Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives

• Published in: Bioelectrochemistry (Amsterdam, Netherlands) Vol. 132; p. 107412
• Main Authors: Pešić, Marko, Bugarinović, Jovana, Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Todosijević, Anka, Stevanović, Dragana, Damljanović, Ivan
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.04.2020; Elsevier BV
• Subjects: [3 + 2] dipolar cycloaddition; Aromatic compounds; Binding; Carboxylates; Crystallography, X-Ray; Cyclic voltammetry; Cycloaddition; Density Functional Theory; Deoxyribonucleic acid; Differential pulse voltammetry; DNA; DNA - metabolism; DNA damage; DNA-binding; Electrochemical analysis; Electrochemical Techniques - methods; Electrochemistry; Ferrocene; Ferrous Compounds - chemistry; Ferrous Compounds - metabolism; Magnetic Resonance Spectroscopy; Metallocenes - chemistry; Metallocenes - metabolism; Molecular docking; Molecular Structure; NMR; Nuclear magnetic resonance; Nucleic acids; Oxidation; Oxidation process; Oxidation-Reduction; Single crystals; Spectrophotometry, Infrared; Voltammetry; X-ray diffraction; Cyclic voltammetry; Differential pulse voltammetry; DNA-binding; [3 + 2] dipolar cycloaddition; Ferrocene
• ISSN: 1567-5394; 1878-562X
• DOI: 10.1016/j.bioelechem.2019.107412

[Display omitted] •A series of ferrocene derivatives have been synthesized via [3 + 2] dipolar cycloaddition.•The electrochemical properties of products were examined by voltammetry tests.•CV and DPV revealed the quasi-reversible one-electron oxidation process.•The DNA-binding capacity of all the products was estimated using CV and DPV.•The DFT calculations confirmed the electrostatic nature of the interactions with DNA. The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives.