5-Chloroanthranilic Acid Schiff Base: Crystal Structure, DNA/BSA Interactions, Molecular Docking and Antioxidant Activity

Abstract

A novel 5ClAA-Schiff base (Schiff base derived from the condensation of 5-chloroanthranilic acid and 4-(dimethylamino)benzaldehyde) has been synthesized. The structure of the 5ClAA-Schiff base was clarified by CHN analysis, FTIR, electronic absorption spectroscopy, ESI-MS and X-ray single crystal diffraction methods. In biological activity studies, the interactions of the 5ClAA-Schiff base with calf thymus DNA (CT-DNA) were examined using fluorescence spectroscopy. The interactions of the 5ClAA-Schiff base with bovine serum albumin (BSA) were investigated using electronic absorption and fluorescence spectroscopy techniques and the BSA quenching mechanism was found. The molecular docking simulation was investigated to explore the interactions between the 5ClAA-Schiff base and biomolecules such as DNA and BSA using in silico techniques. Results confirmed that the 5ClAA-Schiff base was inserted into DNA via a minor groove and into BSA with subdomain IIA. The antioxidant activity of the 5ClAA-Schiff base was also investigated in comparison with the compounds used as standard.

Keywords

• 5-chloroanthranilic acid
• Schiff base
• DNA/BSA interactions
• antioxidant activity

References

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