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Fluorimetric and CD Recognition Between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate

Šmidlehner, Tamara; Košćak, Marta; Božinović, Ksenija; Majhen, Dragomira; Schmuck, Carsten; Piantanida, Ivo (2020) Fluorimetric and CD Recognition Between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate. Molecules, 25 . ISSN 1420-3049

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Abstract

Two novel isosteric conjugates of guanidiniocarbonyl-pyrrole and 6-bromo-TO (thiazole orange) were prepared, differing only in linker connectivity to cyanine (benzothiazole nitrogen vs. quinoline nitrogen). The quinoline analog was significantly more susceptible to aggregation in an aqueous medium, which resulted in induced circular dichroism (ICD ; λ = 450–550 nm) recognition between A-T(U) and G-C basepair containing polynucleotides. The benzothiazole-isostere showed pronounced (four-fold) fluorimetric selectivity toward ds-RNA in comparison to any ds-DNA, at variance to its quinoline-analogue fluorescence being weakly selective to GC-DNA. Preliminary screening on human tumor and normal lung cell lines showed that both dyes very efficiently enter living cells and accumulate in mitochondria, causing moderate cytotoxic effects, and thus could be considered as lead compounds toward novel theragnostic mitochondrial dyes.

Item Type: Article
Uncontrolled Keywords: cyanine dyes ; guanidiniocarbonyl-pyrrole ; ds-DNA/RNA sensing ; fluorescence ; circular dichroism ; mitochondria
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Biology
Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višenamjensko očitavanje DNA/RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSenseIvo PiantanidaIP-2013-11-1477HRZZ
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbesIvo PiantanidaIP-2018-01-5475HRZZ
Depositing User: Ivo Piantanida
Date Deposited: 04 Nov 2020 13:20
Last Modified: 10 Aug 2021 14:14
URI: http://fulir.irb.hr/id/eprint/5975
DOI: 10.3390/molecules25194470

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