing a combination of 1D, 2D-NMR spectroscopy and ESI mass spectrometry in both positive and negative mode. One of the main goals of current investigation was to examine the impact of the introduced steric and electronic properties on interactions with various DNA and RNA. The cyanine dyes induced the triplex formation of consecutive rA/dA-containing nucleic acid helices. In particular, the chlorinated cyanine 3 stabilized all three triplex helices (dAdTdT, rAdTdT, rArUrU) much stronger than corresponding duplex nucleic acid forms (dAdT, rAdT, rArU). The same derivative, showed a strong tendency for H-aggregate formation in the presence of rA chain in single-stranded, double-stranded, or triple-stranded forms. The three monomethines exerted a significant effect on all tumour cell lines’ viability, especially towards HeLa and A549 cell lines (5–6 μM). Colocalization studies revealed that fluorophores 2 and 3 preferentially accumulate in mitochondria, which, in addition to their proven influence on cell viability, makes them promising therapeutic leads.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija

POVEZANOST RADA

Projekti:
--IP-2018-01-4694 - Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavima (DNARNAHyB-MolBio) (Radić Stojković, Marijana) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Iva Zonjić (autor)