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Current Bioactive Compounds

Author(s): Amira Boutarfaia, Lazhar Bechki, Touhami Lanez*, Elhafnaoui Lanez and Mohamed Kadri

DOI: 10.2174/1573407215666191017105239

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Synthesis, Antioxidant Activity, and Determination of Binding Parameters of Meso-Tetra-4-Actophenyl-Porphyrin and its Palladium (II) Complex with Superoxide Anion Radicals

Page: [1063 - 1071] Pages: 9

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Abstract

Background: Meso-tetra-4-actophenyl-porphyrin (TAcPPH2) was synthesized by reacting 4- acetyl-benzaldehyde with pyrrole in propionic acid, and used as a ligand for the synthesis of palladium (II) complex (PdTAcPP). The structure of the ligand and the complex were characterized by NMR and electronic spectroscopy.

Methods: The antioxidant activity and the binding parameters of both the ligand and its complex with superoxide anion radical . (O2 -) were measured using cyclic voltammetry based assay. The assays were based on the measurement of the anodic peak current density of . O2− electrochemically generated by reduction of molecular oxygen in DMF.

Results: The complex PdTAcPP showed the highest antioxidant activity (0.73 ± 0.01 mg/mL) which is four times higher than that of the standard antioxidant α-tocopherol (3.04 ± 0.03 mg/mL).

Discussion: Binding parameters like binding constants, the ratio of binding constants and binding free energies were also measured.

Conclusions: The value of the binding free energy ranging from -7.89 kJmol-1 for TAcPPH2 to -17.59 kJ.mol-1for PdTAcPP suggests an electrostatic interaction of . O2− with TAcPPH2 and PdTAcPP which has been found to be the dominant interaction mode. The kinetics of the interaction reaction of the ligand and complex was quantified having second-order rate constant values equal to 0.2 and 1.3 M-1 s-1, respectively.

Keywords: Porphyrin, homogeneous rate constant, cyclic voltammetry, superoxide anion radical, binding parameters, antioxidant activity coefficient.

Graphical Abstract

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