From a marine neuropeptide to antimicrobial pseudopeptides containing aza-β 3-amino acids: Structure and activity

Journal of Medicinal Chemistry

Volumn 55, Issue 5, 2012, Pages 2025-2034

  Laurencin, Mathieu ^a   Legrand, Baptiste ^b   Duval, Emilie ^c   Henry, Joël ^c   Baudy Floc'h, Michèle ^a   Zatylny Gaudin, Céline ^c   Bondon, Arnaud ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; NEUROPEPTIDE; POLYPEPTIDE ANTIBIOTIC AGENT; PSEUDOPEPTIDE;

AMINO ACID SEQUENCE; ANIMAL CELL; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CIRCULAR DICHROISM; CONTROLLED STUDY; CYTOTOXICITY; MICELLE; MOLLUSC; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ANIMALS; ANTI-BACTERIAL AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; AZA COMPOUNDS; CHO CELLS; CIRCULAR DICHROISM; CRICETINAE; CRICETULUS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HEMOLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEUROPEPTIDES; OLIGOPEPTIDES; RABBITS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84858025734     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2011595     Document Type: Article

References (56)

1. Andreu, D.; Rivas, L. Animal antimicrobial peptides: an overview Biopolymers 1998, 47, 415-433
2. Epand, R. M.; Vogel, H. J. Diversity of antimicrobial peptides and their mechanisms of action Biochim. Biophys. Acta 1999, 1462, 11-28
3. Hancock, R. E.; Sahl, H. G. Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies Nature Biotechnol. 2006, 24, 1551-1557
4. Peschel, A.; Sahl, H. G. The co-evolution of host cationic antimicrobial peptides and microbial resistance Nature Rev. Microbiol. 2006, 4, 529-536
5. Zasloff, M. Antimicrobial peptides of multicellular organisms Nature 2002, 415, 389-395
6. Shai, Y. Mode of action of membrane active antimicrobial peptides Biopolymers 2002, 66, 236-248
7. Brogden, K. A. Antimicrobial peptides: pore formers or metabolic inhibitors in bacteria? Nature Rev. Microbiol. 2005, 3, 238-250
8. Matsuzaki, K. Magainins as paradigm for the mode of action of pore forming polypeptides Biochim. Biophys. Acta 1998, 1376, 391-400
9. Wu, M.; Maier, E.; Benz, R.; Hancock, R. E. Mechanism of interaction of different classes of cationic antimicrobial peptides with planar bilayers and with the cytoplasmic membrane of Escherichia coli Biochemistry 1999, 38, 7235-7242
10. Bechinger, B.; Lohner, K. Detergent-like actions of linear amphipathic cationic antimicrobial peptides Biochim. Biophys. Acta 2006, 1758, 1529-1539
11. Legrand, B.; Laurencin, M.; Sarkis, J.; Duval, E.; Mouret, L.; Hubert, J.-F.; Collen, M.; Vie, V.; Zatylny-Gaudin, C.; Henry, J.; Baudy-Floc'h, M.; Bondon, A. Structure and mechanism of action of a de novo antimicrobial detergent-like peptide Biochim. Biophys. Acta 2011, 1808, 106-116
12. 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
13. 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
14. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. Unexpected relationships between structure and function in alpha, beta-peptides: antimicrobial foldamers with heterogeneous backbones J. Am. Chem. Soc. 2004, 126, 6848-6849
15. 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
16. Song, Y. M.; Park, Y.; Lim, S. S.; Yang, S. T.; Woo, E. R.; Park, I. S.; Lee, J. S.; Kim, J. I.; Hahm, K. S.; Kim, Y.; Shin, S. Y. Cell selectivity and mechanism of action of antimicrobial model peptides containing peptoid residues Biochemistry 2005, 44, 12094-12106
17. 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 2007, 1768, 1506-1517
18. Olsen, C. A.; Bonke, G.; Vedel, L.; Adsersen, A.; Witt, M.; Franzyk, H.; Jaroszewski, J. W. alpha-Peptide/beta-peptoid chimeras Org. Lett. 2007, 9, 1549-1552
19. Shuey, S. W.; Delaney, W. J.; Shah, M. C.; Scialdone, M. A. Antimicrobial beta-peptoids by a block synthesis approach Bioorg. Med. Chem. Lett. 2006, 16, 1245-1248
20. Violette, A.; Fournel, S.; Lamour, K.; Chaloin, O.; Frisch, B.; Briand, J. P.; Monteil, H.; Guichard, G. Mimicking helical antibacterial peptides with nonpeptidic folding oligomers Chem. Biol. 2006, 13, 531-538
21. 3-peptides mimicking a supradominant CD4 T cell epitope presented by nucleosome Mol. Immunol. 2007, 44, 3024-3036
22. Cheguillaume, A.; Salaün, A.; Sinbandhit, S.; Potel, M.; Gall, P.; Baudy-Floc'h, M.; Le Grel, P. Solution synthesis and characterization of hydrazinopeptoidic oligomers J. Org. Chem. 2001, 66, 4923-4929
23. 3-cyclohexapeptides: pseudopeptidic macrocycles with interesting conformational and configurational properties slow pyramidal nitrogen inversion in 24-membered rings J. Org. Chem. 2006, 71, 5638-5645
24. 3-peptides, a new class of foldamers relying on a framework of hydrazinoturns J. Org. Chem. 2005, 70, 6499-6502
25. 3-cyclotetrapeptides J. Org. Chem. 2008, 73, 8579-8582
26. 3-cyclopeptides: a new way of controlling nitrogen chirality J. Am. Chem. Soc. 2009, 131, 14521-14525
27. Henry, J.; Zatylny, C.; Boucaud-Camou, E. Peptidergic control of egg-laying in the cephalopod Sepia officinalis: involvement of FMRFamide and FMRFamide-related peptides Peptides 1999, 20, 1061-1070
28. Brogden, K. A.; Guthmiller, J. M.; Salzet, M.; Zasloff, M. The nervous system and innate immunity: the neuropeptide connection Nature Immunol. 2005, 6, 558-564
29. 3-peptides Tetrahedron Lett. 2007, 48, 5767-5770
30. 3-amino acids via reductive amination of glyoxylic acid Tetrahedron Lett. 2005, 46, 7073-7075
31. 3-amino acids and alpha-amino acids J. Org. Chem. 2005, 70, 10701-10708
32. 3-amino acids with nonproteinogenic hydrophobic side chains for solid-phase syntheses of pseudopeptides Synthesis 2009, 1007-1013
33. Baudy-Floc'h, M.; Zatylny-Gaudin, C.; Henry, J.; Duval, E.; Laurencin, M. (SERB). French patent FR 07 09054 1808, 2007, pp 106-116.
34. Dathe, M.; Nikolenko, H.; Klose, J.; Bienert, M. Cyclization increases the antimicrobial activity and selectivity of arginine- and tryptophan- containing hexapeptides Biochemistry 2004, 43, 9140-9150
35. Wu, J. M.; Wei, S. Y.; Chen, H. L.; Weng, K. Y.; Cheng, H. T.; Cheng, J. W. Solution structure of a novel d -ss-naphthylalanine substituted peptide with potential antibacterial and antifungal activities Biopolymers 2007, 88, 738-745
36. Haug, B. E.; Svendsen, J. S. The role of tryptophan in the antibacterial activity of a 15-residue bovine lactoferricin peptide J. Pept. Sci. 2001, 7, 190-196
37. Hubert, F.; Noel, T.; Roch, P. A member of the arthropod defensin family from edible Mediterranean mussels (Mytilus galloprovincialis) Eur. J. Biochem. 1996, 240, 302-306
38. Sisido, M.; Egusa, S.; Imanishi, Y. One-Dimensional Aromatic Crystals in Solution 0.2. Synthesis, Conformation, and Spectroscopic Properties of Poly(l -2-Naphthylalanine) J. Am. Chem. Soc. 1983, 105, 4077-4082
39. Sisido, M.; Egusa, S.; Imanishi, Y. One-Dimensional Aromatic Crystal in Solution 0.1. Synthesis, Conformation, and Spectroscopic Properties of Poly(l -1-Naphthylalanine) J. Am. Chem. Soc. 1983, 105, 1041-1049
40. Dike, A.; Cowsik, S. M. Solution structure of amphibian tachykinin Uperolein bound to DPC micelles J. Struct. Biol. 2006, 156, 442-452
41. Ivankin, A.; Livne, L.; Mor, A.; Caputo, G. A.; DeGrado, W. F.; Meron, M.; Lin, B.; Gidalevitz, D. Role of the Conformational Rigidity in the Design of Biomimetic Antimicrobial Compounds Angew. Chem., Int. Ed. Engl. 2010, 49, 8462-8465
42. 3-2- Methylidene-amino Acids Bearing Proteinogenic Side Chains-A Survey Chem. Biodiversity 2005, 2, 401-420
43. Mowery, B. P.; Lindner, A. H.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Structure-Activity Relationships among Random Nylon-3 Copolymers That Mimic Antibacterial Host-Defense Peptides J. Am. Chem. Soc. 2009, 131, 9735-9745
44. Goodballe, T.; Nilsson, L. L.; Petersen, P. D.; Jenssen, H. Antimicrobial β-Peptides and α-Peptoids Chem. Biol. Drug Des. 2011, 77, 107-116
45. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. Interplay among folding, sequence, and lipophilicity in the antibacterial and hemolytic activities of α/β-peptides J. Am. Chem. Soc. 2007, 129, 417-428
46. Claudon, P.; Violette, A.; Lamour, K.; Decossas, M.; Fournel, S.; Heurtault, B.; Godet, J.; Mely, Y.; Jamart-Gregoire, B.; Averlant-Petit, M. C.; Briand, J. P.; Duportail, G.; Monteil, H.; Guichard, G. Consequences of Isostructural Main-Chain Modifications for the Design of Antimicrobial Foldamers: Helical Mimics of Host-Defense Peptides Based on a Heterogeneous Amide/Urea Backbone Angew. Chem., Int. Ed. Engl. 2010, 49, 333-336
47. Hetru, C.; Bulet, P. Strategies for the isolation and characterization of antimicrobial peptides of invertebrates Methods Mol. Biol. 1997, 78, 35-49
48. Duval, E.; Zatylny, C.; Laurencin, M.; Baudy-Floc'h, M.; Henry, J. KKKKPLFGLFFGLF: a cationic peptide designed to exert antibacterial activity Peptides 2009, 30, 1608-1612
49. Javadpour, M. M.; Juban, M. M.; Lo, W. C.; Bishop, S. M.; Alberty, J. B.; Cowell, S. M.; Becker, C. L.; McLaughlin, M. L. De novo antimicrobial peptides with low mammalian cell toxicity J. Med. Chem. 1996, 39, 3107-3113
50. Delaglio, F.; Grzesiek, S.; Vuister, G. W.; Zhu, G.; Pfeifer, J.; Bax, A. NMRPipe: a multidimensional spectral processing system based on UNIX pipes J. Biomol. NMR 1995, 6, 277-293
51. Johnson, B. A.; Blevins, R. NMRVIEW: a computer program for the visualization and analysis of NMR data J. Biomol. NMR 1994, 4, 603-614
52. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley-Interscience: New York, 1986.
53. Linge, J. P.; O'Donoghue, S. I.; Nilges, M. Automated assignment of ambiguous nuclear overhauser effects with ARIA Methods Enzymol. 2001, 339, 71-90
54. Koradi, R.; Billeter, M.; Wuthrich, K. MOLMOL: a program for display and analysis of macromolecular structures J. Mol. Graphics 1996, 14 (51-55) 29-32
55. Laskowski, R. A.; Rullmannn, J. A.; MacArthur, M. W.; Kaptein, R.; Thornton, J. M. AQUA and PROCHECK-NMR: programs for checking the quality of protein structures solved by NMR J. Biomol. NMR 1996, 8, 477-486
56. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Crystallography & NMR system: a new software suite for macromolecular structure determination Acta Crystallogr., Sect. D: Biol. Crystallogr. 1998, 54, 905-921