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Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality—Strong Affinity Nucleic Acids Binders
- Source :
- Biomolecules, Biomolecules; Volume 11; Issue 8; Pages: 1075, Biomolecules, Vol 11, Iss 1075, p 1075 (2021)
- Publication Year :
- 2021
-
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.
- Subjects :
- antiproliferative activity
Circular dichroism
Supramolecular chirality
Dimer
Intercalation (chemistry)
cyanine dye
010402 general chemistry
01 natural sciences
Biochemistry
Microbiology
Article
chemistry.chemical_compound
Cell Line, Tumor
Humans
Cyanine
DNA binding
Coloring Agents
Biology
Molecular Biology
Binding Sites
010405 organic chemistry
RNA binding
fluorescence
circular dichroism
DNA
Combinatorial chemistry
QR1-502
Intercalating Agents
3. Good health
0104 chemical sciences
chemistry
Polynucleotide
Nucleic acid
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- Biomolecules, Biomolecules; Volume 11; Issue 8; Pages: 1075, Biomolecules, Vol 11, Iss 1075, p 1075 (2021)
- Accession number :
- edsair.doi.dedup.....1e460e8e968343544f1a750f6b1df796