Solution and biological behaviour of enrofloxacin metalloantibiotics: A route to counteract bacterial resistance (original) (raw)
Abstract
Solution behaviour of enrofloxacin complexes with copper(II), nickel(II), cobalt(II) and zinc(II) in the presence and absence of 1, 10-phenanthroline was studied in aqueous solution, by potentiometry. The results obtained show that under physiological conditions (micromolar concentration range and pH 7.4) only copper(II) forms stable complexes. Binary copper(II)/enrofloxacin and ternary copper(II)/enrofloxacin/phenanthroline complexes were synthesised and characterized by elemental analysis, UV-visible spectroscopy and FTIR. The antimicrobial activity of these complexes and of copper(II)/enrofloxacin and copper(II)/enrofloxacin/ phenanthroline solutions, prepared by mixing of the individual components in the same stoichiometric proportion and concentration range used for the synthesised complexes, was tested against two different Escherichia coli strains. Although, at a glance, the results point to a possible use of both complexes as metalloantibiotics, a detailed analysis shows that, at biological concentrations, the copper(II) binary complex does not exist and the antimicrobial activity observed is a consequence of its dissociation into free enrofloxacin. Consequently, only the ternary complex seems worth pursuing as a possible antimicrobial agent candidate. Moreover, as the biological studies showed, both the synthesised complexes and the solutions prepared by mixing the components exhibited the same behaviour. Hence, a new, faster and accurate methodology to screen metalloantibiotics prior to synthesis of the complexes is proposed.
Loading Preview
Sorry, preview is currently unavailable. You can download the paper by clicking the button above.
References (53)
- A.I. Alvarez, M. Perez, J.G. Prieto, A.J. Molina, R. Real, G. Merino, J. Pharm. Sci. 97 (2008) 3483-3493.
- F.C. Tenover, Am. J. Infect. Control 34 (2006) S3-S10.
- M. Martinez, P. McDermott, R. Walker, Vet. J. 172 (2006) 10-28.
- M.A. Mitchell, J. Exot. Pet. Med. 15 (2006) 66-69.
- I. Turel, Coord. Chem. Rev. 232 (2002) 27-47.
- S.C. Wallis, L.R. Gahan, B.G. Charles, T.W. Hambley, P.A. Duckworth, J. Inorg. Biochem. 62 (1996) 1-16.
- D.L. Ross, C.M. Riley, J. Pharm. Biomed. Anal. 12 (1994) 1325-1331.
- B. Macias, M.V. Villa, I. Rubio, A. Castineiras, J. Borras, J. Inorg. Biochem. 84 (2001) 163-170.
- B. Macias, M.V. Villa, M. Sastre, A. Castineiras, J. Borras, J. Pharm. Sci. 91 (2002) 2416-2423.
- M.P. Lopez-Gresa, R. Ortiz, L. Perello, J. Latorre, M. Liu-Gonzalez, S. Garcia-Granda, M. Perez-Priede, E. Canton, J. Inorg. Biochem. 92 (2002) 65-74.
- G.G. Wu, G.P. Wang, X.C. Fu, L.G. Zhu, Molecules 8 (2003) 287-296.
- A. Serafin, A. Stanczak, Russ. J. Coord. Chem. 35 (2009) 81-95.
- E.Y. Bivian-Castro, F. Cervantes-Lee, G. Mendoza-Diaz, Inorg. Chim. Acta 357 (2004) 349-353.
- E.J. Alvarez, V.H. Vartanian, J.S. Brodbelt, J. Am. Soc. Mass Spectrom. 8 (1997) 620-629.
- Table 4 MIC results obtained for the different formulations in two E. coli strains. Values expressed in µg/mL and nM (in brackets).
- N. Ramirez-Ramirez, G. Mendoza-Diaz, F. Gutierrez-Corona, M. Pedraza-Reyes, J. Biol. Inorg. Chem. 3 (1998) 188-194.
- J. Robles, J. Martín-Polo, L. Alvarez-Valtierra, L. Hinojosa, G. Mendoza-Díaz, Metal- Based Drugs 7 (2000) 301-311.
- J. Hernández-Gil, L. Perelló, R. Ortiz, G. Alzuet, M. González-Álvarez, M. Liu- González, Polyhedron 28 (2009) 138-144.
- E.K. Efthimiadou, Y. Sanakis, M. Katsarou, C.P. Raptopoulou, A. Karaliota, N. Katsaros, G. Psomas, J. Inorg. Biochem. 100 (2006) 1378-1388.
- K.C. Skyrianou, E.K. Efthimiadou, V. Psycharis, A. Terzis, D.P. Kessissoglou, G. Psomas, J. Inorg. Biochem. 103 (2009) 1617-1625.
- K.C. Skyrianou, F. Perdih, I. Turel, D.P. Kessissoglou, G. Psomas, J. Inorg. Biochem. 104 (2010) 161-170.
- A. Garcia-Raso, J.J. Fiol, B. Adrover, V. Moreno, I. Mata, E. Espinosa, E. Molins, J. Inorg. Biochem. 95 (2003) 77-86.
- B. Macias, I. Garcia, M.V. Villa, J. Borras, M. Gonzalez-Alvarez, A. Castineiras, J. Inorg. Biochem. 96 (2003) 367-374.
- D.S. Sigman, A. Mazumder, D.M. Perrin, Chem. Rev. 93 (1993) 2295-2316.
- P. Gameiro, C. Rodrigues, T. Baptista, I. Sousa, B. de Castro, Int. J. Pharm. 334 (2007) 129-136.
- J. Recillas-Mota, M. Flores-Alamo, R. Moreno-Esparza, J. Gracia-Mora, Acta Crystallogr. Sect. E Struct. Rep. Online 63 (2007) M3030-U1551.
- E.K. Efthimiadou, Y. Sanakis, M. Katsarou, C.P. Raptopoulou, A. Karaliota, N. Katsaros, G. Psomas, Polyhedron 27 (2008) 1729-1738.
- G. Gran, Analyst 77 (1952) 661-671.
- J. Inczéby, T. Lengyel, A.M. Ure, Chapter 3, Compendium of Analytical Nomenclature, 3rd EditionIUPAC, 1997.
- P. Gans, A. Sabatini, A. Vacca, Talanta 43 (1996) 1739-1753.
- CLSI, Clinical and Laboratory Standards Institute, Methods for Dilution Antimicro- bial Susceptibility Tests for Bacteria that Grow Aerobically: Approved Standard- Eighth Edition, 2009, CLSI document M07-A8.
- Y. Kawai, K. Matsubayashi, H. Hakusui, Chem. Pharm. Bull. 44 (1996) 1425-1430.
- M. Lizondo, M. Pons, M. Gallardo, J. Estelrich, J. Pharm. Biomed. Anal. 15 (1997) 1845-1849.
- C. Rodrigues, P. Gameiro, S. Reis, J. Lima, B. de Castro, Langmuir 18 (2002) 10231-10236.
- I. Turel, N. Bukovec, E. Farkas, Polyhedron 15 (1996) 269-275.
- F. Quentel, M. Lher, J. Courtotcoupez, Anal. Chim. Acta 97 (1978) 373-383.
- F.B. Erim, H.F.M. Boelens, J.C. Kraak, Anal. Chim. Acta 294 (1994) 155-163.
- H. Sigel, J. Inorg. Nucl. Chem. 37 (1975) 507-509.
- M.S. Luth, L.E. Kapinos, B. Song, B. Lippert, H. Sigel, Dalton Trans. (1999) 357-365.
- A. Fernandez-Botello, A. Holy, V. Moreno, H. Sigel, J. Inorg. Biochem. 98 (2004) 2114-2124.
- R.C. Li, D.E. Nix, J.J. Schentag, Pharm. Res. 11 (1994) 917-920.
- P. Atkins, T. Overton, J. Rourke, M. Weller, F. Armstrong, Shriver & Atkins: Inorganic Chemistry, 4th EditionOxford Univ. Press, Oxford, 2006.
- A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd Edition, Studies in Physical and Theorectical Chemistry Series, Vol 1, Elsevier, Amsterdam, 1984.
- G. Mukherjee, T. Ghosh, J. Inorg. Biochem. 59 (1995) 827-833.
- K.E. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th EditionWiley, New York, 1986.
- G.B. Deacon, R.J. Phillips, Coord. Chem. Rev. 33 (1980) 227-250.
- C. Dendrinou-Samara, G. Tsotsou, L.V. Ekateriniadou, A.H. Kortsaris, C.P. Raptopoulou, A. Terzis, D.A. Kyriakidis, D.P. Kessissoglou, J. Inorg. Biochem. 71 (1998) 171-179.
- CLSI, Performance Standards for Antimicrobial Disk Susceptibility Tests: Approved Standard-Tenth Edition, 2009, CLSI document M02-A10.
- B. Grey, T.R. Steck, Appl. Environ. Microbiol. 67 (2001) 5325-5327.
- S.D. Gupta, B.T.O. Lee, J. Camakaris, H.C. Wu, J. Bacteriol. 177 (1995) 4207-4215.
- P. Drevensek, T. Zupancic, B. Pihlar, R. Jerala, U. Kolitsch, A. Plader, I. Turel, J. Inorg. Biochem. 99 (2005) 432-442.
- M.E. Katsarou, E.K. Efthimiadou, G. Psomas, A. Karaliota, D. Vourloumis, J. Med. Chem. 51 (2008) 470-478.
- A.M. Zoroddu, S. Zanetti, R. Pogni, R. Basosi, J. Inorg. Biochem. 63 (1996) 291-300.