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Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders

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Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P.O. Box 180, 10002 Zagreb, Croatia
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Faculty of Chemistry and Pharmacy, Department of Pharmaceutical and Applied Organic Chemistry, Sofia University “St. Kliment Ohridski”, 1000 Sofia, Bulgaria
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Department of Chemistry, Johannes Gutenberg Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany
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Laboratory of Experimental Therapy, Division of Molecular Medicine, Ruđer Bošković Institute, P.O. Box 180, 10002 Zagreb, Croatia
*
Authors to whom correspondence should be addressed.
These authors contributed equally.
Academic Editor: Michael Van Dyke
Biomolecules 2021, 11(8), 1075; https://doi.org/10.3390/biom11081075
Received: 14 June 2021 / Revised: 15 July 2021 / Accepted: 19 July 2021 / Published: 21 July 2021
(This article belongs to the Special Issue Polynucleotides)
New analogs of the commercial asymmetric monomethine cyanine dyes thiazole orange (TO) and thiazole orange homodimer (TOTO) with hydroxypropyl functionality were synthesized and their properties in the presence of different nucleic acids were studied. The novel compounds showed strong, micromolar and submicromolar affinities to all examined DNA ds-polynucleotides and poly rA–poly rU. The compounds studied showed selectivity towards GC-DNA base pairs over AT-DNA, which included both binding affinity and a strong fluorescence response. CD titrations showed aggregation along the polynucleotide with well-defined supramolecular chirality. The single dipyridinium-bridged dimer showed intercalation at low dye-DNA/RNA ratios. All new cyanine dyes showed potent micromolar antiproliferative activity against cancer cell lines, making them promising theranostic agents. View Full-Text
Keywords: cyanine dye; DNA binding; RNA binding; fluorescence; circular dichroism; antiproliferative activity cyanine dye; DNA binding; RNA binding; fluorescence; circular dichroism; antiproliferative activity
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MDPI and ACS Style

Mikulin, I.; Ljubić, I.; Piantanida, I.; Vasilev, A.; Mondeshki, M.; Kandinska, M.; Uzelac, L.; Martin-Kleiner, I.; Kralj, M.; Tumir, L.-M. Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders. Biomolecules 2021, 11, 1075. https://doi.org/10.3390/biom11081075

AMA Style

Mikulin I, Ljubić I, Piantanida I, Vasilev A, Mondeshki M, Kandinska M, Uzelac L, Martin-Kleiner I, Kralj M, Tumir L-M. Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders. Biomolecules. 2021; 11(8):1075. https://doi.org/10.3390/biom11081075

Chicago/Turabian Style

Mikulin, Ivana, Ivana Ljubić, Ivo Piantanida, Aleksey Vasilev, Mihail Mondeshki, Meglena Kandinska, Lidija Uzelac, Irena Martin-Kleiner, Marijeta Kralj, and Lidija-Marija Tumir. 2021. "Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders" Biomolecules 11, no. 8: 1075. https://doi.org/10.3390/biom11081075

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