Syntheses, Characterizations and Antimicrobial Activity of Three New Mixed Ligand Fe(III) Ce(IV) and Th(IV) Schiff Base Chelates

المؤلفون

  • Bahya M. ALfakhry
  • Miloud M. Miloud
  • Marei M. El-ajaily
  • Najla M. Mohamed
  • Asma ELramli
  • Esraa ELwerfally

DOI:

https://doi.org/10.37375/foej.v1i2.487

الكلمات المفتاحية:

Schiff base, Ethylenediamine, Mixed ligand chelates, Antimicrobial activity, MIC

الملخص

In the present study, a Schiff base (HL1) derived from the condensation reaction      of L-alanine with o-hydroxyacetophenone  in 1:1 molar ratio was synthesized. The Schiff base and ethylenediamine compound were used to form three mixed ligand chelates with iron(III), cerium(IV) and thorium(IV) ions. The compounds were characterized using several analytical and spectroscopic tools [IR, electronic, NMR and mass]. The results showed the bonding behavior between the ligands and metal ions. The antimicrobial activities of the ligands and mixed ligand chelates were investigated against Staphylococcus aureus, Serratia marcescens, Acinetobacter baumannii and Candida albicans using the agar disk diffusion method. The results indicated that the antimicrobial activity of the tested compounds exhibited a fairly good inhibitory effect on the pathogenic microbe’s species. In contrast, the L-alanine showed no antimicrobial activity against A.baumannii. Schiff base, L-alanine, o-hydroxy acetophenone , [Fe(L1) (L3)(OH)] .H2O, [Ce(L1) (L3)(SO4)(H2O)].H2O and [Th(L1)(L3)(NO3)2]. 2H2O showed bacteriostatic activity against the highly susceptible species of pathogenic bacteria (S. aureus and S. marcescens) with MIC reached 50 mg/ml. while ethylenediamine suppressed bacterial growth of these species at a concentration of 25 mg/ml.

 

المراجع

Abu-Dief, A. M., & Mohamed, I. M. (2015). A review on versatile applications of transition metal complexes incorporating Schiff bases, Beni-Suef University Journal of Basic and Applied Sciences, 4(2), 119-133. https://doi.org/10.1016/j.bjbas.2015.05.004

Alassbaly, F.S., Maihub, A.A., Ben-Gweirif, S.F., El-Ajaily, M.M. & Al-Noor, T.H., (2016). Chelation trends and antibacterial activity of some mixed ligand chelates, Saudi Journal of Pathology and Microbiology, 1(2), 29-35. https://doi.org/10.21276/sjpm.2016.1.2.1

Al-Barki, N.S., Maihub, A.A., El-Ajaily, M.M. & Al-Noor, T.H. (2016). Synthesis and Physiochemical Studies of Some Mixed Schiff Bases Complexes. Academic Journal of Chemistry, 1(3), 66-75.

AL-Garawi, S., Tomi, I & AL-Daraji, A. (2012). Synthesis and characterization of new amino acid Schiff bases and studies their effects on the activity of ACP, PAP and NPA enzymes (In Vitro), E-Journal of Chemistry, 9(2), 962-969. https://doi.org/10.1155/2012/218675

Alghool, S., Abd El-Halim, H.F., Abd El-sadek, M.S., Yahia, I.S. & Wahab, L.A. (2013). Synthesis, thermal characterization, and antimicrobial activity of lanthanum, cerium, and thorium complexes of amino acid Schiff base ligand, Journal of thermal analysis and calorimetry, 112(2), 671-681. https://doi.org/10.1007/s10973-012-2628-4

Al-Jeboori, F.H., Al-Shimiesawi, T.A.M., Abd Oun, M.A., Abd ul-Ridha, A. & Abdulla, A.Y (2014). Synthesis and characterization of amino acid (phenylalanine) schiff bases and their metal complexes, Journal of Chemical and Pharmaceutical Research, 6(8), 44-53.

Al-Noor, T.H., Al-barki, N.S., Maihub, A.A. & El-ajaily, M.M. (2017). Synthesis and Spectroscopic Characterization of some Mixed Schiff Base Complexes, International Journal of Science and Research, 6(3), 2421-2426.https://doi.org./10.21275/ART20172143

Alothman, A. A., Albaqami, M. D. & Alshgari, R. A. (2021). Synthesis, spectral characterization, quantum chemical calculations, thermal studies and biological screening of nitrogen and oxygen donor atoms containing Azo-dye Cu(II), Ni(II) and Co(II) complexes, Journal of Molecula Structure, 1223, 128984. https://doi.org/10.1016/j.molstruc.2020.128984

Amani, V., Safari, N., Khavasi, H.R. & Mirzaei, P. (2007). Iron (III) mixed-ligand complexes: Synthesis, characterization and crystal structure determination of iron (III) hetero-ligand complexes containing 1, 10-phenanthroline, 2, 2′-bipyridine, chloride and dimethyl sulfoxide,[Fe (phen) Cl3 (DMSO)] and [Fe (bipy) Cl3 (DMSO)], Polyhedron, 26(17), 4908-4914. https://doi.org/10.1016/j.poly.2007.06.038

Anitha, C., Sumathi, S., Tharmaraj, P. & Sheela, C.D. (2012). Synthesis, characterization, and biological activity of some transition metal complexes derived from novel hydrazone azo Schiff base ligand, International Journal of Inorganic Chemistry, 2011. https://doi.org/10.1155/2011/493942

Ashraf, M.A., Mahmood, K., Wajid, A., Maah, M.J. & Yusoff, I. (2011). Synthesis, characterization and biological activity of Schiff bases, IPCBEE, 10(1), 185.

Atiyah, E. M., Alwan, W. M. & Alkam, H. H. (2020). New mixed ligand complexes of New Schiff base 4,4'-((naphthalen-1-ylimino) methylene) dibenzene-1,3-diol and 8-hydroxy quinoline: Synthesis, Spectral Characterization, Thermal studies and Biological Activities, Systematic Reviews in Pharmacy, 11(8), 725-735. https://doi.org/10.31838/srp.2020.8.104

Chohan, Z.H., Farooq, M.A., Scozzafava, A. & Supuran, C.T. (2002). Antibacterial schiff bases of oxalyl-hydrazine/diamide incorporating pyrrolyl and salicylyl moieties and of their zinc (II) complexes, Journal of Enzyme Inhibition and Medicinal Chemistry, 17(1), 1-7. https://doi.org/10.1080/14756360290005598

Derebe, M.G., Raju, V.J.T. & Retta, N. (2002). Synthesis and characterization of some metal complexes of a Schiff base derived from ninhydrin and α, L-alanine, Bulletin of the Chemical Society of Ethiopia, 16(1), 53-64. https://doi.org/10.4314/bcse.v16i1.20948

Ejidike, I.P. & Ajibade, P.A. (2015). Synthesis, characterization and biological studies of metal (II) complexes of (3E)-3-[(2-{(E)-[1-(2, 4-dihydroxyphenyl) ethylidene] amino} ethyl) imino]-1-phenylbutan-1-one Schiff base, Molecules, 20(6), 9788-9802. https://doi.org/10.3390/molecules20069788

El-Ajaily, M.M., Al-Barki, N.S. & Maihub, A.A., (2016). Mixed Schiff Bases Chelates: Synthesis and Spectroscopic Investigation, Asian Journal of Advanced Basic Sciences, 4(2), 123-130.

M. El-ajaily,M.M., Sarangi, A.K., Mohapatra,R.K., Hassan, S.S., Eldaghare, R.N., Mohapatra, P.K., Raval, M.K., Das, D. Mahal, A., Cipurkovic, A.[i] & Al-Noor, T.H.(2019). transition metal complexes of (E)-2((2-hydroxylbenzylidene) amino- 3-mercaptopropanoic acid: XRD, anticancer, molecular modeling and Molecular docking studies, Chemistry Select., 4, 9999 –10005. DOI: 10.1002/slct.201902306

El-Sherif, A.A. & Eldebss, T.M., (2011). Synthesis, spectral characterization, solution equilibria, in vitro antibacterial and cytotoxic activities of Cu (II), Ni (II), Mn (II), Co (II) and Zn (II) complexes with Schiff base derived from 5-bromosalicylaldehyde and 2- aminomethylthiophene, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(5), 1803-1814. https://doi.org/10.1016/j.saa.2011.05.062

EL-zweay, R .S., EL-ajaily, M. M., Ben-Gweirif, S. F., & Maihub, A.A. (2013). Preparation, characterization and antibacterial activity of some mixed ligand chelates, Journal of the Chemical Society of Pakistan, 35( 1),67-71.

Fugu, M. B., Ndahi, N. P., Paul, B. B & Mustapha, A. N. (2013) Synthesis, characterization and antimicrobial studies of some vanillin Schiff base metal(II) complexes, Journal of Chemical and Pharmaceutical Research, 5(4), 22-28.

Gaballa, A. S., Asker, M. S., Barakat, A. S., & Teleb, S. M. (2007). Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine, Spectrochimica acta. Part A, Molecular and Biomolecular Spectroscopy, 67(1), 114 - 121. https://doi.org/10.1016/j.saa.2006.06.031

Ghosh, T. & Pal, S. (2015). Synthesis and characterization of dodecahedral cerium (IV) and gadolinium (III) complexes with a tetradentate Schiff Base, Journal of Chemical Sciences, 127(7), 1201-1209. https://doi.org/10.1007/s12039-015-0887-x

Gobara, A.G.H. (2017), Synthesis, Characterization and Biological Activity of Some Thiosemicarbazone Ligands and their Complexes with Some M (II) ions, (PhD diss., University of Gezira.

Hamil, A.M., Abdelkarem, M., Hemmet, M. & El-ajaily, M.M. (2012). Synthesis of a New Schiff Base: 2-[2-(E)-(2-hydroxyphenyl)-ethylidene] aminoethyl) ethanimidoyl] phen, International Journal of ChemTech Research, 4(2), 682-685.

Hosny, N.M. & El-Dossoki, F.I. (2008). Schiff base complexes derived from 2- acetylpyridine, leucine, and some metal chlorides: their preparation, characterization,and physical properties, Journal of Chemical & Engineering Data,53(11), 2567-2572. https://doi.org./10.1021/je800415n

Hossian, M.S., Banu, L.A, El-Zahan, M.K, Haque, M.M. (2019). Synthesis, Characterization and Biological Activity Studies of mixed ligand complexes with Schiff base and 2,2 Bipyridine, International Journal of Applied Science-Research and Review, 6 (1:2). https://doi.org./10.21767/2394-9988.100086

Humelnicu, D., Pui, A., Malutan, C., Malutan, T. & Humelnicu, I. (2020). Synthesis, characterization and theoretical investigations of new uranium (VI) and thorium (IV) complexes with 1-furfurylaldehyde-derived Schiff bases as ligands, Journal of Saudi Chemical Society, 24(6), 451-460. https://doi.org/10.1016/j.jscs.2020.04.001

Kan, J.Y., Hsu, Y.L., Chen, Y.H., Chen, T.C., Wang, J.Y. & Kuo, P.L. (2013). Gemifloxacin, a fluoroquinolone antimicrobial drug, inhibits migration and invasion of human colon cancer cells, BioMed research international, 2013. https://doi.org/10.1155/2013/159786

Karipcin, F. & Kabalcilar, E. (2007). Spectroscopic and Thermal Studies on Solid Complexes of 4-(2-pyridylazo) resorcinol with Some Transition Metals, Acta Chimica Slovenica, 54(2), 242-247.

Klamm, B.E., Windorff, C.J., Marsh, M.L., Meeker, D.S. & Albrecht-Schmitt, T.E. (2018). Schiff-base coordination complexes with plutonium (IV) and cerium (IV), Chemical Communications, 54(62), 8634-8636. https://doi.org/10.1039/C8CC03571G

Lakshmi, S. S. & Geetha, K. (2016). Synthesis, characterization and biological studies of amino acid (L-tryptophan) Schiff base transition complexes, Journal of Chemical and pharmaceutical research, 8(1), 668-674.

Lateef, S. M., Sarhan, B.M. & Al-Saedi, W. A. J. (2016). Synthesis, Characterization and Biological Activity for Complexes VO(II), Mn(II), Co(II) and Ni(II) With New Multidentate Ligand [2-((E)-3-(2-hydroxyphenylimino)-1,5-dimethyl-2-phenyl-2,3- dihydro-1H-pyrazol-4-ylimino) acetic Acid][H2L] type (N2), Diyala Journal for pure Sciences, 12(1), 10-27.

Liu, T., Duan, G. & Zeng, Z. (2009). Synthesis and characterization of cerium, thorium, and uranyl complexes with (E)-4-(4-methoxyphenoxy)-4-oxobut-2-enoic acid, Journal of Coordination Chemistry, 62(13), 2203-2211. https://doi.org/10.1080/00958970902769799

Matar, S.A., Talib, W.H., Mustafa, M.S., Mubarak, M.S. & AlDamen, M.A. (2015). Synthesis, characterization, and antimicrobial activity of Schiff bases derived from benzaldehyde and 3, 3′-diaminodipropylamine, Arabian Journal of Chemistry, 8(6), 850- 857. https://doi.org/10.1016/j.arabjc.2012.12.039

McCleverty J. A, Meyer T. J. (2003) Comprehensive Coordination Chemistry II: From Biology to Nanotechnology. 2nd ed, 232- 236, (Elsevier, Amsterdam. Netherlands).

Mostafa, A.A., Al-Askar, A.A., Almaary, K.S., Dawoud, T.M., Sholkamy, E.N. & Bakri, M.M. (2018). Antimicrobial activity of some plant extracts against bacterial strains causing food poisoning diseases, Saudi Journal of Biological Sciences, 25, 361–366. https://doi.org/10.1016/j.sjbs.2017.02.004

Nakamoto, K. (1978). Infrared and Raman Spectra of Inorganic and Coordination Compounds 3rd ed, (Wiley-Interscience, New York).

Ossowicz, P., Janus, E., Schroeder, G. & Rozwadowski, Z. (2013). Spectroscopic studies of amino acid ionic liquid-supported Schiff bases, Molecules, 18(5),4986-5004. https://doi.org/10.3390/molecules18054986

Palanimurugan, A., Dhanalakshmi, A., Selvapandian, P. & Kulandaisamy, A., (2019). Electrochemical behavior, structural, morphological, Calf Thymus-DNA interaction and in-vitro antimicrobial studies of synthesized Schiff base transition metal complexes, Heliyon, 5(7), e02039. https://doi.org/10.1016/j.heliyon.2019.e02039

Patel, R.N., Singh, N., Shukla, K.K., Gundla, V.L.N. & Chauhan, U.K. (2006). Synthesis, characterization and biological activity of ternary copper (II) complexes containing polypyridyl ligands, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 63(1),.21-26. https://doi.org/10.1016/j.saa.2005.04.030

Pervaiz, M., Ahmad, I., Yousaf, M., Kirn, S., Munawar, A., Saeed, Z., Adnan, A., Gulzar, T., Kamal, T., Ahmad, A. & Rashid, A. (2019). Synthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 206, 642-649. https://doi.org/10.1016/j.saa.2018.05.057

Prashanthi, Y. & Kiranmai, K. (2012). Spectroscopic characterization and biological activity of mixed ligand complexes of Ni (II) with 1, 10-phenanthroline and heterocyclic Schiff bases, Bioinorganic chemistry and applications, 2012. https://doi.org/10.1155/2012/948534

Rahman, L.A., Abu-Dief, A.M., Hashem, N.A. & Seleem, A.A. (2015). Recent advances in synthesis, characterization and biological activity of nano sized Schiff base amino acid M (II) complexes, International Journal of Nanomaterials and Chemistry, 1(2), 79-95. https://doi.org/10.12785/ijnc/010205

Salama, M.M., Ahmed, S.G. & Hassan, S.S. (2017). Synthesis, characterizations, biological, and molecular docking studies of some amino acid Schiff bases with their cobalt (II) complexes, Advances in Biological Chemistry, 7(05), 182. https://doi.org/10.4236/abc.2017.75013

Sarı, N. & G ̈urkan, P., 2004. Some novel amino acid-Schiff bases and their complexes synthesis, characterization, solid state conductivity behaviors and potentiometric studies, Z. Naturforsch. 59b, 692 – 698. DOI:10.1515/znb-2004-0610

Selvaganapathy, M. & Raman, N. (2016). Pharmacological activity of a few transition metal complexes: A Short Review, Journal of Chemical Biology and Therapeutics, 1(2), 1-17. https://doi.org10.4172/2572-0406.1000108

Slavin, Y.N., Asnis, J., Häfeli, U.O. & Bach, H. (2017). Metal nanoparticles: understanding the mechanisms behind antibacterial activity, Journal of nanobiotechnology, 15(1),1- 20. doi.org/10.1186/s12951-017-0308-z

Sobola, A. O & Watkins, G. M. (2013). Antimicrobial activity and Cu(II) complexes of Schiff bases derived from ortho-aminophenol and salicylaldehyde derivatives, Journal of Chemical and Pharmaceutical Research, 5(10), 147-154.

Srivastava, S.C. & Newman, L. (1972). Mixed ligand complexes of palladium (II) with chloride and iodide, Inorganic Chemistry, 11(12), 2855-2859. https://doi.org/10.1021/ic50118a001

Tamiru, G., Abebe,A., Abebe, M. & Liyew, M. (2019). Synthesis, structural investigation and biological application of new mono- and binuclear cobalt (II) mixed-ligand complexes containing 1,10-phenanthroline, acetamide and ethylenediamine, Ethiopian Journal of Science and Technology, 12(1), 69-91. https://doi.org./10.4314/ejst.v12i1.4

Thakkar, N.V. & Thakkar, J.R. (2000). Synthesis and characterization of chiral mixed ligand Co(II) complexes of isonitrosopropiophenone and amino acids. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 30(10),1871- 1887. doi.org/10.1080/00945710009351875

Thakur, G.A. & Shaikh, M.M. (2006). Synthesis, characterization, antibacterial and cytotoxicity studies on some mixed ligand Th (IV) complexes, Acta poloniae pharmaceutica, 63(2), 95-100.

Thakur, G.A., Athlekar, S.V., Dharwadkar, S.R. & Shaikh, M.M. (2007). Synthesis and biological activity of mixed ligand dioxouranium (VI) and thorium (IV) complexes, Acta poloniae pharmaceutica, 64(1), 9-15.

التنزيلات

منشور

2023-01-09

كيفية الاقتباس

ALfakhry, B. M., Miloud, M. M., M. El-ajaily, M., Mohamed, N. M., ELramli, A., & ELwerfally, E. (2023). Syntheses, Characterizations and Antimicrobial Activity of Three New Mixed Ligand Fe(III) Ce(IV) and Th(IV) Schiff Base Chelates. المجلة العلمية لكلية التربية, 1(2), 24–1. https://doi.org/10.37375/foej.v1i2.487

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