Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

Eid Abdalrazaq; Abdel Aziz Qasem Jbarah; Taghreed Hashim Al-Noor; Gassan Thabit Shinain; Mohammed Mahdi Jawad

doi:10.22146/ijc.74020

Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

https://doi.org/10.22146/ijc.74020

Eid Abdalrazaq^(1*), Abdel Aziz Qasem Jbarah⁽²⁾, Taghreed Hashim Al-Noor⁽³⁾, Gassan Thabit Shinain⁽⁴⁾, Mohammed Mahdi Jawad⁽⁵⁾

(1) Department of Chemistry, College of Science, Al-Hussein Bin Talal University, Ma’an 71111, Jordan
(2) Department of Chemistry, College of Science, Al-Hussein Bin Talal University, Ma’an 71111, Jordan
(3) Department of Chemistry, Education for Pure Science College - Ibn- Al Haitham, University of Baghdad, Baghdad 10071, Iraq
(4) Department of Chemistry, Education for Pure Science College - Ibn- Al Haitham, University of Baghdad, Baghdad 10071, Iraq
(5) Department of Biology, Education College - Ibn- Al Haitham, University of Baghdad, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract

Mixed ligand metal complexes are synthesized from oxalic acid with Schiff base, and the Schiff base was obtained from trimethoprim and acetylacetone. The synthesized complexes were of the type [M(L₁)(L₂)], where the metal, M, is Ni(II), Cu(II), Cr(III), and Zn(II), L₁ corresponds to the trimethoprim ((Z)-4-((4-amino-5-(3,4,5-trimethoxybenzyl)pyrimidine-2-yl)imino)pentane-2-one) as the first ligand and L₂ represent the oxalate anion ( ) as a second ligand. Characterization of the prepared compounds was performed by elemental analysis, molar conductivity, magnetic measurements, ¹H-NMR, ¹³C-NMR, FT-IR, and Ultraviolet-visible (UV-Vis) spectral studies. The recorded infrared data is reinforced with density functional theory (DFT) calculations. Also, the recorded and calculated IR spectra of the complexes suggested that the coordination of Schiff base is a bidentate ligand with Cu and Ni complexes and a tridentate ligand with Co, Cr, and Zn complexes. The electronic structures of the complexes were investigated by DFT calculations, showing several degrees of HOMO-LUMO energy gaps between complexes. The complexes were studied for their DNA interaction activities. The synthesized ligand and its metal complexes were evaluated for antimicrobial properties against bacterial strains of Bacillus subtilis (G+), Enterobacter cloacae (G-), and Staphylococcus aureus (G+). These complexes considered in this study showed good antimicrobial activity.

Keywords

trimethoprim; oxalic acid complexes; acetyl acetone; Schiff base; antimicrobial activity

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References

[1] El-Sawaf, A.K., El-Essawy, F., Nassar, A.A., and El-Samanody, E.S.A., 2018, Synthesis, spectral, thermal and antimicrobial studies on cobalt(II), nickel(II), copper(II), zinc(II) and palladium(II) complexes containing thiosemicarbazone ligand, J. Mol. Struct., 1157, 381–394.

[2] Muralisankar, M., Haribabu, J., Bhuvanesh, N.S.P., Karvembu, R., and Sreekanth, A., 2016, Synthesis, X-ray crystal structure, DNA/protein binding, DNA cleavage and cytotoxicity studies of N(4) substituted thiosemicarbazone based copper(II)/nickel(II) complexes, Inorg. Chim. Acta, 449, 82–95.

[3] Mathan Kumar, S., Rajesh, J., Anitha, K., Dhahagani, K., Marappan, M., Indra Gandhi, N., and Rajagopal, G., 2015, Synthesis, characterization, crystal structure and cytotoxic properties of thiosemicarbazide Ni(II) and Zn(II) complexes, Spectrochim. Acta, Part A, 142, 292–302.

[4] Pahonţu, E., Julea, F., Chumakov, Y., Petrenco, P., Roşu, T., and Gulea, A., 2017, Synthesis, characterization, crystal structure and antiproliferative activity studies of Cu(II), Ni(II) and Co(II) complexes with 4-benzoyl-5-pyrazolones derived compounds, J. Organomet. Chem., 836-837, 44–55.

[5] Pu, L.M., Zhao, Q., Liu, L.Z., Zhang, H., Long, H.T., and Dong, W.K., 2018, Synthesis and fluorescence properties of a new heterotrinuclear Co(II)-Ce(III)complex constructed from a bis(salamo)-type tetraoxime ligand, Molecules, 23 (4), 804.

[6] Chen, Q.L., 2016, Synthesis and structural characterization of a pyridine oxalato molybdenum(V) complex, Int. J. New Technol. Res., 2 (1), 40–43.

[7] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., 2009, Gaussian-09 Revision E.01, Gaussian, Inc., Wallingford, CT.

[8] Makkonen, I., Ervasti, M.M., Kauppila, V.J., and Harju, A., 2012, Exchange-correlation potentials for inhomogeneous electron systems in two dimensions from exact diagonalization: Comparison with the local-spin-density approximation, Phys. Rev. B, 85, 205140.

[9] Becke, A.D., 2019, Dependence of the virial exciton model on basis set and exact-exchange fraction, J. Chem. Phys., 150, 241101.

[10] Chen, H., Nusspickel, M., Tilly, J., and Booth, G.H., 2021, Variational quantum eigensolver for dynamic correlation functions, Phys. Rev. A, 104 (3), 032405.

[11] Wang, G., Annaberdiyev, A., Melton, C.A., Bennett, M.C., Shulenburger, L., and Mitas, L., 2019, A new generation of effective core potentials from correlated calculations: 4s and 4p Main group elements and first row additions, J. Chem. Phys., 151, 144110.

[12] Hill, J.G., and Shaw, R.A., 2021, Correlation consistent basis sets for explicitly correlated wavefunctions: Pseudopotential-based basis sets for the group 11 (Cu, Ag, Au) and 12 (Zn, Cd, Hg) elements, J. Chem. Phys., 155, 174113.

[13] Hassan, S.S., Shoukry, M.M., and Jbarah, A.A.Q., 2020, Cordination compound of dimethyltin(IV) with N,N,N’,N’-tetraethylethylenediamine: speciation and theoretical approach, J. Mex. Chem. Soc., 64 (2), 24–43.

[14] Dennington, R., Keith, T. A., and Millam, J.M., 2016, GaussView, Version 6, Semichem Inc., Shawnee Mission, KS.

[15] Abu-Yamin, A.A., Jbarah, A.A.Q.M., AlKhalyfeh, K., Matar, S., Alqasaimeh, M., Rüffer, T., and Lang, H., 2022, Crystal structure, spectroscopic studies, DFT calculations, and biological activity of 5-bromosalicylaldehyde–based Schiff bases, J. Mol. Struct., 1262, 132976.

[16] O’boyle, N.M., Tenderholt, A.L., and Langner, K.M., 2008, Cclib: A library for package‐independent computational chemistry algorithms, J. Comput. Chem., 29 (5), 839–845.

[17] Mary Juliet, B.M., and Amaladasan, M., 2014, Preparation and properties of macrocyclic ligand, Int. J. Recent Innovation Trends Comput. Commun., 2 (8), 2102–2105.

[18] Jeffery, G.H., Bassett, J., Mendham, J., and Denney, R.C., 1989, Vogel’s Textbook of Quantitative Chemical Analysis, 5^th Ed., John Wiley & Sons Inc., New York, US.

[19] Orekhov, M.A., 2021, Coordination numbers of bivalent ions in organic solvents, Russ. J. Phys. Chem. A, 95 (10), 2059–2064.

[20] Marcus, R.A., 1964, Chemical and electrochemical electron-transfer theory, Annu. Rev. Phys. Chem., 15 (1), 155–196.

[21] Saheb, V., Sheikhshoaie, I., and Stoeckli-Evans, H., 2012, A novel tridentate Schiff base dioxo-molybdenum(VI) complex: Synthesis, experimental and theoretical studies on its crystal structure, FTIR, UV–visible, ¹H NMR and ¹³C NMR spectra, Spectrochim. Acta, Part A, 95, 29–36.

[22] Agrwal, A., Verma, A., Chantola, N., Verma, S., and Kasana, V., 2022, Synthesis, molecular docking and extensive structure activity relationship of substituted DHP derivatives: A new class of herbicides, J. Environ. Sci. Health, Part B, 57 (5), 379–420.

[23] Odion, E.E., Enadeghe, D.O., and Usifoh, C.O., 2021, Synthesis, characterization and antibacterial assessment of 3,4,5-trimethoxy-3’,4’-dimethoxychalcone and 2,4,6-trimethoxy-3’,4’-dimethoxychalcone, Niger. J. Pharm. Appl. Sci. Res., 10 (2), 1–5.

[24] Jin, R.Y., Sun, X.H., Liu, Y.F., Wong, W., Lu, W.T., and Ma, H.X., 2014, Synthesis, crystal structure, IR, ¹H NMR and theoretical calculations of 1,2,4-triazole Schiff base, J. Mol. Struct., 1062, 13–20.

[25] Aparna, E.P., and Devaky, K.S., 2018, Microwave assisted solid phase synthesis of trisubstituted pyrimidines, J. Chem. Pharm. Res., 10 (8), 67–72.

[26] Jacobsen, N.E., 2017, NMR Data Interpretation Explained: Understanding 1D and 2D NMR Spectra of Organic Compounds and Natural Products, John Wiley & Sons, Inc., Hoboken, New Jersey, US.

[27] Ebrahimi, H.P., Hadi, J.S., Abdulnabi, Z.A., and Bolandnazar, Z., 2014, Spectroscopic, thermal analysis and DFT computational studies of salen-type Schiff base complexes, Spectrochim. Acta, Part A, 117, 485–492.

[28] Adeyemi, J.O., Olasunkanmi, L.O., Fadaka, A.O., Sibuyi, N.R.S., Oyedeji, A.O., and Onwudiwe, D.C., 2022, Synthesis, theoretical calculation, and biological studies of mono- and diphenyltin(IV) complexes of N-methyl-N-hydroxyethyldithiocarbamate, Molecules, 27 (9), 2947.

[29] Al-Noor, T.H., Karam, N.H., Ghanim, F.H., Kindeel, A.S., and Al-Dujaili, A.H., 2017, Synthesis, characterization and liquid crystalline properties of novel benzimidazol-8-hydroxyquinoline complexes, Inorg. Chim. Acta, 466, 612–617.

[30] Nakamoto, K., 2009, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, 6^th Ed., John Wiley & Sons, Inc., Hoboken, New Jersey, US.

[31] Mezey, R.Ș., Máthé, I., Shova, S., Grecu, M.N., and Roșu, T., 2015, Synthesis, characterization and antimicrobial activity of copper(II) complexes with hydrazone derived from 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde, Polyhedron, 102, 684–692.

[32] Bellamy, L.J., 1975, The Infra-Red Spectra of Complex Molecules, Springer, Dordrecht, Netherlands.

[33] Housecroft, C.E., and Sharpe, A.G., 2018, Inorganic Chemistry, 5^th Ed., Pearson Education Limited, Harlow, UK.

[34] Jamil, Y.M.S., Al-Qadasy, J.M.K., Al-Azab, F.M., and Al-Maqtari, M.A., 2018, Synthesis, characterization and antibacterial study of some 3d-metal complexes of paracetamol and 1,10-phenanthroline, Jordan J. Chem., 13 (4), 203–212.

[35] Fleming, G.R., Lewis, N.H.C., Arsenault, E.A., Wu, E.C., and Oldemeyer, S., 2019, "Two-Dimensional Electronic Vibrational Spectroscopy" in Coherent Multidimensional Spectroscopy, Eds. Cho, M., Springer, Singapore, 35–49.

[36] Galić, N., Dijanošić, A., Kontrec, D., and Miljanić, S., 2012, Structural investigation of aroylhydrazones in dimethylsulphoxide/water mixtures, Spectrochim. Acta, Part A, 95, 347–353.

[37] Abbas, S.H., 2017, Synthesis, characterization and biological activity of some nickel(II) mixed ligands complexes of dithiocarbamate and 1,10-phenanthroline, Eur. J. Chem., 8 (4), 367–370.

[38] Yallur, B.C., Krishna, P.M., and Challa, M., 2021, Bivalent Ni(II), Co(II) and Cu(II) complexes of [(E)-[(2-methyl-1,3-thiazol-5-yl)methylidene]amino]thiourea: Synthesis, spectral characterization, DNA and in-vitro anti-bacterial studies, Heliyon, 7 (4), e06838.

[39] Rajendran, N., Periyasamy, A., Kamatchi, N., and Solomon, V., 2020, Synthesis and efficacy of copper(II) complexes bearing N(4)-substituted thiosemicarbazide and diimine co-ligands on plasmid DNA and HeLa cell lines, J. Serb. Chem. Soc., 85 (3), 321–334.

[40] Dance, I.G., Gerloch, M., Lewis, J., Stephens, F.S., and Lions, F., 1966, High-spin five-coordinate cobalt (II), Nature, 210 (5033), 298.

[41] Kafi-Ahmadi, L., and Shirmohammadzadeh, L., 2017, Synthesis of Co(II) and Cr(III) salicylidenic Schiff base complexes derived from thiourea as precursors for nano-sized Co₃O₄ and Cr₂O₃ and their catalytic, antibacterial properties, J. Nanostruct. Chem., 7 (2), 179–190.

[42] Bendjeddou, A., Abbaz, T., Gouasmia, A., and Villemin, D., 2017, Determination of reactive properties of a series of mono-functionalized bis-tetrathiafulvalene employing DFT calculations, ASRJETS, 29 (1), 308–326.

[43] Politzer, P., and Murray, J.S., 2021, "Molecular Electrostatic Potentials: Significance and Applications" in Chemical Reactivity in Confined Systems: Theory, Modelling and Applications, Eds. Chattaraj, P.K., and Chakraborty, D., John Wiley & Sons Ltd, Hoboken, New Jersey, US.

[44] Gadre, S.R., Suresh, C.H., and Mohan, N., 2021, Electrostatic potential topology for probing molecular structure, bonding and reactivity, Molecules, 26 (11), 3289.

[45] da Silva, G.C.Q., Cardozo, T.M., Amarante, G.W., Abreu, C.R.A., and Horta, B.A.C., 2018, Solvent effects on the decarboxylation of trichloroacetic acid: Insights from ab initio molecular dynamics simulations, Phys. Chem. Chem. Phys., 20 (34), 21988–21998.

[46] Muthukkumar, M., Malathy, M., and Rajavel, R., 2015, Antimicrobial and DNA cleavage activities of macrocyclic Cu(II), Ni(II), Co(II), and Zn(II) Schiff base complexes, Chem. Sci. Rev. Lett., 4 (16), 1227–1236.

DOI: https://doi.org/10.22146/ijc.74020