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.
Highlights
Versatile applications of small molecule fluorescent probes targeting DNA/RNA in biochemical and biomedicinal applications have attracted enormous interest and, due to the versatility of applications, have become unavoidable tools for monitoring biological processes [1]
The reaction mixture of Cy-amino overlapped absorbancies of guanidiniocarbonyl-pyrrole (GCP) and triazole moieties and another acid and GCP in acetonitrile with O-(1H-6-Chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium absorption band in the visible range attributed to cyanine dye
Results bind to ds-DNA/RNA with similar affinity (Table 2), it seems that quinoline-tethered cyanines
Summary
Versatile applications of small molecule fluorescent probes targeting DNA/RNA in biochemical and biomedicinal applications have attracted enormous interest and, due to the versatility of applications, have become unavoidable tools for monitoring biological processes [1]. Cyanine analogs are likely the most extensively used family of fluorogenic dyes, their particular advantage being non-emissive in free solution but strong emission fluorescence upon binding to the target [7,8,9]. Derivatives characterized GCP moiety as a very useful building block in the design of new small molecules targeting DNA/RNA, when conjugated with large aromatic fluorophores [10,11,12]. Pyrene-GCP analogs have been shown to be very efficient single-molecule- multipurpose
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