Combination of antimicrobial and endotoxin-neutralizing activities of novel oleoylamines

Antimicrobial Agents and Chemotherapy

Volumn 49, Issue 6, 2005, Pages 2307-2313

  Zorko, Mateja ^a   Majerle, Andreja ^a   Šarlah, David ^b   Keber, Mateja Manček ^a   Mohar, Barbara ^b   Jerala, Roman ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b Laboratory of Organic and Medicinal Chemistry   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

(N OLEOYLPROPYL) N,N BIS[2 (DIETHYLAMINO)ETHYL]AMIDE; (N OLEOYLPROPYL)[N,N BIS(2 AMINOETHYL)]AMIDE; (NALPHA OLEOYLLYSYLPROPYL) N,N BIS[2 (DIETHYLAMINO)ETHYL]AMIDE; ANTIINFECTIVE AGENT; BACTERIUM LIPOPOLYSACCHARIDE; ENDOTOXIN; ETHIDIUM BROMIDE; N,N BIS[2 (GLYCINAMIDO)ETHYL]OLEOYLAMIDE; N1 OLEOYLDIETHYLENETRIAMINE; OLEIC ACID (4 AMINOBUTYL)(3 AMINOPROPYL)AMIDE; OLEIC ACID [4 (2 AMINOETHYLAMINO)BUTYL] [3 (2 AMINOETHYLAMINO)PROPYL]AMIDE; OLEIC ACID BIS(2 AMINOETHYL)AMIDE; OLEIC ACID BIS(2 DIETHYLENETRIAMINE)AMIDE; OLEIC ACID BIS[2 (2 AMINOETHYLAMINO)ETHYL]AMIDE; OLEOLAMINE; OLEOYLAMINE DERIVATIVE; POLYAMINE DERIVATIVE; POLYMYXIN B; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL MEMBRANE; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HEMOLYSIS; HUMAN; HUMAN CELL; LIMULUS LYSATE TEST; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CELL MEMBRANE PERMEABILITY; ENDOTOXINS; ESCHERICHIA COLI; FATTY ACIDS, MONOUNSATURATED; HEMOLYSIS; HUMANS; LIPOPOLYSACCHARIDES; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 19544380592     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.49.6.2307-2313.2005     Document Type: Article

References (31)

1. Asseline, U., M. Chassignol, J. Draus, M. Durand, and J. C. Maurizot. 2003. Synthesis and properties of oligo-2́-deoxyribonucleotides containing internucleotidic phosphoramidate linkages modified with pendant groups ending with either two amino or two hydroxyl functions. Bioorg. Med. Chem. 11: 3499-3511.
2. a.Balaban, A. T. 1982. Highly discriminating distance based topological index. Chem. Phys. Lett. 89:399-404.
3. Blagbrough, I. S., A. J. Geall, and S. A. David. 2000. Lipopolyamines incorporating the tetraamine spermine, bound to an alkyl chain, sequester bacterial lipopolysaccharide. Bioorg. Med. Chem. Lett. 10:1959-1962.
4. Cohen, J. 2002. The immunopathogenesis of sepsis. Nature 420:885-891.
5. Craig, W. A., J. H. Turner, and C. M. Kunin. 1974. Prevention of the generalized Shwartzman reaction and endotoxin lethality by polymyxin B localized in tissues. Infect. Immun. 10:287-292.
6. David, S. A. 2001. Towards a rational development of anti-endotoxin agents: novel approaches to sequestration of bacterial endotoxins with small molecules. J. Mol. Recognit. 14:370-387.
7. David, S. A., B. Bechtel, C. Annaiah, V. I. Mathan, and P. Balaram. 1994. Interaction of cationic amphiphilic drugs with lipid A: implications for development of endotoxin antagonists. Biochim. Biophys. Acta 1212:167-175.
8. David, S. A., R. Silverstein, C. R. Amura, T. Kielian, and D. C. Morrison. 1999. Lipopolyamines: novel antiendotoxin compounds that reduce mortality in experimental sepsis caused by gram-negative bacteria. Antimicrob. Agents Chemother. 43:912-919.
9. Duwe, A. K., C. A. Rupar, G. B. Horsman, and S. I. Vas. 1986. In vitro cytotoxicity and antibiotic activity of polymyxin B nonapeptide. Antimicrob. Agents Chemother. 30:340-341.
10. Govorunov, I. G., N. V. Kosarev, I. Evtodienko, and E. O. Puchkov. 1982. [Permeability of the membrane of the Escherichia coli envelope for ethidium bromide.] Mikrobiologiia 51:731-734. (In Russian.)
11. Holzheimer, R. G. 2001. Antibiotic induced endotoxin release and clinical sepsis: a review. J. Chemother. 13:159-172.
12. Jerala, R., and M. Porro. 2004. Endotoxin neutralizing peptides. Curr. Top. Med. Chem. 4:1173-1184.
13. Jurgens, G., M. Muller, M. H. Koch, and K. Brandenburg. 2001. Interaction of hemoglobin with enterobacterial lipopolysaccharide and lipid A. Physicochemical characterization and biological activity. Eur. J. Biochem. 268:4233-4242.
14. Kang, J. H., M. K. Lee, K. L. Kim, and K. S. Hahm. 1996. Structure-biological activity relationships of 11-residue highly basic peptide segment of bovine lactoferrin. Int. J. Pept. Protein Res. 48:357-363.
15. Leon-Ponte, M., M. G. Kirchhof, T. Sun, T. Stephens, B. Singh, S. Sandhu, and J. Madrenas. 2005. Polycationic lipids inhibit the pro-inflammatory response to LPS. Immunol. Lett. 96:73-83.
16. Lohner, K. 2001. The role of membrane lipid composition in cell targeting of antimicrobial peptides, p. 149-165. In K. Lohner (ed.), Development of novel antimicrobial agents: emerging strategies. Horizon Scientific Press, Norfolk, England.
17. Lohner, K., and E. J. Prenner. 1999. Differential scanning calorimetry and X-ray diffraction studies of the specificity of the interaction of antimicrobial peptides with membrane-mimetic systems. Biochim. Biophys. Acta 1462:141-156.
18. Majerle, A., J. Kidrič, and R. Jerala. 2000. Production of stable isotope enriched antimicrobial peptides in Escherichia coli: an application to the production of a 15N-enriched fragment of lactoferrin. J. Biomol. NMR 18:145-151.
19. Majerle, A., J. Kidrič, and R. Jerala. 2003. Enhancement of antibacterial and lipopolysaccharide binding activities of a human lactoferrin peptide fragment by the addition of acyl chain. J. Antimicrob. Chemother. 51:1159-1165.
20. Reference deleted.
21. Moore, R. A., N. C. Bates, and R. E. Hancock. 1986. Interaction of polycationic antibiotics with Pseudomonas anruginosa lipopolysaccharide and lipid A studied by using dansyl-polymyxin. Antimicrob. Agents Chemother. 29:496-500.
22. Morrison, D. C. 1998. Antibiotic-mediated release of endotoxin and the pathogenesis of gram-negative sepsis. Prog. Clin. Biol. Res. 397:199-207.
23. Mortimer, F. C., D. J. Mason, and V. A. Gant. 2000. Flow cytometric monitoring of antibiotic-induced injury in Escherichia coli using cell-impermeant fluorescent probes. Antimicrob. Agents Chemother. 44:676-681.
24. National Committee for Clinical Laboratory Standards. 2003. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A5. National Committee for Clinical Laboratory Standards, Wayne, Pa.
25. Nikaido, H. 2003. Molecular basis of bacterial outer membrane permeability revisited. Microbiol. Mol. Biol. Rev. 67:593-656.
26. Opal, S. M., J. E. Palardy, N. Parejo, and D. C. Morrison. 2001. Lipopolyamines as a therapeutic strategy in experimental Gram-negative bacterial sepsis. J. Endotoxin Res. 7:35-38.
27. Otvos, L., Jr. 2002. The short proline-rich antibacterial peptide family. Cell Mol. Life Sci. 59:1138-1150.
28. Rifkind, D. 1967. Prevention by polymyxin B of endotoxin lethality in mice. J. Bacteriol. 93:1463-1464.
29. Rustici, A., M. Velucchi, R. Faggioni, M. Sironi, P. Ghezzi, S. Quataert, B. Green, and M. Porro. 1993. Molecular mapping and detoxification of the lipid A binding site by synthetic peptides. Science 259:361-365.
30. Ulevitch, R. J. 2000. Molecular mechanisms of innate immunity. Immunol. Res. 21:49-54.
31. Vaara, M., and T. Vaara. 1983. Polycations as outer membrane- disorganizing agents. Antimicrob. Agents Chemother. 24:114-122.