New insights into the translocation route of enrofloxacin and its metalloantibiotics

Journal of Membrane Biology

Volumn 241, Issue 3, 2011, Pages 117-125

  Ribeiro, C ^a   Lopes, S C ^a   Gameiro, P ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Antimicrobial; Cardiolipin; Enrofloxacin; Escherichia coli membrane; Fluorescence spectroscopy; Metalloantibiotic

Indexed keywords

ANTIINFECTIVE AGENT; ENROFLOXACIN; LIPID; LIPOSOME; METALLOANTIBIOTIC; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG UPTAKE; ESCHERICHIA COLI; FLUORESCENCE SPECTROSCOPY; MONOTHERAPY; PH;

ANTI-BACTERIAL AGENTS; BIOLOGICAL TRANSPORT; CELL MEMBRANE; COORDINATION COMPLEXES; COPPER; DRUG RESISTANCE, BACTERIAL; ESCHERICHIA COLI; FLUOROQUINOLONES; HYDROGEN-ION CONCENTRATION; LIPID BILAYERS; LIPOSOMES; PHENANTHROLINES; PHOSPHOLIPIDS; SPECTROMETRY, FLUORESCENCE; STATIC ELECTRICITY;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 79959715945     PISSN: 00222631     EISSN: 14321424     Source Type: Journal    
DOI: 10.1007/s00232-011-9368-4     Document Type: Article

References (58)

1. Aarestrup FM (2006) Antimicrobial resistance in bacteria of animal origin. ASM Press, Washington, DC
2. Alvarez AI, Pérez M, Prieto JG, Molina AJ, Real R, Merino G (2008) Fluoroquinolone efflux mediated by ABC transporters. J Pharm Sci 97:3483-3493
3. Arouria A, Datheb M, Blumea A (2009) Peptide induced demixing in PG/PE lipid mixtures: a mechanism for the specificity of antimicrobial peptides towards bacterial membranes? Biochim Biophys Acta Biomembr 1788:650-659
4. Bensikaddour H, Snoussi K, Lins L, Bambeke FV, Tulkens PM, Brasseur R, Goormaghtigh E, Mingeot-Leclercq MP (2008) Interactions of ciprofloxacin with DPPC and DPPG: fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis. Biochim Biophys Acta Biomembr 1778:2535-2543
5. Bhunia A, Domadia PN, Torres J, Hallock KJ, Ramamoorthy A, Bhattacharjya S (2010) NMR structure of pardaxin, a pore-forming antimicrobial peptide, in lipopolysaccharide micelles: mechanism of outer membrane permeabilization. J Biol Chem 285:3883-3895
6. Bilski P, Martinez LJ, Koker EB, Chignell CF (1998) Influence of solvent polarity and proticity on the photochemical properties of norfloxacin. Photochem Photobiol 68:20-24 (Pubitemid 128472327)
7. Bryan LE, Bedard J (1991) Impermeability to quinolones in gram-positive and gram-negative bacteria. Eur J Clin Microbiol 10:232-239
8. Cheng JTJ, Hale JD, Elliott M, Hancock REW, Straus SK (2011) The importance of bacterial membrane composition in the structure and function of aurein 2.2 and selected variants. Biochim Biophys Acta Biomembr 1808:622-633
9. Coutinho A, Prieto M (1995) Self-association of the polyene antibiotic nystatin in dipalmitoylphosphatidylcholine vesicles: a time-resolved fluorescence study. Biophys J 69:2541-2557
10. Cuquerella MC, Miranda MA, Bosca F (2006) Role of excited state intramolecular charge transfer in the photophysical properties of norfloxacin and its derivatives. J Phys Chem A 110:2607-2612
11. Dennison SR, Morton LHG, Harris F, Phoenix DA (2008) The impact of membrane lipid composition on antimicrobial function of an [alpha]-helical peptide. Chem Phys Lipids 151:92-102
12. Djurdjevic PT, Jelikicstankov M, Stankov D (1995) Fluorescence reaction and complexation equilibria between norfloxacin and aluminum(III) ion in chloride medium. Anal Chim Acta 300:253-259
13. Drakopoulos AI, Ioannou PC (1997) Spectrofluorometirc study of the acid-base equilibria and complexation behavior of the fluoroquinolones antibiotics ofloxacin, norfloxacin, ciprofloxacin and pefloxacin in aqueous solution. Anal Chim Acta 354:197-204 (Pubitemid 28009247)
14. Efthimiadou EK, Sanakis Y, Katsarou M, Raptopoulou CP, Karaliota A, Katsaros N, Psomas G (2006) Neutral and cationic mononuclear copper(II) complexes with enrofloxacin: structure and biological activity. J Inorg Biochem 100:1378-1388
15. Efthimiadou EK, Sanakis Y, Katsaros N, Karaliota A, Psomas G (2007) Transition metal complexes with the quinolone antibacterial agent pipemidic acid: synthesis, characterization and biological activity. Polyhedron 26:1148-1158
16. Epand RM, Epand RF (2009a) Domains in bacterial membranes and the action of antimicrobial agents. Mol Biosyst 5:580-587
17. Epand RM, Epand RF (2009b) Lipid domains in bacterial membranes and the action of antimicrobial agents. Biochim Biophys Acta Biomembr 1788:289-294
18. Epand RM, Epand RF (2011) Bacterial membrane lipids in the action of antimicrobial agents. J Pept Sci 17:298-305
19. Fresta M, Guccione S, Beccari AR, Furneri PM, Puglisi G (2002) Combining molecular modeling with experimental methodologies: mechanism of membrane permeation and accumulation of ofloxacin. Bioorg Med Chem 10:3871-3889 (Pubitemid 36164686)
20. Haines TH (2009) A new look at cardiolipin. Biochim Biophys Acta Biomembr 1788:1997-2002
21. Hamill P, Brown K, Jenssen H, Hancock RE (2008) Novel antiinfectives: is host defence the answer? Curr Opin Biotechnol 19:628-636
22. Hoch FL (1992) Cardiolipins and biomembrane function (review). Biochim Biophys Acta 1113:71-133
23. Hooper DC (1999) Mechanisms of fluoroquinolone resistance. Drug Resist Updat 2:38-55
24. Hopkins K, Davies R, Threlfall E (2005) Mechanisms of quinolone resistancein Escherichia coli and Salmonella: recent developments. Int J Antimicrob Agents 25:358-373 (Pubitemid 40558766)
25. Kawai Y, Matsubayashi K, Hakusui H (1996) Interaction of quinolones with metal cations in aqueous solution. Chem Pharm Bull 44:1425-1430 (Pubitemid 26301488)
26. Lakowicz J (1999) Principles of fluorescence spectroscopy. Kluwer, New York
27. Lewis RNAH, McElhaney RN (2009) The physicochemical properties of cardiolipin bilayers and cardiolipin-containing lipid membranes. Biochim Biophys Acta Biomembr 1788:2069-2079
28. Lindner B, Wiese A, Brandenburg K, Seydel U, Dalhoff A (2002) Lack of interaction of fluoroquinolones with lipopolysaccharides. Antimicrob Agents Chemother 46:1568-1570 (Pubitemid 34415347)
29. Lizondo M, Pons M, Gallardo M, Estelrich J (1997) Physicochemical properties of enrofloxacin. J Pharmaceut Biomed 15:1845-1849 (Pubitemid 27341990)
30. LohnerK(2009)Newstrategies for novel antibiotics: peptides targeting bacterial cell membranes. Gen Physiol Biophys 28:105-116
31. Lohner K, Blondelle SE (2005) Molecular mechanisms of membrane perturbation by antimicrobial peptides and the use of biophysical studies in the design of novel peptide antibiotics. Comb Chem High Throughput Screen 8:241-256 (Pubitemid 40488604)
32. Lohner K, Latal A, Degovics G, Garidel P (2001) Packing characteristics of a model system mimicking cytoplasmic bacterial membranes. Chem Phys Lipids 111:177-192 (Pubitemid 32702027)
33. Lopes SC, Goormaghtigh E, Cabral BJ, Castanho MA (2004) Filipin orientation revealed by linear dichroism. Implication for a model of action. J Am Chem Soc 126:5396-5402 (Pubitemid 38596351)
34. Lopes S, Neves C, Eaton P, Gameiro P (2010) Cardiolipin, a key component to mimic the E. coli bacterial membrane in model systems revealed by dynamic light scattering and steady-state fluorescence anisotropy. Anal Bioanal Chem 398:1357-1366
35. Mahendran KR, Hajjar E, Mach T, Lovelle M, Kumar A, Sousa I, Spiga E, Weingart H, Gameiro P, Winterhalter M (2010) Molecular basis of enrofloxacin translocation through OmpF, an outer membrane channel of Escherichia coli - when binding does not imply translocation. J Phys Chem B 114:5170-5179
36. Maniti O, Alves I, Trugnan G, Ayala-Sanmartin J (2010) Distinct behaviour of the homeodomain derived cell penetrating peptide penetratin in interaction with different phospholipids. PLoS One 5:e15819
37. Martinez M, McDermott P, Walker R (2006) Pharmacology of the fluoroquinolones: a perspective for the use in domestic animals. Vet J 172:10-28 (Pubitemid 43869434)
38. Meras ID, Pena AMdl, Caceres MIR, Lopez FS (1998) Simultaneous fluorometric determination of nalidixic acid and 7-hydroxymethylnalidixic acid by partial least squares calibration. Talanta 45:899-907
39. Mileykovskaya E (2007) Subcellular localization of Escherichia coli osmosensory transporter ProP: focus on cardiolipin membrane domains. Mol Microbiol 64:1419-1422
40. Mitchell MA (2006) Enrofloxacin. J Exot Pet Med 15:66-69
41. Murzyn K, Róg T, Pasenkiewicz-Gierula M (2005) Phosphatidylethanolamine-phosphatidylglycerol bilayer as a model of the inner bacterial membrane. Biophys J 88:1091-1103 (Pubitemid 40975941)
42. Pagès J, James C, Winterhalter M (2008) The porin and the permeating antibiotic: a selective diffusion barrier in gram-negative bacteria. Nat Rev Microbiol 6:893-903
43. Park H-R, Oh C-H, Lee H-C, Lim SR, Yang K, Bark K-M (2004) Spectroscopic properties of various quinolone antibiotics in aqueous - organic solvent mixtures. Photochem Photobiol 80:554-564 (Pubitemid 40174485)
44. Pate MN, Parmar PA, Gandhi DS (2010) Square pyramidal copper(II) complexes with forth generation fluoroquinolone and neutral bidentate ligand: structure, antibacterial, SOD mimic and DNA-interaction studies. Bioorg Med Chem 18:1227-1235
45. Pávez P, Herrera B, Toro-Labbé A, Encinas MV (2007) Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics. Photochem Photobiol 83:511-519 (Pubitemid 46854944)
46. Pozo Navas B, Lohner K, Deutsch G, Sevcsik E, Riske KA, Dimova R, Garidel P, Pabst G (2005) Composition dependence of vesicle morphology and mixing properties in a bacterial model membrane system. Biochim Biophys Acta Biomembr 1716:40-48 (Pubitemid 41377148)
47. Rodrigues C, Gameiro P, Reis S, Lima JLFC, Castro Bd (2002) Interaction of grepafloxacin with large unilamellar liposomes: partition and fluorescence studies reveal the importance of charge interactions. Langmuir 18:10231-10236
48. Romantsov T, Guan Z, Wood JM (2009) Cardiolipin and the osmotic stress responses of bacteria. Biochim Biophys Acta Biomembr 1788:2092-2100
49. Ross DL, Riley CM (1994) Dissociation and complexation of the fluoroquinolone antimicrobials - an update. J Pharm Biomed 12:1325-1331
50. Santos NC, Prieto M, Castanho MARB (2003) Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods. Biochim Biophys Acta Biomembr 1612:123-135 (Pubitemid 36629567)
51. Saraiva R, Lopes S, Ferreira M, Novais F, Pereira E, Feio MJ, Gameiro P (2010) Solution and biological behaviour of enrofloxacin metalloantibiotics: a route to counteract bacterial resistance? J Inorg Biochem 104:843-850
52. Schlame M (2008) Glycerolipids. Cardiolipin synthesis for the assembly of bacterial and mitochondrial membranes (thematic review). J Lipid Res 49:1607-1620
53. Seral C, Barcia-Macay M, Mingeot-Leclercq MP, Tulkens PM, Bambeke FV (2005) Comparative activity of quinolones (ciprofloxacin, levofloxacin, moxifloxacin and garenoxacin) against extracellular and intracellular infection by Listeria monocytogenes and Staphylococcus aureus in J774 macrophages. J Antimicrob Chemother 55:511-517 (Pubitemid 40542592)
54. Tossi A, Sandri L, Giangaspero A (2000) Amphipathic, alpha-helical antimicrobial peptides. Biopolymers 55:4-30
55. Valeur B (2002) Molecular fluorescence: principles and applications. Wiley, New York
56. Van Bambeke F, Michot JM, Van Eldere J, Tulkens PM (2005) Quinolones in 2005: an update. Clin Microbiol Infect 11: 256-280 (Pubitemid 40443832)
57. Weitman H, Roslaniec M, Frimer AA, Afri M, Freeman D, Mazur Y, Ehrenberg B (2001) Solvatochromic effects in the electronic absorption and nuclear magnetic resonance spectra of hypericin in organic solvents and in lipid bilayers. Photochem Photobiol 73:110-118
58. Yeagle P (1987) The membranes of cells. Academic Press, New York