Journal
DYES AND PIGMENTS
Volume 207, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2022.110715
Keywords
Thiazole orange dyes; DNA; RNA recognition; Triplex helix formation; H -aggregate; Mitochondrial dyes; Cell viability
Funding
- Croatian Science Foundation [IP-2018-01-4694]
- Bulgarian National Science Fund (BNSF) [59/1]
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A series of dicationic monomethine cyanine dyes were synthesized with structural alterations to examine their interactions with DNA and RNA. The chlorinated cyanine dye showed strong stability in triplex helices and tendency for H-aggregate formation. These dyes exerted a significant effect on tumor cell viability, especially in HeLa and A549 cell lines. Fluorophores 2 and 3 preferentially accumulated in mitochondria and showed promising therapeutic potential.
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 mu M). 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.
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