Antimicrobial activity of small β-peptidomimetics based on the pharmacophore model of short cationic antimicrobial peptides

Journal of Medicinal Chemistry

Volumn 53, Issue 2, 2010, Pages 595-606

  Hansen, Terkel ^a   Alst, Tore ^a   Havelkova, Martina ^a   Strøm, Morten B ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN A; PEPTIDOMIMETIC AGENT; POLYPEPTIDE ANTIBIOTIC AGENT;

ANTIMICROBIAL ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHARMACOPHORE; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

ANTI-INFECTIVE AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; CHYMOTRYPSIN; DRUG DESIGN; ERYTHROCYTES; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR MIMICRY; OLIGOPEPTIDES; STAPHYLOCOCCUS AUREUS;

EID: 77249095412     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901052r     Document Type: Article

References (52)

1. Rice, L. B. Antimicrobial resistance in Gram-positive bacteria. Am. J. Med. 2006, 119, S11-S19.
2. Todd, B. Beyond MRSA: VISA and VRSA: what will ward off these pathogens in health care facilities? Am. J. Nurs. 2006, 106, 28-30.
3. Gang, R. K.; Sanyal, S. C.; Bang, R. L.; Mokaddas, E.; Lari, A. R. Staphylococcal septicaemia in burns. Burns 2000, 26, 359-366.
4. Klevens, M. R.; Morrison, M. A.; Nadle, J.; Petit, S.; Gersman, K.; Ray, S.; Harrison, L. H.; Lynfield, R.; Dumyati, G.; Townes, J. M.; Craig, A. S.; Zell, E. R.; Fosheim, G. F.; McDouglas, L. K.; Carey, R. B.; Fridkin, S. K. Invasive methicillin-resistant Staphylococcus aureus infections in the united states. J. Am. Med. Assoc. 2007, 298, 1763-1771.
5. Severin, A.; Tabei, K.; Tenover, F.; Chung, M.; Clarke, N.; Tomasz, A. High level oxacillin and vancomycin resistance and altered cell wall composition in Staphylococcus aureus carrying the staphylococcal mecA and the enterococcal vanA gene complex. J. Biol. Chem. 2004, 279, 3398-3407.
6. National Nosocomial Infections Surveillance (NNIS) System Report, Data Summary from January 1990-May 1999, Issued June 1999. Am. J. Infect. Control 1999, 27, 520-532.
7. Projan, S. J.; Bradford, P. A. Late stage antibacterial drugs in the clinical pipeline. Curr. Opin. Microbiol. 2007, 10, 441-446.
8. Projan, S. J. Why is big Pharma getting out of antibacterial drug discovery? Curr. Opin. Microbiol. 2003, 6, 427-430.
9. Poupard, J. A. Is the pharmaceutical industry responding to the challenge of increasing bacterial resistance? Clin. Microbiol. Newslett. 2006, 28, 13-15.
10. Projan, S. J. Whither antibacterial drug discovery? Drug Discovery Today 2008, 13, 279-280.
11. Boman, H. G.; Nilsson, I.; Rasmuson, B. Inducible antibacterial defence system in Drosophila. Nature 1972, 237, 232-235.
12. Zasloff, M. Magainins, a class of antimicrobial peptides from Xenopus skin: isolation, characterization of two active forms, and partial cDNA sequence of a precursor. Proc. Natl. Acad. Sci. U.S. A. 1987, 84, 5449-5453.
13. Zasloff, M.; Martin, B.; Chen, H.-C. Antimicrobial activity of synthetic magainin peptides and several analogues. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 910-913.
14. Giuliani, A.; Pirri, G.; Nicoletto, S. F. Antimicrobial peptides: an overview of a promising class of therapeutics. Cent. Eur. J. Biol. 2007, 2, 1-33.
15. Boman, H. G. Antibacterial peptides: basic facts and emerging concepts. J. Intern. Med. 2003, 254, 197-215.
16. Latham, P. W. Therapeutic peptides revisited. Nat. Biotechnol. 1999, 17, 755-757.
17. Strøm, M. B.; Haug, B. E.; Skar, M. L.; Stensen, W.; Stiberg, T.; Svendsen, J. S. The pharmacophore of short cationic antibacterial peptides. J. Med. Chem. 2003, 46, 1567-1570.
18. Haug, B. E.; Stensen, W.; Stiberg, T.; Svendsen, J. S. Bulky nonproteinogenic amino acids permit the design of very small and effective cationic antibacterial peptides. J. Med. Chem. 2004, 47, 4159-4162.
19. Cronin, J. R.; Yuen, G. U.; Pizzarello, S. Gas chromatographic-mass spectral analysis of the five-carbon β-, γ-, and δ-amino alkanoic acids. Anal. Biochem. 1982, 124, 139-149.
20. Masond, M. S.; Abd El-Hamid, O. H. Structural chemistry of amino acid complexes. Transition Met. Chem. 1989, 14, 233-234.
21. Gupta, A.; Loew, G. H.; Lawless, J. Interaction of metal ions and amino acids: possible mechanisms for the adsorption of amino acids on homoionic smectite clays. Inorg. Chem. 2002, 22, 111-120.
22. Carpino, L. A.; El-Faham, A. Tetramethylfluoroformamidinium hexafluorophosphate: a rapid-acting peptide coupling reagent for solution and solid phase peptide synthesis. J. Am. Chem. Soc. 1995, 117, 5401-5402.
23. Porter, E. A.; Weisblum, B.; Gellman, S. H. Mimicry of hostdefense peptides by unnatural oligomers: antimicrobial β-peptides. J. Am. Chem. Soc. 2002, 124, 7324-7330.
24. Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. De novo design of antibacterial β-peptides. J. Am. Chem. Soc. 1999, 121, 12200-12201.
25. Arvidsson, P. I.; Ryder, N. S.; Weiss, H. M.; Gross, G.; Kretz, O.; Woessner, R.; Seebach, D. Antibiotic and hemolytic activity of a beta2/beta3 peptide capable of folding into a 12/10-helical secondary structure. ChemBioChem 2003, 4, 1345-1347.
26. Raguse, T. L.; Porter, E. A.; Weisblum, B.; Gellman, S. H. Structure-activity studies of 14-helical antimicrobial β-peptides: probing the relationship between conformational stability and antimicrobial potency. J. Am. Chem. Soc. 2002, 124, 12774-12785.
27. Arvidsson, P. I.; Frackenpohl, J.; Ryder, N. S.; Liechty, B.; Petersen, F.; Zimmermann, H.; Camenisch, G. P.; Woessner, R.; Seebach, D. On the antimicrobial and hemolytic activities of amphiphilic β-peptides. ChemBioChem 2001, 2, 771-773.
28. Seebach, D. D. Biological and pharmacokinetic studies with β-peptides. Chimia 1998, 52, 734.
29. Hintermann, T.; Seebach, D. The biological stability of β-peptides. No interactions between α-and β-peptidic structures? Chimia 1997, 51, 244-247.
30. Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. D. The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases. ChemBioChem 2001, 2, 445-455.
31. Kang, J. H.; Lee, M. K.; Kim, K. L.; Hahm, K.-S. Structurebiological activity relationships of 11-residue highly basic peptide segment of bovine lactoferrin. Int. J. Pept. Protein Res. 1996, 48, 357-363.
32. Collins, J. M.; Leadbeater,N. E. Microwave energy: a versatile tool for the biosciences. Org. Biomol. Chem. 2007, 5, 1141-1150.
33. Burrell, M. M. Enzymes of Molecular Biology; Humana Press: Totowa, NJ, 1993; p 370.
34. Wessolowski, A.; Bienert, M.; Dathe, M. Antimicrobial activity of arginine- and tryptophan-rich hexapeptides: the effects of aromatic clusters, D-amino acid substitution and cyclization. J. Pept. Res. 2004, 64, 159-169.
35. Shai, Y. Mode of action of membrane active antimicrobial peptides. Biopolymers (Pept. Sci.) 2002, 66, 236-248.
36. Hicks, R. P.; Bhonsle, J. B.; Venugopal, D.; Koser, B. W.; Magill, A. J. De novo design of selective antibiotic peptides by incorporation of unnatural amino acids. J. Med. Chem. 2007, 50, 3026-3036.
37. Klüver, E.; Adermann, K.; Schulz, A. Synthesis and structureactivity relationship of β-defensins, multifunctional peptides of the immune system. J. Pept. Sci. 2006, 12, 243-257.
38. Hagmann, W. K. The many roles for fluorine in medicinal chemistry. J. Med. Chem. 2008, 51, 4359-4369.
39. Bohm, H. J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Muller, K.; Obst-Sander, U.; Stahl, M. Fluorine in medicinal chemistry. ChemBioChem 2004, 5, 637-643.
40. Gimenez, D.; Andreu, C.; del Olmo, M.-l.; Varea, T.; Diaz, D.; Asensio, G. The introduction of fluorine atoms or trifluoromethyl groups in short cationic peptides enhances their antimicrobial activity. Bioorg. Med. Chem. 2006, 14, 6971-6978.
41. Zhao, Z.; Koeplinger, K. A.; Padbury, G. E.; Hauer, M. J.; Bundy, G. L.; Banitt, L. S.; Schwartz, T. M.; Zimmermann, D. C.; Harbach, P. R.; Mayo, J. K.; Aaron, C. S. Bioactivation of 6,7-Dimethyl-2,4-di-1-pyrrolidinyl-7H-pyrrolo[2,3-d]pyrimidine (U-89843) to Reactive Intermediates That Bind Covalently to Macromolecules and Produce Genotoxicity1. Chem. Res. Toxicol. 1996, 9, 1230-1239.
42. Diana, G. D.; Rudewicz, P.; Pevear, D. C.; Nitz, T. J.; Aldous, S. C.; Aldous, D. J.; Robinson, D. T.; Draper, T.; Dutko, F. J. Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism. J. Med. Chem. 2002, 38, 1355-1371.
43. Park, K.; Kitteringham, N. R.; O'Neill, P. M. Metabolism of fluorine-containing drugs. Annu. Rev. Pharmacol. 2001, 41, 443-470.
44. Hester, J. B.; Gibson, J. K.; Buchanan, L. V.; Cimini, M. G.; Clark, M. A.; Emmert, D. E.; Glavanovich, M. A.; Imbordino, R. J.; LeMay, R. J.; McMillan, M. W.; Perricone, S. C.; Squires, D. M.; Walters, R. R. Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias: Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential. J. Med. Chem. 2001, 44, 1099-1115.
45. Chan, D. I. D. Tryptophan- and arginine-rich antimicrobial peptides: structures and mechanisms of action. Biochim. Biophys. Acta, Biomembr. 2006, 1758, 1184-1202.
46. Haug, B. E.; Stensen, W.; Kalaaji, M.; Rekdal, O.; Svendsen, J. S. Synthetic antimicrobial peptidomimetics with therapeutic potential. J. Med. Chem. 2008, 51, 4306-4314.
47. Mookherjee, N.; Hancock, R. E. W. Cationic host defence peptides: innate immune regulatory peptides as a novel approach for treating infections. Cell. Mol. Life Sci. 2007, 64, 922-933.
48. Haug, B. E.; Stensen, W.; Svendsen, J. S. Application of the Suzuki-Miyaura cross-coupling to increase antimicrobial potency generates promising novel antibacterials. Bioorg. Med. Chem. Lett. 2007, 17, 2361-2364.
49. Tew, G. N.; Clements, D.; Tang, H.; Arnt, L.; Scott, R. W. Antimicrobial activity of an abiotic host defense peptide mimic. Biochim. Biophys. Acta, Biomembr. 2006, 1758, 1387-1392.
50. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis. Springer-Verlag: New York, 1994.
51. 3,3-amino acids: a turn motif for β-peptides. Helv. Chim. Acta 1998, 81, 2218-2243.
52. Chan, W. C.; White, P. D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Oxford University Press: Oxford, 2000; 346 p.