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 title Project leader Project code Project type Višenamjensko očitavanje DNA/RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSense Ivo Piantanida IP-2013-11-1477 HRZZ Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbes Ivo Piantanida IP-2018-01-5475 HRZZ
Depositing User:	Ivo Piantanida
Date Deposited:	04 Nov 2020 13:20
URI:	http://fulir.irb.hr/id/eprint/5975
DOI:	10.3390/molecules25194470

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