6533b822fe1ef96bd127cee0
RESEARCH PRODUCT
Acid–base behaviour and binding to double stranded DNA/RNA of benzo[g]phthalazine-based ligands
Eudald CarbonellRoberto TejeroMaría J. R. YuntaEnrique García-españaLucrecia CampayoFernando Gómez-contrerasMercedes CanoCristina Galiana-rosellóÁLvaro Martínez-camarenaAna M. SanzMario InclánJorge González-garcíaJorge González-garcíaPilar Navarrosubject
Circular dichroismChemistryStereochemistryIntercalation (chemistry)Protonation02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnologyDiprotic acid01 natural sciencesCatalysis0104 chemical scienceschemistry.chemical_compoundMaterials ChemistryNucleic acidMoiety0210 nano-technologyPhthalazineDNAdescription
The affinity and the binding mode of two benzo[g]phthalazine compounds, functionalized with one or two 2-(imidazole-4-yl)-ethylamine groups, to DNA and RNA models have been evaluated by means of UV-Vis, fluorescence and circular dichroism (CD) spectroscopies in combination with viscometry and molecular dynamics. Both organic molecules bind strongly to all nucleic acid models via the intercalation mode in the duplex structure, especially compound 1. Intriguingly, 1 exhibits different emission responses depending on the base composition of duplex DNA/RNAs, which points out the possibility of using it as a base selective nucleic acid probe. Moreover, the acid-base behaviour of both compounds has been studied by pH-metric titrations and UV-Vis and emission fluorescence techniques to investigate the unexplored basicity of this type of compound. 1 behaves as a triprotic base whilst 2 is a diprotic base with the protonation of the benzo[g]phthalazine moiety occurring in the physiological pH range.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-01 | New Journal of Chemistry |