A new approach to counteract bacteria resistance: A comparative study between moxifloxacin and a new moxifloxacin derivative in different model systems of bacterial membrane

Chemical Biology and Drug Design

Volumn 81, Issue 2, 2013, Pages 265-274

  Lopes, Silvia C ^a   Ribeiro, Carla ^a   Gameiro, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

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

Indexed keywords

ANTIBIOTIC AGENT; COPPER MOXIFLOXACIN PHENANTHROLINE COMPLEX; MOXIFLOXACIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL MEMBRANE; COMPARATIVE STUDY; COMPLEX FORMATION; CONTROLLED STUDY; ESCHERICHIA COLI; FLUORESCENCE SPECTROSCOPY; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; AZA COMPOUNDS; CELL MEMBRANE; DRUG RESISTANCE, MICROBIAL; ESCHERICHIA COLI; LIPOSOMES; QUINOLINES; SPECTROMETRY, FLUORESCENCE;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; MAMMALIA;

EID: 84872310072     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12071     Document Type: Article

References (59)

1. Evans H.L., Lefrak S.N., Lyman J., Smith R.L., Chong T.W., McElearney S.T., Schulman A.R., Hughes M.G., Raymond D.P., Pruett T.L., Sawyer R.G. (2007) Cost of gram-negative resistance. Crit Care Med;35:89-95.
2. Jones K.E., Patel N.G., Levy M.A., Storeygard A., Balk D., Gittleman J.L., Daszak P. (2008) Global trends in emerging infectious diseases. Nature;451:990-993.
3. Andersson D., Hughes D. (2010) Antibiotic resistance and its cost: is it possible to reverse resistance?Nat Rev Microbiol;8:260-271.
4. Beringer P., Wong-Beringer A., Rho J. (1998) Economic aspects of antibacterial adverse effects. Pharmacoeconomics;13:35-49.
5. Findlay B., Zhanel G., Schweizer F. (2010) Cationic amphiphiles, a new generation of antimicrobials inspired by the natural antimicrobial peptide scaffold. Antimicrob Agents Chemother;54:4049-4058.
6. Gong Y., Ma M., Luo Y., Bong D. (2008) Functional determinants of a synthetic vesicle fusion system. J Am Chem Soc;130:6196-6205.
7. Hurdle J.G., O'Neill A.J., Chopra I., Lee R.E. (2011) Targeting bacterial membrane function: an underexploited mechanism for treating persistent infections. Nat Rev Microbiol;9:62-75.
8. Huang Y., Huang J., Chen Y. (2010) Alpha-helical cationic antimicrobial peptides: relationships of structure and function. Protein Cell;1:143-152.
9. Arouri A., Dathe M., Blume A. (2009) Peptide induced demixing in PG/PE lipid mixtures: a mechanism for the specificity of antimicrobial peptides towards bacterial membranes?Biochim Biophys Acta;1788:650-659.
10. Epand R., Epand R. (2009) Lipid domains in bacterial membranes and the action of antimicrobial agents. Biochim Biophys Acta;1788:289-294.
11. Epand R., Maloy L., Ramamoorthy A., Epand R. (2010) Amphipathic helical cationic antimicrobial peptides promote rapid formation of crystalline states in the presence of phosphatidylglycerol: lipid clustering in anionic membranes. Biophys J;98:2564-2573.
12. Epand R., Wang G., Berno B., Epand R. (2009) Lipid segregation explains selective toxicity of a series of fragments derived from the human cathelicidin LL-37. Antimicrob Agents Chemother;53:3705-3714.
13. Haney E., Nathoo S., Vogel H., Prenner E. (2010) Induction of non-lamellar lipid phases by antimicrobial peptides: a potential link to mode of action. Chem Phys Lipids;163:82-93.
14. Pokorny A., Almeida P. (2004) Kinetics of dye efflux and lipid flip-flop induced by δ-lysin in phosphatidylcholine vesicles and the mechanism of graded release by amphipathic, α-helical peptides. Biochemistry;43:8846-8885.
15. Pokorny A., Almeida P. (2005) Permeabilization of raft-containing lipid vesicles by δ-lysin: a mechanism for cell sensitivity to cytotoxic peptides. Biochemistry;44:9538-9544.
16. Pokorny A., Birkbeck T., Almeida P. (2002) Mechanism and kinetics of δ-lysin interaction with phospholipid vesicles. Biochemistry;41:11044-11056.
17. Epand R., Epand R. (2011) Bacterial membrane lipids in the action of antimicrobial agents. J Pept Sci;17:298-305.
18. Lohner K. (2001) The Role of Membrane Lipid Composition in Cell Targeting of Antimicrobial Peptides. Norfolk: Horizon Scientific Press.
19. Lopes S.C.D.N., Fedorov A., Castanho M.A.R.B. (2006) Chiral recognition of D-kyotorphin by lipidic membranes: relevance toward improved analgesic efficiency. ChemMedChem;1:723-728.
20. Lopes S.C.D.N., Soares C.M., Baptista A.M., Goormaghtigh E., Costa Cabral B.J., Castanho M.A.R.B. (2006) Conformational and orientational guidance of the analgesic dipeptide kyotorphin induced by lipidic membranes: putative correlation toward receptor docking. J Phys Chem B;110:3385-3394.
21. Oliphant C., Green G. (2002) Quinolones: a comprehensive review. Am Fam Physician;65:455-464.
22. Caeiro J., Iannini P. (2003) Moxifloxacin (Avelox): a novel fluoroquinolone with a broad spectrum of activity. Expert Rev Anti Infect Ther;1:363-370.
23. Spigaglia P., Barbanti F., Mastrantonio P. (2011) Multidrug resistance in European Clostridium difficile clinical isolates. J Antimicrob Chemother;66:2227-2234.
24. Skyrianou K.C., Efthimiadou E.K., Psycharis V., Terzis A., Kessissoglou D.P., Psomas G. (2009) Nickel-quinolones interaction. Part 1 - Nickel(II) complexes with the antibacterial drug sparfloxacin: structure and biological properties. J Inorg Biochem;103:1617-1625.
25. Skyrianou K.C., Perdih F., Turel I., Kessissoglou D.P., Psomas G. (2010) Nickel-quinolones interaction. Part 2 - interaction of nickel(II) with the antibacterial drug oxolinic acid. J Inorg Biochem;104:161-170.
26. Hernández-Gil J., Perelló L., Ortiz R., Alzuet G., González-Álvarez M., Liu-González M. (2009) Synthesis, structure and biological properties of several binary and ternary complexes of copper(II) with ciprofloxacin and 1, 10 phenanthroline. Polyhedron;28:138-144.
27. Patitungkho S., Adsule S., Dandawate P., Padhye S., Ahmad A., Sarkar F.H. (2011) Synthesis, characterization and anti-tumor activity of moxifloxacin-Copper complexes against breast cancer cell lines. Bioorg Med Chem Lett;21:1802-1806.
28. Katsarou M.E., Efthimiadou E.K., Psomas G., Karaliota A., Vourloumis D. (2008) Novel Copper(II) complex of N-Propyl-norfloxacin and 1, 10-phenanthroline with enhanced antileukemic and DNA nuclease activities. J Med Chem;51:470-478.
29. López-Gresa M.P., Ortiz R., Perelló L., Latorre J., Liu-González M., García-Granda S., Pérez-Priede M., Cantón E. (2002) Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin): spectroscopic and X-ray structural char-acterization. Antibacterial studies. J Inorg Biochem;92:65-74.
30. Saraiva R., Lopes S., Ferreira M., Novais F., Pereira E., Feio M.J., Gameiro P. (2010) Solution and biological behaviour of enrofloxacin metalloantibiotics: a route to counteract bacterial resistance?J Inorg Biochem;104:843-850.
31. Pate M., Parmar P., Gandhi D. (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.
32. Ribeiro C., Lopes S., Gameiro P. (2011) New insights into the translocation route of enrofloxacin and its metalloantibiotics. J Membr Biol;241:117-125.
33. Murzyn K., Róg T., Pasenkiewicz-Gierula M. (2005) Phosphatidylethanolamine-phosphatidylglycerol bilayer as a model of the inner bacterial membrane. Biophys J;88:1091-1103.
34. 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.
35. Pozo Navas B., Lohner K., Deutsch G., Sevcsik E., Riske K.A., Dimova R., Garidel P., Pabst G. (2005) Composition dependence of vesicle morphology and mixing properties in a bacterial model membrane system. Biochim Biophys Acta;1716:40-48.
36. 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.
37. Dahlberg M., Maliniak A. (2008) Molecular dynamics simulations of cardiolipin bilayers. J Phys Chem B;112:11655-11663.
38. Lopes S., Neves C., Eaton P., Gameiro P. (2012) Improved model systems for bacterial membranes from differing species: the importance of varying composition in PE/PG/cardiolipin ternary mixtures. Mol Membr Biol;29:207-217.
39. Hoch F. (1992) Cardiolipins and biomembrane function. Biochim Biophys Acta;1113:71-133.
40. Mileykovskaya E. (2007) Subcellular localization of Escherichia coli osmosensory transporter ProP: focus on cardiolipin membrane domains. Mol Microbiol;64:1419-1422.
41. Schlame M., Ren M. (2009) The role of cardiolipin in the structural organization of mitochondrial membranes. Biochim Biophys Acta;1788:2080-2083.
42. Domènech Ò., Morros A., Cabañas M.E., Montero M.T., Hernández-Borrell J. (2007) Thermal response of domains in cardiolipin content bilayers. Ultramicroscopy;107:943-947.
43. Romantsov T., Guan Z., Wood J. (2009) Cardiolipin and the osmotic stress responses of bacteria. Biochim Biophys Acta;1788:2092-2100.
44. Lewis R., Zweytick D., Pabst G., Lohner K., McElhaney R. (2007) Calorimetric, X ray diffraction, and spectroscopic studies of the thermotropic phase behavior and organization of tetramyristoyl cardiolipin membranes. Biophys J;92:3166-3177.
45. Lewis R., McElhaney R. (2009) The physicochemical properties of cardiolipin bilayers and cardiolipin-containing lipid membranes. Biochim Biophys Acta;1788:2069-2079.
46. Hadjicharalambous C., Sheynis T., Jelinek R., Shanahan M., Ouellette A., Gizeli E. (2008) Mechanisms of alpha-defensin bactericidal action: comparative membrane disruption by Cryptdin-4 and its disulfide-null analogue. Biochemistry;47:12626-12634.
47. Lakowicz J. (1999) Principles of Fluorescence Spectroscopy. New York: Kluwer.
48. Rodrigues C., Gameiro P., Reis S., Lima J., de Castro B. (2001) Interaction of grepafloxacin with large unilamellar liposomes: partition and fluorescence studies reveal the importance of charge interactions. Langmuir;18:10231-10236.
49. 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.
50. Santos N., Prieto M., Castanho M. (2003) Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods. Biochim Biophys Acta;1612:123-135.
51. Neves P., Leite A., Rangel M., de Castro B., Gameiro P. (2007) Influence of structural factors on the enhanced activity of moxifloxacin: a fluorescence and EPR spectroscopic study. Anal Bioanal Chem;387:1543-1552.
52. Sousa I., Claro V., Pereira J.L., Amaral A.L., Cunha-Silva L., de Castro B., Feio M.J., Pereira E., Gameiro P. (2012) Synthesis, characterization and antibacterial studies of a Copper(II) levofloxacin ternary complex. J Inorg Biochem;110:64-71.
53. Pávez P., Herrera B., Toro-Labbé A., Encinas M. (2007) Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics. Photochem Photobiol;83:511-519.
54. Weitman H., Roslaniec M., Frimer A., 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.
55. Park H.-R., Oh C.-H., Lee H.-C., Lim S., Yang K., Bark K.-M. (2004) Spectroscopic properties of various quinolone antibiotics in aqueous - organic solvent mixtures. Photochem Photobiol;80:554-564.
56. Bilski P., Martinez L., Koker E., Chignell C. (1998) Influence of solvent polarity and proticity on the photochemical properties of norfloxacin. Photochem Photobiol;68:20-24.
57. Cuquerella M., Miranda M., 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.
58. Yeagle P. (1987) The Membranes of Cells. New York: Academic Press, Inc.
59. Allegrini P., Pluschke G., Seelig J. (1984) Cardiolipin conformation and dynamics in bilayer membranes as seen by deuterium magnetic resonance. Biochemistry;23:6452-6458.