1- MSc Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran, Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran , firstname.lastname@example.org 2- PhD Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran, Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran 3- MSc Department of Microbiology, Faculty of Science, Ilam University, Ilam, Iran, Department of Microbiology, Faculty of Science, Ilam University, Ilam, Iran 4- MSc Department of Microbiology, Pharmaceutical Sciences Branchl, Islamic Azad university Tehran, Tehran, Iran, Department of Microbiology, Pharmaceutical Sciences Branchl, Islamic Azad university Tehran, Tehran, Iran 5- PhD Department of biology, Faculty of Science, Islamic Azad University, North Branch Tehran, Tehran, Iran, Department of biology, Faculty of Science, Islamic Azad University, North Branch Tehran, Tehran, Iran
Abstract: (613 Views)
ABSTRACT Backgroundandobjectives: Synthesis and characterization of several metal complexes (metal ions: Co2+, Ti4+ and Ce3+) of macroacyclic Schiff base ligand have been reported. The Schiff base ligand is prepared from the condensation reaction of 1, 4-di-(4-fluoro-2-aminophenoxy) butane with salicylaldehyde in ethanol. In addition, antibacterial activity of metal ions, Schiff base ligand and their complexes have been investigated. Recent studies show that many Schiff base complexes have antibacterial activity against Gram-positive and Gram-negative bacteria. Therefore, we aimed to synthesize new Schiff base complexes and evaluate their antibacterial activity against a number of Gram-positive and Gram-negative bacteria. Methods: Schiff base ligand and their complexes were characterized by mass spectrometry and IR, H-NMR and C-NMR spectroscopy. The in vitro antibacterial activity of the Schiff base ligand, metal ions and their complexes were evaluated against some Gram-positive and Gram-negative bacteria by disk diffusion method and determining minimum inhibitory concentration. Results: In this study, the Schiff base complexes had good antibacterial activity, but the Schiff base ligand and metal ions did not show any antibacterial effect. In some cases, the antibacterial effect of the complexes was higher than that of the standard antibiotics tetracycline and gentamycin. The titanium complex showed the highest antibacterial activity in both methods. This complex created the largest growth inhibition zone (diameter: 100mm) against Staphylococcus aureus, and had the lowest minimum inhibitory concentration against Bacillus subtilis (6.75 mg/ml). Conclusion: The compounds synthesized in our study have strong antibacterial activity. Keywords: Schiff base complex, Schiff base ligand, antibacterial activity, Staphylococcus aureus, Bacillus subtilis.
Type of Study: Original Paper |
Subject: Special Received: 2017/08/2 | Accepted: 2017/08/2 | Published: 2017/08/2
1. Gupta KC, Sutar AK. Catalytic activities of Schiff base transition metal complexes. Coordination Chemistry Reviews. 2008; 252(12): 1420-1450. [DOI:10.1016/j.ccr.2007.09.005]
2. Wadher SJ, Puranik MP, Karande NA, Yeole PG. Synthesis and biological evaluation of Schiff base of dapsone and their derivative as antimicrobial agents. International Journal of PharmTechResearch. 2009; 1(1): 22-33.
3. Sinha D, Tiwari AK, Singh S, Shukla G, Mishra P, Chandra H, Mishra AK. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. European journal of medicinal chemistry. 2008; 43 (1): 160-5. [DOI:10.1016/j.ejmech.2007.03.022]
4. Bhargavi G, Rajasekharan MV, Costes JP, Tuchagues JP. Synthesis, crystal structure and magnetic properties of dimeric Mn(III) Schiff base complexes including pseudohalide ligands: Ferromagnetic interactions through phenoxo bridges and single molecule magnetism. Polyhedron. 2009; 28(7): 1253-1260. [DOI:10.1016/j.poly.2009.02.024]
5. da Silva CM, da Silva DL, Modolo LV, Alves RB, deResende MA, Martins CVB, et al. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research. 2011; 2(1): 1-8. [DOI:10.1016/j.jare.2010.05.004]
6. Singh K, Barwa MS, Tyagi P. Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone. Polyhedron. 2006; 41(1): 147-153. [DOI:10.1016/j.ejmech.2005.06.006]
7. Keypour H, Shayesteh M, Rezaeivala M, Chalabian F, Elerman Y, Buyukgungor O. Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu (II), Ni (II) Co (II), Zn (II), and Cd (II) complexes of a new potentially hexadentate N2O4 Schiff base ligand. Journal of Molecular Structure. 2013; 1032(2): 62-69. [DOI:10.1016/j.molstruc.2012.07.056]
8. Keypour H, Shayesteh M, Rezaeivala M, Chalabian F, Valencia L. Synthesis and characterization of a series of transition metal complexes with a new symmetrical polyoxaaza macroacyclic Schiff base ligand: X-ray crystal structure of cobalt (II) and nickel (II) complexes and their antibacterial properties. SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy. 2013; 101 (1) 59-66. [DOI:10.1016/j.saa.2012.09.048]
9. Khanmohammadi H, Amani S, Abnosi MH, Khavasi HR. New asymmetric heptaaza Schiff base macrocyclic complex of Mn(II): Crystal structure, biological and DFT studies, SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy. 2010; 77(2)342-347. [DOI:10.1016/j.saa.2010.02.001]
10. Faridbod F, Ganjali MR Dinarvand, R, Norouzi P, Riahi S. Schiff's bases and crown ethers as supramolecular sensing materials in the construction of potentiometric membrane sensors. Sensors. 2008; 8 (3): 1645-1703. doi: 10.3390/s8031645. [DOI:10.3390/s8031645]
11. Rosu T, Pahontu E, Maxim C, Georgescu R, Stanica N, Almajan GL, et al. Synthesis, characterization and antibacterial activity of some new complexes of Cu(II), Ni(II), VO(II), Mn(II) with Schiff base derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one. Polyhedron. 2010; 29(2): 757-766. [DOI:10.1016/j.poly.2009.10.017]
12. Cimernman Z, Galic N, Bosner B. The Schiff bases of salicylaldehyde and aminopyridines as highly sensitive analytical reagents. Analyticachimicaacta. 1997; 343(1): 145-153. [DOI:10.1016/S0003-2670(96)00587-9]
13. Yousifa EA, Majeeda AS, Salih NA. Synthesis, characterization and preliminary in vitro antibacterialscreening activity of metal complex derivatives of2-[(5-styryl-[1,3,4]thiadiazol-2-ylimino)-methyl]-phenol. Taibah University for Science. 2014; 8(1): 26-30. [DOI:10.1016/j.jtusci.2013.09.003]
14. hat MA,Al-Omar MA, Siddiqui N. Antimicrobial activity of Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives: an in vitro evaluation. Medicinal Chemistry Research. 2013; 22(9): 4455-4458. [DOI:10.1007/s00044-012-0452-9]
15. Shukla S, Srivastava RS, Shrivastava SK, Sodhi A, Kumar P. Synthesis, characterization, in vitro anticancer activity, and docking of Schiff bases of 4-amino-1,2-naphthoquinone. Medicinal Chemistry Research. 2013; 22(4): 1604-1617. [DOI:10.1007/s00044-012-0150-7]
16. Nair MS, Arish D, Joseyphus RS. Synthesis, characterization, antifungal, antibacterial and DNA cleavage studies of some heterocyclic Schiff base metal complexes. Saudi Chemical Society. 2012; 16(1): 83-88. [DOI:10.1016/j.jscs.2010.11.002]
17. Basak S, Sen S, Banerjee S, Mitra S, Rosair G, Rodriguez MTG. Three new pseudohalide bridged dinuclear Zn(II) Schiff base complexes: Synthesis, crystal structures and fluorescence studies. Polyhedron. 2007; 26(17): 5104-5112. [DOI:10.1016/j.poly.2007.07.025]
18. Nayak S, Gamez PP, Kozlevcˇar B, Pevec AA, Roubeau O, Dehnen S, et al. Coordination compounds from the planar tridentate Schiff-base ligand 2-methoxy-6-((quinolin-8-ylimino)methyl)phenol (mqmpH) with several transition metal ions: Use of [FeIII(mqmp)(CH3OH)Cl2] in the catalytic oxidation of alkanes and alkenes. Polyhedron. 2010; 29(11): 2291-2296. [DOI:10.1016/j.poly.2010.04.035]
19. Siddiqi KS, Khan S, Nami SAA, El-ajaily MM. Polynuclear transition metal complexes with thiocarbo -hydrazide and dithiocarbamates. Spectrochimica Acta. 2007; 67(3): 995-1002. [DOI:10.1016/j.saa.2006.09.019]
20. Desai RM, Shah RM, Shah VH. Preparation and Antimicrobial Screening of Cu (II), Ni (II), Zn (II), Cd (II) Complexes. EJournal of chemistry. 2006; 3(12): 137-141. [DOI:10.1155/2006/897673]
21. Brooks GF, Carroll KC, Butel JS, Morse SA, Mietzner TA. Jawetz, Melnick & Adelberg's medical microbiology; 26th ed. New York: McGraw Hill. 2013; 209-222.
22. Gheibi N, Saboury A A, Mansuri TH. The inhibition effect of some n-alkyl dithiocarbamates on mushroom tyrosinase. Journal of Enzyme Inhibition and Medicinal Chemistry. 2005; 20(4): 393-399. [DOI:10.1080/14756360500179903]
23. Kosanic M, Rankovic B. Screening of antimicrobial activity of some lichen species in vitro. Kragujevac Journal of Science. 2010; 32(2): 65-72.
24. Sanez MT, Garcia MD, Rowe JG. Antibicrobial activity and phytochemical studies of some lichens from south of spain. Fitoterapia 2006; 77(3) 156-159. [DOI:10.1016/j.fitote.2005.12.001]
25. Mobinikhaledi A, Jabbarpour M. Preparation, characterization, and biological activity of some new Schiff bases derived from aminophenoxyalkyloxybenzenamines and salicylaldehyde in the presence of p-TSA, and their Zn(II) and Cu(II) complexes. Research on Chemical Intermediates. 2015; 41(2): 511-523. [DOI:10.1007/s11164-013-1205-1]
26. Patil M, Hunoor R, Gudasi K. Transition metal complexes of a new hexadentate macroacyclic N 2O 4-donor Schiff base: Inhibitory activity against bacteria and fungi. European Journal of Medicinal Chemistry. 2010; 45(7): 2981-2986. [DOI:10.1016/j.ejmech.2010.03.025]
27. Abdallah SM, Zayed MA, Mohamed GG. Synthesis and spectroscopic characterization of new tetradentate Schiff base and its coordination compounds of NOON donor atoms and their antibacterial and antifungal activity. Journal of Chemistry. 2010; 3(2): 103-113. [DOI:10.1016/j.arabjc.2010.02.006]
Tamoradi T, Goudarziafshar H, Rashki S, Katouzian F, Chalabian F. Synthesis of New Schiff Base Ligand and Its Complexes in The Presence of Some Transition Metal Ion and Evaluation of Their Antibacterial Properties. mljgoums. 2017; 11 (2) :5-10 URL: http://goums.ac.ir/mljgoums/article-1-969-en.html