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

Mikulin, Ivana; Ljubić, Ivana; Piantanida, Ivo; Vasilev, Aleksey; Mondeshki, Mihail; Kandinska, Meglena; Uzelac, Lidija; Martin-Kleiner, Irena; Kralj, Marijeta; Tumir, Lidija-Marija (2021) Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders. Biomolecules, 11 (8). ISSN 2218-273X

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: cyanine dye ; DNA binding ; RNA binding ; fluorescence ; circular dichroism ; antiproliferative activity
Subjects: NATURAL SCIENCES > Biology
Divisions: Division of Molecular Medicine
Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteinaPiantanida, IvoIP-2018-01-5475HRZZ
Depositing User: Sofija Konjević
Date Deposited: 06 Aug 2021 09:16
Last Modified: 06 Aug 2021 09:16
URI: http://fulir.irb.hr/id/eprint/6518
DOI: 10.3390/biom11081075

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