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