Synthesis, characterization and antimicrobial activities of some metal(II) amino acids’ complexes

Temitayo Olufunmilayo Aiyelabola, Isaac Ayoola Ojo, Adeleke Clement Adebajo, Grace Olufunmilayo Ogunlusi, Olayinka Oyetunji, Ezekiel Olugbenga Akinkunmi, Adebowale Olusoji Adeoye

Adis Pharma Inc., 5238 Palmetto Place, Mississauga, ON L5M OC8, Canada.
Department of Chemistry, Faculty of Science, Obafemi Awolowo University, Ile-Ife, Nigeria.
Department of Chemistry, University of Botswana, Gaborone, Botswana.
Department of Pharmaceutics, Faculty of Pharmacy, Obafemi Awolowo University, Ile-Ife, Nigeria.
Department of Pharmacognosy, Faculty of Pharmacy, Obafemi Awolowo University, Ile-Ife, Nigeria.

DOI: 10.4236/abc.2012.23034                

Abstract

Metal(II) coordination compounds of glycine and ph-enylalanine were synthesized and characterized using infrared and electronic spectroscopic, and magnetic susceptibility measurements. The complexes were tested for antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Methicillin Resistant Staphy-lococcus aureus (MRSA), Escherichia coli, Pseudo-monas aeruginosa, Proteus vulgaris and Candida albicans. The stoichiometric reaction between the metal (II) ions and ligands in molar ratio M:L (1:3) [where M = Mn, Co, Ni, Cu and Cd; L= glycine; phenylalanine] resulted in the formation of five-coordinate square pyramidal dinuclear geometry for both copper complexes and six-coordinate octa-hedral geometry for the other complexes. The spectroscopic and magnetic moment data suggested that the ligands coordinated via both their amino and carboxylate ion moieties. The complexes demonstrated better activities against one or more of the tested microbes than acriflavine, the standard drug used.

Keywords

Glycine; Phenylalanine; Coordination Compound; Antimicrobial; Chelation

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Saha, S., Dhanasekaran, D., Chandraleka, S., Thajuddin, N. and Panneerselvam, A. (2010) Synthesis, characterization and antimicrobial activity of cobalt metal complexes against drug resistant bacterial and fungal pathogens. Advances in Biological Research, 4, 224-229.
[2]	Mulligan, M.E. and Murray-Leisure, K. (1993) Methicillin-resistant Staphylococcus aureus: A consensus review of the microbiology, pathogenesis, and epidemiology with implications for prevention and management. American Journal of Medicine, 94, 313-328. Hdoi:10.1016/0002-9343(93)90063-U
[3]	Farrell, N. (2003) Metal complexes as drugs and chemotherapeutic agents. Comprehensive Coordination Chemistry, 9, 809-840.
[4]	Faúndez, G., Troncoso, M., Navarrete, P. and Figueroa, G. (2004) Antimicrobial activity of copper surfaces against suspensions of Salmonella enterica and Campylobacter jejuni. Bio-Medical Central Microbiology, 4, 19-26.
[5]	Johari, R., Kumar, G., Kumar, D. and Singh, S. (2009) Synthesis and antibacterial activity of M(II) schiff-base complex. Journal of the Indian Chemistry Council, 26, 23-27.
[6]	Chang, E., Simmers, C. and Knight, A., (2010) Cobalt complexes as antiviral and antibacterial agents. Pharmaceuticals, 3, 1711-1728. Hdoi:10.3390/ph3061711
[7]	Husseiny, A.F., Aazam, E.S. and Al Shebary, J. (2008) Synthesis, characterization and antibacterial activity of schiff-base ligand incorporating coumarin moiety and it metal complexes. Inorganic Chemistry, 3, 64-68.
[8]	Chohan, Z.H., Arif, M., Akhtar, M.A. and Supuran, C.T. (2006) Metal based antibacterial and antifungal agents: Synthesis, characterization and in-vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds. Bioinorganic Chemistry and Applications, 2006, 1-11. Hdoi:10.1155/BCA/2006/83131
[9]	Rehman, S., Ikram, M., Rehman, S., Faiz, A. and Shahnawaz, A. (2010) Synthesis, characterization and antimicrobial studies of transition metal complexes of imidazole derivative. Bulletin of Chemical Society of Ethiopia, 24, 201-207.
[10]	Nomiya, K., Takahashi, S., Noguchi, R., Nemoto, S., Takayama, T. and Oda, M. (2000) Synthesis and characterization of water-soluble silver(I) complexes with L- histidine (H2his) and (S)-(-)-2-pyrrolidone-5-carboxylic acid (H2pyrrld) showing a wide spectrum of effective antibacterial and antifungal activities. Crystal structures of chiral helical polymers [Ag(Hhis)]n and {[Ag(Hpyrrld)]2}n in the solid state. Inorganic Chemistry, 39, 3301-3311. Hdoi:10.1021/ic990526o
[11]	Legler, A., Kazachenko, A., Kazbanov, V. and Per’ yanova, O. (2001) Synthesis and antimicrobial activity of silver complexes with arginine and glutamic acid. Pharmaceutical Chemistry, 35, 35-36. Hdoi:10.1023/A:1014098810078
[12]	Aiyelabola, T., Ojo, I. and Akinkunmi, O. (2012) Structural and antimicrobial studies of coordination compounds of phenylalanine and glycine. International Journal of Chemistry, 4, 49-59. Hdoi:10.5539/ijc.v4n2p49
[13]	Nomiya, K. and Yokoyama, H. (2002) Synthesis, crystal structures anti antimicrobial activities of polymeric silver(I) complexes with three amino-acids [aspartic acid (H2asp), glycine (Hgly) and asparagines (Hasn)]. Journal of Chemical Society, Dalton Transaction, 2483-2490. Hdoi:10.1039/b200684g
[14]	Murray, P.R., Baroon, E.J., Pfaller, M.A., Tenover, F.C. and Yolke, R.H. (1995) Manual of clinical microbiology. 6th Edition, American Society for Microbiology, Washington DC, 56-77.
[15]	Youssef, N.S. and Hegab, K.H. (2005) Synthesis and Characterization of Some Transition Metal complexes of thiosemicarbazones derived from 2-acetylpyrrole and 2- acetylfuran. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 35, 391-399. Hdoi:10.1081/SIM-200059215
[16]	Greenwood, N.N. and Earnshaw, A. (1997) Coordination compounds. Butterworth-Heinemann, Hong Kong, 1060- 1090.
[17]	Osowole, A. (2011) Synthesis, characterization and magnetic and thermal studies on some metal(II) thiophenyl schiff base complexes. International Journal of Inorganic Chemistry, 2011, 1-7. Hdoi:10.1155/2011/650186
[18]	Dawood, Z.F., Mohammed, T.J. and Sharif, M.R. (2009) New nickel(II) complexes with benzilbis (semicarbazone) and dithiocarbamate ligands. Iraqi Journal of Veterinary Sciences, 23, 135-141.
[19]	Osowole, A.A., Woods, J.A.O. and Odunola, O.A. (2000). Synthesis and characterization of synthesis and physico-chemical properties of some copper(ii) β-ketoamines and their adducts with 2,2-bipyridine and 1,10-phenan- throline.some nickel(II) β-ketoamines and their adducts with 2,2-bipyridine and 1,10-phenanthroline. Synthesis and Reactivity of Inorganic and Metal Organic Chemistry, 32, 783-799. Hdoi:10.1081/SIM-120004446
[20]	Ballhausen, C.J. (1962) An introduction to ligand field theory. McGraw Hill, New York.
[21]	Sathisha, M., Revankar, V. and Pai, K. (2008) Synthesis, structure, electrochemistry and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against Ehrlich ascites carcinoma in Swiss albino mice. Metal Based Drugs, 2008, 362-375.
[22]	Miessler, G.L. and Tarr, D.A. (1999) Coordination compounds. Pearson Prentice Hall, New York, 315-316.
[23]	Cotton, F.A. and Wilkinson, G. (1981) Advanced inorganic chemistry. John Wiley and Sons, New York, 628- 816.
[24]	Lever, A.B.P. (1986) Inorganic electronic spectroscopy. Elsevier, London, 481-579
[25]	Fessenden, R.J. and Fessenden, J.S. (1990) Organic chemistry. Harness and Nabie Inc., 1048.
[26]	Nakamoto, K. (2009) Complexes of amino acids. In: K. Nakamoto, Ed., Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York, 66-74.
[27]	Elzahany, E.A., Hegab, K.H., Safaa, K.H. and Youssef, N.S. (2008) Synthesis, characterization and biological activity of some transition metal complexes with Schiff Bases derived from 2-formylindole, salicyladehyde and N-amino rhodanine. Australian Journal of Basic and Applied Sciences, 2, 210-220.
[28]	Fahmideh, S., Lotf, A.S. and Shahriar, G. (2010) Synthesis, characterization and anti-tumour activity of Fe(III) schiff base complexes with unsymmetric tetradentate li- gands. Bulletin of Chemical Society of Ethiopia, 24, 193- 199.
[29]	Konstantinovic, S., Radovanovic, C., Cakic, Z. and Vasic, V. (2003) Synthesis and characterization of Cd(II), Ni(II), Cu(II) and Zn(II) complexes with 3-salicylidenehydra- zono-2-indolinone. Journal of the Serbian Chemical Society, 68, 641-647. Hdoi:10.2298/JSC0309641K
[30]	Pavia, D., Lampman G. and Kriz G. (2001) Introduction to spectroscopy, a guide for students of organic chemistry. Brooks and Cole, Florence.
[31]	Saunders, D.L. (2009) Isolation of lead-amino acid and mercury-amino acid complexes with characterization in the solid state, the solution state, and the gas phase. Ph.D. Thesis, Department of Chemistry, Dalhousie University, Halifax.
[32]	Ibrahim, M., Wang, F., Lou, M., Xie, G., Li, B., Bo, Z., Zhang, G., Liu, H. and Wareth, A. (2011) Copper as an antibacterial agent for human pathogenic multidrug resistant Burkholderia cepacia complex bacteria. Journal of Bioscience and Bioengineering, 112, 570-576. Hdoi:10.1016/j.jbiosc.2011.08.017
[33]	Abushelaibi, A. (2005) antimicrobial effects of copper and brass ions on the growth of Listeria Monocytogenes at different temperatures, pH and nutrients. Ph.D. Thesis, Department of Food Science, Agricultural and Mechanical College, Louisiana State University, Louisiana.
[34]	Centre for Applied Microbiology and Research (2000) Hhttp://www.copper.org/about/pressreleases/2000/DemonstratePotential.html
[35]	Copper Development Centre (2004) Antimicrobial: Copper. Hhttp://www.copper.org.sg/publications/cca/0309/pg06_japan_research.html
[36]	Kabbani, A.T., Hammud, H.H. and Ghannoum, A.M. (2007) Preparation and antibacterial activity of copper and cobalt complexes of 4-chloro-3-nitrobenzoate with a nitrogen donor ligand. Pharmaceutical Chemistry Bulletin, 55, 446-450. Hdoi:10.1248/cpb.55.446
[37]	Chohan, Z.H., Scozzafava, A. and Supuran, C.T. (2006) Synthesis of biologically active Co(II), Cu(II), Ni(II) and Zn(II) complexes of symmetrically 1,1’-disubstituted fer- rocene derived compounds. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33, 241-257. Hdoi:10.1081/SIM-120017783
[38]	Chohan, Z.H., Farooq, M.A., Scozzafava, A. and Supuran, C.T. (2002) Antibacterial schiff bases of oxalyl-hydrazine; diamide incorporating pyrrolyl and salicylyl moieties and of their zinc(II). Journal of Enzyme Inhibition and Medicinal Chemistry, 17, 1-7. Hdoi:10.1080/14756360290005598
[39]	Garba, S. and Salihu, L. (2011) Antibacterial activities of 2-O-butyl-1-O-(2’-ethylhexyl) benzene-1,8-dicarboxylate and 1-phenyl-1,4-pentanedione isolated from Vitellaria paradoxa root bark. Asian Journal of Scientific Research, 4, 149-157. Hdoi:10.3923/ajsr.2011.149.157
[40]	Stanila, A., Marcu, A., Rusu, D., Rusu, M. and David, L. (2007) Spectroscopic studies of some copper (II) complexes with amino acids. Journal of Molecular Structure, 364-368. Hdoi:10.1016/j.molstruc.2006.11.048