Synthesis of Cu(II), Ni(II), Co(II), and Mn(II) Complexes with Ciprofloxacin and Their Evaluation of Antimicrobial, Antioxidant and Anti-Tubercular Activity

Ketan S. Patel, Jiten C. Patel, Hitesh R. Dholariya, Vishal K. Patel, Kanuprasad D. Patel

Chemistry Department, Shree P. M. Patel College of Peramedical Science & Technology, Sardar Patel University, Gujarat- India.
Chemistry Department, V. P. & R. P. T. P. Science College, Sardar Patel University, Vallabh Vidhyanagar, Gujarat-India.

DOI: 10.4236/ojmetal.2012.23008                

Abstract

Co(II), Ni(II), Cu(II) and Mn(II) complexes synthesized by reflux of 6-bromo-3-(3-(4-chlorophenyl)acryloyl)-2H- chromen-2-one, Ciprofloxacin and various transition metal. ¹H, ¹³C, IR and ESI Mass confirm the formation of ligand. The metal complexes were characterized on the basis of various spectroscopic techniques like IR studies and elemental analysis while the geometry of complexes was octahedral which is confirmed by electronic spectra and thermogravimetric analysis. The compounds were subjected to antimicrobial, antioxidant and anti-tubercular activity screening using serial broth dilution method and Minimum Inhibitory Concentration (MIC) is determined. Mn(II) complex has shown significant antifungal activity with an MIC of 6.25 μg/ml while Cu(II) complex is noticeable for antibacterial activity at the same concentration. Anti-TB activity of the ligand has enhanced on complexation with Ni(II) and Co(II) ions. While Ni(II) complex shows superior antioxidant activity than other complexes.

Keywords

Transition Metal Complex; Ciprofloxacin; Biological Activity

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	E. L. Que, D. W. Domaille and C. J. Chang, “Metals in Neurobiology: Probing Their Chemistry and Biology with Molecular Imaging,” Chemical Reviews, Vol. 108, No. 5, 2008, pp. 1517-1549.
[2]	A. W. Czarnik, “Desperately Seeking Sensors,” Chemistry & Biology, Vol. 2, No. 7, 1995, pp. 423-428.
[3]	K. W. Huang, H. Yang, Z. G. Zhou, M. X. Yu, F. Y. Li, X. Gao, T. Yi and C. H. Huang, “Multisignal Chemosensor for Cr3+ and Its Application in Bioimaging,” Organic Letters, Vol. 10, No. 12, 2008, pp. 2557-2560.
[4]	I. Kostova, I. Manolov, S. Konstantinov and M. Karaivanova, “Synthesis, Physicochemical Characterisation and Cytotoxic Screening of New Complexes of Cerium, Lanthanum and Neodymium with Warfarin and Coumachlor Sodium Salts,” European Journal of Medicinal Chemistry, Vol. 34, No. 1, 1999, pp. 63-68.
[5]	I. Kostova, I. Manolov, I. Nicolova and N. Danchev, “New Metal Complexes of 4-Methyl-7-hydroxycoumarin Sodium Salt and Their Pharmacological Activity,” II Farmaco, Vol. 56, No. 9, 2001, pp. 707-713.
[6]	I. Kostova, I. Manolov, I. Nicolova, S. Konstantinov and M. Karaivanova, “New Lanthanide Complexes of 4Methyl-7-Hydroxycoumarin and Their Pharmacological Activity,” European Journal of Medicinal Chemistry, Vol. 36, No. 4, 2001, pp. 339-347.
[7]	W. Martindale, “Martindale—The Extra Pharmacopeia,” 30th Edition, The Pharmaceutical Press, London, 1993.
[8]	P. Ball, “The Quinolones,” Academic Press, San Diego, 2000.
[9]	G. Sheehan, N. S. Y. Chew, “The History of Quinolones” In: A. R. Ronald, D. E. Low, Eds., Fluoroquinolone Antibiotics, Birkhauser, Basel, 2003, pp. 1-10.
[10]	I. Turel, “The Interactions of Metal Ions with Quinolone Antibacterial Agents,” Coordination Chemistry Reviews, Vol. 232, No. 1-2, 2002, pp. 27-47.
[11]	B. E. Scully, M. Nakatomi, C. Ores, S. Davidson, H. C. Neu, “Ciprofloxacin Therapy in Cystic Fibrosis,” The American Journal of Medicine, Vol. 82, No. 4A, 1987, pp. 196-201.
[12]	Z. A. Siddiqi, M. Khalid, S. Kumar, M. Shahid and S. Noor, “Antimicrobial and SOD Activities of Novel Transition Metal Complexes of Pyridine-2,6-dicarboxylic Acid Containing 4-Picoline as Auxiliary Ligand,” European Journal of Medicinal Chemistry, Vol. 45, No. 1, 2010, pp. 264-269.
[13]	S. Delaney, M. Pascaly, P. K. Bhattacharya, K. Han and J. K. Barton, “Oxidative Damage by Ruthenium Complexes Containing the Dipyridophenazine Ligand or Its Derivatives: A Focus on Intercalation,” Inorganic Chemistry, Vol. 41, No. 7, 2002, pp. 1966-1974.
[14]	K. Serbest, A. Colak, S. Güner, S. Karab?cek and F. Kormali, “Copper(II)—Manganese(II) Complexes of 3,3’-(1,3Propanediyldiimine)bis-(3-methyl-2-butanone)dioxime with Superoxide Dismutase-Like Activity,” Transition Metal Chemistry, Vol. 26, No. 6, 2001, pp. 625-629.
[15]	A. I. Vogel, “Textbook of Practical Organic Chemistry,” 5th Edition, Longman, London, 1989.
[16]	G. Wanare, R. Aher, N. Kawathekar, R. Ranjan and N. K. Kaushik, “Synthesis of Novel α-Pyranochalcones and Pyrazoline Derivatives as Plasmodium Falciparum Growth Inhibitors,” Bioorganic & Medicinal Chemistry Letters, Vol. 20, No. 15, 2010, pp. 4675-4678.
[17]	O. M. Abdelhafez, K. M. Amin, R. Z. Batran, T. J. Maher, S. A. Nada and S. Sethumadhvan, “Synthesis, Anticoagulant and PIVKA-II Induced by New 4-Hydroxycoumarin Derivatives Original Research Article,” Bioorganic & Medicinal Chemistry, Vol. 18, No. 10, 2010, pp. 33713378.
[18]	D. H. Jani, H. S. Patel, H. Keharia and C. K. Modi, “Novel Drug-Based Fe(III) Heterochelates: Synthetic, Spectroscopic, Thermal and in-Vitro Antibacterial Significance,” Applied Organometallic Chemistry, Vol. 24, No. 2, 2010, pp. 99-111.
[19]	R. Wise, J. M. Andrews and J. P. Ashby, “Activity of Daptomycin against Gram-Positive Pathogens: A Comparison with Other Agents and the Determination of a Tentative Breakpoint,” Journal of Antimicrobial Chemotherapy, Vol. 48, No. 4, 2001, pp. 563-567.
[20]	I. F. F. Benziea and J. J. Strain, “The Ferric Reducing Ability of Plasma (FRAP) as a Measure of ‘Antioxidant Power’: The FRAP Assay,” Analytical Biochemistry, Vol. 239, No. 1, 1996, pp. 70-76.
[21]	I. Kostova, G. Momekov, M. Zaharieva and M. Karaivanova, “Cytotoxic Activity of New Lanthanum (III) Complexes of Bis-Coumarins,” European Journal of Medicinal Chemistry, Vol. 40, No. 6, 2005, pp. 542-551.
[22]	P. George, “Mononuclear Metal Complexes with Ciprofloxacin: Synthesis, Characterization and DNA-Binding Properties,” Journal of Inorganic Biochemistry, Vol. 102, No. 12, 2008, pp. 1798-1811.
[23]	J. R. Anacona and I. J. Rodriguez, “Synthesis and AntiBacterial Activity of Cephalexin Metal Complexes,” Journal of Coordination Chemistry, Vol. 57, No. 15, 2004, pp. 1263-1269.
[24]	I. Leban, I. Turel and N. Bukovec, “Crystal Structure and Characterization of the Bismuth(III) Compound with Quinolone Family Member (Ciprofloxacin). Antibacterial Study,” Journal of Inorganic Biochemistry, Vol. 66, No. 4, 1997, pp. 241-245.
[25]	K. S. Patel, J. C. Patel, H. R. Dholariya and K. D. Patel, “Multiple Heating Rate Kinetic Parameters, Thermal, X-Ray Diffraction Studies of Newly Synthesized Octahedral Copper Complexes Based on Bromo-Coumarins along with Their Antioxidant, Anti-Tubercular and Antimicrobial Activity Evaluation,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 96, 2012, pp. 468-479.
[26]	J. C. Patel, H. R. Dholariya, K. S Patel and K. D. Patel, “Spectral, Thermal, Biological and Multi-Heating Rate Kinetic Properties of Cu(II) Complexes Containing N2O2 Donor Ligands: 1,10-Phenanthroline and Acyl Coumarins,” Applied Organometallic Chemistry.
[27]	P. K. Panchal and M. N. Patel, “Toxic Effect of Transition Metal Complexes on Salmonella Typhi, Escherichia Coli and Serratia Marcescens,” Toxicological & Environmental Chemistry, Vol. 87, No. 3, 2005, pp. 407-414.
[28]	K. B. Gudasi, M. S. Patil, R. S. Vadavi, R. V. Shenoy, S. A. Patil and M. Nethaji, “X-Ray Crystal Structure of the N-(2-hydroxy-1-naphthalidene)phenylglycine Schiff Base. Synthesis and Characterization of Its Transition Metal Complexes,” Chemistry and Materials Science, Vol. 31, No. 5, 2006, pp. 580-585.
[29]	K. C. Patel and D. E. Goldberg, “Aralkylpolyamine Complexes-III: Some Thiocyanate and Selenocyanate Complexes of Copper(II), Nickel(II) and Cobalt(II) with n-benzylethylenediamine and N,N’-dibenzylethylenediamine,” Journal of Inorganic and Nuclear Chemistry, Vol. 34, No. 2, 1972, pp. 637-649.
[30]	A. L. Abuhijleh, C. Woods and I. Y. Ahmed, “Synthesis and Molecular Structure of Monomeric Copper(II) Acetates with 2-Methylimidazole and 1,2-Dimethylimidazole,” Inorganica Chimica Acta, Vol. 190, No. 1, 1991, pp. 11-17.
[31]	D. P. Singh, R. Kumar, V. Malik and P. Tyagi, “Synthesis and Characterization of Complexes of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) with Macrocycle 3,4,11,12Tetraoxo-1,2,5,6,9,10,13,14-octaaza-cyclohexadeca-6,8,14,16-tetraene and Their Biological Screening,” Transition Metal Chemistry, Vol. 32, No. 8, 2007, pp. 10511055.
[32]	M. C. Jain, A. K. Shrivastava and P. C. Jain, “Some Tetragonally Distorted Copper(II) Complexes of 4-Benzylamidothiosemicarbazide and Its Thiosemicarbazone,” Inorganica Chimica Acta, Vol. 23, 1977, pp. 199-203.
[33]	E. Canpolat, A. Yciazi and M. Kaya, “Synthesis and Characterization of Mononuclear Cobalt(II), Nickel(II), Copper(II), Zinc(II), Cadmium(II) and Dinuclear Uranyl(VI) Complexes with N,N-bis(2-{[(2,2-dimethyl-1,3-dioxolan4-yl)methyl]amino}butyl)N’,N’-dihydroxyethanediimida-mide,” Transition Metal Chemistry, Vol. 31, No. 3, 2006, pp. 653-657.
[34]	A. M. Rahman, M. I. Choudhary and W. J. Thomsen, “Bioassay Techniques for Drug Development,” Harwood Academic, Netherlands, 2001.
[35]	J. Lv, T. T. Liu, S. Cai, X. Wang, L. Liu and Y. M. Wang, “Synthesis, Structure and Biological Activity of Cobalt(II) and Copper(II) Complexes of Valine-Derived Schiff Bases,” Journal of Inorganic Biochemistry, Vol. 100, No. 11, 2006, pp. 1888-1096.
[36]	Z. H. Chohan, C. T. Supuran and A. Scozzafava, “Metalloantibiotics: Synthesis and Antibacterial Activity of Cobalt(II), Copper(II), Nickel(II) and Zinc(II) Complexes of Kefzol,” Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 19, No. 1, 2004, pp. 79-84.