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

doi:10.3390/molecules25194470

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

^1,†

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^3,‡ and

^1,*

Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička Cesta 54, 10000 Zagreb, Croatia

Division of Molecular Biology, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

Institute of Organic Chemistry, University of Duisburg-Essen, 45141 Essen, Germany

Author to whom correspondence should be addressed.

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Present address: National Institute of Chemistry, Hajdrihova 19, P.O. Box 660, SI-1001 Ljubljana, Slovenia.

^‡

This work is dedicated to the late Prof. Dr. Carsten Schmuck, in memory of his invaluable contribution to our research.

Academic Editor: Ugo Caruso

Molecules 2020, 25(19), 4470; https://doi.org/10.3390/molecules25194470

Received: 7 September 2020 / Revised: 25 September 2020 / Accepted: 27 September 2020 / Published: 29 September 2020

(This article belongs to the Special Issue Advances in DNA and RNA Sensing)

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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. View Full-Text

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

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Šmidlehner, T.; Košćak, M.; Božinović, K.; Majhen, D.; Schmuck, C.; Piantanida, I. Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate. Molecules 2020, 25, 4470. https://doi.org/10.3390/molecules25194470

AMA Style

Šmidlehner T, Košćak M, Božinović K, Majhen D, Schmuck C, Piantanida I. Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate. Molecules. 2020; 25(19):4470. https://doi.org/10.3390/molecules25194470

Chicago/Turabian Style

Šmidlehner, Tamara, Marta Košćak, Ksenija Božinović, Dragomira Majhen, Carsten Schmuck, and Ivo Piantanida. 2020. "Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate" Molecules 25, no. 19: 4470. https://doi.org/10.3390/molecules25194470

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

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