Short alkylated peptoid mimics of antimicrobial lipopeptides

Antimicrobial Agents and Chemotherapy

Volumn 55, Issue 1, 2011, Pages 417-420

  Chongsiriwatana, Nathaniel P ^a   Miller, Tyler M ^b,c   Wetzler, Modi ^c   Vakulenko, Sergei ^d   Karlsson, Amy J ^d   Palecek, Sean P ^d   Mobashery, Shahriar ^e   Barron, Annelise E ^a,b,c  

^a Northwestern University   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c Stanford University   (United States)

^d University of Wisconsin Madison   (United States)

^e UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; GLYCINE DERIVATIVE; LIPOPEPTIDE; MELITTIN; MONOMER; N 4(AMINOBUTYL)GLYCINE; N 4(PHENYLETHYL)GLYCINE; PEPTOID; PEXIGANAN ACETATE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG POTENCY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HEMOLYSIS; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

ANTI-INFECTIVE AGENTS; CELLS, CULTURED; HEMOLYSIS; HUMANS; LIPOPEPTIDES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PEPTOIDS;

EID: 78650649448     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01080-10     Document Type: Article

References (38)

1. Andreu, D., and L. Rivas. 1998. Animal antimicrobial peptides: an overview. Biopolymers 47:415-433.
2. Armand, P., K. Kirshenbaum, A. Falicov, R. L. Dunbrack, Jr., K. A. Dill, R. N. Zuckermann, and F. E. Cohen. 1997. Chiral N-substituted glycines can form stable helical conformations. Folding Des. 2:369-375.
3. Armand, P., K. Kirshenbaum, R. A. Goldsmith, S. Farr-Jones, A. E. Barron, K. T. V. Truong, K. A. Dill, D. F. Mierke, F. E. Cohen, R. N. Zuckermann, and E. K. Bradley. 1998. NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains. Proc. Natl. Acad. Sci. U. S. A. 95:4309-4314.
4. Avrahami, D., and Y. Shai. 2003. Bestowing antifungal and antibacterial activities by lipophilic acid conjugation to D,L-amino acid-containing antimicrobial peptides: a plausible mode of action. Biochemistry 42:14946-14956.
5. Bessalle, R., A. Kapitkovsky, A. Gorea, I. Shalit, and M. Fridkin. 1990. All-D-magainin: chirality, antimicrobial activity and proteolytic resistance. FEBS Lett. 274:151-155.
6. Chongsiriwatana, N. P., J. A. Patch, A. M. Czyzewski, M. T. Dohm, A. Ivankin, D. Gidalevitz, R. N. Zuckermann, and A. E. Barron. 2008. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides. Proc. Natl. Acad. Sci. U. S. A. 105:2794-2799.
7. CLSI. 2006. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 6th ed. CLSI, Wayne, PA.
8. Ge, Y., D. MacDonald, M. M. Henry, H. I. Hait, K. A. Nelson, B. A. Lipsky, M. A. Zasloff, and K. J. Holroyd. 1999. In vitro susceptibility to pexiganan of bacteria isolated from infected diabetic foot ulcers. Diagn. Microbiol. Infect. Dis. 35:45-53.
9. Goodson, B., A. Ehrhardt, S. Ng, J. Nuss, K. Johnson, M. Giedlin, R. Yamamoto, W. H. Moos, A. Krebber, M. Ladner, M. B. Giacona, C. Vitt, and J. Winter. 1999. Characterization of novel antimicrobial peptoids. Antimicrob. Agents Chemother. 43:1429-1434.
10. Hancock, R. E., and M. G. Scott. 2000. The role of antimicrobial peptides in animal defenses. Proc. Natl. Acad. Sci. U. S. A. 97:8856-8861.
11. Hancock, R. E. W., and H.-G. Sahl. 2006. Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nat. Biotechnol. 24: 1551-1557.
12. Ishitsuka, Y., L. Arnt, J. Majewski, S. Frey, M. Ratajczek, K. Kjaer, G. N. Tew, and K. Y. C. Lee. 2006. Amphiphilic poly(phenyleneethynylene)s can mimic antimicrobial peptide membrane disordering effect by membrane insertion. J. Am. Chem. Soc. 128:13123-13129.
13. Japelj, B., M. Zorko, A. Majerle, P. Pristovsek, S. Sanchez-Gomez, G. Martinez de Tejada, I. Moriyon, S. E. Blondelle, K. Brandenburg, J. Andrae, K. Lohner, and R. Jerala. 2007. The acyl group as the central element of the structural organization of antimicrobial lipopeptide. J. Am. Chem. Soc. 129: 1022-1023.
14. Jenssen, H., P. Hamill, and R. E. W. Hancock. 2006. Peptide antimicrobial agents. Clin. Microbiol. Rev. 19:491-511.
15. Kamysz, W., C. Silvestri, O. Cirioni, A. Giacometti, A. Licci, A. Della Vittoria, M. Okroj, and G. Scalise. 2007. In vitro activities of the lipopeptides palmitoyl (Pal)-Lys-Lys-NH2 and Pal-Lys-Lys alone and in combination with antimicrobial agents against multiresistant Gram-positive cocci. Antimicrob. Agents Chemother. 51:354-358.
16. Kirshenbaum, K., A. E. Barron, R. A. Goldsmith, P. Armand, E. K. Bradley, K. T. V. Truong, K. A. Dill, F. E. Cohen, and R. N. Zuckermann. 1998. Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure. Proc. Natl. Acad. Sci. U. S. A. 95:4303-4308.
17. Laverty, G., M. McLaughlin, C. Shaw, S. P. Gorman, and B. F. Gilmore. 2010. Antimicrobial activity of short, synthetic cationic lipopeptides. Chem. Biol. Drug Des. 75:563-569.
18. Lipinski, C. A., F. Lombardo, B. W. Dominy, and P. J. Feeney. 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 23:3-25.
19. Lockwood, N. A., J. R. Haseman, M. V. Tirrell, and K. H. Mayo. 2004. Acylation of SC4 dodecapeptide increases bactericidal potency against Gram-positive bacteria, including drug-resistant strains. Biochem. J. 378:93-103.
20. Majerle, A., J. Kidric, 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.
21. Mak, P., J. Pohl, A. Dubin, M. S. Reed, S. E. Bowers, M. T. Fallon, and W. M. Shafer. 2003. The increased bactericidal activity of a fatty acid-modified synthetic antimicrobial peptide of human cathepsin G correlates with its enhanced capacity to interact with model membranes. Int. J. Antimicrob. Agents 21:13-19.
22. Makovitzki, A., D. Avrahami, and Y. Shai. 2006. Ultrashort antibacterial and antifungal lipopeptides. Proc. Natl. Acad. Sci. U. S. A. 103:15997-16002.
23. Makovitzki, A., J. Baram, and Y. Shai. 2008. Antimicrobial lipopolypeptides composed of palmitoyl di-and tricationic peptides: in vitro and in vivo activities, self-assembly to nanostructures, and a plausible mode of action. Biochemistry 47:10630-10636.
24. Miller, S. M., R. J. Simon, S. Ng, R. N. Zuckermann, J. M. Kerr, and W. H. Moos. 1995. Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers. Drug Dev. Res. 35:20-32.
25. NCCLS. 2002. Method for broth dilution antifungal susceptibility testing of yeasts. Approved standard, 2nd ed. NCCLS, Wayne, PA.
26. Patch, J. A., and A. E. Barron. 2003. Helical peptoid mimics of magainin-2 amide. J. Am. Chem. Soc. 125:12092-12093.
27. Peggion, C., F. Formaggio, M. Crisma, R. F. Epand, R. M. Epand, and C. Toniolo. 2003. Trichogin: a paradigm for lipopeptaibols. J. Pept. Sci. 9:679-689.
28. Peschel, A., and H.-G. Sahl. 2006. The co-evolution of host cationic antimicrobial peptides and microbial resistance. Nat. Rev. Microbiol. 4:529-536.
29. Porter, E. A., X. Wang, H. S. Lee, B. Weisblum, and S. H. Gellman. 2000. Non-haemolytic beta-amino-acid oligomers. Nature 404:565.
30. Porter, E. A., B. Weisblum, and S. H. Gellman. 2002. Mimicry of hostdefense peptides by unnatural oligomers: antimicrobial beta-peptides. J. Am. Chem. Soc. 124:7324-7330.
31. Porter, E. A., B. Weisblum, and S. H. Gellman. 2005. Use of parallel synthesis to probe structure-activity relationships among 12-helical beta-peptides: evidence of a limit on antimicrobial activity. J. Am. Chem. Soc. 127: 11516-11529.
32. Seebach, D., M. Overhand, F. N. M. Kuehnle, and B. Martinoni. 1996. Beta-peptides. Synthesis by Arndt-Eistert homologation with concomitant peptide coupling. Structure determination by NMR and CD spectroscopy and by x-ray crystallography. Helical secondary structure of a beta-hexapeptide in solution and its stability towards pepsin. Helv. Chim. Acta 79:913-941.
33. Tew, G. N., D. Liu, B. Chen, R. J. Doerksen, J. Kaplan, P. J. Carroll, M. L. Klein, and W. F. DeGrado. 2002. De novo design of biomimetic antimicrobial polymers. Proc. Natl. Acad. Sci. U. S. A. 99:5110-5114.
34. Tsubery, H., I. Ofek, S. Cohen, and M. Fridkin. 2001. N-terminal modifications of polymyxin B nonapeptide and their effect on antibacterial activity. Peptides 22:1675-1681.
35. Uchida, M., G. McDermott, M. Wetzler, M. A. Le Gros, M. Myllys, C. Knoechel, A. E. Barron, and C. A. Larabell. 2009. Soft X-ray tomography of phenotypic switching and the cellular response to antifungal peptoids in Candida albicans. Proc. Natl. Acad. Sci. U. S. A. 106:19375-19380.
36. Wu, C. W., K. Kirshenbaum, T. J. Sanborn, J. A. Patch, K. Huang, K. A. Dill, R. N. Zuckermann, and A. E. Barron. 2003. Structural and spectroscopic studies of peptoid oligomers with alpha-chiral aliphatic side chains. J. Am. Chem. Soc. 125:13525-13530.
37. Wu, C. W., T. J. Sanborn, K. Huang, R. N. Zuckermann, and A. E. Barron. 2001. Peptoid oligomers with alpha-chiral, aromatic side chains: sequence requirements for the formation of stable peptoid helices. J. Am. Chem. Soc. 123:6778-6784.
38. Zuckermann, R. N., J. M. Kerr, S. B. H. Kent, and W. H. Moos. 1992. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 114:10646-10647.