Synthesis, Characterization, X-Ray Diffraction Analysis of A Tridentate Schiff Base Ligand and Its Complexes with Co(II), Fe(II), Pd(II) and Ru(II): Bioactivity Studies

Document Type : Research Article

Authors

1 Department of Food Processing, Vocational School of Technical Sciences, Muş Alparslan University, 49250 Muş, TURKEY

2 Department of Chemistry, Faculty of Arts and Sciences, Muş Alparslan University, 49250 Muş, TURKEY

3 Department of Molecular Biology and Genetics, Faculty of Arts and Sciences, Muş Alparslan University, 49250 Muş, TURKEY

4 Department of Chemistry, Faculty of Arts and Sciences, Hitit University, 19100 Çorum, TURKEY

Abstract

This study reports the synthesis of Co(II), Fe(II), Pd(II), and Ru(II) complexes with Schiff base obtained by the condensation of 2-amino-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate with salicylaldehyde. The characterization of the ligand and its complexes was arranged and studied by FT-IR, UV-Vis., 1H and 13C NMR, microanalyses (C, H, N, S), X-Ray Diffraction (XRD) analysis, magnetic susceptibility, mass spectra, and ThermoGravimetry Analysis (TGA) and further was screened for antimicrobial, antioxidant and antiradical activities. The antioxidant activity of the ligand and its metal complexes was examined by using different methods including the total antioxidant activity method, total reduction method, and DPPH. The antimicrobial activities of Schiff base and metal complexes were investigated on bacterial and fungal strains. DNA cleavage experiments of metal complexes with supercoiled pBR322 DNA were detected by gel electrophoresis in the being of H2O2.

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References

[1] Iftikhar B., Javed K., Khan M.S.U., Akhter Z., Mirza B., Mckee V., Synthesis, Characterization and Biological Assay of Salicylaldehyde Schiff Base Cu(II) Complexes and Their Precursors, J. Mol. Struct., 1155: 337-348 (2018).
[2] Yang J., Shi R., Zhou P., Qiu Q., Li H., Asymmetric Schiff Bases Derived from Diaminomaleonitrile and Their Metal Complexes, J. Mol. Struct., 1106: 242-258 (2016).
[3] Liu X., Manzur C., Novoa N., Celedón S., Carrillo D., Hamon J.R., Multi Dentate Unsymmetrically-Substituted Schiff Bases and Their Metal Complexes: Synthesis, Functional Materials Properties, and Applications to Catalysis, Coord. Chem. Rev., 357: 144-172 (2018).
[4] Zakerhamidi M.S., Nejati K., Sorkhabi S.G., Saati M., Substituent and Solvent Effects on the Spectroscopic Properties and Dipole Moments of Hydroxylbenzaldehyde Azo Dye and Related Schiff Bases, J. Mol. Liq., 180: 225-234 (2013).
[5] Arroudj S., Bouchouit M., Bouchouit K., Bouraiou A., Messaadia L., Kulyk B., Figa V., Bouacida S., Sofiani Z., Taboukhat S., Synthesis, Spectral, Optical Properties and Theoretical Calculations on Schiff Bases Ligands Containing o-Tolidine, Op. Mater., 56: 116-120 (2016).
[6] Satheesh C.E., Kumar P.R., Sharma P., Lingaraju K., Palakshamurthy B.S., Naika H.R., Synthesis, Characterization and Antimicrobial Activity of New Palladium and Nickel Complexes Containing Schiff Bases, Inorg. Chim. Acta, 442: 1-9 (2016).
[7] Deilami A.B., Salehi M., Arab A., Amiri A., Synthesis, Crystal Structure, Electrochemical Properties and DFT Calculations of Three New Zn(II), Ni(II) and Co(III) Complexes Based on 5-Bromo-2-((allylimino)methyl)phenol Schiff-Based Ligand, Inorg. Chim. Acta, 476: 93-100 (2018).
[8] Tan Y-X., Zhang Z-J., Liu Y., Yu J-X., Zhu X-M., Kuang D-Z., Jiang WJ., Synthesis, Crystal Structure and Biological Activity of the Schiff Base Organotin(IV) Complexes Based on Salicylaldehyde-o-aminophenol, J. Mol. Struct., 1149: 874-881 (2017).
[9] Yang J., Shi R., Zhou P., Qiu Q., Li H., Asymmetric Schiff Bases Derived from Diamino Malenitrile and Their Metal Complexes, J. Mol. Struct., 1106: 242-258 (2016).
[10] Zaltariov M.F., Avadanei M., Balan M., Peptanariu D., Vornicu N., Shova S., Synthesis, Structural Characterization and Biological Studies of New Schiff Bases Containing Trimethylsilyl Groups, J. Mol. Struct., 1175: 624-631 (2019).
[11] Sumrra S.H., Habiba U., Zafar W., Imran M., Chohan Z.H., A Review on the Efficacy and Medicinal Applications of Metal-Based Triazole Derivatives, J. Coord. Chem., 73: 2838-2877 (2020).
[12] Buldurun K., Turan N., Aras A., Mantarcı A., Turkan F., Bursal E., Spectroscopic and Structural Characterization, Enzyme Inhibitions, and Antioxidant Effects of New Ru(II) and Ni(II) Complexes of Schiff Base, Chem. Biodivers., 16(8): e1900243 (2019).
[13] Araújo E.L., Hellen de F.G.B., Dockal E.R., Cavalheiro É.T.G., Synthesis, Characterization and Biological Activity of Cu(II), Ni(II) and Zn(II) Complexes of Biopolymeric Schiff Bases of Salicylaldehydes and Chitosan, Int. J. Biol. Macromol., 95: 168-176 (2017).
[14] Parsaee Z., Mohammadi K., Synthesis, Characterization, Nano-Sized Binuclear Nickel Complexes, DFT Calculations and Antibacterial Evaluation of New Macrocyclic Schiff Base Compounds, J. Mol. Struct., 1137: 512-523 (2017).
[15] Szady-Chełmieniecka A., Kołodziej B., Morawiak M., Kamieński B., Schiff W., Spectroscopic Studies of the Intramolecular Hydrogen Bonding in o-Hydroxy Schiff Bases, Derived from Diamino Maleonitrile, and Their Deprotonation Reaction Products, Spectrochim. Acta, Part A, 189: 330-341 (2018).
[16] Buldurun K., Turan K., Bursal E., Aras A., Mantarcı A., Çolak N., Türkan F. Gülçin İ., Synthesis, Characterization, Powder X-Ray Diffraction Analysis, Thermal Stability, Antioxidant Properties and Enzyme Inhibitions of M(II)-Schiff Base Ligand Complexes, J. Biomol. Struct. Dyn., 39: 6480-6487 (2021).
[17] Ceyhan G., Çelik C., Urus S., Demirtaş I., Elmastaş M., Tümer M., Antioxidant, Electrochemical, Thermal, Antimicrobial and Alkane Oxidation Properties of Tridentate Schiff Base Ligands and Their Metal Complexes, Spectrochim. Acta, Part A, 81: 184-198 (2011).
[18] Tadavi S.K., Yadav A.A., Bendre R.S., Synthesis and Characterization of A Novel Schiff Base of 1,2-Diamino Propane with Substituted Salicyaldehyde and Its Transition Metal Complexes: Single Crystal Structures and Biological Activities, J. Mol. Struct., 1152: 223-231 (2018).
[19] Taha Z.A., Hijazi A.K., Ababneh T.S., Mhaidat I., Ajlouni A.M., Al-Hassan K.A., Mitzithra C., Hamilakis S., Danladi F., Altalafha A.Y., Photophysical Properties and Computational Study of Newly Synthesized Lanthanide Complexes with N-(2-Carboxyphenyl) Salicylideneimine Schiff Base Ligand, J. Lumin., 18: 230-239 (2017).
[20] Özdemir Ö., Novel Symmetric Diimine-Schiff Bases and Asymmetric Triimine-Schiff Bases as Chemo Sensors for the Detection of Various Metal Ions, J. Mol. Struct., 1125: 260-271 (2016).
[21] Pervaiz M., Ahmad I., Yousaf M., Kirn S., Munawar A., Saeed Z., Adnan A., Gulzar T., Kamal T., Ahmad A., Rashid A., Synthesis, Spectral and Antimicrobial Studies of Amino Acid Derivative Schiff Base Metal (Co, Mn, Cu and Cd) Complexes, Spectrochim. Acta, Part A, 206: 642-649 (2019).
[22] Patil S.A., Unki S.N., Kulkarni A.D., Naik V.H., Badami P.S., Co(II), Ni(II) and Cu(II) Complexes with Coumarin-8-yl Schiff-Bases: Spectroscopic, in Vitro Antimicrobial, DNA Cleavage and Fluorescence Studies, Spectrochim. Acta, Part A, 79: 1128-1136 (2011).
[23] Khalid S., Sumrra S.H., Chohan Z.H., Isatin Endowed Metal Chelates as Antibacterial and Antifungal Agents, Sains Malays., 49: 1891-1904 (2020).
[24] Bursal E., Turkan F., Buldurun K., Turan N., Aras A., Çolak N., Murahari M., Yergeri M.C., Transition Metal Complexes of A Multidentate Schiff Base Ligand Containing Pyridine: Synthesis, Characterization, Enzyme Inhibitions, Antioxidant Properties, and Molecular Docking Studies, Biometals, 34: 393-406 (2021).
[25] Nair M.S., Arish D., Joseyphus R.S., Synthesis, Characterization, Antifungal, Antibacterial and DNA Cleavage Studies of Some Heterocyclic Schiff Base Metal Complexes, J. Saudi. Chem. Soc., 16: 83-88 (2012).
[26] Turan N., Adigüzel R., Buldurun K., Bursal E., Spectroscopic, Thermal and Antioxidant Properties of Novel Mixed Ligand-Metal Complexes Obtained from Saccharinate Complexes and Azo Dye Ligand (Mnppa), Int. J. Pharmacol., 12: 92-100 (2016).
[27] Gaber M., El-Ghamry H.A., Fathalla S.K., Ni(II), Pd(II) and Pt(II) Complexes of (1H-1,2,4-triazole-3-ylimino)methyl]naphthalene-2-ol. Structural, Spectroscopic, Biological, Cytotoxicity, Antioxidant and DNA Binding, Spectrochim. Acta, Part A, 139: 396-404 (2015).
[28] Sumrra S., Hanif M., Chohan Z.H., Design, Synthesis and in Vitro Bactericidal/Fungicidal Screening of Some Vanadyl (IV) Complexes with Mono-and Di-Substituted ONS Donor Triazoles, J. Enzyme Inhib. Med. Chem., 30: 800-808 (2015).
[29] Ali M.A., Mirza A.H., Ting W.Y., Hamid M.H.S.A., Bernhardt P.V., Butcher R.J., Mixed-Ligand Nickel(II) and Copper(II) Complexes of Tridentate ONS and NNS Ligands Derived from S-Alkyldithiocarbazates with the Saccharination as a Co-Ligand, Polyhedron, 48: 167-173 (2012).
[30] Daravath S., Kumar M.P., Rambabu A., Vamsikrishna N., Shivaraj N.G., Design, Synthesis, Spectral Characterization, DNA Interaction and Biological Activity Studies of Copper(II), Cobalt(II) and Nickel(II) Complexes of 6-Amino Benzothiazole Derivatives, J. Mol. Struct., 1144: 147-158 (2017).
[31] Turan N., Buldurun K., Gündüz B., Çolak N., Synthesis and Structures of Fe(II), Zn(II) and Pd(II) Complexes with A Schiff Base Derived from Methyl 2-Amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c] pyridine-3-carboxylate and Comparison of Their Optical Constants for Different Solvents and Molarities, J. Nanoelectron. Optoelectron., 12: 1028-1040 (2017).
[32] Pandiarajan D., Ramesh R., Ruthenium(II) Half-Sandwich Complexes Containing Thioamides: Synthesis, Structures and Catalytic Transfer Hydrogenation of Ketones, J. Organomet. Chem., 723: 26-35 (2013).
[33] Kilic A., Savci A., Alan Y., Beyazsakal L., The Synthesis of Novel Boronate Esters and N-Heterocyclic Carbene (NHC)-Stabilized Boronate Esters: Spectroscopy, Antimicrobial and Antioxidant Studies, J. Organomet. Chem., 917: 121268 (2020).
[34] Blois M.S., Antioxidant Determinations by the Use of a Stable Free Radical, Nature, 26: 1199-1200 (1958).
[35] Turan N., Buldurun K., Alan Y., Savci A., Çolak N., Mantarci A., Synthesis, Characterization, Antioxidant, Antimicrobial and DNA Binding Properties of Ruthenium(II), Cobalt(II) and Nickel(II) Complexes of Schiff Base Containing o-Vanillin, Res. Chem. Intermediat., 45: 3525-3540 (2019).
[36] Londershausen M., Approaches to New Parasiticides, Pestic. Sci., 48(4): 269-292 (1996).
[37] Gönül İ., Synthesis and Structural Characterization of ONO Type Tridentate Ligands and Their Co(II) and Ni(II) Complexes: Investigation of Electrical Conductivity and Antioxidant Properties, Inorg. Chim. Acta, 495: 1-8 (2019).
[38] Buldurun K., Turan N., Savcı A., Çolak N., Synthesis, Structural Characterization and Biological Activities of Metal(II) Complexes with Schiff Bases Derived from 5-Bromosalicylaldehyde: Ru(II) Complexes Transfer Hydrogenation, J. Saudi. Chem. Soc., 23: 205-214 (2019).
[39] Yeğiner G., Gülcan M., Işık S., Ürüt G.Ö., Özdemir S., Kurtoğlu M., Transition Metal(II) Complexes with A Novel Azo-Azomethine Schiff Base Ligand: Synthesis, Structural and Spectroscopic Characterization, Thermal Properties and Biological Applications, J. Fluoresc., 27: 2239-2251 (2017).
[40] Çalık H.S., Ispir I, Karabuga S., Aslantaş M., Ruthenium(II) Complexes of NO Ligands: Synthesis, Characterization and Application in Transfer Hydrogenation of Carbonyl Compounds, J. Organomet. Chem., 801: 122-129 (2016).
[41] Ramesh M., Vetkatachalam G., Half-Sandwich (Η6-p-Cymene) Ruthenium(II) Complexes Bearing 5-Amino-1-methyl-3-phenylpyrazole Schiff Base Ligands: Synthesis, Structure and Catalytic Transfer Hydrogenation of Ketones, J. Organomet. Chem., 880: 47-55 (2019).
[42] Ekennia A.C., Osowole A.A., Olasunkanmi L.O., Onwudiwe D.C., Olubiyi O.O., Ebenso E.E., Synthesis, Characterization, DFT Calculations and Molecular Docking Studies of Metal(II) Complexes, J. Mol. Struct., 1150: 279-292 (2017).
[43] Sathishkumar P.N., Raveendran N., Bhuvanesh N.S.P., Karwembu R., Chemoselective Transfer Hydrogenation of Nitroarenes, Ketones and Aldehydes Using Acylthiourea Based Ru(II)(p-Cymene) Complexes as Precatalysts, J. Organomet. Chem., 876: 57-65 (2018).
[44] Turan N., Buldurun K., Çolak N., Özdemir İ., Preparation and Spectroscopic Studies of Fe(II), Ru(II), Pd(II) and Zn(II) Complexes of Schiff Base Containing Terephthalaldehyde and Their Transfer Hydrogenation and Suzuki-Miyaura Coupling Reaction, Open. Chem., 17: 571-580 (2019).
[45] Turan N., Savci A., Buldurun K., Alan Y., Adigüzel R., Synthesis and Chemical Structure Elucidation of Two Schiff Base Ligands, Their Iron(II) and Zinc(II) Complexes, and Antiradical, Antimicrobial, Antioxidant Properties, Lett. Org. Chem., 13: 343-351 (2016).
[46] More M.S., Joshi P.G., Mishra Y.K., Khanna P.K., Metal Complexes Driven from Schiff Bases and Semicarbazones for Biomedical and Allied Applications: A Review, Mater. Today Chem., 14: 100195 (2019).
[47] Ünver Y., Deniz S., Çelik F., Akar Z., Küçük M., Sancak K., Synthesis of New 1,2,4-Triazole Compounds Containing Schiff and Mannich Bases (Morpholine) with Antioxidant and Antimicrobial Activities, J. Enzyme. Inhib. Med. Chem., 31: 89-95 (2016).
[48] Aboafia S.A., Elsayed S.A., El-Sayed A.K.A., El-Hendawy A.M., New Transition Metal Complexes of 2,4-Dihydroxybenzaldehyde Benzoylhydrazone Schiff Base (H2dhbh): Synthesis, Spectroscopic Characterization, DNA Binding/Cleavage and Antioxidant Activity, J. Mol. Struct., 1158: 39-50 (2018).
[49] Devagi G., Dallemer F., Kalaivani P., Prabhakaran R., Organometallic Ruthenium(II) Complexes Containing NS Donor Schiff Bases: Synthesis, Structure, Electrochemistry, DNA/BSA Binding, DNA Cleavage, Radical Scavenging and Antibacterial Activities, J. Organomet. Chem., 854: 1-14 (2018).
[50] Hellas C.M.Y., Chan H.L., Yang M., Determination of Mode of Interactions Between Novel Drugs and Calf Thymus DNA by Using Quartz Crystal Resonator, Sensors Actuat. B, 81: 283-288 (2002).
[51] Rehman A., Choudhary M.I., Thomsen W.J., “Bioassay Techniques for Drug Development”, Harwood Academic Publishers, Amsterdam, The Netherlands, pp. 9, (2001).
[52] Shungu D.L., Weinberg E., Cerami A.T., Evaluation of Three Broth Disk Methods for Testing the Susceptibility of Anaerobic Bacteria to Imipenem, J. Clin. Microbiol., 21: 875-879 (1985).
[53] Bakirdere E.G., Fellah M.F., Canpolat E., Kaya M., Synthesis and Characterization of A New 2-{(E)-[(4-aminophenyl)imino]methyl}-6-bromo-4-chlorophenol and Its Complexes with Co(II), Ni(II), Cu(II), and Zn(II): An Experimental and DFT Study, Synth. React. Inorg. Metal-Org. Nano-Metal Chem., 45: 1337 (2015).
[54] Amjad M., Sumrra S.H., Akram M.S., Chohan Z.H., Metal-Based Ethanolamine-Derived Compounds:
A Note on Their Synthesis, Characterization and Bioactivity, J. Enzyme Inhib. Med. Chem., 31: 88-97 (2016).
[55] Dharamaraj N., Viswanathamurthi P., Natarajan K., Ruthenium (II) Complexes Contain Bidentate Schiff Bases and Their Antifungal Activity, Trans. Met. Chem., 26: 105-109 (2001).
[56] Anacona J.R., Rodriguez A., Synthesis and Antibacterial Activity of Ceftriaxone Metal Complexes, Trans. Met. Chem., 30: 897 (2005).
[57] Venkateswarlu K., Kumar M.P., Rambabu A., Vamsikrishna N., Daravath S., Rangan K., Crystal Structure, DNA Binding, Cleavage, Antioxidant and Antibacterial Studies of Cu(II), Ni(II) and Co(III) Complexes with 2-((Furan-2-yl)methylimino)methyl)- 6-ethoxyphenol Schiff Base, J. Mol. Struct., 1160: 198-207 (2018).
Iranian Journal of Chemistry and Chemical Engineering
Volume 41, Issue 8 - Serial Number 118
August 2022
Pages 2635-2649

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