Synthetic mimics of antimicrobial peptides from triaryl scaffolds

Journal of Medicinal Chemistry

Volumn 54, Issue 7, 2011, Pages 2241-2254

  Thaker, Hitesh D ^a   Sgolastra, Federica ^a   Clements, Dylan ^b   Scott, Richard W ^b   Tew, Gregory N ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b PolyMedix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEXIGANAN ACETATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYPEPTIDE ANTIBIOTIC AGENT;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONFORMATION; CONTROLLED STUDY; DRUG CONFORMATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ERYTHROCYTE; ESCHERICHIA COLI; HEMOLYSIS; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS;

AMINO ACID SEQUENCE; ANTIMICROBIAL CATIONIC PEPTIDES; BACTERIA; DRUG DESIGN; HEMOLYSIS; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PEPTIDOMIMETICS;

EID: 79953802893     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101410t     Document Type: Article

References (53)

1. Neu, H. C. The crisis in antibiotic resistance Science 1992, 257, 1064-1073
2. Brown, K.; Hancock, R. Cationic host defense (antimicrobial) peptides Curr. Opin. Immunol. 2006, 18, 24-30 (Pubitemid 43049644)
3. McPhee, J. B.; Hancock, R. E. W. Function and therapeutic potential of host defence peptides J. Pept. Sci. 2005, 11, 677-687 (Pubitemid 41684254)
4. Giuliani, A.; Pirri, G.; Bozzi, A.; Giulio, A.; Aschi, M.; Rinaldi, A. C. Antimicrobial peptides: natural templates for synthetic membrane-active compounds Cell. Mol. Life Sci. 2008, 65, 2450-2460
5. Zasloff, M. Antimicrobial peptides of multicellular organisms Nature 2002, 415, 389-395 (Pubitemid 34100944)
6. 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 (Pubitemid 46597762)
7. Hancock, R. E.; Lehrer, R. Cationic peptides: a new source of antibiotics Trends Biotechnol. 1998, 16, 82-8 (Pubitemid 28055477)
8. Hancock, R. E. W.; Sahl, H.-G. Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies Nat. Biotechnol. 2006, 24, 1551-1557 (Pubitemid 44967479)
9. Brogden, K. A. Antimicrobial peptides: pore formers or metabolic inhibitors in bacteria Nat. Rev. Microbiol. 2005, 3, 238-250 (Pubitemid 40298223)
10. Perron, G. G.; Zasloff, M.; Bell, G. Experimental evolution of resistance to an antimicrobial peptide Proc. R. Soc., Ser. B 2006, 273, 251-256 (Pubitemid 46768100)
11. Mor, A. Peptide-based antibiotics: a potential answer to raging antimicrobial resistance Drug Dev. Res. 2000, 50, 440-447
12. Koczulla, A. R.; Bals, R. Antimicrobial peptides: current status and therapeutic potential Drugs 2003, 63, 389-406 (Pubitemid 36259526)
13. Marr, A.; Gooderham, W.; Hancock, R. Antibacterial peptides for therapeutic use: obstacles and realistic outlook Curr. Opin. Pharmacol. 2006, 6, 468-472 (Pubitemid 44340665)
14. Bradshaw, J. Cationic antimicrobial peptides: issues for potential clinical use BioDrugs 2003, 17, 233-240 (Pubitemid 36999949)
15. Rotem, S.; Mor, A. Antimicrobial peptide mimics for improved therapeutic properties Biochim. Biophys. Acta, Biomembr. 2009, 1788, 1582-1592
16. Som, A.; Vemparala, S.; Ivanov, I.; Tew, G. N. Synthetic mimics of antimicrobial peptides Biopolymers 2008, 90, 83-93
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.S.A. 2008, 105, 2794-2799 (Pubitemid 351723623)
18. Liu, D.; DeGrado, W. F. De novo design, synthesis, and characterization of antimicrobial β-peptides J. Am. Chem. Soc. 2001, 123, 7553-7559 (Pubitemid 32899391)
19. Porter, E. A.; Weisblum, B.; Gellman, S. H. Mimicry of host-defense peptides by unnatural oligomers: antimicrobial beta-peptides J. Am. Chem. Soc. 2002, 124, 7324-7330 (Pubitemid 34670441)
20. Porter, E. A.; Wang, X.; Lee, H. S.; Weisblum, B.; Gellman, S. H. Non-haemolytic beta-amino-acid oligomers Nature 2000, 404, 565
21. Dartois, V.; Sanchez-Quesada, J.; Cabezas, E.; Chi, E.; Dubbelde, C.; Dunn, C.; Granja, J.; Gritzen, C.; Weinberger, D.; Ghadiri, M. R.; Parr, T. R., Jr. Systemic antibacterial activity of novel synthetic cyclic peptides Antimicrob. Agents Chemother. 2005, 49, 3302-3310 (Pubitemid 41060575)
22. Tew, G. N.; Liu, D.; Chen, B.; Doerksen, R. J.; Kaplan, J.; Carroll, P. J.; Klein, M. L.; DeGrado, W. F. De novo design of biomimetic antimicrobial polymers Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5110-5114 (Pubitemid 34411511)
23. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R. F.; Epand, R. M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mimicry of antimicrobial host-defense peptides by random copolymers J. Am. Chem. Soc. 2007, 129, 15474-15476
24. Arnt, L.; Nusslein, K.; Tew, G. N. Nonhemolytic abiogenic polymers as antimicrobial peptide mimics J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3860-3864
25. Lienkamp, K.; Madkour, A. E.; Musante, A.; Nelson, C. F.; Nusslein, K.; Tew, G. N. Antimicrobial polymers prepared by ROMP with unprecedented selectivity: a molecular construction kit approach J. Am. Chem. Soc. 2008, 130, 9836-9843
26. Kuroda, K.; DeGrado, W. F. Antimicrobial synthetic polymers: amphiphilic polymethacrylate derivatives Abstr. Pap. - Am. Chem. Soc. 2004, 228, U356-U356
27. Radzishevsky, I. S.; Kovachi, T.; Porat, Y.; Ziserman, L.; Zaknoon, F.; Danino, D.; Mor, A. Structure-activity relationships of antibacterial acyl-lysine oligomers Chem. Biol. 2008, 15, 354-362 (Pubitemid 351508428)
28. Zaknoon, F.; Sarig, H.; Rotem, S.; Livne, L.; Ivankin, A.; Gidalevitz, D.; Mor, A. Antibacterial properties and mode of action of a short acyl-lysyl oligomer Antimicrob. Agents Chemother. 2009, 53, 3422-3429
29. Choi, S.; Isaacs, A.; Clements, D.; Liu, D.; Kim, H.; Scott, R. W.; Winkler, J. D.; DeGrado, W. F. De novo design and in vivo activity of conformationally restrained antimicrobial arylamide foldamers Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 6968-6973
30. Tang, H.; Doerksen, R.; Jones, T.; Klein, M.; Tew, G. Biomimetic facially amphiphilic antibacterial oligomers with conformationally stiff backbones Chem. Biol. 2006, 13, 427-435
31. Tang, H.; Doerksen, R. J.; Tew, G. N. Synthesis of urea oligomers and their antibacterial activity Chem. Commun. 2005, 1537
32. Liu, D.; Choi, S.; Chen, B.; Doerksen, R. J.; Clements, D. J.; Winkler, J. D.; Klein, M. L.; DeGrado, W. F. Nontoxic membrane-active antimicrobial arylamide oligomers Angew. Chem., Int. Ed. 2004, 43, 1158-1162 (Pubitemid 39257984)
33. Scott, R. W.; DeGrado, W. F.; Tew, G. N. De novo designed synthetic mimics of antimicrobial peptides Curr. Opin. Biotechnol. 2008, 19, 620-627
34. Arnt, L.; Rennie, J. R.; Linser, S.; Willumeit, R.; Tew, G. N. Membrane activity of biomimetic facially amphiphilic antibiotics J. Phys. Chem. B 2006, 110, 3527-3532
35. Tew, G. N.; Clements, D.; Tang, H.; Arnt, L.; Scott, R. W. Antimicrobial activity of an abiotic host defense peptide mimic Biochim. Biophys. Acta 2006, 1758, 1387-1392 (Pubitemid 44436076)
36. Tew, G. N.; Scott, R. W.; Klein, M. L.; Degrado, W. F. De novo design of antimicrobial polymers, foldamers, and small molecules: from discovery to practical applications Acc. Chem. Res. 2010, 43, 30-39
37. Poriel, C.; Liang, J. J.; Rault-Berthelot, J.; Barriere, F.; Cocherel, N.; Slawin, A. M.; Horhant, D.; Virboul, M.; Alcaraz, G.; Audebrand, N.; Vignau, L.; Huby, N.; Wantz, G.; Hirsch, L. Dispirofluorene-indenofluorene derivatives as new building blocks for blue organic electroluminescent devices and electroactive polymers Chemistry 2007, 13, 10055-10069
38. Baudoin, O.; Guenard, D.; Gueritte, F. Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls J. Org. Chem. 2000, 65, 9268-9271 (Pubitemid 32015198)
39. Horn, J.; Marsden, S. P.; Nelson, A.; House, D.; Weingarten, G. G. Convergent, regiospecific synthesis of quinolines from o -aminophenylboronates Org. Lett. 2008, 10, 4117-4120
40. Phukan, K.; Ganguly, M.; Devi, N. Mild and useful method for N-acylation of amines Synth. Commun. 2009, 39, 2694-2701
41. Symons, M. C. R. Structure in solvents and solutions. NMR and vibrational spectroscopic studies Chem. Soc. Rev. 1983, 12, 1-34
42. 1H NMR chemical shifts J. Phys. Chem. A 1999, 103, 8121-8124
43. Reeves, L. W.; Allan, E. A.; Stromme, K. O. Nuclear shielding parameters for protons in hydrogen bonds. II. Correlation of chemical shifts in intramolecular hydrogen bonds with infrared stretching frequencies Can. J. Chem. 1960, 38, 1249-1254
44. Dudek, G. O. Spectroscopic studies of ketoenol equilibria. VIII. Schiff base spectroscopic correlations J. Org. Chem. 1965, 30, 548-552
45. Lomas, J. S.; Adenier, A.; Cordier, C.; Lacroix, J.-C. Hydrogen bonding and solvent effects in heteroaryldi(1-adamantyl)methanols: an NMR and IR spectroscopic study J. Chem. Soc., Perkin Trans. 2 1998, 2647-2652 (Pubitemid 128432944)
46. Rusu, V. H.; Ramos, M. N.; Da Silva, J. B. P. Hydrogen bonds between hydrogen fluoride and aromatic azines: an ab initio study Int. J. Quantum Chem. 2006, 106, 2811-2817 (Pubitemid 44476077)
47. Steinberg, D. A.; Hurst, M. A.; Fujii, C. A.; Kung, A. H.; Ho, J. F.; Cheng, F. C.; Loury, D. J.; Fiddes, J. C. Protegrin-1: a broad-spectrum, rapidly microbicidal peptide with in vivo activity Antimicrob. Agents Chemother. 1997, 41, 1738-1742 (Pubitemid 27339878)
48. Yan, H.; Hancock, R. E. Synergistic interactions between mammalian antimicrobial defense peptides Antimicrob. Agents Chemother. 2001, 45, 1558-1560 (Pubitemid 32374135)
49. Ge, Y.; MacDonald, D. L.; Holroyd, K. J.; Thornsberry, C.; Wexler, H.; Zasloff, M. In vitro antibacterial properties of pexiganan, an analog of magainin Antimicrob. Agents Chemother. 1999, 43, 782-788 (Pubitemid 29165740)
50. Hansen, T.; Alst, T.; Havelkova, M.; Strom, M. B. Antimicrobial activity of small beta-peptidomimetics based on the pharmacophore model of short cationic antimicrobial peptides J. Med. Chem. 2010, 53, 595-606
51. Gabriel, G. J.; Tew, G. N. Conformationally rigid proteomimetics: a case study in designing antimicrobial aryl oligomers Org. Biomol. Chem. 2008, 6, 417-423 (Pubitemid 351161726)
52. Sangster, J. Octanol-Water Partitioning Coefficients: Fundamentals and Physical Chemistry; Wiley: Chichester, U.K., 1997.
53. Sheppeck, J. E.; Kar, H.; Hong, H. A convenient and scaleable procedure for removing the Fmoc group in solution Tetrahedron Lett. 2000, 41, 5329-5333 (Pubitemid 30450788)