Antimicrobial activity of peptidomimetics against multidrug-resistant Escherichia coli: A comparative study of different backbones

Journal of Medicinal Chemistry

Volumn 55, Issue 16, 2012, Pages 7253-7261

  Jahnsen, Rasmus D ^a   Frimodt Møller, Niels ^b   Franzyk, Henrik ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b HVIDOVRE HOSPITAL   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; CATION; CEFOTAXIME; CIPROFLOXACIN; GENTAMICIN; MONOMER; PEPTIDOMIMETIC AGENT; PEPTOID;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ESCHERICHIA COLI; HEMOLYSIS; HUMAN; HUMAN CELL; KLEBSIELLA PNEUMONIAE; MULTIDRUG RESISTANCE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; CIRCULAR DICHROISM; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG STABILITY; ENTEROBACTERIACEAE; ESCHERICHIA COLI; HELA CELLS; HUMANS; MICROBIAL SENSITIVITY TESTS; PEPTIDOMIMETICS; PROTEIN STRUCTURE, SECONDARY; SOLID-PHASE SYNTHESIS TECHNIQUES; STRUCTURE-ACTIVITY RELATIONSHIP; UNILAMELLAR LIPOSOMES;

EID: 84866943640     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300820a     Document Type: Article

References (42)

1. ECDC. Annual Report of the European Antimicrobial Resistance Survillance Network; European Centre for Disease Prevention and Control: Stockholm, 2010.
2. WHO. Impacts of Antimcrobial Growth Promoter Termination in Denmark; WHO/CDS/CPE/ZFK/2003.1; World Health Organization: Foulum, 2003.
3. Projan, S. J. Why is Big Pharma getting out of antibacterial drug discovery? Curr. Opin. Microbiol. 2003, 6, 427-430.
4. Hammerum, A. M.; Lester, C. H.; Jakobsen, L.; Porsbo, L. J. Faecal carriage of extended-spectrum β-lactamase-producing and AmpC β-lactamase-producing bacteria among Danish army recruits. Clin. Microbiol. Infect. 2011, 17, 566-568.
5. Campos, J.; Oteo, J.; Perez-Vazquez, M. Extended-spectrum β-lactamase producing Escherichia coli: changing epidemiology and clinical impact. Curr. Opin. Infect. Dis. 2010, 23, 320-326.
6. Nordmann, P.; Poirel, L.; Lagrutta, E.; Taylor, P.; Pham, J. Emergence of Metallo-/?-Lactamase NDM-1-Producing Multidrug-Resistant Escherichia coli in Australia. Antimicrob. Agents Chemother. 2010, 54, 4914-4916.
7. Talbot, G. H.; Bradley, J.; Edwards, J. E.; Gilbert, D.; Scheld, M.; Bartlett, J. G Bad Bugs Need Drugs: An Update on the Development Pipeline from the Antimicrobial Availability Task Force of the Infectious Diseases Society of America. Clin. Infect. Dis. 2006, 42, 657-668.
8. Paterson, D. L. Resistance in Gram-negative bacteria: Enter-obacteriaceae. Am. J. Infect. Control 2006, 34, S20-S28 discussion S64-S73.
9. Zasloff, M. Antimicrobial peptides of multicellular organisms. Nature 2002, 415, 389-395.
10. Hancock, R E.; Sahl, H. G Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nature Biotechnol. 2006, 24, 1551 - 1557.
11. Rotem, S.; Mor, A. Antimicrobial peptide mimics for improved therapeutic properties. Biochim. Biophys. Acta, Biomembr. 2009, 1788, 1582-1592.
12. Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. De Novo Design of Antibacterial β-Peptides. J. Am. Chem. Soc. 1999, 121, 12200-12201.
13. Zuckermann, R N; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 1992, 114, 10646-10647.
14. Hamper, B. C.; Kolodziej, S. A.; Scates, A. M.; Smith, R G; Cortez, E. Solid Phase Synthesis of/7-Peptoids: N-Substituted ß-Aminopropionic Acid Oligomers. J. Org. Chem. 1998, 63, 708-718.
15. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. Interplay among folding, sequence, and lipophilicity in the antibacterial and hemolytic activities of a//7-peptides. J. Am. Chem. Soc. 2007, 129, 417-428.
16. Ryge, T. S.; Frimodt-Møller, N; Hansen, P. R Antimicrobial activities of twenty lysine-peptoid hybrids against clinically relevant bacteria and fungi. Chemotherapy 2008, 54, 152-6.
17. Chongsiriwatana, N. P.; Patch, J. A.; Czyzewski, A M.; Dohm, M. T.; Ivankin, A.; Gidalevitz, D.; Zuckermann, R N; Barron, A. E. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides. Proc. Natl. Acad. Sci. U.SA. 2008, 105, 2794-2799.
18. Olsen, C. A.; Ziegler, H. L.; Nielsen, H. M.; Frimodt-Møller, N.; Jaroszewski, J. W.; Franzyk, H. Antimicrobial, hemolytic, and cytotoxic activities of/7-peptoid-peptide hybrid oligomers: improved properties compared to natural AMPs. ChemBioChem 2010, 11, 1356-60.
19. Olsen, C. A.; Bonke, G; Vedel, L.; Adsersen, A; Witt, M.; Franzyk, H; Jaroszewski, J. W. a-Peptide//7-peptoid chimeras. Org. Lett. 2007, 9, 1549-1552.
20. Park, K H; Nan, Y. H; Park, Y.; Kim, J. I.; Park, I. S.; Hahm, K S.; Shin, S. Y. Cell specificity, anti-inflammatory activity, and plausible bactericidal mechanism of designed Trp-rich model antimicrobial peptides. Biochim. Biophys. Acta, Biomembr. 2009, 1788, 1193-1203.
21. Bonke, G; Vedel, L.; Witt, M.; Jaroszewski, J. W.; Olsen, C. A.; Franzyk, H. Dimeric building blocks for solid-phase synthesis of a-peptide-/7-peptoid chimeras. Synthesis 2008, 2381-2390.
22. Kruijtzer, J. A. W.; Hofmeyer, L. J. F.; Heerma, W.; Versluis, C.; Liskamp, R M. J. Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines: The synthesis of (retro) peptoids of Leu-enkephalin and substance P. Chem.-Eur. J. 1998, 4, 1570-1580.
23. Noack, M.; Gottlich, R Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines. Eur. J. Org. Chem. 2002, 2002, 3171-3178.
24. Østergaard, S.; Holm, A. Peptomers: A Versatile Approach for the Preparation of Diverse Combinatorial Peptidomimetic Bead Libraries. Mol. Divers. 1997, 3, 17-27.
25. Zhang, X. A.; Oglecka, K; Sandgren, S.; Belting, M.; Esbjorner, E. K; Norden, B.; Graslund, A. Dual functions of the human antimicrobial peptide LL-37-Target membrane perturbation and host cell cargo delivery. Biochim. Biophys. Acta, Biomembr. 2010, 1798, 2201-2208.
26. Godballe, T.; Nilsson, L. L.; Petersen, P. D.; Jenssen, H. Antimicrobial Peptides and a-Peptoids. Chem. Biol. Drug. Des. 2011, 77, 107-116.
27. ECDC. Annual Epidemiological Report 2011; European Centre for Disease Control and Prevention: Stockholm, 2011.
28. ECDC. Updated Risk Assessment on the Spread of NDM and Its Variants within Europe; European Centre for Disease Prevention and Control: Stockholm, 2011.
29. Jenssen, H.; Hamill, P.; Hancock, R E. W. Peptide Antimicrobial Agents. Clin. Microbiol. Rev. 2006, 19, 491-511.
30. Wu, C. W.; Sanborn, T. J.; Huang, K; Zuckermann, R N; Barron, A. E. Peptoid Oligomers with a-Chiral, Aromatic Side Chains: Sequence Requirements for the Formation of Stable Peptoid Helices. J. Am. Chem. Soc. 2001, 123, 6778-6784.
31. Wu, C. W.; Kirshenbaum, K; Sanborn, T. J.; Patch, J. A.; Huang, K; Dill, K A.; Zuckermann, R N; Barron, A. E. Structural and Spectroscopic Studies of Peptoid Oligomers with a-Chiral Aliphatic Side Chains. J. Am. Chem. Soc. 2003, 125, 13525-13530.
32. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R F.; Epand, R M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mmicry of antimicrobial host-defense peptides by random copolymers. J. Am. Chem. Soc. 2007, 129, 15474-15476.
33. Martinek, T. A; Fulop, F. Side-chain control of/7-peptide secondary structures. Eur. J. Biochem. 2003, 270, 3657-3666.
34. Simon, R J.; Kania, R S.; Zuckermann, R N; Huebner, V D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K. Peptoids: a modular approach to drug discovery. Proc. Natl. Acad. Sci. U.SA. 1992, 89, 9367-9371.
35. Hansen, T.; Alst, T.; Havelkova, M.; Strøm, M. B. Antimicrobial Activity of Small/7-Peptidomimetics Based on the Pharmacophore Model of Short Cationic Antimicrobial Peptides. J. Med. Chem. 2009, 53, 595-606.
36. Chen, Y. X.; Mant, C. T.; Farmer, S. W.; Hancock, R E. W.; Vasil, M. L.; Hodges, R S. Rational design of a-helical antimicrobial peptides with enhanced activities and specificity/therapeutic index. J. Biol. Chem. 2005, 280, 12316-12329.
37. Zhu, W. L.; Song, Y. M.; Park, Y.; Park, K H; Yang, S. T.; Kim, J. I.; Park, I. S.; Hahm, K. S.; Shin, S. Y. Substitution of the leucine zipper sequence in melittin with peptoid residues affects self-association, cell selectivity, and mode of action. Biochim. Biophys. Acta, Biomembr. 2007, 1768, 1506-1517.
38. Slaninova, J.; Mlsova, V; Kroupova, H; Alan, L.; Tumova, T.; Monincova, L.; Borovickova, L.; Fucik, V; Cerovsky, V Toxicity study of antimicrobial peptides from wild bee venom and their analogs toward mammalian normal and cancer cells. Peptides 2012, 33, 18-26.
39. Mygind, P. H; Fischer, R L.; Schnorr, K M.; Hansen, M. T.; Sonksen, C. P.; Ludvigsen, S.; Raventos, D.; Buskov, S.; Christensen, B.; De Maria, L.; Taboureau, O.; Yaver, D.; Elvig-Jorgensen, S. G; Sorensen, M. V; Christensen, B. E.; Kjaerulff, S.; Frimodt-Møller, N; Lehrer, R I.; Zasloff, M.; Kristensen, H.-H. Plectasin is a peptide antibiotic with therapeutic potential from a saprophytic fungus. Nature 2005, 437, 975-980.
40. Hope, M. J.; Bally, M. B.; Webb, G.; Cullis, P. R Production of Large Unilamellar Vesicles by a Rapid Extrusion Procedure- Characterization of Size Distribution, Trapped Volume and Ability to Maintain a Membrane-Potential. Biochim. Biophys. Acta 1985, 812, 55-65.
41. Foged, C.; Franzyk, H; Bahrami, S.; Frokjaer, S.; Jaroszewski, J. W.; Nielsen, H. M.; Olsen, C. A. Cellular uptake and membrane-destabilising properties of a-peptide//7-peptoid chimeras: lessons for the design of new cell-penetrating peptides. Biochim. Biophys. Acta, Biomembr. 2008, 1778, 2487-2495.
42. Greenfield, N. J. Using circular dichroism spectra to estimate protein secondary structure. Nature Protoc. 2006, 1, 2876-2890.