DNA Binding Properties of Novel Pyrrolyl Quinones Derivatives: Insights from Spectroscopic, Electrophoretic and Computational Studies

High Resolution Image Download MS PowerPoint Slide In this work, we report the synthesis and Deoxyribonucleic acid (DNA)-binding properties of a new series of pyrrolyl quinone derivatives. These compounds were prepared from 2,5-dimethyl-1,4-benzoquinone through Michael-type addition/oxidation and electrophilic aromatic substitution reactions using pyrrole and bis-pyrrole nucleophiles. Additional structural diversification was achieved by reacting the pyrrolyl quinone intermediate either with 1-aminoanthracene or with acetone, affording new pyrrolyl quinone derivatives through distinct synthetic pathways. Owing to the electron-deficient π-conjugated nature of the pyrrolyl quinone scaffold, their ability to interact with DNA was investigated by ultraviolet–visible (UV–vis) spectroscopy, gel electrophoresis, viscosity studies and molecular docking analyses. The combined results demonstrate that these new pyrrolyl quinone derivatives interact with DNA, highlighting the potential of this scaffold as a promising platform for molecular recognition and future drug-design applications.