Solution studies on binary and ternary complexes of copper(II) with some fluoroquinolones and 1,10-phenanthroline: Antimicrobial activity of ternary metalloantibiotics

International Journal of Pharmaceutics

Volumn 334, Issue 1-2, 2007, Pages 129-136

  Gameiro, Paula ^a   Rodrigues, Catarina ^b   Baptista, Teresa ^b   Sousa, Isabel ^a   de Castro, Baltazar ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b Instituto Universitário de Ciências da Saúde do Norte   (Portugal)

Author keywords

Antibacterial activity; Distribution diagrams; Fluoroquinolones; Ternary complexes

Indexed keywords

COPPER COMPLEX; NORFLOXACIN; NORFLOXACIN 1,10 PHENANTHROLINE COPPER; OFLOXACIN; OFLOXACIN 1,10 PHENANTHROLINE COPPER; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG STABILITY; NONHUMAN; PH; POTENTIOMETRY; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTI-BACTERIAL AGENTS; COPPER; DRUG DESIGN; DRUG RESISTANCE, MICROBIAL; DRUG STABILITY; LIGANDS; MICROBIAL SENSITIVITY TESTS; NORFLOXACIN; OFLOXACIN; PHENANTHROLINES; POTENTIOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33947286695     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2006.10.035     Document Type: Article

References (45)

1. Alvarez J.E., Vartanian H.V., and Brodbelt S.J. Metal complexation reactions of quinolone antibiotics in a quadrupole ion trap. Anal. Chem. 69 (1997) 1147-1155
2. Anderson E.V., Gootz D.T., and Osheroff N. Topoisomerase IV catalysis and the mechanism of quinolone action. J. Biol. Chem. 273 (1998) 17879-17885
3. Bivian-Castro Y.E., Cervantes-Lee F., and Mendoza-Diaz G. Synthesis, characterization and crystal structure of copper(II) ternary complex with cinoxacin and histamine. Inorg. Chim. Acta 357 (2004) 349-353
4. 2 incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae. Diag. Microbiol. Infect. Dis. 42 (2002) 65-69
5. Chevalier J., Malle'a M., and Page's J.M. Comparative aspects of the diffusion of norfloxacin, cefepime and spermine through the F porin channel of Enterobacter cloacae. J. Biochem. 348 (2000) 223-227
6. Connors K.A. Binding Constants: The Measurement of Molecular Complex Stability (1987), John Wiley, New York
7. Erim B.F., Boelens M.H.F., and Kraak C.J. Applicability of capillary zone electrophoresis to study metal complexation in solution. Anal. Chim. Acta 294 (1994) 155-163
8. Fernandez-Botello A., Holy A., Moreno V., and Sigel H. Intramolecular stacking interactions in ternary copper(II) complexes formed by a heteroaromatic amine and 9-[2-(2-phosphonoethoxy)ethyl]adenine, a relative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine. J. Inorg. Biochem. 98 (2004) 2114-2124
9. Fraústo J.J.R., and Williams R.J.P. The Biological Chemistry of the Elements: The Inorganic Chemistry of Life (1994), Oxford University Press, New York
10. Gans P., Sabatini A., and Vacca A. Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta 43 (1996) 1739-1753
11. Garcia-Raso A., Fiol J.J., Adrover B., Moreno V., Mata I., Espinosa E., and Molins E. Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline. J. Inorg. Biochem. 95 (2003) 77-86
12. Gran G. Determination of the equivalence point in potentiometric titrations 2. Analyst 77 (1952) 661-671
13. Hegde S.S., Vetting W.M., Roderick L.S., Mitchenall A.L., Maxwell A., Takiff E.H., and Blanchard S.J. A fluoroquinolone resistance protein from Mycobacterium tuberculosis that mimics DNA. Science 308 (2005) 1480-1483
14. Kawai Y., Matsubayashi K., and Hakusui H. Interaction of quinolones with metal cations in aqueous solution. Chem. Pharm. Bull. 44 (1996) 1425-1430
15. Khodursky B.A., and Cozzarelli R.N. The mechanism of inhibition of topoisomerase IV by quinolone antibacterials. J. Biol. Chem. 273 (1998) 27668-27677
16. Levine C., Hiasa H., and Marians K. DNA gyrase and topoisomerase IV: biochemical activities, physiological roles during chromosome replication, and drug sensitivities. Biochim. Biophys. Acta 1400 (1998) 29-43
17. Lopez-Gresa P.M., Ortiz R., Perello L., Latorre J., Liu-Gonzalez M., Garcia-Granda S., Perez-Priede M., and Canton E. Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin)-spectroscopic and X-ray structural characterization. Antibacterial studies. J. Inorg. Biochem. 92 (2002) 65-74
18. Luth S.M., Kapinos E.L., Song B., Lippert B., and Sigel H. Extent of intramolecular stacking interactions in the mixed-ligand complexes formed in aqueous solution by copper(II), 2,2′-bipyridine or 1,10-phenanthroline and 2′-deoxyguanosine 5′-monophosphate. J. Chem. Soc., Dalton Trans. (1999) 357-365
19. Marians J.K., and Hiasa H. Mechanism of quinolone action-A drug-induced structural perturbation of the DNA precedes strand cleavage by topoisomerase IV. J. Biol. Chem. 272 (1997) 9401-9409
20. Macias B., Villa V.M., Rubio I., Castineiras A., and Borras J. Complexes of Ni(II) and Cu(II) with ofloxacin crystal structure of a new Cu(II) ofloxacin complex. J. Inorg. Biochem. 84 (2001) 163-170
21. Macias B., Villa V.M., Sastre M., Castineiras A., and Borras J. Complexes of Co(II) and Zn(II) with ofloxacin. Crystal structure of [Co(oflo)(2)(MeOH)(2)]·4MeOH. J. Pharm. Sci. 91 (2002) 2416-2423
22. Macias B., Garcia I., Villa V.M., Borras J., Gonzalez-Alvarez M., and Castineiras A. Oxidative DNA damage of mixed copper(II) complexes with sulfonamides and 1,10-phenanthroline-crystal structure of [Cu(N-quinolin-8-yl-p-toluenesulfonamidate)(2) (1,10-phenanthroline)]. J. Inorg. Biochem. 96 (2003) 367-374
23. Ming L.J. Structure and function of metalloantibiotics. Med. Res. Rev. 23 (2003) 697-762
24. National Committee for Clinical Laboratory Standards. Approved Standard M7-A5. Methods for dilution antimicrobial Susceptibility tests for bacteria that grow aerobically, 5th ed. National Committee for Clinical Laboratory Standards, Wayne, 2000.
25. Neves P., Berkane E., Gameiro P., Winterhalter M., and Castro d.B. Interaction between quinolones antibiotics and bacterial outer membrane porin OmpF. Biophys. Chem. 113 (2005) 123-128
26. Piddock V.L.J. Fluoroquinolone resistance in Salmonella serovars isolated from humans and food animals. Fems Microbiol. Rev. 26 (2002) 3-16
27. Piddock V.L.J., Ricci V., Pumbwe L., Everett J.M., and Griggs J.D. Fluoroquinolone resistance in Campylobacter species from man and animals: detection of mutations in topoisomerase genes. J. Antimicrob. Chemother. 51 (2003) 19-26
28. Prilipov A., Phale S.P., Gelder V.P., Rosenbusch P.J., and Koebnik R. Coupling site-directed mutagenesis with high-level expression: large scale production of mutant porins from E. coli. Fems Microbiol. Lett. 163 (1998) 65-72
29. Quentel F., Lher M., and Courtotcoupez J. Stability of organometallic complexes in propylene carbonate saturated with water. 2. 1,10-Phenanthroline complexes of copper(Ii), cadmium(Ii), zinc(Ii) and lead(Ii). Anal. Chim. Acta 97 (1978) 373-383
30. Ramirez-Ramirez N., Mendoza-Diaz G., Gutierrez-Corona F., and Pedraza-Reyes M. Determination of the intracellular targets and in vitro activity of a new class of chemical nuclease complexes derived from antibiotics of the quinolone family. J. Biol. Inorg. Chem. 3 (1998) 188-194
31. Robles J., Martin-Polo J., lvarez-Valtierra L., Hinojosa L., and Mendoza-Di{dotless}az G. A theoretical-experimental study on the structure and activity of certain quinolones and the interaction of their Cu(II)-complexes on a DNA model. Metal-Based Drugs 7 (2000) 301-311
32. Ross L.D., and Riley M.C. Dissociation and complexation of the fluoroquinolone antimicrobials-an update. J. Pharm. Biomed. Anal. 12 (1994) 1325-1331
33. Ross L.D., and Riley M.C. Dissociation and complexation of the fluoroquinolone antimicrobials-an update. J. Pharm. Biomed. Anal. 12 (1994) 1325-1331
34. Sigel H. Ternary complexes in solution. 19. Relation between ligand basicity and complex stability-method for estimation of stability-constants. J. Inorg. Nucl. Chem. 37 (1975) 507-509
35. Shen L.L., and Pernet A.G. Mechanism of inhibition of DNA Gyrase by analogs of nalidixic-acid-the target of drugs is DNA. Proc. Natl. Acad. Sci. 82 (1985) 307-311
36. Shen L.L., Baranowski J., and Pernet G.A. Mechanism of inhibition of DNA Gyrase by quinolone antibacterials-specificity and cooperativity of drug-binding to DNA. Biochemistry 28 (1989) 3879-3885
37. Shen L.L., Mitscher A.L., Sharma N.P., Odonnell J.T., Chu T.D.W., Cooper S.C., Rosen T., and Pernet G.A. Mechanism of inhibition of DNA gyrase by quinolone antibacterials-a Cooperative Drug-DNA Binding Model. Biochemistry 28 (1989) 3886-3894
38. Shen L.L., Kohlbrenner E.W., Weigl D., and Baranowski J. Mechanism of quinolone inhibition of DNA gyrase-appearance of unique norfloxacin binding-sites in enzyme-DNA complexes. J. Biol. Chem. 264 (1989) 2973-2978
39. Sigman S.D., Mazumder A., and Perrin M.D. Chemical nucleases. Chem. Rev. 93 (1993) 2295-2316
40. Takei M., Fukuda H., Kishii R., and Hosaka M. Target preference of 15 quinolones against Staphylococcus aureus, based on antibacterial activities and target inhibition. Antimicrob. Agents Chemother. 45 (2001) 3544-3547
41. Turel I. The interactions of metal ions with quinolone antibacterial agents. Coord. Chem. Rev. 232 (2002) 27-47
42. Wallis C.S., Gahan R.L., Charles G.B., Hambley W.T., and Duckworth A.P. Copper(II) complexes of the fluoroquinolone antimicrobial ciproffoxacin. synthesis, X-ray structural characterization, and potentiometric study. J. Inorg. Biochem. 62 (1996) 1-16
43. Weigel M.L., Anderson J.G., and Tenover C.F. DNA gyrase and topoisomerase IV mutations associated with fluoroquinolone resistance in Proteus mirabilis. Antimicrob. Agents Chemother. 46 (2002) 2582-2587
44. Wu G.G., Wang P.G., Fu C.X., and Zhu G.L. Synthesis, crystal structure, stacking effect and antibacterial studies of a novel quaternary copper (II) complex with quinolone. Molecules 8 (2003) 287-296
45. Yun-Liang Y., Tsai-Ling L., and Hsiu-Jung L. Molecular mechanisms of fluoroquinolone resistance in klebsiella. Curr. Drug Targets-Infect. Disorders 4 (2004) 295-302