Biophysical studies of the interaction of squalamine and other cationic amphiphilic molecules with bacterial and eukaryotic membranes: importance of the distribution coefficient in membrane selectivity

Chemistry and Physics of Lipids

Volumn 163, Issue 2, 2010, Pages 131-140

  Di Pasquale, Eric ^a   Salmi Smail, Chanaz ^b   Brunel, Jean Michel ^c   Sanchez, Patrick ^a   Fantini, Jacques ^a   Maresca, Marc ^a  

^a University of Mediterranée   (France)

^b INSERM   (France)

^c AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

Cationic amphipathic antimicrobial; Distribution coefficient; Lipid bilayer; Lipid monolayer; Polymyxin B; Squalamine

Indexed keywords

AMPHOPHILE; CALCIUM; CETRIMIDE; LIPOPOLYSACCHARIDE; POLYMYXIN B; SQUALAMINE;

ARTICLE; BACTERIAL MEMBRANE; BIOPHYSICS; CONTROLLED STUDY; DRUG STRUCTURE; EUKARYOTE; KINETICS; LIPID BILAYER; LIPID MONOLAYER; NONHUMAN; PRIORITY JOURNAL; PROKARYOTE; SENSITIVITY ANALYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; CALCIUM; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CETRIMONIUM COMPOUNDS; CHOLESTANOLS; DETERGENTS; ESCHERICHIA COLI; KINETICS; LIPID BILAYERS; LIPOPOLYSACCHARIDES; MICE; POLYMYXIN B;

BACTERIA (MICROORGANISMS); EUKARYOTA; PROKARYOTA;

EID: 74349088909     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2009.10.006     Document Type: Article

References (39)

1. Brunel J.M., Salmi C., Loncle C., Vidal N., and Letourneux Y. Squalamine: a polyvalent drug of the future?. Curr. Cancer Drug Targets 5 (2005) 267-272
2. Carr Jr. C., and Morrison D.C. Mechanism of polymyxin B-mediated lysis of lipopolysaccharide-treated erythrocytes. Infect. Immun. 49 (1985) 84-89
3. Chen C.C., and Feingold D.S. Locus of divalent cation inhibition of the bactericidal action of polymyxin B. Antimicrob. Agents Chemother. 2 (1972) 331-335
4. Chen W.H., Shao X.B., Moellering R., Wennersten C., and Regen S.L. A bioconjugate approach toward squalamine mimics: insight into the mechanism of biological action. Bioconjug. Chem. 17 (2006) 1582-1591
5. Clausell A., Busquets M.A., Pujol M., Alsina A., and Cajal Y. Polymyxin B-lipid interactions in Langmuir-Blodgett monolayers of Escherichia coli lipids: a thermodynamic and atomic force microscopy study. Biopolymers 75 (2004) 480-490
6. Clausell A., Rabanal F., Garcia-Subirats M., Asunción Alsina M., and Cajal Y. Synthesis and membrane action of polymyxin B analogues. Luminescence 20 (2005) 117-123
7. Clausell A., Garcia-Subirats M., Pujol M., Busquets M.A., Rabanal F., and Cajal Y. Gram-negative outer and inner membrane models: insertion of cyclic cationic lipopeptides. J. Phys. Chem. B 111 (2007) 551-563
8. Ding B., Guan Q., Walsh J.P., Boswell J.S., Winter T.W., Winter E.S., Boyd S.S., Li C., and Savage P.B. Correlation of the antibacterial activities of cationic peptide antibiotics and cationic steroid antibiotics. J. Med. Chem. 45 (2001) 663-669
9. Di Pasquale E., Chahinian H., Sanchez P., and Fantini J. The insertion and transport of anandamide in synthetic lipid membranes are both cholesterol-dependent. PLoS ONE 4 (2009) e4989
10. Fantini J., Cook D.G., Nathanson N., Spitalnik S.L., and Gonzalez-Scarano F. Infection of colonic epithelial cell lines by type 1 human immunodeficiency virus is associated with cell surface expression of galactosylceramide, a potential alternative gp120 receptor. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 2700-2704
11. Hartmann W., Galla H.J., and Sackmann E. Polymyxin binding to charged lipid membranes. An example of cooperative lipid-protein interaction. Biochim. Biophys. Acta 510 (1978) 124-139
12. Katsu T., Yoshimura S., Tsuchiya T., and Fujita Y. Temperature dependence of action of polymyxin B on Escherichia coli. J. Biochem. 95 (1984) 1645-1653
13. Katsu T., Nakagawa H., and Yasuda K. Interaction between polyamines and bacterial outer membranes as investigated with ion-selective electrodes. Antimicrob. Agents Chemother. 46 (2002) 1073-1079
14. Katz M., Tsubery H., Kolusheva S., Shames A., Fridkin M., and Jelinek R. Lipid binding and membrane penetration of polymyxin B derivatives studied in a biomimetic vesicle system. Biochem. J. 375 (2003) 405-413
15. Kubinyi H. Nonlinear dependence of biological activity on hydrophobic character: the bilinear model. Farmaco Sci. 34 (1979) 248-276
16. Leo A., Hansch C., and Elkins D. Partition coefficients and their uses. Chem. Rev. 71 (1971) 525-616
17. Maloy W.L., and Kari U.P. Structure-activity studies on magainins and other host defense peptides. Biopolymers 37 (1995) 105-122
18. McBroom A.J., and Kuehn M.J. Release of outer membrane vesicles by Gram-negative bacteria is a novel envelope stress response. Mol. Microbiol. 63 (2007) 545-558
19. Moore K.S., Wehrli S., Roder H., Rogers M., Forrest Jr. J.N., McCrimmon D., and Zasloff M. Squalamine: an aminosterol antibiotic from the shark. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 1354-1358
20. Niven G.W., and Mulholland F. Cell membrane integrity and lysis in Lactococcus lactis: the detection of a population of permeable cells in post-logarithmic phase cultures. J. Appl. Microbiol. 84 (1998) 90-96
21. Ran S., Downes A., and Thorpe P.E. Increased exposure of anionic phospholipids on the surface of tumor blood vessels. Cancer Res. 62 (2002) 6132-6140
22. Salmi C., Loncle C., Vidal N., Letourneux Y., Fantini J., Maresca M., Taïeb N., Pagès J.M., and Brunel J.M. Squalamine: an appropriate strategy against the emergence of multidrug resistant Gram-negative bacteria?. PLoS ONE 3 (2008) e2765
23. Salmi C., Loncle C., Vidal N., Laget M., Letourneux Y., and Brunel J.M. Antimicrobial activities of 3-amino- and polyaminosterol analogues of squalamine and trodusquemine. J. Enzyme Inhib. Med. Chem. 23 (2008) 860-865
24. Sangster J. Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry. Vol. 2 of Wiley Series in Solution Chemistry (1997), John Wiley & Sons Ltd., Chichester
25. Savage P.B., and Li C. Cholic acid derivatives: novel antimicrobials. Expert Opin. Investig. Drugs 9 (2000) 263-272
26. Savage P.B., Li C., Taotafa U., Ding B., and Guan Q. Antibacterial properties of cationic steroid antibiotics. FEMS Microbiol. Lett. 217 (2002) 1-7
27. Selinsky B.S., Zhou Z., Fojtik K.G., Jones S.R., Dollahon N.R., and Shinnar A.E. The aminosterol antibiotic squalamine permeabilizes large unilamellar phospholipid vesicles. Biochim. Biophys. Acta 1370 (1998) 218-234
28. Selinsky B.S., Smith R., Frangiosi A., Vonbaur B., and Pedersen L. Squalamine is not a proton ionophore. Biochim. Biophys. Acta 1464 (2000) 135-141
29. 2+. Biochim. Biophys. Acta 643 (1981) 626-635
30. Sixl F., and Galla H.J. Calorimetric investigation of polymyxin binding to phosphatidic acid bilayers. Biochim. Biophys. Acta 693 (1982) 466-478
31. Ti Tien H. Bilayer Lipid Membranes (BLM): Theory and Practice (1974), Marcel Dekker Inc., New York
32. Tsubery H., Ofek I., Cohen S., and Fridkin M. The functional association of polymyxin B with bacterial lipopolysaccharide is stereospecific: studies on polymyxin B nonapeptide. Biochemistry 39 (2000) 11837-11844
33. Tsubery H., Ofek I., Cohen S., and Fridkin M. N-terminal modifications of polymyxin B nonapeptide and their effect on antibacterial activity. Peptides 22 (2001) 1675-1681
34. Tsubery H., Ofek I., Cohen S., Eisenstein M., and Fridkin M. Modulation of the hydrophobic domain of polymyxin B nonapeptide: effect on outer-membrane permeabilization and lipopolysaccharide neutralization. Mol. Pharmacol. 62 (2002) 1036-1042
35. Vaara M., and Vaara T. Polycations as outer membrane-disorganizing agents. Antimicrob. Agents Chemother. 24 (1983) 114-122
36. Wiese A., Münstermann M., Gutsmann T., Lindner B., Kawahara K., Zähringer U., and Seydel U. Molecular mechanisms of polymyxin B-membrane interactions: direct correlation between surface charge density and self-promoted transport. J. Membr. Biol. 162 (1998) 127-138
37. Wiese A., Gutsmann T., and Seydel U. Towards antibacterial strategies: studies on the mechanisms of interaction between antibacterial peptides and model membranes. J. Endotoxin Res. 9 (2003) 67-84
38. Wilton D.C. Anionic phospholipids and the regulation of cell functions. Biochem. Soc. Trans. 26 (1998) 378-383
39. Xiong Y.Q., Mukhopadhyay K., Yeaman M.R., Adler-Moore J., and Bayer A.S. Functional interrelationships between cell membrane and cell wall in antimicrobial peptide-mediated killing of Staphylococcus aureus. Antimicrob. Agents Chemother. 49 (2005) 3114-3121