Analogous oligo-acyl-lysines with distinct antibacterial mechanisms

FASEB Journal

Volumn 22, Issue 8, 2008, Pages 2652-2661

  Rotem, Shahar ^a   Radzishevsky, Inna S ^a   Bourdetsky, Dmitry ^a   Navon Venezia, Shiri ^b   Carmeli, Yehuda ^b   Mor, Amram ^a,b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b TEL AVIV SOURASKY MEDICAL CENTER   (Israel)

Author keywords

Host defense peptides; Intracellular targets; Mechanism of action; Peptidomimetics

Indexed keywords

ANTIINFECTIVE AGENT; DNA; OLIGO ACYL LYSINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL KINETICS; BINDING AFFINITY; CONTROLLED STUDY; DRUG STABILITY; DRUG STRUCTURE; ESCHERICHIA COLI; FEMALE; HEMOLYSIS; HOST RESISTANCE; HUMAN; HUMAN CELL; MALE; MEMBRANE DAMAGE; MORTALITY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTIMICROBIAL CATIONIC PEPTIDES; CELL MEMBRANE; DNA, BACTERIAL; ESCHERICHIA COLI; ESCHERICHIA COLI INFECTIONS; FEMALE; HEMOLYSIS; HUMANS; KLEBSIELLA PNEUMONIAE; LYSINE; MEMBRANE POTENTIALS; MICE; MICE, INBRED ICR; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PERITONITIS; SALMONELLA TYPHIMURIUM; SEPSIS; SURFACE PLASMON RESONANCE;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; QUERCUS;

EID: 48749098846     PISSN: 08926638     EISSN: None     Source Type: Journal    
DOI: 10.1096/fj.07-105015     Document Type: Article

References (50)

1. Hancock, R. E., and Sahl, H. G. (2006) Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nat. Biotechnol. 24, 1551-1557
2. Jenssen, H., Hamill, P., and Hancock, R. E. (2006) Peptide antimicrobial agents. Clin. Microbiol. Rev. 19, 491-511
3. Zasloff, M. (2002) Antimicrobial peptides of multicellular organisms. Nature 415, 389-395
4. Goldman, M. J., Anderson, G. M., Stolzenberg, E. D., Kari, U. P., Zasloff, M., and Wilson, J. M. (1997) Human beta-defensin-1 is a salt-sensitive antibiotic in lung that is inactivated in cystic fibrosis. Cell 88, 553-560
5. Lee, I. H., Cho, Y., and Lehrer, R. I. (1997) Effects of pH and salinity on the antimicrobial properties of clavanins. Infect. Immun. 65, 2898-2903
6. Minahk, C. J., and Morero, R. D. (2003) Inhibition of enterocin CRL35 antibiotic activity by mono- and divalent ions. Lett. Appl. Microbiol. 37, 374-379
7. Radzishevsky, I. S., Rotem, S., Zaknoon, F., Gaidukov, L., Dagan, A., and Mor, A. (2005) Effects of acyl versus aminoacyl conjugation on the properties of antimicrobial peptides. Antimicrob. Agents Chemother. 49, 2412-2420
8. Rozek, A., Powers, J. P., Friedrich, C. L., and Hancock, R. E. (2003) Structure-based design of an indolicidin peptide analogue with increased protease stability. Biochemistry 42, 14130-14138
9. Bradshaw, J. (2003) Cationic antimicrobial peptides: issues for potential clinical use. BioDrugs 17, 233-240
10. Gordon, Y. J., Romanowski, E. G., and McDermott, A. M. (2005) A review of antimicrobial peptides and their therapeutic potential as anti-infective drugs. Curr. Eye Res. 30, 505-515
11. Iverson, B. L. (1997) Betas are brought into the fold. Nature 385, 113-115
12. Kirshenbaum, K., Barron, A. E., Goldsmith, R. A., Armand, P., Bradley, E. K., Truong, K. T., Dill, K. A., Cohen, F. E., and Zuckermann, R. N. (1998) Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure. Proc. Natl. Acad. Sci. U. S. A. 95, 4303-4308
13. Tew, G. N., Liu, D., Chen, B., Doerksen, R. J., Kaplan, J., Carroll, P. J., Klein, M. L., and DeGrado, W. F. (2002) De novo design of biomimetic antimicrobial polymers. Proc. Natl. Acad. Sci. U. S. A. 99, 5110-5114
14. Liu, D., and DeGrado, W. F. (2001) De novo design, synthesis, and characterization of antimicrobial beta-peptides. J. Am. Chem. Soc. 123, 7553-7559
15. Patch, J. A., and Barron, A. E. (2003) Helical peptoid mimics of magainin-2 amide. J. Am. Chem. Soc. 125, 12092-12093
16. Oppenheim, J. J., and Yang, D. (2005) Alarmins: chemotactic activators of immune responses. Curr. Opin. Immunol. 17, 359-365
17. Yang, D., Biragyn, A., Hoover, D. M., Lubkowski, J., and Oppenheim, J. J. (2004) Multiple roles of antimicrobial defensins, cathelicidins, and eosinophil-derived neurotoxin in host defense. Annu. Rev. Immunol. 22, 181-215
18. Shai, Y. (2002) Mode of action of membrane active antimicrobial peptides. Biopolymers 66, 236-248
19. Cociancich, S., Ghazi, A., Hetru, C., Hoffmann, J. A., and Letellier, L. (1993) Insect defensin, an inducible antibacterial peptide, forms voltage-dependent channels in Micrococcus luteus. J. Biol. Chem. 268, 19239-19245
20. Sahl, H. G., Pag, U., Bonness, S., Wagner, S., Antcheva, N., and Tossi, A. (2005) Mammalian defensins: structures and mechanism of antibiotic activity. J. Leukoc. Biol. 77, 466-475
21. Kragol, G., Lovas, S., Varadi, G., Condie, B. A., Hoffmann, R., and Otvos, L., Jr. (2001) The antibacterial peptide pyrrhocoricin inhibits the ATPase actions of DnaK and prevents chaperone-assisted protein folding. Biochemistry 40, 3016-3026
22. Patrzykat, A., Friedrich, C. L., Zhang, L., Mendoza, V., and Hancock, R. E. (2002) Sublethal concentrations of pleurocidinderived antimicrobial peptides inhibit macromolecular synthesis in Escherichia coli. Antimicrob. Agents Chemother. 46, 605-614
23. Mor, A., Hani, K., and Nicolas, P. (1994) The vertebrate peptide antibiotics dermaseptins have overlapping structural features but target specific microorganisms. J. Biol. Chem. 269, 31635-31641
24. Selsted, M. E., Tang, Y. Q., Morris, W. L., McGuire, P. A., Novotny, M. J., Smith, W., Henschen, A. H., and Cullor, J. S. (1993) Purification, primary structures, and antibacterial activities of beta-defensins, a new family of antimicrobial peptides from bovine neutrophils. J. Biol. Chem. 268, 6641-6648
25. Matsuzaki, K., Mitani, Y., Akada, K. Y., Murase, O., Yoneyama, S., Zasloff, M., and Miyajima, K. (1998) Mechanism of synergism between antimicrobial peptides magainin 2 and PGLa. Biochemistry 37, 15144-15153
26. Park, C. B., Yi, K. S., Matsuzaki, K., Kim, M. S., and Kim, S. C. (2000) Structure-activity analysis of buforin II, a histone H2A-derived antimicrobial peptide: the proline hinge is responsible for the cell-penetrating ability of buforin II. Proc. Natl. Acad. Sci. U. S. A. 97, 8245-8250
27. Radzishevsky, I., Krugliak, M., Ginsburg, H., and Mor, A. (2007) Antiplasmodial activity of lauryl-lysine oligomers. Antimicrob. Agents Chemother. 51, 1753-1759
28. Radzishevsky, I. S., Rotem, S., Bourdetsky, D., Navon-Venezia, S., Carmeli, Y., and Mor, A. (2007) Improved antimicrobial peptides based on acyl-lysine oligomers. Nat. Biotechnol. 25, 657-659
29. Lockwood, N. A., Haseman, J. R., Tirrell, M. V., and Mayo, K. H. (2004) Acylation of SC4 dodecapeptide increases bactericidal potency against Gram-positive bacteria, including drug-resistant strains. Biochem. J. 378, 93-103
30. Avrahami, D., and Shai, Y. (2002) Conjugation of a magainin analogue with lipophilic acids controls hydrophobicity, solution assembly, and cell selectivity. Biochemistry 41, 2254-2263
31. Majerle, A., Kidric, J., and Jerala, R. (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
32. Fields, G. B., and Noble, R. L. (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein. Res. 35, 161-214
33. Hoben, H. J., and Somasegaran, P. (1982) Comparison of the pour, spread, and drop plate methods for enumeration of Rhizobium Spp. in inoculants made from presterilized peat. Appl. Environ. Microbiol. 44, 1246-1247
34. Rydlo, T., Rotem, S., and Mor, A. (2006) Antibacterial properties of dermaseptin S4 derivatives under extreme incubation conditions. Antimicrob. Agents Chemother. 50, 490-497
35. Tossi, A., Scocchi, M., Zanetti, M., Gennaro, R., Storici, P., and Romeo, D. (1997) An approach combining rapid cDNA amplification and chemical synthesis for the identification of novel, cathelicidin-derived, antimicrobial peptides. Methods Mol. Biol. 78, 133-150
36. Moore, R. A., Bates, N. C., and Hancock, R. E. (1986) Interaction of polycationic antibiotics with Pseudomonas-aeruginosa lipopolysaccharide and lipid-A studied by using dansyl-polymyxin. Antimicrob. Agents Chemother. 29, 496-500
37. Gaidukov, L., Fish, A., and Mor, A. (2003) Analysis of membrane-binding properties of dermaseptin analogues: relationships between binding and cytotoxicity. Biochemistry 42, 12866-12874
38. Lehrer, R. I., Barton, A., Daher, K. A., Harwig, S. S., Ganz, T., and Selsted, M. E. (1989) Interaction of human defensins with Escherichia coli. Mechanism of bactericidal activity. J. Clin. Invest. 84, 553-561
39. Zhang, L., Dhillon, P., Yan, H., Farmer, S., and Hancock, R. E. (2000) Interactions of bacterial cationic peptide antibiotics with outer and cytoplasmic membranes of Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 44, 3317-3321
40. Frimodt-Moller, N., Knudsen, J. D., and Espersen, F. (1999) The mouse peritonitis/sepsis model. In Handbook of Animal Models of Infection (Zak, O., and Sande, M. A., eds) pp. 127-136, Academic, London, UK
41. Schwetz, B. A. (2001) From the Food and Drug Administration. JAMA 285, 724
42. Hancock, R. E. (1997) Peptide antibiotics. Lancet 349, 418-422
43. Wu, M., Maier, E., Benz, R., Hancock, R. E. (1999) Mechanism of interaction of different classes of cationic antimicrobial peptides with planar bilayers and with the cytoplasmic membrane of Escherichia coli. Biochemistry 38, 7235-7242
44. Yeaman, M. R., Bayer, A. S., Koo, S. P., Foss, W., and Sullam, P. M. (1998) Platelet microbicidal proteins and neutrophil defensin disrupt the Staphylococcus aureus cytoplasmic membrane by distinct mechanisms of action. J. Clin. Invest. 101, 178-187
45. Boman, H. G., Agerberth, B., and Boman, A. (1993) Mechanisms of action on Escherichia coli of cecropin P1 and PR-39, two antibacterial peptides from pig intestine. Infect. Immun. 61, 2978-2984
46. Xiong, Y. Q., Yeaman, M. R., and Bayer, A. S. (1999) In vitro antibacterial activities of platelet microbicidal protein and neutrophil defensin against Staphylococcus aureus are influenced by antibiotics differing in mechanism of action. Antimicrob. Agents Chemother. 43, 1111-1117
47. Marynka, K., Rotem, S., Portnaya, I., Cogan, U., and Mor, A. (2007) In vitro discriminative antipseudomonal properties resulting from acyl substitution of N-terminal sequence of derma-septin s4 derivatives. Chem. Biol. 14, 75-85
48. Rotem, S., Radzishevsky, I., and Mor, A. (2006) physicochemical properties that enhance discriminative antibacterial activity of short dermaseptin derivatives. Antimicrob. Agents Chemother. 50, 2666-2672
49. Shalev, D. E., Rotem, S., Fish, A., and Mor, A. (2006) Consequences of N-acylation on structure and membrane binding properties of dermaseptin derivative K4-S4-(1-13). J. Biol. Chem. 281, 9432-9438
50. Morton, C. O., dos Santos, S. C., and Coote, P. (2007) An amphibian-derived, cationic, alpha-helical antimicrobial peptide kills yeast by caspase-independent but AIF-dependent programmed cell death. Molec. Microbiol. 65, 494-507