Preparation, Characterization, and Biological Activity of La(III), Nd(III), Er(III), Gd(III), and Dy(III) Complexes with Schiff Base Resulted from Reaction of 4-Antipyrinecarboxaldehyde and 2-Aminobenzothiazole

https://doi.org/10.22146/ijc.87262

Kawther Adeeb Hussein(1*), Naser Shaalan(2), Aliaa Khauon Lafta(3), Janan Majeed Al Akeedi(4)

(1) Department of Chemistry, College of Science, Al-Nahrain University, Jadria, Baghdad 10072, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(3) Iraqi Center for Cancer and Medical Genetics Research, Mustansiriyah University, Baghdad 10052, Iraq
(4) Department of Medical Laboratory Techniques, University Al-Farabi, Baghdad 10022, Iraq
(*) Corresponding Author

Abstract


The research includes the preparation of several complexes of the internal transition elements lanthanide (Ln = La, Nd, Er, Gd, and Dy) containing the 4f shell, with Schiff bases resulting from condensation reactions between 4-antipyrinecarboxaldehyde and 2-aminobenzothiazoles. Schiff's base was identified using FTIR spectra, UV-vis spectroscopy, elemental microanalysis CHNSO, nuclear magnetic resonance, mass spectrometry, and TGA thermal analysis. The complexes were studied and identified with elemental microanalysis CHNSO, FTIR spectroscopy, UV-vis spectroscopy, TGA thermal analysis, conductivity measurement, and magnetic sensitivity. The result showed that these complexes were classified as homogeneous bidentate complexes with the general formula of [Ln2(L)2(NO3)6]·6H2O. The physical measurements indicated that the prepared complexes are non-electrolyte and paramagnetic. Some compounds prepared in vitro were evaluated for their antibacterial activity against four types of pathogenic strains Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumonia, and using the agar disc spreading method for the evaluation. The results showed that some of these complexes have good antibacterial activity compared to the biological activity of the ligand. Also, the biological activity of Schiff's base and the prepared complexes were evaluated against three types of fungi (Candida albicans, Tropical fungi, and Scandal fungi), and they showed great activity against the prepared complexes.


Keywords


4-antipyrinecarboxaldehyde; biological activities; lanthanide complexes; Schiff bases



References

[1] Cotton, S., 2013, Lanthanide and actinide chemistry, John Wiley & Sons, Hoboken, New Jersey, US.

[2] Gupta, I., Singh, S., Bhagwan, S., and Singh, D., 2021, Rare earth (RE) doped phosphors and their emerging applications: A review, Ceram. Int., 47 (14), 19282–19303.

[3] Wang, C., 2023, Theory and Application of Rare Earth Materials, Springer Singapore, Singapore.

[4] Cossard, A., Desmarais, J.K., Casassa, S., Gatti, C., and Erba, A., 2021, Charge density analysis of actinide compounds from the quantum theory of atoms in molecules and crystals, J. Phys. Chem. Lett., 12 (7), 1862–1868.

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

[6] 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.

[7] Liu, Y., 2021, Durabilité des revêtements de barrière thermique pulvérisé au plasma atmosphérique dopés aux terres rares pour le diagnostic thermique et structurel, Dissertation, Institut Supérieur de l'Aéronautique et de l'Espace, Toulouse, France.

[8] Salman, A.D., Juzsakova, T., Mohsen, S., Abdullah, T.A., Le, P.C., Sebestyen, V., Sluser, B., and Cretescu, I., 2022, Scandium recovery methods from mining, metallurgical extractive industries, and industrial wastes, Materials, 15 (7), 2376.

[9] Razavi, R., and Amiri, M., 2022, “Rare earth-based ceramic nanomaterials—manganites, ferrites, cobaltites, and nickelates” in Advanced Rare Earth-Based Ceramic Nanomaterials, Eds. Zinatloo-Ajabshir, S., Elsevier, Amsterdam, Netherlands, 205–230.

[10] Patil, A.S., Patil, A.V., Dighavkar, C.G., Adole, V.A., and Tupe, U.J., 2022, Synthesis techniques and applications of rare earth metal oxides semiconductors: A review, Chem. Phys. Lett., 796, 139555.

[11] Bünzli, J.C.G., 2016, “Chapter 287 - Lanthanide Luminescence: From a Mystery to Rationalization, Understanding, and Applications” in Handbook on the Physics and Chemistry of Rare Earths, Vol. 50, Eds., Bünzli, J.C.G., and Pecharsky, V.K., Elsevier, Amsterdam, Netherlands, 141–176.

[12] Koper, G.H.M., and Terpstra, M., 2012, Improving the Properties of Permanent Magnets: A Study of Patents, Patent Applications and Other Literature, Springer Dordrecht, Berlin, Germany.

[13] Wang, K., Han, C., Shao, Z., Qiu, J., Wang, S., and Liu, S., 2021, Perovskite oxide catalysts for advanced oxidation reactions, Adv. Funct. Mater., 31 (30), 2102089.

[14] Maity, U.K., Manoravi, P., Joseph, M., and Sivaraman, N., 2022, Laser-induced breakdown spectroscopy for simultaneous determination of lighter lanthanides in actinide matrix in aqueous medium, Spectrochim. Acta, Part B, 190, 106393.

[15] Aaseth, J., and Berlinger, B., 2022, “Lanthanum” in Handbook on the Toxicology of Metals, 5th Ed., Eds. Nordberg, G.F., and Costa, M., Academic Press, Cambridge, Massachusetts, US, 419–425.

[16] Hasan, M.M., Bithe, S.A., Neher, B., and Ahmed, F., 2022, Polythiophene as a sensor model for chlorofluorocarbon, fluorine, and oxygen gas using DFT calculations, J. Mol. Model., 28 (3), 59.

[17] Arnold, B., 2022, Zircon, Zirconium, Zirconia-Similar Names, Different Materials, Springer Berlin, Heidelberg, Germany.

[18] Hasegawa, M., Ohmagari, H., Tanaka, H., and Machida, K., 2022, Luminescence of lanthanide complexes: From fundamental to prospective approaches related to water- and molecular-stimuli, J. Photochem. Photobiol., C, 50, 100484.

[19] Lima, A.T., Kirkelund, G.M., Ntuli, F., and Ottosen, L.M., 2022, Rare earth elements extractability from residual waste materials, Proceedings of the 9th International Conference on Engineering for Waste and Biomass Valorisation, Technical University of Denmark, Copenhagen, Denmark, 27-30 July 2022, 699–700.

[20] Krüger, L., 2020, “Rare Earth Elements—A Treasure Locked in AMD?” in Recovery of Byproducts from Acid Mine Drainage Treatment, Eds Fosso-Kankeu, E., Wolkersdorfer, C., and Burges, J., John Wiley & Sons, Inc., Hoboken, NJ, US, 263–313.

[21] Jin, S., Li, R., Huang, H., Jiang, N., Lin, J., Wang, S., Zheng, Y., Chen, X., and Chen, D., 2022, Compact ultrabroadband light-emitting diodes based on lanthanide-doped lead-free double perovskites, Light: Sci. Appl., 11 (1), 52.

[22] Lei, Y.H., Jiang, J.H., Li, X., Li, Q.G., and Li, C.H., 2022, A nine‐coordinated bismuth(III) Schiff‐base complex: Design, synthesis, computational studies, and antimicrobial activity, Appl. Organomet. Chem., 36 (2), e6523.

[23] Shahi, S., Roghani-Mamaqani, H., Talebi, S., and Mardani, H., 2022, Chemical stimuli-induced reversible bond cleavage in covalently crosslinked hydrogels, Coord. Chem. Rev., 455, 214368.

[24] Troschke, E., Oschatz, M., and Ilic, I.K., 2021, Schiff‐bases for sustainable battery and supercapacitor electrodes, Exploration, 1 (3), 20210128.

[25] Faujdar, E., and Singh, R.K., 2021, Study on alkylated Schiff base of a triazole with 3,5-di-tert-butyl-4-hydroxybenzaldehyde as a novel multifunctional lubricant additive, Fuel, 302, 121158.

[26] Akagawa, M., 2021, Protein carbonylation: Molecular mechanisms, biological implications, and analytical approaches, Free Radical Res., 55 (4), 307–320.

[27] Fuentes-Lemus, E., Hägglund, P., López-Alarcón, C., and Davies, M.J., 2021, Oxidative crosslinking of peptides and proteins: Mechanisms of formation, detection, characterization and quantification, Molecules, 27 (1), 15.

[28] Battin, S.N., 2019, Vanillin-Aminoquinoline Schiff Bases and their Co(II), Ni(II) and Cu(II) Complexes, Lulu Press, Inc., Morrisville, North Carolina, US.

[29] Hussein, K.A., and Shaalan, N., 2022, Synthesis, characterization, and antibacterial activity of lanthanide metal complexes with Schiff base ligand produced from reaction of 4,4-methylene diantipyrine with ethylenediamine, Indones. J. Chem., 22 (5), 1365–1375.

[30] Hussein, K.A., Mahdi, S., and Shaalan, N., 2023, Synthesis, spectroscopy of new lanthanide complexes with Schiff base derived from (4-antipyrinecarboxaldehyde with ethylene di-amine) and study the bioactivity, Baghdad Sci. J., 20 (2), 305–305.

[31] Hammoda, R.G., and Shaalan, N., 2023, Synthesis of Zn(II) and Co(II) complexes with a Schiff base derived from malonic acid dihydrazide for photo-stabilizers of polystyrene, Indones. J. Chem., 23 (5), 1324–1340.

[32] Taha, Z.A., Ajlouni, A.M., Al-Hassan, K.A., Hijazi, A.K., and Faiq, A.B., 2011, Syntheses, characterization, biological activity, and fluorescence properties of bis-(salicylaldehyde)-1, 3-propylenediimine Schiff base ligand and its lanthanide complexes, Spectrochim. Acta, Part A, 81 (1), 317–323.

[33] Nandiyanto, A.B.D., Ragadhita, R., and Fiandini, M., 2023, Interpretation of Fourier transforms infrared spectra (FTIR): A practical approach in the polymer/plastic thermal decomposition, Indones. J. Sci. Technol., 8 (1), 113–126.

[34] Kariaka, N.S., Kolotilov, S.V., Gawryszewska, P., Kasprzycka, E., Weselski, M., Dyakonenko, V.V., Shishkina, S.V., Trush, V.A., and Amirkhanov, V.M., 2019, Structures and spectral and magnetic properties of a series of carbacylamidophosphate pentanuclear lanthanide(III) hydroxo complexes, Inorg. Chem., 58 (21), 14682–14692.

[35] Teran, R., Guevara, R., Mora, J., Dobronski, L., Barreiro-Costa, O., Beske, T., Pérez-Barrera, J., Araya-Maturana, R., Rojas-Silva, P., Poveda, A., and Heredia-Moya, J., 2019, Characterization of antimicrobial, antioxidant, and leishmanicidal activities of Schiff base derivatives of 4-aminoantipyrine, Molecules, 24 (15), 2696.

[36] Al-Shaheen, A.J., and Al-Bergas, A.F., 2020, Synthesis and identification of some complexes of 4-[N-(2,4-dihydroxybenzylidene) imino] antipyrinyl with serine (L1) or with theronine (L2) ligands and evaluation of their bacteria activities, J. Educ. Sci., 29 (4), 42–61.

[37] Niessen, W.M., and Falck, D., 2015, “Introduction to Mass Spectrometry, a Tutorial” in Analyzing Biomolecular Interactions by Mass Spectrometry, Eds. Kool, J., and Niessen, W.M.A., Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 1–54.

[38] Hassan, S.A., Lateef, S.M., and Majeed, I.Y., 2020, Structural, spectral and thermal studies of new bidentate Schiff base ligand type (NO) derived from mebendazol and 4-aminoantipyrine and it's metal complexes and evaluation of their biological activity, Res. J. Pharm. Technol., 13 (6), 3001–3006.

[39] 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.

[40] Cruz-Navarro, A., Rivera, J.M., Durán-Hernández, J., Castillo-Blum, S., Flores-Parra, A., Sánchez, M., Hernández-Ahuactzi, I., and Colorado-Peralta, R., 2018, Luminescence properties and DFT calculations of lanthanide(III) complexes (Ln= La, Nd, Sm, Eu, Gd, Tb, Dy) with 2,6-bis(5-methyl-benzimidazol-2-yl) pyridine, J. Mol. Struct., 1164, 209–216.

[41] Anonymous, 2021, Physical Chemistry (LibreTexts), https://chem.libretexts.org/@go/page/9054, accessed January 31, 2022.

[42] Ferenc, W., Sadowski, P., Cristóvão, B., and Sarzyński, J., 2013, Investigation of some physicochemical properties of 4-nitrocinnamates of lanthanides(III), J. Chil. Chem. Soc., 58 (2), 1753–1758.

[43] Sorace, L., and Gatteschi, D., 2015, “Electronic Structure and Magnetic Properties of Lanthanide Molecular Complexes” in Lanthanides and Actinides in Molecular Magnetism, Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 1–26.

[44] Hussain, A., Gadadhar, S., Goswami, T.K., Karande, A.A., and Chakravarty, A.R., 2012, Photo-induced DNA cleavage activity and remarkable photocytotoxicity of lanthanide(III) complexes of a polypyridyl ligand, Dalton Trans., 41 (3), 885–895.

[45] Abbas, A.K., 2016, Preparation, characterization and biological evaluation of some lanthanide(ΙΙΙ) ions complexes with 3-(1-methyl-2-benzimidazolylazo)-tyrosine, Baghdad. Sci. J., 13 (2), 128–128.

[46] Zhang, F., Huang, F., Yao, X., Jin, Y., Chen, Q., Liu, F., and Li, G., 2015, Pyridine Carboxylate Lanthanide Coordination Complexes with 1D and 2D Structure, J. Inorg. Organomet. Polym. Mater., 25 (5), 1183–1188.

[47] Obaid, S.M.H., Jarad, A.J., and Salih Al-Hamdani, A.A., 2020, Synthesis, characterization and biological activity of mixed ligand metal salts complexes with various ligands, J. Phys.: Conf. Ser., 1660 (1), 012028.

[48] Holland, N., Pang, X., Herzberg, W., Bor, J., and Lorenz, E., 2021, Combination of physics based simulation and machine learning for PV power forecasting of large power plants, The 38th European Photovoltaic Solar Energy Conference and Exhibition (EU PVSEC), Lisbon, Portugal, 6-10 September 2021.

[49] Shaalan, N., 2022, Preparation, spectroscopy, biological activities and thermodynamic studies of new complexes of some metal ions with 2-[5-(2-hydroxy-phenyl)-1,3,4-thiadiazol-2-ylimino]-methyl-naphthalen-1-ol], Baghdad Sci. J., 19 (4), 829–829.

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

[51] 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.

[52] Jarrahpour, A.A., Motamedifar, M., Pakshir, K., Hadi, N., and Zarei, M., 2004, Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities, Molecules, 9 (10), 815–824.

[53] Wang, C., Fan, L., Pan, Z., Fan, S., Shi, L., Li, X., Zhao, J., Wu, L., Yang, G., and Xu, C., 2022, Synthesis of novel indole Schiff base compounds and their antifungal activities, Molecules, 27 (20), 6858.



DOI: https://doi.org/10.22146/ijc.87262

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