Synthesis, Characterization and in Vitro Antimicrobial Screening of the Xanthate Derivatives and their Iron(II) Complexes

Document Type: Research Article

Authors

1 Department of Chemistry, University of Sistan and Baluchestan, Zahedan, I.R. IRAN

2 Department of Nanotechnology and Advanced Materials, Materials and Energy Research Center, Karaj, I.R. IRAN

3 Department of Biology and Microbiology, University of Sistan and Baluchestan, Zahedan, I.R. IRAN

4 Islamic Azad University, Neyshabur Branch, Neyshabur, I.R. IRAN

Abstract

Seven reported xanthate ligands and their new Fe(II) complexes of formulaNa[Fe(R-OCSS)3], where R is ethyl-, propyl-, butyl-, pentyl-, Hexyl-, heptyl- and octyl-xanthate have been synthesized. They have been characterized using elemental analysis, molar conductance, FT-IR, UV-Vis and 1H NMR spectroscopic techniques and melting-, decomposition-points for ligands and complexes respectively. All the ligands and their Fe(II) complexes have been evaluated for their antimicrobial activity against four gram-positive bacteria, four gram-negative bacteria and three fungi by agar disc diffusion technique. The MIC values of the compounds exhibited significant antifungal activity but showed lower antibacterial activity. The iron(II) complexes are found to possess higher antimicrobial activity than their counterpart ligands thus improving its antimicrobial efficacy. Hydrocarbon chain length of the ligands coordinated to Fe(II) centers seemed to be important for their antifungal as well as antibacterial activities.

Keywords

Main Subjects


[1] Antonio F.S., Débora F.B., Lis R.V. F., Natália A.C., Geziel R.A., Margareth B., Alberto A.C., Ademir N., Daniela C.M.R., Ademir D.A., Study of the Antimicrobial Activity of Metal Complexes and Their Ligands Through Bioassays Applied to
Plant Extracts
, Rev. Bras. Farmacogn., 24: 309-315 (2014).

[2] Bouchoucha A., Terbouche A., Zaouani M., Derridj F., Djebbar S., Iron and Nickel Complexes with Heterocyclic Ligands: Stability, Synthesis, Spectral Characterization, Antimicrobial Activity, Acute and Subacute Toxicity, J. Trace Elem. Med Biol.,27: 191-202 (2013).

[3] Sabounchei S.J., Pourshahbaz M., Salehzadeh S., Bayat M., Karamian R., Asadbegy M., Khavasi H.R., New Chlorine Bridged Vinuclear Silver(I) Complexes of Bidentate Phosphorus Ylides: Synthesis, Spectroscopy, Theoretical and Anti-Bacterial Studies, Polyhedron, 85: 652-664 (2015).

[6]  Alijanianzadeh M., Saboury A.A., Mansuri-Torshizi H., Haghbeen K., Moosavi-Movahedi A.A., The Inhibitory Effect of Some New Synthesized Xanthates on Mushroom Tyrosinase Activities, J. Enzyme Inhibition and Medicinal Chemistry, 22: 239-246 (2007).

[8]  Saboury A.A., Alijanianzadeh M., Mansouri- Torshizi H., The Role of Alkyl Chain Length in the Inhibitory Effect n-alkyl Xanthates on Mushroom Tyrosinase Activities, Acta Biochim. Pol., 54: 183-191 (2007).

[9] Geraldo M.D., Daniele C.M., Camila A.C., Jaqueline A.F.d., Isabella P.F., Eucler B.P., James L.W., Solange M.S.V.W., Klaus K., Isolda C.M., Heloisa B., Synthesis, Characterisation and Biological Aspects of Copper(II) Dithiocarbamate Complexes, [Cu{S2CNR(CH2CH2OH)}2], (R=Me, Et, Pr and CH2CH2OH), J. Mol. Struct, 988: 1-8 (2011).

[13] Saad E.A., Hasan A.M., Synthesis and Characterization of Mn(II), Fe(II) and Co(II) Complexes with 4-Hydroxypiperidinedithiocarbamate and their Adducts with Neutral Bases, Raf. J. Sci., 25: 53-61 (2014).

[16] Núñez C., Fernández-Lodeiro A., Fernández-Lodeiro J., Carballo J., Capelo J.L., Lodeiro C., Synthesis, Spectroscopic Studies and in Vitro Antibacterial Activity of Ibuprofen and Its Derived Metal Complexes, Inorg. Chem. Commun., 45: 61-65 (2014).

[17] Xu B., Kong X.L., Zhou T., Qiu D.H., Chen Y.L., Liu M.S., Yang R.H., Hider R.C., Synthesis, Iron(III)-Binding Affinity and in Vitro Evaluation of 3-Hydroxypyridin-4-One Hexadentate Ligands as Potential Antimicrobial Agents, Bioorg. Med. Chem. Let., 21: 6376-6380 (2011).

[20] Nakamoto K., “Infrared and Raman Spectra of Inorganic And Coordination Compound”, 4th ed. New York. John Wiley and sons. (1986).

[21] Damian C.O.,Tanvir A., Christien A.S., Fe(II) and Fe(III) Complexes of N-ethyl-N-phenyl Dithiocarbamate: Electrical Conductivity Studies and Thermal Properties, Electrochimica Acta, 127: 283-289 (2014).

[22] Narges A., Hassan M.T., Maryam N., Farshad H. Sh., Cytotoxicity of Diimine Palladium (II) Complexes of Alkyldithiocarbamate Derivatives on Human Lung, Ovary and Liver Cells, I. J. Pharm. Res., 11: 689-695 (2012).

[23] Nabipour H., Ghammamy S., Ashuri Sh., Aghbolagh Z. Sh., Synthesis of a New Dithiocarbamate Compound and Study of Its Biological Properties, Org. Chem. J., 2: 75-80 (2010).

[24] Jayaraju A., Musthak Ahamad M., Rao R.M., Sreeramulu J., Synthesis, Characterization and Biological Evaluation of Novel Dithiocarbamate Metal Complexes, Der. Pharma. Chemica., 4: 1191-1194 (2012).

[26] Yahui Z., Zhao C., Yongdan C., Chuanyao S., FTIR Studies of Xanthate Adsorption on Chalcopyrite, Pentlandite and Pyrite Surfaces, J. Mol. Struct., 1048: 434-440 (2013).

[28] Nicholas G. S., Eric A.S., Ian R.Sh., Benjamin L.I., Bryan D., Sylvanna V.K., Benjamin F. Gh., Atta M.A., Eric C.B., Synthesis of Zinc and Cadmium O-Alkyl Thiocarbonate and Dithiocarbonate Complexes and a Cationic Zinc Hydrosulfide Complex, Inorganica. Chimica. Acta., 386: 83-92 (2012).

[30] Yu-Wen L., Shu-Tao L., Facile Synthesis and Antifungal Activity of Dithiocarbamate Derivatives Bearing an Amide Moiety, J. Serb. Chem. Soc., 80: 1367-1374 (2015).

[31] Loth M., Meddah B., TirTouil A., Len C., Verstraete W., Antifungal Activity of Synthesized Dithiocarbamate Derivatives on Fusariumoxysporum f sp. Albedinisin Algeria, J. Chem. Pharm. Res., 7: 49-53 (2015).

[32] Yamini Y., Tamaddon T., Sensing of Iron by Solid Phase Spectrophotometry, Iran. J. Chem.Chem. Eng. (IJCCE), 21: 91-96 (2002).