Synthesis, Characterization and Microbial Evaluation of Metal Complexes of Molybdenum with Ofloxacin (Levo (S-form) and Dextro (R-form)) Isomers
DOI:
https://doi.org/10.12970/2308-8044.2014.02.01.1Keywords:
Antibacterial, synthesis, levofloxacin, ofloxacin, molybdenum.Abstract
The article describes the interaction of molybdenum with dextrofloxacin and levofloxacin (isomers of ofloxacin) antibiotic drugs. Characterization of compounds was made by UV-Vis, FT–IR, 1H NMR, elemental and thermogravimetric analyses. The green colored Mo–dextrofloxacin and yellow colored Mo–levofloxacin complexes were isolated. After complete characterization, the chemical formulae of the complexes were established as [MoO2(R-Oflox)2] or [MoO2(Dextro)2] and [MoO2(Levo)2] or [MoO2(S-Oflox)2]. The microbial evaluation was made by well diffusion method for both ligands and their metal complexes against two bacterial strains, S. aureus and E. coli. It was observed that the antibacterial action of Mo–dextrofloxacin and Mo-levofloxacin was significantly higher than the dextrofloxacin and levofloxacin alone against S. aureus, while no action was observed against E. coli.
References
Ming L-J. Structure and function of “metalloantibiotics”. Med Res Rev 2003; 23: 697-762. http://dx.doi.org/10.1002/med.10052
Sabale PM, Kaur P, Patel Y, Patel J, Patel R. Metalloantibiotics in therapy: an overview. J Chem Pharm Res 2012; 4: 4921-36.
Wu G, Wang G, Fu X, Zhu L. Synthesis, crystal structure, stacking effect and antibacterial studies of a novel quaternary copper (II) complex with quinolone. Molecules 2003; 8: 287- 96. http://dx.doi.org/10.3390/80200287
Sadeek SA, El-Shwiniy WH. Metal complexes of the third generation quinolone antibacterial drug sparfloxacin: preparation, structure, and microbial evaluation. J Coord Chem 2010; 63: 3471-82. http://dx.doi.org/10.1080/00958972.2010.514049
Imran M, Iqbal J, Iqbal S, Ijaz N. In vitro antibacterial studies of ciprofloxacin–imines and their complexes with Cu(II),Ni(II),Co(II), and Zn(II). Turk J Biol 2007; 31: 67–72.
Shaikh AR, Giridhar R, Megraud F, Yadav MR. Metalloantibiotics: synthesis, characterization and antimicrobial evaluation of bismuth–fluoroquinolone complexes against Helicobacter pylori. Acta Pharm 2009; 59: 259-71. http://dx.doi.org/10.2478/v10007-009-0027-6
Obaleye JA, Akinremi CA, Balogun EA, Adebayo JO, Omotow AB. Synthesis, characterisation, antimicrobial and toxicological studies of some metal complexes of norfloxacin and ofloxacin. Centrepoint (Science Edition) 2009; 16: 37-56.
Turel I. The interactions of metal ions with quinolone antibacterial agents. Coord Chem Rev 2002; 232: 27-47. http://dx.doi.org/10.1016/S0010-8545(02)00027-9
Okeri HA, Arhewoh IM. Analytical profile of the fluoroquinolone antibacterials. I. Ofloxacin. Afri J Biotech 2008; 7: 670-80.
ivec P, Perdih F, Turel I, Giester G, Psomas G. Different types of copper complexes with the quinolone antimicrobial drugs ofloxacin and norfloxacin: structure, DNA– and albumin–binding. J Inorg Biochem 2012; 117: 35-47. http://dx.doi.org/10.1016/j.jinorgbio.2012.08.008
Mohd A, Khan AAP, Bano S, Siddiqi KS. Interaction and fluorescence quenching study of levofloxacin with divalent toxic metal ions. Eurasian J Anal Chem 2010; 5: 177-86.
Azcurra AI, Yudi LM, Baruzzi AM, Kakiuchi T. Interfacial behavior of ofloxacin–Fe(III) complex at the water /1,2– dichloroethane interface: a voltfluorometric and chronofluorometric study. J Electroanal Chem 2001; 506: 138-42. http://dx.doi.org/10.1016/S0022-0728(01)00493-4
De PK, Sahana B, Rakshit S. Enhancement of dissolution rate and stability study of ofloxacin solid dispersion. Der Pharmacia Sinica 2011; 2: 169-81.
Macıas B, Villa MV, Rubio I, Castineiras A, Borras J. Complexes of Ni(II) and Cu(II) with ofloxacin Crystal structure of a new Cu(II) ofloxacin complex. J Inorg Biochem 2001; 84: 163-70. http://dx.doi.org/10.1016/S0162-0134(01)00182-9
Sultana N, Arayne MS, Rizvi SBS, Haroon U, Mesaik MA. Synthesis, spectroscopic, and biological evaluation of some levofloxacin metal complexes. Med Chem Res 2013; 22: 1371-7. http://dx.doi.org/10.1007/s00044-012-0132-9
Drevensek P, Kosmrlj J, Giester G, et al. X–Ray crystallographic, NMR and antimicrobial activity studies of magnesium complexes of fluoroquinolones–racemic ofloxacin and its S–form, levofloxacin. J Inorg Biochem 2006; 100: 1755-63. http://dx.doi.org/10.1016/j.jinorgbio.2006.06.011
Li Y, Chai Y, Yuan R, Liang W. Synthesis and application of a new copper(II) complex containing oflx and leof. Russ J Inorg Chem 2008; 53: 704-6. http://dx.doi.org/10.1134/S0036023608050070
Akinremi CA, Obaleye JA, Amolegbe SA, Adediji JF, Bamigboye MO. Biological activities of some fluoroquinolones–metal complexes. Int J Med Biomed Res 2012; 1: 24-34. http://dx.doi.org/10.14194/ijmbr.115
Park H-R, Oh C-H, Lee H-C, Choi JG, Jung B-I, Bark K-M. Quenching of ofloxacin and flumequine fluorescence by divalent transition metal cations. Bull Korean Chem Soc 2006; 27: 2002-10. http://dx.doi.org/10.5012/bkcs.2006.27.12.2002
Chen C, Chen K, Long Q, Ma M, Ding F. Structural characterization and DNA–binding properties of Sm(III) complex with ofloxacin using spectroscopic methods. Spectroscopy 2009; 23: 103-11. http://dx.doi.org/10.1155/2009/769146
Chen C-Y, Chen Q-Z, Wang X-F, Liu M-S, Chen Y-F. Synthesis, characterization, DNA binding properties, and biological activities of a mixed ligand copper(II) complex of ofloxacin. Trans Met Chem 2009; 34: 757-63. http://dx.doi.org/10.1007/s11243-009-9259-z
Park H-R, Oh C-H, Lee H-C, Choi JG, Jung B-I, Bark K-M. Quenching of ofloxacin and flumequine fluorescence by divalent transition metal cations. Bull Korean Chem Soc 2006; 27: 2002-10. http://dx.doi.org/10.5012/bkcs.2006.27.12.2002
Lewis J, Wilkins RG. Modern coordination chemistry, Interscience Publishers, New York 1960.
El-Shwiniy WH, El-Attar MS, Sadeek SA. Metal Complexes of enrofloxacin part I: preparation, spectroscopic, thermal analyses studies and antimicrobial evaluation. J Korean Chem Soc 2013; 57: 52-62. http://dx.doi.org/10.5012/jkcs.2013.57.1.52
Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley, New York 1978.
Manimekalai R, Kalpanadevi K, Sinduja CR. Coordination aspects of newly synthesized complexes of some divalent transition metals with 2,4-dichlorophenoxy acetate and hydrazine. Chem Sci Trans 2013. http://dx.doi.org/10.7598/cst2013.406
Psomas G. Mononuclear metal complexes with ciprofloxacin: Synthesis, characterization and DNA-binding properties. J Inorg Biochem 2008; 102: 1798-811. http://dx.doi.org/10.1016/j.jinorgbio.2008.05.012
Gusina L, Bulhac I, Dragancea D, Simonov YA, Shova S. Structural and spectroscopic characterization of dioxomolybdenum(VI) complexes with schiff bases derived from isonicotinoylhydrazide. Rev Roum Chim 2011; 56: 981- 5.
Sovilj SP, Miti D, Drakuli BJ, Milenkovi M. Spectroscopic properties and antimicrobial activity of dioxomolybdenum(VI) complexes with heterocyclic S,S’-ligands. J Serb Chem Soc 2012; 77: 53-66. http://dx.doi.org/10.2298/JSC110328160S
Patil SK, Naik VM, Mallur NB. Synthesis, spectral and antibacterial studies of oxomolybdenum (V) and dioxomolybdenum (VI) complexes with 2–imidazolyl mercaptoaceto hydrazone. Der Pharma Chemica 2012; 4: 1812-8.
Rao DP, Yadav HS, Yadava AK, Singh S, Yadav US. Synthesis and characterization of cis–dioxomolybdenum(VI) complexes having furil as a precursor molecule. J Serb Chem Soc 2012; 77: 1205-10. http://dx.doi.org/10.2298/JSC111110020R
Maurya RC, Sutradhar D, Sahu S, Bohre P. Synthesis, characterization and 3d molecular modeling of some new 8– coordinate cis–dioxomolybdenum vi) chelates involving (o, n, o)–donor coordination matrix of schiff bases derived from 4– amino–2,3–dimethyl–1–phenyl–2–pyrazolin–5–one and some –diketoenolates. Rasayan J Chem 2008; 1: 395-412.
Zhou Z–H, Wang H, Yu P, Olmstead MM, Cramer SP. Structure and spectroscopy of a bidentate bis–homocitrate dioxo–molybdenum(VI) complex: Insights relevant to the structure and properties of the FeMo–cofactor in nitrogenase. J Inorg Biochem 2013; 118: 100-6. http://dx.doi.org/10.1016/j.jinorgbio.2012.10.001
Vieira LMM, de Almeida MV, Lourenço MCS, Bezerra FAFM, Fontes APS. Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones. European J Med Chem 2009; 44: 4107-11. http://dx.doi.org/10.1016/j.ejmech.2009.05.001
Sadeek SA, El–Shwiniy WH. Preparation, structure and microbial evaluation of metal complexes of the second generation quinolone antibacterial drug lomefloxacin. J Mol Struct 2010; 981: 130-8. http://dx.doi.org/10.1016/j.molstruc.2010.07.041
Sadeek SA, El–Shwiniy WH. Metal complexes of the fourth generation quinolone antimicrobial drug gatifloxacin: Synthesis, structure and biological evaluation. J Mol Struct 2010; 977: 243-53. http://dx.doi.org/10.1016/j.molstruc.2010.05.041
Sadeek SA, El–Shwiniy WH, Zordok WA, El-Didamony AM. Synthesis, spectroscopic, thermal and biological activity investigation of new Y(III) and Pd(II) Norfloxacin complexes. J Argent Chem Soc 2009; 97: 128-48.
Joseph NRJ, Sakthivel A, Jeyamurugan R. Synthesis, structural characterization and antimicrobial studies of novel schiff base copper(II) complexes. J Chil Chem Soc 2009; 54: 354-7.
