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

Versatile applications of small molecule fluorescent probes targeting DNA/RNA and proteins in biochemical and biomedicinal applications have attracted enormous interest which is why they became unavoidable tools for monitoring biological processes. 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 ;  = 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-analog 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.

cyanine dyes ; guanidiniocarbonyl-pyrrole ; ds-DNA/RNA sensing ; fluorescence ; circular dichroism ; mitochondria

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