6533b820fe1ef96bd127a412

RESEARCH PRODUCT

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

Aleksey VasilevIvo PiantanidaMeglena I. KandinskaMihail MondeshkiIvana LjubićLidija UzelacIvana MikulinLidija-marija TumirMarijeta KraljIrena Martin-kleiner

subject

antiproliferative activityCircular dichroismSupramolecular chiralityDimerIntercalation (chemistry)cyanine dye010402 general chemistry01 natural sciencesBiochemistryMicrobiologyArticlechemistry.chemical_compoundCell Line TumorHumansCyanineDNA bindingColoring AgentsBiologyMolecular BiologyBinding Sites010405 organic chemistrycyanine dye ; DNA binding ; RNA binding ; fluorescence ; circular dichroism ; antiproliferative activityDNARNA bindingCombinatorial chemistryQR1-502Intercalating Agents3. Good health0104 chemical sciencescircular dichroismchemistryPolynucleotideNucleic acidcyanine dye; DNA binding; RNA binding; fluorescence; circular dichroism; antiproliferative activityfluorescenceDNA

description

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.

yearjournalcountryeditionlanguage
2021-07-21
10.3390/biom11081075https://doi.org/10.3390/biom11081075