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Current Bioactive Compounds

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ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

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Research Article

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

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

Volume 16, Issue 7, 2020

Page: [1063 - 1071] Pages: 9

DOI: 10.2174/1573407215666191017105239

Price: $65

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

[1]
Ighodaro, O.M.; Akinloye, O.A. First line defence antioxidants-Superoxide Dismutase (SOD), catalase (CAT) and Glutathione Peroxidase (GPX): Their fundamental role in the entire antioxidant defence grid. Alex. J. Med., 2017, 54(4), 287-293.
[http://dx.doi.org/10.1016/j.ajme.2017.09.001]
[2]
Sen, S.; Chakraborty, R.; Sridhar, C.; Reddy, Y.S.R.; De, B. Free radicals, antioxidants, diseases and phytomedicines: Current status and future prospect. Int. J. Pharm. Sci. Rev. Res., 2010, 3(1), 91-100.
[3]
Giustarini, D.; Dalle-Donne, I.; Tsikas, D.; Rossi, R. Oxidative stress and human diseases: Origin, link, measurement, mechanisms, and biomarkers. Crit. Rev. Clin. Lab. Sci., 2009, 46(5-6), 241-281.
[http://dx.doi.org/10.3109/10408360903142326]
[4]
Lanez, T.; Henni, M.; Hemmami, H. Development of cyclic voltammetric method for the study of the interaction of antioxidant standards with superoxide anion radicals case of α-tocopherol. St. Cerc. St. CICBIA, 2015, 16(2), 161-168.
[5]
Lanez, T.; Hemmami, H. Antioxidant activities of N-ferrocenylmethyl-2- and -3-nitroaniline and determination of their binding parameters with superoxide anion radicals. Curr. Pharm. Anal., 2017, 13(00), 1-7.
[6]
Ahmed, S.; Shakeel, F. Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical. Czech. J. Food Sci., 2012, 30(2), 153-163.
[7]
Ahmed, S.; Shakeel, F. Voltammetric determination of antioxidant character in Berberis lycium Royel, Zanthoxylum armatum and Morus nigra Linn plants. Pak. J. Pharm. Sci., 2012, 25(3), 501-507.
[8]
Thompson, S.J.; Brennan, M.R.; Lee, S.Y.; Dong, G. Synthesis and applications of rhodium porphyrin complexes. Chem. Soc. Rev., 2018, 47(3), 929-981.
[http://dx.doi.org/10.1039/C7CS00582B]
[9]
Kadri, M.; Hou, J.; Dorcet, V.; Roisnel, T.; Bechki, L.; Miloudi, A.; Bruneau, C.; Gramage-Doria, R. Palladium-catalysed cross-coupling reactions controlled by noncovalent Zn-N interactions. Chemistry, 2017, 23(21), 5033-5043.
[http://dx.doi.org/10.1002/chem.201604780]
[10]
Huang, H.; Song, W.; Rieffel, J.; Lovell, J.F. Emerging applications of porphyrins in photomedicine. Front. Phys., 2015, 3, 1-15.
[http://dx.doi.org/10.1007/s11467-015-0501-1]
[11]
Alves, E.; Faustino, M.A.F.; Maria Neves, G.P.M.S.; Cunha, Â.; Nadais, H.; Almeida, A. Potential applications of porphyrins in photodynamic inactivation beyond the medical scope. J. Photochem. Photobiol. Chem., 2015, 22, 34-57.
[http://dx.doi.org/10.1016/j.jphotochemrev.2014.09.003]
[12]
Brett, C.M.A.; Brett, A.M.O. Electrochemistry: Principles, Methods and Applications; Oxford Science University Publications: Oxford, 1993, pp. 427-435.
[13]
Molyneux, P. The use of the stable free radical Diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. Sci. Technol., 2004, 26, 211-219.
[14]
Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. LWT - Food. Sci. Tech. (Paris), 1995, 28(1), 25-30.
[15]
Antolovich, M.; Prenzler, P.D.; Patsalides, E.; McDonald, S.; Robards, K. Methods for testing antioxidant activity. Analyst (Lond.), 2002, 127(1), 183-198.
[http://dx.doi.org/10.1039/b009171p]
[16]
Korotkova, E.I.; Karbainov, Y.A.; Avramchik, O.A. Investigation of antioxidant and catalytic properties of some biologically active substances by voltammetry. Anal. Bioanal. Chem., 2003, 375(3), 465-468.
[http://dx.doi.org/10.1007/s00216-002-1687-y]
[17]
Pisoschi, A.M.; Cheregi, M.C.; Danet, A.F. Total antioxidant capacity of some commercial fruit juices: Electrochemical and spectrophotometrical approaches. Molecules, 2009, 14(1), 480-493.
[http://dx.doi.org/10.3390/molecules14010480]
[18]
Milardović, S.; Iveković, D.; Grabarić, B.S. A novel amperometric method for antioxidant activity determination using DPPH free radical. Bioelectrochemistry, 2006, 68(2), 175-180.
[http://dx.doi.org/10.1016/j.bioelechem.2005.06.005]
[19]
Milardovic, S.; Ivekovic, D.; Rumenjak, V.; Grabaric, B.S. Use of DPPH⋅DPPH redox couple for biamperometric determination of antioxidant activity. Electroanalysis, 2005, 17(20), 1847-1853.
[http://dx.doi.org/10.1002/elan.200503312]
[20]
Pellegrini, N.; Serafini, M.; Colombi, B.; Del Rio, D.; Salvatore, S.; Bianchi, M.; Brighenti, F. Total antioxidant capacity of plant foods, beverages and oils consumed in Italy assessed by three different in vitro assays. J. Nutr., 2003, 133(9), 2812-2819.
[http://dx.doi.org/10.1093/jn/133.9.2812]
[21]
Miller, N.J.; Rice-Evans, C.; Davies, M.J.; Gopinathan, V.; Milner, A. A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin. Sci. (Lond.), 1993, 84(4), 407-412.
[http://dx.doi.org/10.1042/cs0840407]
[22]
Gil, M.I.; Tomás-Barberán, F.A.; Hess-Pierce, B.; Kader, A.A. Antioxidant capacities, phenolic compounds, carotenoids, and vitamin C contents of nectarine, peach, and plum cultivars from California. J. Agric. Food Chem., 2002, 50(17), 4976-4982.
[http://dx.doi.org/10.1021/jf020136b]
[23]
Nicholson, R.S.; Shain, I. Theory of stationary electrode polarography. Single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. J. Anal. Chem., 1964, 36(4), 706-723.
[http://dx.doi.org/10.1021/ac60210a007]
[24]
Muhammad, H.; Hanif, M.; Tahiri, I.A.; Versiani, M.A.; Shah, F.; Khaliq, O. Electrochemical behavior of superoxide anion radical towards quinones: A mechanistic approach. Res. Chem. Intermed., 2018, 44(10), 6387-6400.
[http://dx.doi.org/10.1007/s11164-018-3496-8]

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