Synthesis, Characterization, and Antibacterial Activity of Lanthanide Metal Complexes with Schiff Base Ligand Produced from Reaction of 4,4-Methylene Diantipyrine with Ethylenediamine

https://doi.org/10.22146/ijc.74214

Kawther Adeeb Hussein(1*), Naser Shaalan(2)

(1) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract


An environmentally friendly method for the synthesis of Schiff bases was described by combining 4,4-methylenediantipyrine with ethylenediamine. The complex was prepared in a classical way, the usual condensation reaction method. A series of metal complexes were prepared from reactions of lanthanide nitrate salts [Nd+3, La+3, Er+3, Gd+3, and Dy+3] with a Schiff base ligand. The structures of the complexes were confirmed by analytical studies, spectral measurements, and thermal studies, and the prepared ligand was characterized using microanalysis technique, UV-Visible, infrared, nuclear magnetic resonance 1H-NMR and 13C-NMR, mass spectrometry, and thermogravimetric analysis (TGA), and the addition of conductivity measurement and magnetic moment of complexes. The results showed that these complexes have a consistency of 10 in which the elements are bonded with the ligand through the two nitrogen atoms at C=N and that the bonding ratio between the metal:ligand is in 1:2 ratio. By using agar disc-spreading, we tested several in vitro compounds for their antibacterial activity against four pathogenic bacteria, including Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae. The majority of the complexes demonstrated antibacterial activity.

Keywords


Schiff’s bases; lanthanide complexes; biological activity; 4,4-methylene diantipyrine



References

[1] Paderni, D., Giorgi, L., Fusi, V., Formica, M., Ambrosi, G., and Micheloni, M., 2021, Chemical sensors for rare earth metal ions, Coord. Chem. Rev., 429, 213639.

[2] Bünzli, J.C.G., 2014, Review: Lanthanide coordination chemistry: From old concepts to coordination polymers, J. Coord. Chem., 67 (23-24), 3706–3733.

[3] Atwood, D.A., 2013, The Rare Earth Elements: Fundamentals and Applications, John Wiley & Sons, Hoboken, New Jersey, US.

[4] Alghool, S., Zoromba, M.S., and Abd El-Halim, H.F., 2013, Lanthanide amino acid Schiff base complexes: Synthesis, spectroscopic characterization, physical properties and in vitro antimicrobial studies, J. Rare Earths, 31 (7), 715–721.

[5] Chundawat, N.S., Jadoun, S., Zarrintaj, P., and Chauhan, N.P.S., 2021, Lanthanide complexes as anticancer agents: A review, Polyhedron, 207, 115387.

[6] Vernon, R.E., 2021, The location and composition of Group 3 of the periodic table, Found. Chem., 23 (2), 155–197.

[7] Wedal, J.C., and Evans, W.J., 2021, A rare-earth metal retrospective to stimulate all fields, J. Am. Chem. Soc., 143 (44), 18354–18367.

[8] Zasimov, P., Amidani, L., Retegan, M., Walter, O., Caciuffo, R., and Kvashnina, K.O., 2022, HERFD-XANES and RIXS Study on the electronic structure of trivalent lanthanides across a series of isostructural compounds, Inorg. Chem., 61 (4), 1817–1830.

[9] Cotton, S., 2013, Lanthanide and Actinide Chemistry, John Wiley & Sons, Chichester, UK.

[10] Nehra, K., Dalal, A., Hooda, A., Bhagwan, S., Saini, R.K., Mari, B., Kumar, S., and Singh, D., 2022, Lanthanides β-diketonate complexes as energy-efficient emissive materials: A review, J. Mol. Struct., 1249, 131531.

[11] Pari, G., Mookerjee, A., and Bhattacharya, A.K., 2005, First-principles electronic structure calculations of R3Al5O12 (R being the rare-earth elements Ce–Lu), Phys. B, 365 (1-4), 163–172.

[12] Prats, H., and Stamatakis, M., 2022, Atomistic and electronic structure of metal clusters supported on transition metal carbides: Implications for catalysis, J. Mater. Chem. A, 10 (3), 1522–1534.

[13] Al-Qahtani, S.D., Alzahrani, S.O., Snari, R.M., Al-Ahmed, Z.A., Alkhamis, K., Alhasani, M., and El-Metwaly, N.M., 2022, Preparation of photoluminescent and photochromic smart glass window using sol-gel technique and lanthanides-activated aluminate phosphor, Ceram. Int., 48 (12), 17489–17498.

[14] Malik, M.A., Dar, O.A., Gull, P., Wani, M.Y., and Hashmi, A.A., 2018, Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy, MedChemComm, 9 (3), 409–436.

[15] Patil, C.J., Patil, M.C., and Patil, M.C., 2019, Reduction of azomethine bond of organic compound: Part-2. Formation of aldimine and ketimine and their catalytic hydrogenation, Int. J. Pharm. Biol. Arch., 10 (2), 134–137.

[16] Xu, Y., Shi, Y., Lei, F., and Dai, L., 2020, A novel and green cellulose-based Schiff base-Cu (II) complex and its excellent antibacterial activity, Carbohydr. Polym., 230, 115671.

[17] Panda, J., Raiguru, B.P., Mishra, M., Mohapatra, S., and Nayak, S., 2022, Recent advances in the synthesis of imidazo[1,2‐a]pyridines: A brief review, ChemistrySelect, 7 (3), e202103987.

[18] Soleimani, E., Taheri, S.A.N., and Sargolzaei, M., 2017, Synthesis, characterization, theoretical and biological studies of a new macrocycle Schiff base with Co(II), Ni(II), Cu(II) and Zn(II) complexes, J. Chil. Chem. Soc., 62 (4), 3731–3740.

[19] Jirjees, V.Y., Suleman, V.T., Al-Hamdani, A.A., and Ahmed, S.D., 2019, Preparation, spectroscopic characterization and theoretical studies of transition metal complexes with 1-[(2-(1H-indol-3-yl) ethylimino) methyl]naphthalene-2-ol ligand, Asian J. Chem., 31 (11), 2430–2438.

[20] Rasheed, A.M., Al-Bayati, S.M.M., Al-Hasani, R.A.M., and Shakir, M.A., 2021, Synthesizing, structuring, and characterizing bioactivities of Cr(III), La(III), and Ce(III) complexes with nitrogen, oxygen, and Sulpher donor bidentate Schiff base ligands, Baghdad Sci. J., 18 (4), 1545–1551.

[21] Ajlouni, A.M., Abu-Salem, Q., Taha, Z.A., Hijazi, A.K., and Al Momani, W., 2016, Synthesis, characterization, biological activities and luminescent properties of lanthanide complexes with [2-thiophenecarboxylic acid, 2-(2-pyridinylmethylene)hydrazide] Schiff bases ligand, J. Rare Earths, 34 (10), 986–993.

[22] Al Zoubi, W., Mohamed, S.G., Al-Hamdani, A.A.S., Mahendradhany, A.P., and Ko, Y.G., 2018, Acyclic and cyclic imines and their metal complexes: Recent progress in biomaterials and corrosion applications, RSC Adv., 8 (41), 23294–23318.

[23] El-Ansary, A.L., and Abdel-Kader, N.S., 2012, Synthesis, characterization of La(III), Nd(III), and Er(III) complexes with Schiff bases derived from benzopyran-4-one and thier fluorescence study, Int. J. Inorg. Chem., 2012, 901415.

[24] Raczuk, E., Dmochowska, B., Samaszko-Fiertek, J., and Madaj, J., 2022, Different Schiff bases—Structure, importance and classification, Molecules, 27 (3), 787.

[25] Yusuf, T.L., Oladipo, S.D., Zamisa, S., Kumalo, H.M., Lawal, I.A., Lawal, M.M., and Mabuba, N., 2021, Design of new Schiff-base copper(II) complexes: Synthesis, crystal structures, DFT study, and binding potency toward cytochrome P450 3A4, ACS Omega, 6 (21), 13704–13718.

[26] Raman, N., Johnson Raja, S., and Sakthivel, A., 2009, Transition metal complexes with Schiff-base ligands: 4-Aminoantipyrine based derivatives–A review, J. Coord. Chem., 62 (5), 691–709.

[27] Shaalan, N., Abed, A.Y., Alkubaisi, H.M., and Mahde, S., 2019, Synthesis, spectroscopy, biological activities and thermodynamic studies for new complexes of some lanthanide metals with Schiff's bases derived from [2-acetylth-iophene] with [2,5-dihydrazino-1,3,4-thiadiazole], Res. J. Chem. Environ., 23, 181–187.

[28] Shaalan, N., Khalaf, W.M., and Mahdi, S., 2022, Preparation and characterization of new tetra-dentate N2O2 Schiff base with some of metal ions complexes, Indones. J. Chem., 22 (1), 62–71.

[29] Shaalan, N.D., and Abdulwahhab, S.M., 2021, Synthesis, characterization and biological activity study of some new metal complexes with Schiff’s bases derived from [o-vanillin] with [2-amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole], Egypt. J. Chem., 64 (8), 4059–4067.

[30] Martinez-Gomez, N.C., Vu, H.N., and Skovran, E., 2016, Lanthanide chemistry: From coordination in chemical complexes shaping our technology to coordination in enzymes shaping bacterial metabolism, Inorg. Chem., 55 (20), 10083–10089.

[31] Akram, E., Shaalan, N., Rashad., A.A., Hasan, A., Al-Amiery, A., and Yousif, E., 2016, Study of structural and optical properties of new films derived PVC-2-[5-phenyl-1,3,4-thiadiazol-2-ylimino-methyl]-benzoic acid, Res. J. Pharm., Biol. Chem. Sci., 7 (5), 2836–2844.

[32] Kareem, M.J., Al‐Hamdani, A.A.S., Jirjees, V.Y., Khan, M.E., Allaf, A.W., and Al Zoubi, W., 2021, Preparation, spectroscopic study of Schiff base derived from dopamine and metal Ni(II), Pd(II), and Pt(IV) complexes, and activity determination as antioxidants, J. Phys. Org. Chem., 34 (3), e4156.

[33] Obaid, S.M.H., Sultan, J.S., and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological efficacies from some new dinuclear metal complexes for base 3-(3,4-dihydroxy-phenyl)-2-[(2-hydroxy-3-methylperoxy-benzylidene)-amino]-2-methyl propionic acid, Indones. J. Chem., 20 (6), 1311–1322.

[34] Halli, M.B., and Sumathi, R.B., 2017, Synthesis, physico-chemical investigations and biological screening of metal (II) complexes with Schiff base derived from naphthofuran-2-carbohydrazide and citral, Arabian J. Chem., 10, S1748–S1759.

[35] Sönmez, M., Sogukomerogullari, H.G., Öztemel, F., and Berber, İ., 2014, Synthesis and biological evaluation of a novel ONS tridentate Schiff base bearing pyrimidine ring and some metal complexes, Med. Chem. Res., 23 (7), 3451–3457.

[36] Fouad, R., 2020, Synthesis and characterization of lanthanide complexes as potential therapeutic agents, J. Coord. Chem., 73 (14), 2015–2028.

[37] Jawad, S.A.A., and Ahmed, H.A., 2021, Synthesis, characterization and study of amide ligand type N2S2 and metal complexes with di valance manganese, zinc and tri valance iron, Ann. Rom. Soc. Cell Biol., 25 (3), 8511–8520.

[38] Kohale, R.L., Pawade, V.B., Dhoble, S.J., and Deshmukh, A.H., 2020, Optical Properties of Phosphate and Pyrophosphate Compounds, Woodhead Publishing, Sawston, UK.

[39] Al Zoubi, W., Kim, M.J., Yoon, D.K., Al-Hamdani, A.A.S., Kim, Y.G., and Ko, Y.G., 2020, Effect of organic compounds and rough inorganic layer formed by plasma electrolytic oxidation on photocatalytic performance, J. Alloys Compd., 823, 153787.

[40] Hussein, K.A., and Shaalan, N., 2021, Synthesis, spectroscopy and biological activities studies for new complexes of some lanthanide metals with Schiff’s bases derived from dimedone with 4-aminoantipyrine, Chem. Methodol., 6 (2), 103–113.

[41] Satten, R.A., 1953, Analysis of the spectrum of the Nd+++ ion in the bromate crystal, J. Chem. Phys., 21 (4), 637–648.

[42] Pallares, R.M., and Abergel, R.J., 2020, Transforming lanthanide and actinide chemistry with nanoparticles, Nanoscale, 12 (3), 1339–1348.

[43] Wanja, D.W., Mbuthia, P.G., Waruiru, R.M., Bebora, L.C., Ngowi, H.A., and Nyaga, P.N., 2020, Antibiotic and disinfectant susceptibility patterns of bacteria isolated from farmed fish in Kirinyaga county, Kenya, Int. J. Microbiol., 2020, 8897338.

[44] Obaid, S.M., Jarad, A.J., and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological activity of mixed ligand metal salts complexes with various ligands, J. Phys.: Conf. Ser., 1660, 012028.

[45] Tavares, T.D., Antunes, J.C., Padrão, J., Ribeiro, A.I., Zille, A., Amorim, M.T.P., Ferreira, F., and Felgueiras, H.P., 2020, Activity of specialized biomolecules against gram-positive and gram-negative bacteria, Antibiotics, 9 (6), 314.

[46] Delcour, A.H., 2009, Outer membrane permeability and antibiotic resistance, Biochim. Biophys. Acta, Proteins Proteomics, 1794 (5), 808–816.

[47] Sherif, S.H., Kure, D.A., Moges, E.A., and Argaw, B., 2021, Synthesis, characterization, and antibacterial, activity, evaluation of 4-amino antipyrine derivatives and their transition metal complexes, Am. J. Biosci. Bioeng., 9 (1), 8–12.



DOI: https://doi.org/10.22146/ijc.74214

Article Metrics

Abstract views : 2417 | views : 1081 | views : 519


Copyright (c) 2022 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.