Antibiotic and Hemolytic Activity of a β2/β 3 Peptide Capable of Folding into a 12/10-Helical Secondary Structure

ChemBioChem

Volumn 4, Issue 12, 2003, Pages 1345-1347

  Arvidsson, Per I ^a   Ryder, Neil S ^b   Weiss, H Markus ^c   Gross, Gerhard ^c   Kretz, Olivier ^c   Woessner, Ralph ^c   Seebach, Dieter ^d  

^a UPPSALA UNIVERSITY   (Sweden)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^c NOVARTIS PHARMA AG   (Switzerland)

^d ETH ZURICH   (Switzerland)

Author keywords

Amphiphiles; Antibiotics; Helical stuctures; Peptides; Peptidomimetic

Indexed keywords

BETA NONAPEPTIDE; BETA PHENYLALANYL BETA VALYL BETA PHENYLALANYL BETA LEUCYL BETA LYSYL BETA LEUCYL BETA LYSYL BETA LEUCYL BETA PHENYLALANINE; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BIOMIMETICS; DNA HELIX; DRUG STRUCTURE; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; HEMOLYSIS; KLEBSIELLA PNEUMONIAE; NONHUMAN; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE;

AMINO ACID SEQUENCE; ANIMALS; ANTI-INFECTIVE AGENTS; CIRCULAR DICHROISM; ERYTHROCYTES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HEMOLYSIN PROTEINS; HUMANS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; RATS;

ENTEROCOCCUS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; KLEBSIELLA; KLEBSIELLA PNEUMONIAE; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS; STREPTOCOCCUS PNEUMONIAE;

EID: 0347417960     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300698     Document Type: Article

References (42)

1. a) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893;
2. b) J. A. Patch, A. E. Barron, Curr. Opin. Chem. Biol. 2002, 6, 872;
3. c) G. N. Tew, D. Liu, B. Chen, R. J. Doerksen, J. Kaplan, P. J. Carrol, M. L. Klein, W. F. DeGrado, Proc. Natl. Acad. Sci. USA 2002, 99, 5110.
4. a) D. Seebach, J. L. Matthews, Chem. Commun. 1997, 2015;
5. b) K. Gademann, T. Hintermann, J.V. Schreiber, Curr. Med. Chem. 1999, 6, 905;
6. c) P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219.
7. a) Y. Hamuro, J. P. Schneider, W. F. DeGrado, J. Am. Chem. Soc. 1999, 121, 12200;
8. b) E. A. Porter, X. Wang, H.-S. Lee, B. Weisblum, S. H. Gellman, Nature 2000, 404, 565 (erratum: 2000, 405, 298);
9. c) P. I. Arvidsson, J. Frackenpohl, N. S. Ryder, B. Liechty, F. Petersen, H. Zimmermann, G. P. Camenisch, R. Woessner, D. Seebach, ChemBioChem 2001, 2, 771;
10. d) D. Liu, W. F. DeGrado, J. Am. Chem. Soc. 2001, 123, 7553;
11. e) E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 7324;
12. f) T. L. Raguse, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 12774;
13. g) R. F. Epand, N. Umezawa, E. A. Porter, S. Gellman, R. M. Epand, Eur. J. Biochem. 2003, 270, 1240.
14. K. Gademann, D. Seebach, Helv. Chim. Acta 2001, 84, 2924.
15. a) K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem. 1999, 111, 1302; Angew. Chem. Int. Ed. 1999, 38, 1223;
16. a) K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem. 1999, 111, 1302; Angew. Chem. Int. Ed. 1999, 38, 1223;
17. b) K. Gademann, T. Kimmerlin, D. Hoyer, D. Seebach, J. Med. Chem. 2001, 44, 2460;
18. c) D. Seebach, R. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503;
19. d) C. Nunn, M. Rueping, D. Langenegger, E. Schuepbach, T. Kimmerlin, P. Micuch, K. Hurt, D. Seebach, D. Hoyer, Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 95.
20. a) T. Hintermann, D. Seebach, Chimia 1997, 51, 244;
21. b) D. Seebach, S. Abele, J. V. Schreiber, B. Martinoni, A. K. Nussbaum, H. Schild, H. Schulz, H. Hennecke, R. Woessner, F. Bitsch, Chimia 1998, 52, 734;
22. c) J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber, D. Seebach, ChemBioChem 2001, 2, 445.
23. H. Wiegand, B. Wirz, A. Schweitzer, G. P. Camenisch, M. I. R. Perez, G. Gross, R. Woessner, R. Voges, P. I. Arvidsson, J. Frackenpohl, D. Seebach, Biopharm. Drug Dispos. 2002, 23, 251.
24. a) H. G. Boman, Annu. Rev. Immunol. 1995, 13, 61;
25. b) P. Nicolas, A. Mor, Annu. Rev. Microbiol. 1995, 49, 277;
26. c) A. Tossi, L. Sandri, A. Giangaspero, Biopolymers 2000, 55, 4;
27. d) M. B. Strøm, B. E. Haug, M. K. Skar, W. Stensen, T. Stiberg, J. S. Svendsen, J. Med. Chem. 2003, 46, 1567.
28. a) R. E. W. Hancock, Lancet 1997, 349, 418;
29. b) A. R. Koczulla, R. Bals, Drugs 2003, 63, 389;
30. c) M. R. Yeaman, N. Y. Yount, Pharmacol. Rev. 2003, 55, 27.
31. D. Seebach, M. Overhand, F. N. M. Kuehnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913.
32. a) D. Seebach, K. Gademann, J.V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033;
33. b) D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. L. Matthews, J. V. Schreiber, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1998, 81, 932;
34. c) M. Rueping, J. V. Schreiber, G. Lelais, B. Jaun, D. Seebach, Helv. Chim. Acta 2002, 85, 2577;
35. d) A full 750 MHz NMR measurement of 1 has been performed, the NH region displayed good dispersion (suggesting the presence of a preferred conformation) ; a full analysis, which might lead to a structural assignment, is underway.
36. P. I. Arvidsson, J. Frackenpohl, D. Seebach, Helv. Chim. Acta 2003, 86, 1522.
37. a) M. Rueping, B. Jaun, D. Seebach, Chem. Commun. 2000, 2267;
38. b) P. I. Arvidsson, M. Rueping, D. Seebach, Chem. Commun. 2001, 649;
39. c) T. L. Raguse, J. R. Lai, S. H. Gellman, J. Am. Chem. Soc. 2003, 125, 5592.
40. M. Werder, H. Hauser, S. Abele, D. Seebach, Helv. Chim. Acta 1999, 82, 1774.
41. a) Z. Q. Li, R. B. Merrifield, I. A. Boman, H. G. Boman, FEBS Lett. 1988, 231, 299;
42. b) J. H. Cuervo, B. Rodriguez, R. A. Houghten, Pept. Res. 1988, 1, 81.