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Synthesis, Spectroscopy of New Lanthanide Complexes with Schiff Base Derived From (4-Antipyrinecarboxaldehyde with Ethylene Di-Amine) and Study the Bioactivity

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DOI:

https://doi.org/10.21123/bsj.2022.7088

Keywords:

4-antipyrinecarboxaldhyed, Biological Activity, Metal complexes (lanthanide), Schiff’s bases, Thermogravimetric Analysis

Abstract

The study involved preparing a new compound by combining Schiff bases generated from compounds for antipyrine, including lanthanide ions (lanthanum, neodymium, erbium, gadolinium, and dysprosium). The preparation of the ligand from condensation reactions (4-antipyrinecarboxaldehyde with ethylene di-amine) at room temperature, and was characterization using spectroscopic and analytical studies ( FT-IR, UV-visible spectra, 1H-NMR, mass spectrometry, (C.H.N.O), thermogravimetric analysis (TGA), in addition to the magnetic susceptibility and conductivity measurement of the synthesis complexes, among the results we obtained from the tests, we showed that the ligand behaves with the (triple Valence) lanthanide ions, the multidentate behavior through two oxygen atoms of the carbonyl group and two nitrogen atoms of the azomethine group with all the prepared complexes in a molar ratio (1:1). The participation of six groups of bidentate nitrate in the coordination and indicating that their complexes have values of magnetic moment and paramagnetic character and, based on the results of those measurements, the geometrical shape of the complexes was proposed. The biological activity of the prepared complexes was studied using the antibacterial activity, as the results of its effectiveness showed the direction of the bacteria used (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae) at the concentration of 1×10-3M

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Author Biography

Shatha Mahdi , Ministry of Education, Al-Karkh Second Education Directorate, Baghdad, Iraq.

Department of Chemistry - master

References

Al-Labban HM, Sadiq HM, Aljanaby AA. Synthesis, Characterization and study biological activity of some Schiff bases derivatives from 4-amino antipyrine as a starting material. J Phys Conf Ser. 2019 Sep 1; 1294 ( 5): 052007 . IOP Publishing. doi:10.1088/1742-6596/1294/5/052007

Kareem MJ, Al-Hamdani AA, Ko YG, Al Zoubi W, Mohammed SG. Synthesis, characterization, and determination antioxidant activities for new Schiff base complexes derived from 2-(1H-indol-3-yl)-ethylamine and metal ion complexes. J Mol Struct. 2021 May 5; 1231: 129669. https://doi.org/10.1016/j.molstruc.2020.129669

Xu Y, Shi Y, Lei F, Dai L. A novel and green cellulose-based Schiff base-Cu (II) complex and its excellent antibacterial activity. Carbohydr Polym. 2020 Feb 15; 230:115671. https://doi.org/10.1016/j.carbpol.2019.115671

Jirjees VY, Al‐Hamdani AA, Wannas NM, Farqad A R, Dib A, Al Zoubi W. Spectroscopic characterization for new model from Schiff base and its complexes. J Phys Org Chem. 2021 Apr; 34(4):e4169. DOI: 10.1002/poc.4169

Al Zoubi W, Kim MJ, Yoon DK, Al-Hamdani AA, Kim YG, Ko YG. Effect of organic compounds and rough inorganic layer formed by plasma electrolytic oxidation on photo catalytic performance. J Alloys Compd. 2020 May 15; 823: 153787. https://doi.org/10.1016/j.jallcom.2020.153787

Shaalan N, Khalaf WM, Mahdi S. Preparation and Characterization of New Tetra-Dentate N 2 O 2 Schiff Base with Some of Metal Ions Complexes. Indones J Chem. 2022; 22 (1): 62 – 71. https://doi.org/10.22146/ijc.66118

Antony R, Arun T, Manickam ST. A review on applications of chitosan-based Schiff bases. Int J Biol Macromol. 2019 May 15; 129: 615-33. https://doi.org/10.1016/j.ijbiomac.2019.02.047

Morsy NM, Hassan AS, Hafez TS, Mahran MR, Sadawe IA, Gbaj AM. Synthesis, antitumor activity, enzyme assay, DNA binding and molecular docking of Bis-Schiff bases of pyrazoles. J. Iran. Chem. Soc. 2021 Jan; 18(1):47-59. https://doi.org/10.1007/s13738-020-02004-y

Sabir SS, Hussein KB, Mohamad MY. Synthesis of some lanthanide complexes with (o-V2Nph. H2) Schiff-base ligand. Polytechnic J. 2018;8(2):264-76. https://doi.org/10.25156/ptj.2017.7.3.78

Maihub AA, Sofian SM, Awin AA, Belaid AK, Bensaber SM, Hermann A, et al. Antimicrobial activity of some pyrazolidin- 3-one Schiff base derivatives and their complexes with selected metal ions. Clin Trials. 2018; 2018:55-64.

Teran R, Guevara R, Mora J, Dobronski L, Barreiro-Costa O, Beske T, et al. Characterization of antimicrobial, antioxidant, and leishmanicidal activities of Schiff base derivatives of 4- aminoantipyrine. Molecules. 2019 Jan; 24(15):2696. https://doi.org/10.3390/molecules24152696

Mohamed Wannas N, Al‐Hamdani AA, Al Zoubi W. Spectroscopic characterization for new complexes with 2, 2′‐(5, 5‐dimethylcyclohexane‐1, 3‐diylidene) bis (azan‐1‐yl‐1‐ylidene) dibenzoic acid. J Phys Org Chem. 2020 Nov;33(11):e4099. https://doi.org/10.1002/poc.4099

Ommenya FK, Nyawade EA, Andala DM, Kinyua J. Synthesis, characterization and antibacterial activity of Schiff base, 4-Chloro-2-{(E)-[(4-fluorophenyl) imino] methyl} phenol metal (II) complexes. J Chem. 2020 Mar 30; 2020. https://doi.org/10.1155/2020/1745236

Kaczmarek MT, Zabiszak M, Nowak M, Jastrzab R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord Chem Rev. 2018 Sep 1; 370: 42-54. https://doi.org/10.1016/j.ccr.2018.05.012

Hassan SA, Lateef SM, Majeed IY. Structural, Spectral and Thermal studies of new bidentate Schiff base ligand type (NO) derived from Mebendazol and 4-Aminoantipyrine and its metal complexes and evaluation of their biological activity. Res J Pharm Technol 2020; 13(6): 3001-6. DOI: 10.5958/0974-360X.2020.00531.4

Kareem MJ, Al‐Hamdani AA, Jirjees VY, Khan ME, Allaf AW, Al Zoubi W. 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. 2021 Mar; 34(3): e4156. https://doi.org/10.1002/poc.4156

Blinova I, Muna M, Heinlaan M, Lukjanova A, Kahru A. Potential hazard of lanthanides and lanthanide-based nanoparticles to aquatic ecosystems: data gaps, challenges and future research needs derived from bibliometric analysis. J Nanomater. 2020 Feb; 10(2): 328. https://doi.org/10.3390/nano10020328

Al Zoubi W, Mohamed SG, Al-Hamdani AA, Mahendradhany AP, Ko YG. Acyclic and cyclic imines and their metal complexes: recent progress in biomaterials and corrosion applications. Rsc Adv. 2018; 8(41): 23294-318. DOI: 10.1039/C8RA01890A

Marin R, Brunet G, Murugesu M. Shining New Light on Multifunctional Lanthanide Single‐Molecule Magnets. Angew Chem Int Ed. 2021 Jan 25; 60 (4): 1728-46. https://doi.org/10.1002/anie.201910299

Gagné OC. Bond-length distributions for ions bonded to oxygen: results for the lanthanides and actinides and discussion of the f-block contraction. Acta Crystallogr B: Struct Sci Cryst Eng Mater. 2018 Feb 1; 74 (1): 49-62. https://doi.org/10.1107/S2052520617017425

Olyshevets I, Ovchynnikov V, Kariaka N, Dyakonenko V, Shishkina S, Sliva T, et al. Lanthanide complexes based on a new bis-chelating carbacylamidophosphate (CAPh) scorpionate-like ligand. Rsc Adv. 2020; 10(42): 24808-16. DOI: 10.1039/D0RA04714G

Liu T, Chen J. Extraction and separation of heavy rare earth elements: A review. Sep Purif Technol. 2021 Dec 1; 276:119263. https://doi.org/10.1021/acssuschemeng.1c06964

Hussein SS, Mohamad MY. Synthesis of some lanthanide complexes with (o-V2Nph. H2) Schiff-base ligand. Polytechnic J. 2018; 8(2): 264-76. https://doi.org/10.25156/ptj.2017.7.3.78

Abbas AK. Lanthanide Ions Complexes of 2-(4-amino antipyrine)-L-Tryptophane (AAT): Preparation, Identification and Antimicrobial Assay. Iraqi J Sci. 2015; 56(4C): 3297-309.

Hussein KA, Shaalan N 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. 2021; 11: 103-113. https://dx.doi.org/10.22034/chemm.2022.2.3

Martinez-Gomez NC, Vu HN, Skovran E. Lanthanide chemistry: from coordination in chemical complexes shaping our technology to coordination in enzymes shaping bacterial metabolism. Inorg chem. 2016 Oct 17; 55(20): 10083-9. https://doi.org/10.1021/acs.inorgchem.6b00919

Ebosie NP, Ogwuegbu MO, Onyedika GO, Onwumere FC. Biological and analytical applications of Schiff base metal complexes derived from salicylidene-4-aminoantipyrine and its derivatives: A review. J Iran Chem Soc. 2021 Dec; 18(12): 3145-75. https://doi.org/10.1007/s13738-021-02265-1

Remes C, Paun A, Zarafu I, Tudose M, Caproiu MT, Ionita G, et al. Chemical and biological evaluation of some new antipyrine derivatives with particular properties. Bioorg. Chem. 2012 Apr 1; 41:6-12. https://doi.org/10.1016/j.bioorg.2011.12.003

Chavan RR, Hosamani KM. Microwave-assisted synthesis, computational studies and antibacterial/anti-inflammatory activities of compounds based on coumarin-pyrazole hybrid. R Soc Sci Open. 2018 May 2; 5(5): 172435. https://doi.org/10.1098/rsos.172435

Shaalan N, Abed AY, Alkubaisi HM, Mahde M,Synthesis, Spectroscopy, Biological Activities and Thermodynamic Studies for New Complexes of Some Lanthanide Metals with Schiff's Bases derived from [2-acetylthiophene] with [2,5-dihydrazino-1,3,4-thiadiazole]. Res J Chem Environ. 2019; 23: 181-187.

Zabiszak M, Nowak M, Hnatejko Z, Grajewski J, Ogawa K, Kaczmarek MT, et al. Thermodynamic and spectroscopic studies of the complexes formed in tartaric acid and lanthanide (III) ions binary systems. Molecules. 2020 Jan; 25(5): 1121. https://doi.org/10.3390/molecules25051121

Shalan N, Hussein Y. Preparation, spectral characterization, structural study, and evaluation of antibacterial activity of metal complexes with Schiff base derived from (N, Ń-bis (1,5- dimethyl-2-phenyl-1,2-dihydro-pyrazolidine-3-one)-1,2 diamino ethane). Res J Pharm Biol Chem Sci. 2018; 9 (1): 376–385.

Muslah SI, Alabdali AJ, Shaalan ND. Synthesis of Binuclear Complexes of Cu (II), Ni (II) and Cr (III) Metal Ions Derived from Di-Imine Compound as Biterminal Binding Site Ligand. (ANJS). 2020 Nov 30; 23(4): 19-28. DOI: 10.22401/ANJS.23.4.04

Teran R, Guevara R, Mora J, Dobronski L, Barreiro-Costa O, Beske T, et al. Characterization of antimicrobial,antioxidant, and leishmanicidal activities of Schiff base derivatives of 4-aminoantipyrine. Molecules. 2019 Jan; 24(15): 2696. https://doi.org/10.3390/molecules24152696

Kariaka NS, Kolotilov SV, Gawryszewska P, Kasprzycka E, Weselski M, Dyakonenko VV, et al. Structures and Spectral and Magnetic Properties of a Series of Carbacylamidophosphate Pentanuclear Lanthanide (III) Hydroxo Complexes. Inorg Chem. 2019 Oct 24;58(21):14682-92. https://doi.org/10.1021/acs.inorgchem.9b02354

Al-Shaheen AJ, Al-Bergas AF. Synthesis and Identification of Some Complexes of 4-[N-(2, 4-Dihydroxybenzylidene) imino] Antipyrinyl with Serine (L1) or with Threonine (L2) Ligands and Evaluation of Their Bacteria Activities. J Sci Educ Technol. 2020; 29(4). http://dx.doi.org/10.33899/edusj.1999.163310

Niessen WM, Falck D. Introduction to mass spectrometry, a tutorial. Analyzing Biomolecular Interactions by Mass Spectrometry. 2015 Feb 13; 1: 1-54, https://doi.org/10.1002/9783527673391.ch1.

Shaalan N. Preparation and spectroscopic study, biological and thermodynamic activity of new complexes of some metal ions with 2-[5-(2-hydroxy-phenyl)-4, 3, 1-thiadiazol-2-ylimino]-methyl-naphthalene-1-ol. Baghdad Sci J. 2022: 829-837. https://doi.org/10.21123/bsj.2022.19.4.0829

Cruz-Navarro A, Rivera JM, Durán-Hernández J, Castillo-Blum S, Flores-Parra A, Sánchez M, et al. 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. 2018 Jul 15; 1164: 209-16. https://doi.org/10.1016/j.molstruc.2018.03.065

Hovhannesyan G, Boudon V, Lepers M. Transition intensities of trivalent lanthanide ions in solids: Extending the Judd-Ofelt theory. J Lumin. 2022 Jan 1; 241: 118456. https://doi.org/10.1016/j.jlumin.2021.118456

Aguzue OC, Adedayo A, Phillip OA. Mechanochemical Synthesis and Potentiation of the Antimicrobial Activity of 4-[3-(4- methoxyphenyl)-allylideneamino]-1,5-dimethyl-2-phenyl pyrazol-3- one by Metal Chelation. J Math Sci Lett. 2020 Mar 10; 8(2): 15-21. https://doi.org/10.37134/jsml.vol8.2.3.2020

Misra SN, Sommerer SO. Absorption spectra of lanthanide complexes in solution. Appl Spectrosc Rev. 1991 Sep 1; 26(3): 151-202. https://doi.org/10.1080/05704929108050880

Hovhannesyan G, Boudon V, Lepers M. Transition intensities of trivalent lanthanide ions in solids: Revisiting the Judd-Ofelt theory. arXiv preprint arXiv. 2021 Jun 4, 2106: 02502 https://doi.org/10.1016/j.jlumin.2021.118456

Abbas AK. Preparation, Characterization and Biological Evaluation of some Lanthanide (ΙΙΙ) ions Complexes with 3-(1-methyl-2-benzimidazolylazo)-Tyrosine. Baghdad Sci J. 2016; 13: 128-142. http://dx.doi.org/10.21123/bsj.2016.13.2.2NCC.0128

Runowski M, Stopikowska N, Lis S. UV-Vis-NIR absorption spectra of lanthanide oxides and fluorides. Dalton Trans. 2020; 49(7):2129-37. https://doi.org/10.1039/C9DT04921E

Zhang F, Huang F, Yao X, Jin Y, Chen Q, Liu F,then et al. Pyridine Carboxylate Lanthanide Coordination Complexes with 1D and 2D Structure. J Inorg Organomet Polym Mater. 2015 Sep; 25(5): 1183-8. https://doi.org/10.1007/s10904-015-0226-1

Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal. 2016 Apr 1; 6(2): 71-9. https://doi.org/10.1016/j.jpha.2015.11.005

Shaalan N, Mahdi S. 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. 2021; 64, (8), 4059 – 4067. https://dx.doi.org/10.21608/ejchem.2021.66235.3432

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