Aslıhan DALMAZ, Sefa DURMUŞ, Gorkem DULGER, Başaran DÜLGER

Synthesis and Characterization of Dimeric Thio-Schiff Bases by Nano Cerium Oxide and Examination of Their Antimicrobial Activities

In this work, firstly, CeO2 nanoparticles, which can be used as catalysts in many reactions, were synthesized by preparing aqueous solution of cerium(III) nitrate hexahydrate in basic medium. In the second step, the synthesis of dimeric thio Schiff bases was carried out using two different methods. Effect of catalyst on some parameters such as reaction time and yield of product were investigated. The antimicrobial activities of the ligands have been screened in vitro against the organisms Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae (Gram negative bacteria), Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus cereus (Gram positive bacteria) and Candida albicans, C. tropicalis, C. guilliermondii, C. glabrata by Disc Diffusion and Microdilution methods. At the same time, antimicrobial activities of ligands were compared to standard antibiotics (Cefotaxime, Amoxicillin/clavulanic acid, Posacanazole, Nystatin and Gentamicin). Generally, the results obtained in this research showed that all tested ligands exhibited more effect towards Gram positive bacteria and Candida species as compared to standard antibiotics.

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[1] K. Schermanz, “Catalysis by ceria and related materials,” World Scientific, London, Chapter I, 2002.

[2] A. M. Thompson, “Oxides of the Rare Earths,” John Wiley & Sons, New York, 1978.

[3] J. D. McCullough and K. N. Trueblood, “The crystal structure of baddeleyite (monoclinic ZrO2),” Acta Crystallographica, vol. 12, pp. 507-511, 1959.

[4] B. Schmidt, S. Lindman, W. Tong, G. Lindeberg, A. Gogoll, Z. Lai, M. Sohtell, “Design, Synthesis, and Biological Activities of Four Angiotensin II Receptor Ligands with γ-Turn Mimetics Replacing Amino Acid Residues 3−5,” Journal of Medicinal Chemistry, vol. 40, pp. 903-919, 1997.

[5] B. D. Palmer, G. W Rewcastle, A. M. Thompson, M. Boyd, H. H. Showalter, A.D. Sercel, W. A. Denny, “Tyrosine Kinase Inhibitors. 4. Structure-Activity Relationships among N- and 3-Substituted 2,2'-Dithiobis(1H-indoles) for in vitro Inhibition of Receptor and Nonreceptor Protein Tyrosine Kinases,” Journal of Medicinal Chemistry, vol. 38, pp. 58-67, 1995.

[6] S. Murtaza, A. Abbas, K. Iftikhar, S. Shamim, M.S. Akhtar, Z. Razzaq, K. Naseem, A.M. Elgorban, “Synthesis, biological activities and docking studies of novel 2,4-dihydroxybenzaldehyde based Schiff base,” Medicinal Chemistry Research, vol. 25, pp. 2860-2871, 2016.

[7] P. Khatkar, S. Asija and N. Singh, “Synthesis, spektral studies and in vitro antimicrobial activity of soma new Di/Triorganotin (IV) complexes of Schiff base derived from 2-benzoylpyridine,” Journal of the Serbian Chemical Society, vol. 82, pp. 13–23, 2017.

[8] M. G. Bhowon, S. Jhaumeer-Laulloo, N. Soukhee, A. Allibacus, V. Shiboo, “Synthesis, catalytic and antibacterial activity of 2-aminophenyldisulphide,” Journal of Coordination Chemistry, vol. 60, pp. 1335-1343, 2007.

[9] G. G. Mohamed, M. M. Omar and A.M. Hindy, “Metal Complexes of Schiff Bases: Preparation, Characterization, and Biological Activity,” Turkish Journal of Chemistry, vol. 30, pp. 361-382, 2006.

[10] S. C. C. Oliveira, C. K. Z. Andrade, R. M. Varela, J. M. G. Molinillo, F. A. Macías, “Phytotoxicity Study of OrthoDisubstituted Disulfides and Their Acyl Derivatives,” American Chemical Society Omega, vol. 4, pp. 2362−2368, 2019.

[11] F. N. Moghadam, M. Amirnasr, K. Eskandari, S. Meghdadia, “A new disulfide Schiff base as versatile “OFF-ON-OFF” fluorescent colorimetric chemosensor for sequential detection of CN− and Fe3+ ions: Combined experimental and theoretical studies,” Royal Society of Chemistry, vol. 1, pp. 1-3, 2019.

[12] S. M. A. Hamour, A. O'bichere, J. L. Peters, P. J. McDonald, “Patient perceptions of MRSA,” Annals of the Royal College of Surgeons of England, vol. 85, pp. 123-125, 2003.

[13] Y. Narain, S. Jhaumeer-Laulloo, and M. G. Bhowon, “Structure-activity relationship of Schiff base derivatives of bis (aminophenyl) disulfide and p-vanillin as antimicrobial agents,” International Journal of Biological and Chemical Science, vol. 4, pp. 69-74, 2010.

[14] S. Durmus, A. Dalmaz, M. Ozdincer, S. Sivrikaya, “Preparation of Lanthanide Oxide Nanoparticles: An efficient catalyst for the synthesis of dimeric disulphide Schiff Bases,” CBU Journal of Science, vol. 13, pp. 25, 2017.

[15] Saima, A. G. Lavekar, R. Kumar, A. K. Sinha, “Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis (phenylene) bis (benzylideneimine) via sequential oxidative coupling– condensation reactions in one pot from aminothiophenol and benzaldehyde,” Journal of Molecular Catalysis B: Enzymatic, vol. 116, pp. 113-123, 2015.

[16] S. Chandra and R. Kumar, “Synthesis and spectral studies on mononuclear complexes of chromium(III) and manganese(II) with 12-membered tetradentate N2O2, N2S2 and N4 donor macrocyclic ligands,” Transition Metal Chemistry, vol. 29, pp. 269, 2004.

[17] S. Sarkar and K. Dey, “Synthesis and Spectroscopic Characterization of Some Transition Metal complexes of a new hexadentate N2S2O2 Schiff Base Ligand,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 62, pp. 383-393, 2005.

[18] M. Rasouli, M. Morshedi, M. Amirnasr, M. Z. S. Alexandra, R. Randall, “Synthesis, Crystal Structure and Electrochemical Properties of Cu(I) Coordination Polymers with Two New NS)2 Schiff-base Ligands Containing Long Flexible Spacers,” Journal of Coordination Chemistry, vol. 66, pp. 1974-1984, 2013.

[19] Clinical and Laboratory Standards Institute (CLSI), reference method for broth dilution antifungal susceptibility testing of yeasts, approved standard – third edition. CLSI document M27-A3; Wayne, PA 2008.

[20] Clinical and Laboratory Standards Institute, methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, approved standard –ninth edition. CLSI document M07-A9; Wayne, PA 2012.

[21] R. N. Jones, A. L. Barry, T. L. Gaven, J. A. Washington, E. H. Lennette, A. Balows, “Antibacterial Activities of Ciprofloxacin, Norfloxacin, Oxolinic Acid, Cinoxacin, and Nalidixic Acid,” Antimicrobial Agents and Chemotherapy, vol. 25, p. 972-977, 1984,.

[22] M. G. Bhowon, S. Jhaumeer-Laulloo and M. Dowlut, “Synthesis, catalytic and characterization of bis(2-aminophenyl) disulphide imine derivatives and their ruthenium complexes,” Transition Metal Chemistry, vol. 30, pp. 35-39, 2005.

[23] E. Labisbal, A. Blas, J. A .García-Vázquez, J. Romero, M. L. Durán, A. Sousa, “The synthesis of tin(IV) complexes of 2-(2- mercaptophenyl)-imino-phenols by the electrochemical cleavage of a disulphide bond: The crystal structure of bis{2-(2- mercaptophenyl)imino-4,6-dimethoxyphenoxy}tin(IV),” Polyhedron, vol. 11, pp. 227-233, 1992.

[24] E. Labisbal, J. A. García-Vázquez, C. Gómez, A. Macias, J. Romero, A. Sousa, U. Englert, D. E. Fenton, “The synthesis of zinc(II) complexes of 2-(2- mercaptophenyl)-imino-phenol by electrochemical cleavage of a disulfide bond: the crystal structure of {(2,2’- bipyridine)[2-(2-mercaptophenyl)iminophenoxy]}zinc(II),” Inorganic Chimica Acta, vol. 203, pp. 671-, 1993.

[25] M. Behpour, S. M. Ghoreishi, N. Mohammadi, N. Soltani, M. SalavatiNiasari, “Investigation of some Schiff base compounds containing disulfide bond as HCl corrosion inhibitors for mild steel,” Corrosion Science, vol. 52, pp. 4046-4057, 2010.

[26] C. Praveen, K. H. Kumar, D. Muralidharan, P. T. Perumal, “Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: a new oxidant for 2- substituted benzothiazoles and benzoxazoles,” Tetrahedron, vol. 64, pp. 2369-2374, 2008.

[27] S. Bharti, M. Choudhary, B. Mohan, S. P. Rawat, S. R. Sharma, K. Ahmad, “Syntheses, spectroscopic, characterization, SOD-like properties and antibacterial activities of dimer copper (II) and nickel(II) complexes based on imine ligands containing 2-aminothiophenol moiety: X-ray crystal structure determination of disulfide Schiff Bases,” Journal of Molecular Structure, vol.1164, pp. 137-154, 2018.

[28] A. Goszczyńska, H. Kwiecień, K. Fijałkowski, “Synthesis and antibacterial activity of Schiff bases and amines derived from alkyl 2-(2-formyl-4- nitrophenoxy) alkanoates,” Medicinal Chemistry Research, vol. 24, pp. 3561- 3577, 2015.