Effective antimicrobial and anti-endotoxin activity of cationic peptides based on lactoferricin: A biophysical and microbiological study

Anti-Infective Agents in Medicinal Chemistry

Volumn 9, Issue 1, 2010, Pages 9-22

  Brandenburg, Klaus ^a   Howe, Jö̈rg ^a   Sánchez Gómez, Susana ^h   Garidel, Patrick ^b   Roessle, Manfred ^c   Andrä, Jörg ^a   Jerala, Roman ^d   Zweytick, Dagmar ^e   Lohner, Karl ^e   Rappolt, Michael ^f   Blondelle, Sylvie ^g   Moriyon, Ignacio ^h   De Tejada, Guillermo Martinez ^h  

^a RESEARCH CENTER BORSTEL   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^d NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^e ERICH SCHMID INSTITUTE OF MATERIALS SCIENCE   (Austria)

^f SINCROTRONE TRIESTE   (Italy)

^g TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

^h UNIVERSITY OF NAVARRA   (Spain)

Author keywords

Antimicrobial peptides; Lactoferricin; Lipopolysaccharide; Sepsis; Small angle X ray scattering

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIUM LIPOPOLYSACCHARIDE; HYDROCARBON; LACTOFERRICIN; OCTANOYLPHENYLALANYLTRYPTOPHYLARGINYLARGINYLPHENYLALANYLTRYPTOPHYLARGINYLARGININE; OCTANOYLPHENYLALANYLTRYPTOPHYLARGINYLISOLEUCYLARGINYLISOLEUCYLARGINYLARGININE; PHENYLALANYLTRYPTOPHYLARGINYLARGINYLPHENYLALANYLTRYPTOPHYLARGINYLARGININE; PHENYLALANYLTRYPTOPHYLARGINYLISOLEUCYLARGINYLISOLEUCYLARGINYLARGININE; TS 140 15; TS 140 27; UNCLASSIFIED DRUG; VS 1 55; VS 1 60;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL CELL; BACTERIUM ISOLATE; CONTROLLED STUDY; DISEASE MODEL; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG DETERMINATION; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; MOLECULAR INTERACTION; MOLECULAR MECHANICS; MOUSE; NONHUMAN; PARAMETER; PEPTIDE SYNTHESIS; SEPSIS;

EID: 77950854159     PISSN: 18715214     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152110790886736     Document Type: Article

References (45)

1. Rietschel, E.T.; Kirikae, T.; Loppnow, H.; Zabel, P.; Ulmer, J.; Brade, H.; Seydel, U.; Zähringer, U.; Schlaak, M.; Flad, H.-D.; Schade, U. In: Molecular aspects of inflammation, Sies, H.; Flohe, L.; Zimmer, G.; Eds. Springer-Verlag; Berlin, Heidelberg, New York, 1991, pp. 207-231
2. Tapping, R.I. and Tobias, P.S. Cellular binding of soluble CD14 requires lipopolysaccharide (LPS) and LPS-binding protein. J. Biol. Chem., 1997, 272, 23157-23164. (Pubitemid 27392446)
3. Jerala, R. Structural biology of the LPS recognition. Int. J. Med. Microbiol., 2007, 297, 353-363. (Pubitemid 47188054)
4. Zähringer, U.; Lindner, B.; Rietschel, E.T., in Endotoxin in Health and Disease,Brade, Opal, Vogel, and Morrison. Eds. Marcel Dekker; New York 1999, pp. 93-114.
5. Vogel, H.J.; Schibli, D.J.; Jing, W.; Lohmeier-Vogel, E.M.; Epand, R.F.; Epand, R.M. Towards a structure-function analysis of bovine lactoferricin and related tryptophan-and arginine-containing peptides. Biochem. Cell Biol., 2002, 80, 49-63. (Pubitemid 34194228)
6. Baynes, R.D.; Bezwoda, W.R., In: Lactoferrin: Structure and Function, Hutchens, W.T.; Rumball, S.V.; Lönnerdal, B. Eds. Advances in Experimental Medicine and Biology. Plenum Press; New York 1994; pp. 133-141.
7. Wakabayashi, H.; Takase, M.; Tomita, M. Lactoferricin derived from milk protein lactoferrin. Curr. Pharm. Des., 2003, 9, 1277-1287. (Pubitemid 36592136)
8. Chapple, D.S.; Mason, D.J.; Joannou, C.L.; Odell, E.W.; Gant, V.; Evans, R.W. Structure-function relationship of antibacterial synthetic peptides homologous to a helical surface region on human lactoferrin against Escherichia coli serotype O111. Infect. Immun., 1998, 66, 2434-2440. (Pubitemid 28261735)
9. Galanos, C.; Lüderitz, O.; Westphal, O. A new method for the extraction of R lipopolysaccharides. Eur. J. Biol., 1969, 9, 245-249.
10. Rietschel, E.T.; Brade, H.; Holst, O.; Brade, L.; Müller-Loennies, S.; Mamat, U.; Zähringer, U.; Beckmann, F.; Seydel, U.; Brandenburg, K.; Ulmer, A.J.; Mattern, T.; Heine, H.; Schletter, J.; Hauschildt, S.; Loppnow, H.; Schönbeck, U.; Flad, H.-D.; Schade, U.F.; Di Padova, F.; Kusumoto, S.; Schumann, R.R. Bacterial endotoxin: Chemical constitution, biological recognition, host response, and immunological detoxification. Curr. Top. Microbiol. Immunol., 1996, 276, 39-81. (Pubitemid 28012915)
11. Leong, D.; Diaz, R.; Milner, K.; Rudbach, J.; Wilson, J.B. Some sructural and bological poperties of Brucella endotoxin. Infect. Immun., 1970, 7, 174-182.
12. Hirschfeld, M.; Ma, Y.; Weis, J.H.; Vogel, S.N.; Weis, J.J. Cutting edge: Repurification of lipopolysaccharide eliminates signaling through both human and murine toll-like receptor, 2. J. Immunol., 2000, 765, 618-622. (Pubitemid 30484724)
13. Brandenburg, K.; David, A.; Howe, J.; Koch, M.H.; Andrä, J.; Garidel, P. Temperature dependence of the binding of endotoxins to the polycationic peptides polymyxin B and its nonapeptide. Biophys. J., 2005, 88, 1845-1858. (Pubitemid 40976198)
14. Blume, A.; Garidel, P. In: From Macromolecules to Man, Kemp, R. Ed. Elsevier; Amsterdam 1999, pp. 109-173.
15. Paridel, P.; Johann, C.; Blume, A. Thermodynamics of lipid organization and domain formation in phospholipid bilayers. J. Liposome Res., 2000, 70, 131-158.
16. Koch, M.H.J. and Bordas, J. X-ray diffraction and scattering on disordered systems using synchrotron radiation. Nucl. Instr. Methods, 1983, 208, 461-469.
17. Roessle, M.; Klaering, R.; Ristau, U.; Robrahn, B.; Jahn, D.; Gehrmann, T.; Konarev, P.; Round, A.; Fiedler, S; Hermes,C.; Svergun, D. Upgrade of the small-angle X-ray scattering beamline at the European Molecular Biology Laboratory, Hamburg. J. Appl. Crystallogr., 2007, 40, 190-194. (Pubitemid 46732685)
18. Brandenburg, K.; Funari, S.S.; Koch, M.H.J.; Seydel, U. Investigation into the acyl chain packing of endotoxins and phospholipids under near physiological conditions by WAXS and FTIR spectros-copy. J. Struct. Biol., 1999, 128, 175-186. (Pubitemid 30039059)
19. Rappolt, M.; Hodzic, A.; Sartori, B.; Ollivon, M.; Laggner, P. Conformational and hydrational properties during the L(beta)-to L(alpha)-and L(alpha)-to H(II)-phase transition in phosphatidyle-thanolamine. Chem. Phys. Lipids, 2008, 154, 46-55.
20. Worthington, C.R. and Khare, R.S. Structure determination of lipid bilayers. Biophys. J., 1978, 23, 407-425.
21. Garidel, P.; Rappolt, M.; Schromm, A.B.; Howe, J.; Lohner, K.; Andrä, J.; Koch, M.H.; Brandenburg, K. Divalent cations affect chain mobility and aggregate structure of lipopolysaccharide from Salmonella minnesota reflected in a decrease of its biological activity. Biochim. Biophys. Acta, 2005, 1715, 122-131. (Pubitemid 41219700)
22. Rappolt, M. In: Advances in Planar Lipid Bilayers and Liposomes, Leitmanova-Liu, A.; Ed. Elsevier; Amsterdam, 2006, pp. 253-283.
23. Pabst, G.; Rappolt, M.; Amenitsch, H.; Laggner, P. Structural information from multilamellar liposomes at full hydration: full q-range fitting with high quality x-ray data. Phys. Rev. E. Stat. Phys. Plasmas, 2000, 62, 4000-4009.
24. Schromm, A.B.; Brandenburg, K.; Rietschel, E.Th.; Flad, H.-D.; Carroll, S.F.; Seydel, U. Lipopolysaccharide binding protein (LBP) mediates CD14-independent intercalation of lipopolysaccharide into phospholipid membranes. FEBS Lett., 1996, 399, 267-271. (Pubitemid 26426864)
25. Jürgens, G.; Müller, M.; Koch, M.H.J.; Brandenburg, K. Interaction of hemoglobin with enterobacterial lipopolysaccharide and lipid A: Physicochemical characterization and biological activity. Eur. J. Biochem., 2001, 268, 4233-4242. (Pubitemid 32862884)
26. Andrä, J.; Monreal, D.; Martinez de Tejada, G..; Olak, C.; Brezesinski, G.; Gomez, S.S.; Goldmann, T.; Bartels, R.; Brandenburg, K.; Moriyon, I. Rationale for the design of shortened derivatives of the NK-lysin-derived antimicrobial peptide NK-2 with improved activity against Gram-negative pathogens. J. Biol. Chem., 2007, 282, 14719-14728. (Pubitemid 47093359)
27. Galanos, C.; Freudenberg, M.A.; Reutter, W. Galactosamine-induced sensitization to the lethal effects of endotoxin. Proc. Natl. Acad. Sci. USA, 1979, 76, 5939-5943. (Pubitemid 10216692)
28. Seydel, U.; Oikawa, M.; Fukase, K.; Kusumoto, S.; Brandenburg, K. Intrinsic conformation of lipid A is responsible for agonistic and antagonistic activity. Eur. J. Biochem., 2000, 267, 3032-3039. (Pubitemid 30321351)
29. Andrä, J.; Lohner, K.; Blondelle, S.E.; Jerala, R.; Moriyon, I.; Koch, M.H.; Garidel, P.; Brandenburg, K. Enhancement of endotoxin neutralization by coupling of a C12-alkyl chain to a lactofer-ricin-derived peptide. Biochem. J., 2005, 385, 135-143.
30. Brandenburg, K.; Moriyon, I.; Arraiza, M.D.; Lehwark-Yvetot, G.; Koch, M.H.J.; Seydel, U. Biophysical investigations into the interaction of lipopolysaccharide with polymyxins. Thermochim. Acta, 2002, 382, 189-198.
31. Brandenburg, K.; Koch, M.H.J.; Seydel, U. Phase diagramm of deep rough mutant lipopolysaccharide from Salmonella minnesota R595. J. Struct. Biol., 1992, 108, 93-106.
32. Rosenfeld, Y. and Shai, Y. Lipopolysaccharide (Endotoxin)-host defense antibacterial peptides interactions: role in bacterial resistance and prevention of sepsis. Biochim. Biophys. Acta, 2006, 1758, 1513-1522. (Pubitemid 44436084)
33. Rosenfeld, Y.; Papo, N.; Shai, Y. Endotoxin (lipopolysaccharide) neutralization by innate immunity host-defense peptides. Peptide properties and plausible modes of action. J. Biol. Chem., 2006, 281, 1636-1643. (Pubitemid 43752480)
34. Tobias, P.S.; Soldau, K.; Iovine, N.M.; Elsbach, P.; Weiss, J. Lipopolysaccharide (LPS)-binding proteins BPI and LBP form different types of complexes with LPS. J. Biol. Chem., 1997, 272, 18682-18685. (Pubitemid 27318211)
35. Andrä, J.; Howe, J.; Garidel, P.; Rössle, M.; Richter, W.; Leiva-Leon, J.; Moriyon, I.; Bartels, R.; Gutsmann, T.; Brandenburg, K. Mechanism of interaction of optimized Limulus-derived cyclic peptides with endotoxins: thermodynamic, biophysical and microbiological analysis. Biochem. J., 2007, 406, 297-307. (Pubitemid 47310960)
36. Chen, X.; Howe, J.; Andrä, J.; Rösle, M.; Richter, W.; da Silva, A.P.; Krensky, A.M.; Clayberger, C.; Brandenburg, K. Biophysical analysis of the interaction of granulysin-derived peptides with enterobacterial endotoxins. Biochim. Biophys. Acta, 2007, 1768, 2421-2431. (Pubitemid 47542311)
37. Resman, N.; Vasl, J.; Oblak, A.; Pristovsek, P.; Gioannini, T.L.; Weiss, J.P.; Jerala, R. Essential roles of hydrophobic residues in both MD-2 and toll-like receptor 4 in activation by endotoxin. J. Biol. Chem., 2009, 284, 15052-15060.
38. Brandenburg, K. and Wiese, A. Endotoxins: relationships between structure, function, and activity. Curr. Top. Med. Chem., 2004, 4, 1127-1146.
39. Beutler, B. TLR4: central component of the sole mammalian LPS sensor. Curr. Opin. Immunol., 2000, 12, 20-26. (Pubitemid 30093446)
40. Gutsmann, T.; Schromm, A.B.; Koch, M.H.J.; Kusumoto, S.; Fukase, K.; Oikawa, M.; Seydel, U.; Brandenburg, K. Lipopolysaccharide-binding protein-mediated interaction of lipid A from different origin with phospholipid membranes. Phys. Chem. Chem. Phys., 2000, 2, 4521-4528.
41. Okuda, D.; Yomogida, S.; Tamura, H.; Nagaoka, I. Determination of the antibacterial and lipopolysaccharide-neutralizing regions of guinea pig neutrophil cathelicidin peptide CAP11. Antimicrob. Agents Chemother., 2006, 50, 2602-2607. (Pubitemid 44198677)
42. Motzkus, D.; Schulz-Maronde, S.; Heitland, A.; Schulz, A.; Forssmann, W.G.; Jubner, M.; Maronde, E. The novel beta-defensin DEFB123 prevents lipopolysaccharide-mediated effects in vitro and in vivo. FASEB J., 2006, 20, 1701-1702. (Pubitemid 44943777)
43. Mookherjee, N.; Rehaume, L.M.; Hancock, R.E. Cathelicidins and functional analogues as antisepsis molecules. Expert. Opin. Ther. Targets, 2007, 11, 993-1004. (Pubitemid 47240677)
44. Scott, M.G.; Rosenberger, C.M.;Gold, M.R.; Finlay, B.B.; Hancock, R.E. An alpha-helical cationic antimicrobial peptide selectively modulates macrophage responses to lipopolysaccharide and directly alters macrophage gene expression. J. Immunol., 165, 165, 3358-3365.
45. Ren, J.D.; Gu, J.S.; Gao, H.F.; Xia, P.Y.; Xiao, G.X. A synthetic cyclic peptide derived from Limulus anti-lipopolysaccharide factor neutralizes endotoxin in vitro and in vivo. Int. Immunopharmacol., 2008, 8, 775-781.