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Antioxidant activity and superoxide anion radical interaction with 2-(ferrocenylmethylamino) benzonitrile and 3-(ferrocenylmethylamino) benzonitrile

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Abstract

Cyclic voltammetry was used to explore the interaction of (ferrocenylmethylamino) benzonitrile (FMAB) with superoxide anion radical (\({\text{O}}_{2}^{. - }\)), electrochemically generated by the reduction in commercial molecular oxygen in acetonitrile. The difference in the electrochemical behavior of \({\text{O}}_{2}^{. - }\) in the absence and presence of FMAB, including shifts in peak potential and decrease in anodic peak current, was successfully investigated for the determination of interaction parameters such as the binding constant, ratio of binding constants, binding free energy and mode of interaction. The anodic peak potential shifts and the magnitude of binding free energy ΔG suggest the electrostatic interaction of \({\text{O}}_{2}^{. - }\) with FMAB as the dominant mode, whereas the negative sign of ΔG indicates the spontaneity of the interaction. The antioxidant activity of FMAB derivatives was also evaluated using spectrophotometrical and electrochemical techniques. The spectrophotometrical assays were carried out using 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH), while the electrochemical assays were determined by measuring the oxidation peak current of \({\text{O}}_{2}^{. - }\). The activity was found to be highest for 3FMAB in both DPPH and \({\text{O}}_{2}^{. - }\) radicals scavenging methods (0.0183) and (0.0090 mg/mL), respectively, which is equal to half the antioxidant activity of standard antioxidant ascorbic acid (0.0117) and (0.0041 mg/mL).

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Acknowledgments

The authors are grateful to the Ministry of Higher Education and Scientific Research for the financial support to this project (B00L01UN390120110001). We also acknowledge the assistance of M. Ali Tliba from the Laboratoire de Valorisation et Technologie des Ressources Sahariennes (VTRS) staff.

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Lanez, T., Henni, M. Antioxidant activity and superoxide anion radical interaction with 2-(ferrocenylmethylamino) benzonitrile and 3-(ferrocenylmethylamino) benzonitrile. J IRAN CHEM SOC 13, 1741–1748 (2016). https://doi.org/10.1007/s13738-016-0891-1

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