Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes
Coordination compounds of transition metals with norfloxacin (Nor) have potential to improve its effectiveness, as already discussed for some compounds found in the literature. The complexes in the solid state were prepared by precipitation of the respective metal cation (M = Mn(II), Co(II), Ni(II), Cu(II) and Zn(II)) with a norfloxacin sodium salt solution. The thermal behavior under oxidative and pyrolysis conditions was investigated employing thermogravimetry and differential thermal analysis (TG/DTG–DTA) and evolved gas analysis (EGA/TG-FTIR), and the complexes were characterized by elemental analysis (EA), EDTA complexometric titration, infrared spectroscopy (FTIR) and X-ray powder diffraction (XRD). By these results, the minimum formula was established as [M(Nor)2(H2O)2]·nH2O, where n = 3 (Ni), 2.5 (Mn Co, Zn), or 2 (Cu). The evolved gases identified during thermal decomposition of Ni and Cu complexes were ethylene, CO2 and CO for Ni; CO2 and ethane for Cu. Also, antimicrobial activity of the complexes was evaluated by in vitro susceptibility test using the agar diffusion method, and the results were compared with the uncomplexed molecule. It was found that norfloxacin complexation modifies its antibacterial activity. The activity depends on the type of metal ion and microorganism; Mn(II), Co(II) and Zn(II) complexes significantly increased activity against the tested gram-negative bacteria.
KeywordsNorfloxacin Complexes Thermal behavior Antibacterial activity
The authors thank FAPESP (Proc. 2017/14936-9), CNPq (Proc. 421469/2016-1) and CAPES Foundation (Brazil) for financial support and PhD Patricia Neves Mendes (UNIFAL-MG) for the aid in the statistical tests.
- 1.Mazuel C. Norfloxacin. Anal Profiles Drug Subst. 1991; 557–600. http://linkinghub.elsevier.com/retrieve/pii/S0099542808605407.
- 6.Kamble R, Sharma S, Mehta P. Norfloxacin mixed solvency based solid dispersions: An in vitro and in vivo investigation. J Taibah Univ Sci. 2017;11:512–22. http://linkinghub.elsevier.com/retrieve/pii/S1658365517300122.
- 14.Mehta JV, Gajera SB, Patel MN. Antimalarial, antimicrobial, cytotoxic, DNA interaction and SOD like activities of tetrahedral copper(II) complexes. Spectrochim Acta Part A Mol Biomol Spectrosc. 2015;136:1881–92. http://linkinghub.elsevier.com/retrieve/pii/S138614251401600X.
- 15.Sarkar K, Sen K. Some drugs in action: metal ions do influence the activity! Int J Pharm Sci Res. 2015;6:1–13.Google Scholar
- 18.Wang Y-J, Lin Q-Y, Feng J, Wang N. Diaquabis (norfloxacinato) manganese(II) 2,2′-bipyridine solvate tetrahydrate. Acta Crystallogr Sect E Struct Reports Online. International Union of Crystallography; 2009;65:m806–m806. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969423/.
- 19.Teixeira JA, Nunes WDG, Fernandes RP, do Nascimento ALCS, Caires FJ, Ionashiro M. Thermal behavior in oxidative and pyrolysis conditions and characterization of some metal p-aminobenzoate compounds using TG–DTA, EGA and DSC-photovisual system. J Anal Appl Pyrolysis, 2017. http://linkinghub.elsevier.com/retrieve/pii/S0165237017306526.
- 21.Xu ZP, Zeng HC. Thermal evolution of cobalt hydroxides: a comparative study of their various structural phases. J Mater Chem. 1998;8:2499–506. http://xlink.rsc.org/?DOI=a804767g.
- 22.Stein SE. “Infrared spectra” by NIST mass spec data center. In: Linstrom PJ, Mallard WG, editors. NIST Chem. WebBook, NIST Stand. Ref. Database Number 69. Gaithersburg, MD: National Institute of Standards and Technology; [cited 2017 Sep 12]. http://webbook.nist.gov/chemistry/.
- 23.Sahoo S, Chakraborti CK, Mishra SC, Nanda UN, Naik S. FTIR and XRD investigations of some fluoroquinolones. Int J Pharm Pharm Sci. 2011;3:165–70.Google Scholar
- 25.Gouvea LR, Martins DA, Batista DDGJ, de Maria Nazaré CS, Louro SR, Barbeira PJ, et al. Norfloxacin Zn(II)-based complexes: acid base ionization constant determination, DNA and albumin binding properties and the biological effect against Trypanosoma cruzi. Biometals. 2013;26:813–25.CrossRefGoogle Scholar
- 26.Martins DA, Gouvea LR, Muniz GSV, Louro SRW, Batista D da GJ, Soeiro MDNC, et al. Norfloxacin and N-Donor mixed-ligand Copper(II) complexes: synthesis, albumin interaction, and anti-Trypanosoma cruzi activity. Bioinorg Chem Appl 2016;2016:1–11. http://www.hindawi.com/journals/bca/2016/5027404/.CrossRefGoogle Scholar
- 28.Deacon G, Phillips RJ. Relationships between the carbon–oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord Chem Rev. 1980 [cited 2014 Apr 28];33:227–50. http://www.sciencedirect.com/science/article/pii/S0010854500804555.
- 29.Sha J-Q, Li X, Qiu H-B, Zhang Y-H, Yan H. Nickel complexes of the different quinolone antibacterial drugs: synthesis, structure and interaction with DNA. Inorg Chim Acta. 2012;383:178–84. http://linkinghub.elsevier.com/retrieve/pii/S0020169311009108.