Synthesis, characterization, cyclic voltammetry, and molecular docking studies of the antioxidant activities of superoxide anion radicals towards meso-tetramethophenyl-porphyrin and  meso-tetrabiphenyl-porphyrin

Lalmi ZERROUK; Lazhar BECHKI; Elhafnaoui LANEZ; Touhami LANEZ

doi:10.55779/nsb16211823

Authors

Lalmi ZERROUK Kasdi Merbah University, Faculty of Mathematics and Material Sciences, Department of Chemistry, 30000 Ouargla; University of Eloued, VTRS Laboratory, Department of Chemistry, Faculty of Exact Sciences, B.P.789, 39000 Eloued (DZ)
Lazhar BECHKI Kasdi Merbah University, Faculty of Mathematics and Material Sciences, Department of Chemistry, 30000 Ouargla; Kasdi Merbah University, VPRS Laboratory, Department of Chemistry, Faculty of Mathematics and Material Sciences, 30000 Ouargla (DZ)
Elhafnaoui LANEZ University of Eloued, Faculty of Biology, Department of Cellular and Molecular Biology, 39000 Eloued; University of Eloued, VTRS Laboratory, Department of Chemistry, Faculty of Exact Sciences, B.P.789, 39000 Eloued (DZ)
Touhami LANEZ University of Eloued, VTRS Laboratory, Department of Chemistry, Faculty of Exact Sciences, B.P.789, 39000 Eloued (DZ)

DOI:

https://doi.org/10.55779/nsb16211823

Keywords:

antioxidant activity coefficient, binding free energy, cyclic voltammetry, homogeneous rate constant, molecular docking study, porphyrin

Abstract

The investigation employed cyclic voltammetry (CV) assays to assess the scavenging efficacy of two recently developed compounds, namely meso-tetramethophenyl-porphyrin TPPH₂(o-methyl) and meso-tetrabiphenyl-porphyrin (TbiPPH₂), against the superoxide anion radical ( ). The IC₅₀ values derived from the CV assays indicated significant scavenging activity for both compounds, with TbPPH₂ exhibiting superior potency (85.79 ± 0.11 µg ml^-1) compared to the standard antioxidant alpha-tocopherol (353.27 ± 3.21 µg ml^-1). Additionally, molecular docking simulations elucidated the interaction of the investigated compounds with specific amino acid residues of glutathione reductase through hydrogen bonding and hydrophobic interactions. The in vitro and in silico results were concordant, highlighting TbiPPH₂ as the least active compound against glutathione reductase, boasting the highest inhibitory concentration of 0.63 μM and the lowest docking score of -35.36 kJ mol^-1, thus positioning it as a promising candidate for antioxidant applications.

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References

Abu-Melha S (2019). Efficient synthesis of meso-substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents. Archiv der Pharmazie 352(2). https://doi.org/10.1002/ardp.201800221

Ahmed A, Omar WAE, El-Asmy HA, Abou-Zeid L, Fadda AA (2020). Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives. Dyes and Pigments 183. https://doi.org/10.1016/j.dyepig.2020.108728

Ahmed S, Shakeel F (2012a). Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical. Czech Journal of Food Sciences 30(2):153-163. https://doi.org/10.17221/447/2010-cjfs

Ahmed S, Shakeel F (2012b). Voltammetric determination of antioxidant character in Berberis lycium Royel, Zanthoxylum armatum and Morus nigra Linn plants. Pakistan Journal of Pharmaceutical Sciences 25(3):501-507. https://www.pjps.pk/uploads/pdfs/CD-PJPS-25-3-12/Paper-2.pdf

Al-Darraji MN, Jasim SAَ, Aldeen ODAS, Ghasemian A, Rasheed M (2022). The effect of LL37 antimicrobial peptide on FOXE1 and lncRNA PTCSC 2 genes expression in colorectal cancer (CRC) and normal cells. Asian Pacific Journal of Cancer Prevention 23(10):3437-3442. https://doi.org/10.31557/APJCP.2022.23.10.3437

Al-Darraji MN, Saqban LH, Rasheed M, Hussein AJ, Mutar TF (2022). Association of candidate genes polymorphisms in Iraqi patients with chronic kidney disease. Journal of Advanced Biotechnology and Experimental Therapeutics 5(3):687-701. https://doi.org/10.5455/jabet.2022.d147

Antolovich M, Prenzler PD, Patsalides E, McDonald S, Robards K (2002). Erratum: Methods for testing antioxidant activity. Analyst 127(3):430. https://doi.org/10.1039/B009171P

Boutarfaia A, Bechki L, Lanez T, Lanez E, Kadri M (2019a). Synthesis, antioxidant activity, and determination of binding parameters of Meso-Tetra-4-Actophenyl-Porphyrin and its Palladium (II) complex with superoxide anion radicals. Current Bioactive Compounds 16(7):1063-1071. https://doi.org/10.2174/1573407215666191017105239

Boutarfaia A, Bechki L, Lanez T, Lanez E, Kadri M (2019b). Synthesis, antioxidant activity, and determination of binding parameters of Meso-Tetra-4-Actophenyl-Porphyrin and its Palladium (II) complex with superoxide anion radicals. Current Bioactive Compounds 16(7):1063-1071. https://doi.org/10.2174/1573407215666191017105239

Brand-Williams W, Cuvelier ME, Berset C (1995). Use of a free radical method to evaluate antioxidant activity. LWT - Food Science and Technology 28(1):25-30. https://doi.org/10.1016/S0023-6438(95)80008-5

Brett C, Oliveira Brett AM (1993). Electrochemistry: principles, methods, and applications. Electrochemistry 67(2):444. https://cir.nii.ac.jp/crid/1130282271129959296

Eitrich T, Kless A, Druska C, Meyer W, Grotendorst J (2007). Classification of highly unbalanced CYP450 data of drugs using cost sensitive machine learning techniques. Journal of Chemical Information and Modeling 47(1):92-103. https://doi.org/10.1021/ci6002619

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR (2009). Gaussian 09. Wallingford, CT: Gaussian. http://dx.doi.org/10.1007/978-1-4684-7424-4

Gil MI, Tomás-Barberán FA, Hess-Pierce B, Kader AA (2002). Antioxidant capacities, phenolic compounds, carotenoids, and vitamin C contents of nectarine, peach, and plum cultivars from California. Journal of Agricultural and Food Chemistry 50(17):4976-4982. https://doi.org/10.1021/jf020136b

Giustarini D, Dalle-Donne I, Tsikas D, Rossi R (2009). Oxidative stress and human diseases: Origin, link, measurement, mechanisms, and biomarkers. Critical Reviews in Clinical Laboratory Sciences 46(5-6):241-81. https://doi.org/10.3109/10408360903142326

Ighodaro OM, Akinloye OA (2018). First line defence antioxidants-superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPX): Their fundamental role in the entire antioxidant defence grid. Alexandria Journal of Medicine 54(4):287-293. https://doi.org/10.1016/j.ajme.2017.09.001

Karplus PA, Schulz GE (1989). Substrate binding and catalysis by glutathione reductase as derived from refined enzyme: Substrate crystal structures at 2Å resolution. Journal of Molecular Biology 210(1):163-180. https://doi.org/10.1016/0022-2836(89)90298-2

Kedadra A, Lanez T, Lanez E, Hemmami H, Henni M (2022). Synthesis and antioxidant activity of six novel N-ferrocenylmethyl-N-(nitrophenyl)and-N-(cyanophenyl)-acetamides: Cyclic voltammetry and molecular docking studies. Journal of Electrochemical Science and Engineering 12(2):293-304. https://doi.org/10.5599/jese.1162

Khennoufa A, Bechki L, Lanez T, Lanez E, Zegheb N (2021). Spectrophotometric, voltammetric and molecular docking studies of binding interaction of N-ferrocenylmethylnitroanilines with bovine serum albumin. Journal of Molecular Structure 1224. https://doi.org/10.1016/j.molstruc.2020.129052

Kim S, Thiessen PA, Bolton EE, Chen J, Fu G, Gindulyte A (2016). PubChem substance and compound databases. Nucleic Acids Research 44(D1):D1202-1213. https://doi.org/10.1093/nar/gkv951

Korotkova EI, Karbainov YA, Avramchik OA (2003). Investigation of antioxidant and catalytic properties of some biologically active substances by voltammetry. Analytical and Bioanalytical Chemistry 375(3):465-468. https://doi.org/10.1007/s00216-002-1687-y

Lanez E, Bechki L, Lanez T (2019a). Antioxidant Activities, Binding Parameters, and Electrochemical Behavior of Superoxide Anion Radicals Twords 1-Ferrocenylmethylthymine and 1-Ferrocenylmethylcytosine. Current Physical Chemistry 10(1):10-22. https://doi.org/10.2174/1877946809666190424143752

Lanez E, Bechki L, Lanez T (2019b). Computational molecular docking, voltammetric and spectroscopic DNA interaction studies of 9N-(Ferrocenylmethyl)adenine. Chemistry and Chemical Technology 13(1):11-17. https://doi.org/10.23939/chcht13.01.011

Lanez E, Zegheb N, Lanez T (2023). In silico ADME, toxicological analysis, molecular docking studies and Molecular dynamics simulation of Afzelin with potential antibacterial effects against Staphylococcus aureus. Turkish Computational and Theoretical Chemistry 7(3):10-16. https://doi.org/10.33435/TCANDTC.1196422

Lanez T, Hemmami H (2016). Antioxidant activities of N-ferrocenylmethyl-2- and -3-nitroaniline and determination of their binding parameters with superoxide anion radicals. Current Pharmaceutical Analysis 13(2):110-116. https://doi.org/10.2174/1573412912666160831145524

Lanez T, Henni M, Hemmami H (2015). Development of cyclic voltammetric method for the study of the interaction of antioxidant standards with superoxide anion radicals case of α-tocopherol. Scientific Study and Research: Chemistry and Chemical Engineering, Biotechnology, Food Industry 16(2):161-168. https://pubs.ub.ro/dwnl.php?id=CSCC6201502V02S01A0006

Laraoui H, Lanez E, Zegheb N, Adaika A, Lanez T, Benkhaled M (2023). Anti-diabetic activity of flavonol glucosides from Fumana montana Pomel: In vitro analysis, in silico docking, ADMET prediction, and molecular dynamics simulations. ChemistrySelect 8(8). https://doi.org/10.1002/slct.202204512

Li J, Fu A, Zhang L (2019). An overview of scoring functions used for protein–ligand interactions in molecular docking. Interdisciplinary Sciences – Computational Life Sciences 11(2):320-8. https://doi.org/10.1007/s12539-019-00327-w

Meraghni M, Lanez T, Lanez E, Bechki L, Kennoufa A (2023). Experimental and theoretical study on corrosion inhibition of mild steel by meso-tetraphenyl-porphyrin derivatives in acid solution. Journal of Electrochemical Science and Engineering 13(2):217-229. https://doi.org/10.5599/jese.1400

Milardović S, Iveković D, Grabarić BS (2006). A novel amperometric method for antioxidant activity determination using DPPH free radical. Bioelectrochemistry 68(2):175-180. https://doi.org/10.1016/j.bioelechem.2005.06.005

Milardovic S, Iveković D, Rumenjak V, Grabarić BS (2005). Use of DPPH•|DPPH redox couple for biamperometric determination of antioxidant activity. Electroanalysis 17(20):1847-1853. https://doi.org/10.1002/elan.200503312

Miller NJ, Rice-Evans C, Davies MJ, Gopinathan V, Milner A (1993). A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clinical Science 84(4):407-412. https://doi.org/10.1042/cs0840407

Molyneux P (2004). The use of the stable free radical Diphenylpicryl-Hydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin Journal of Science and Technology 26:211-219.

Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry 19(14). https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B

Morris GM, Huey R, Olson AJ (2008). UNIT using AutoDock for ligand-receptor docking. Current Protocols in Bioinformatics 24(24):8-14. https://doi.org/10.1002/0471250953.bi0814s24

Muhammad H, Hanif M, Tahiri IA, Versiani MA, Shah F, Khaliq O, … Ahemd S (2018). Electrochemical behavior of superoxide anion radical towards quinones: a mechanistic approach. Research on Chemical Intermediates 44(10):6387-400. https://doi.org/10.1007/s11164-018-3496-8

Nicholson RS, Shain I (1964). Correction: Theory of stationary electrode polarography: single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. Analytical Chemistry 36(7):1212. https://doi.org/10.1021/ac60213a053

Patra JK, Baek KH (2017). Green biosynthesis of magnetic iron oxide (Fe3O4) nanoparticles using the aqueous extracts of food processing wastes under photo-catalyzed condition and investigation of their antimicrobial and antioxidant activity. Journal of Photochemistry and Photobiology B: Biology 173:291-300. https://doi.org/10.1016/j.jphotobiol.2017.05.045

Pisoschi AM, Cheregi MC, Danet AF (2009). Total antioxidant capacity of some commercial fruit juices: Electrochemical and spectrophotometrical approaches. Molecules 14(1):480-93. https://doi.org/10.3390/molecules14010480

Rasheed M, Saleem MM, Marzoog TR, Taki MM, Bouras D, Hashim IA, ... Sarhan MA (2023). Effect of caffeine-loaded silver nanoparticles on minerals concentration and antibacterial activity in rats. Journal of Advanced Biotechnology and Experimental Therapeutics 6(2):495-509. https://doi.org/10.5455/jabet.2023.d144

Salentin S, Schreiber S, Haupt VJ, Adasme MF, Schroeder M (2015). PLIP: Fully automated protein-ligand interaction profiler. Nucleic Acids Research 43(W1):W443-447. https://doi.org/10.1093/nar/gkv315

Sen S, Chakraborty R, Sridhar C, Reddy YSR, De B (2010). Free radicals, antioxidants, diseases and phytomedicines: Current status and future prospect. International Journal of Pharmaceutical Sciences Review and Research 3(1):91-100.

Sengul M, Yildiz H, Gungor N, Cetin B, Eser Z, Ercisli S (2009). Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. Pakistan Journal of Pharmaceutical Sciences 22(1):102-6.

Silvino ACR, Costa GL, De Araújo FCF, Ascher DB, Pires DEV, Fontes CJF, ... Sousa TN (2016). Variation in Human Cytochrome P-450 drug-metabolism genes: A gateway to the understanding of plasmodium vivax relapses. PLoS One 11(7):e0160172. https://doi.org/10.1371/journal.pone.0160172

Steffen C, Thomas K, Huniar U, Hellweg A, Rubner O, Schroer A (2010). AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. Journal of Computational Chemistry 31(16):2967-70. https://doi.org/10.1002/jcc.21256

Terkeltaub RA, Furst DE, Digiacinto JL, Kook KA, Davis MW (2011). Novel evidence-based colchicine dose-reduction algorithm to predict and prevent colchicine toxicity in the presence of cytochrome P450 3A4/P-glycoprotein inhibitors. Arthritis and Rheumatism 63(8):2226-2237. https://doi.org/10.1002/art.30389

Thompson SJ, Brennan MR, Lee SY, Dong G (2018). Synthesis and applications of rhodium porphyrin complexes. Chemical Society Reviews 47(3):929-981. https://doi.org/10.1039/c7cs00582b

Yao Y, Han X, Yang X, Zhao J, Chai C (2021). Detection of hydrazine at MXene/ZIF-8 nanocomposite modified electrode. Chinese Journal of Chemistry 39(2):330-336. https://doi.org/10.1002/cjoc.202000398

Zahno A, Brecht K, Morand R, Maseneni S, Török M, Lindinger PW, ... Krähenbühl S (2011). The role of CYP3A4 in amiodarone-associated toxicity on HepG2 cells. Biochemical Pharmacology 81(3):432-441. https://doi.org/10.1016/j.bcp.2010.11.002

Zaiz T, Lanez T (2015). Corrosion inhibition of carbon steel XC70 in H2SO4 solution by ferrocene derivative 3-(ferrocenylmethylamine)benzonitrile. Journal of Fundamental and Applied Sciences 4(2):182. https://doi.org/10.4314/jfas.v4i2.8

Zuriaga-Monroy C, Oviedo-Roa R, Montiel-Sánchez LE, Vega-Paz A, Marín-Cruz J, Martínez-Magadán JM (2016). Theoretical study of the aliphatic-chain length’s electronic effect on the corrosion inhibition activity of methylimidazole-based ionic liquids. Industrial and Engineering Chemistry Research 55(12):3506-3516. https://doi.org/10.1021/acs.iecr.5b03884