An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA
| Autor: | Jelena Rupar, Vladimir Dobričić, Mara M. Aleksić, Olivera Čudina, Jasmina Brborić |
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| Rok vydání: | 2020 |
| Předmět: |
Interaction
Square wave voltammetry Dimer Intercalation (chemistry) Biophysics 9-Chloroacridine redox mechanism 02 engineering and technology Electrochemistry Photochemistry 01 natural sciences Redox chemistry.chemical_compound dsDNA-electrochemical biosensor Molecule Physical and Theoretical Chemistry Electrodes Chemistry 010401 analytical chemistry DNA Electrochemical Techniques General Medicine 021001 nanoscience & nanotechnology Binding constant 0104 chemical sciences Molecular Docking Simulation Monomer Molecular docking Acridines 0210 nano-technology Oxidation-Reduction Biosensor |
| Zdroj: | Bioelectrochemistry |
| Popis: | The electrochemical behavior of 9-chloroacridine (9Cl-A), a precursor molecule for synthesis of acridine derivatives with cytostatic activity, is a complex, pH-dependent, diffusion-controlled irreversible process. Oxidation of 9Cl-A initiates with the formation of a cation radical monomer, continues via the formation of a dimer subsequent oxidation to new cation radical. Reduction of 9Cl-A produces radical monomers which are stabilized by dimer formation. The investigation was performed using cyclic, differential pulse and square wave voltammetry at a glassy carbon electrode. The interaction between 9Cl-A and double-stranded DNA (dsDNA) was investigated using a multilayer dsDNA-electrochemical biosensor and 9Cl-A solutions from 1.0 × 10 - 7 M (the lowest 9Cl-A concentration whose interaction with DNA was possible to detect) up to 1 × 10 - 4 M . These allowed the binding constant, K = 3.45 × 10 5 M - 1 and change in Gibbs free energy of the formed adsorbed complex to be calculated. Complex formation was a spontaneous process proceeding via 9Cl-A intercalation into dsDNA inducing structural changes. The intercalation of 9Cl-A into dsDNA was supported by molecular docking analysis. The combination of simple methodology and the use of biosensors to investigate DNA interactions is a powerful tool to offer insight into aspects of drug design during pharmaceutical development. |
| Databáze: | OpenAIRE |
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