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Pyrrolocytosine-pyrene conjugates as fluorescent and CD probes for a fine sensing of ds- polynucleotide secondary structure and specific recognition of poly G

Three novel pyrene-pyrrolocytosine (PyrrC) conjugates efficiently bind to ds-DNA/RNA grooves. The compounds exhibit DNA/RNA secondary structure-dependent fluorimetric selectivity. The most pronounced differentiation was observed between poly (dAdT)2 and poly A – poly U. Moreover, the most flexible conjugate showed specific fluorescence band at 470 nm with poly (dAdT)2 . Different induced circular dichroism (I)CD response of rigid and flexible pyrene-pyrrC conjugates upon A-T(U) binding, revealed fine structural tuning of pyrene position within DNA/RNA binding site. Novel conjugates showed till now unmatched specific fluorimetric recognition of poly G in respect to other ss-RNA, attributed to the synergistic effect of pyrene intercalation combined with H-bonding recognition of complementary basepair. The most prominent response of poly G was observed for the most rigid conjugate, having conveniently pre-organized conformation. All conjugates efficiently entered into human cells, showing no cytotoxicity, thus being promising lead compounds for the further development of cellular or biochemical spectrophotometric probes.

Pyrrolocytosine ; Pyrene ; DNA/RNA binding ; Fluorescence ; circular dichroism

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