Properties and structure-activity studies of cyclic β-hairpin peptidomimetics based on the cationic antimicrobial peptide protegrin I

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 6, 2005, Pages 2055-2064

  Robinson, John A ^a   Shankaramma, Sasalu C ^a   Jetter, Peter ^a   Kienzl, Ursula ^a   Schwendener, Reto A ^b   Vrijbloed, Jan W ^c   Obrecht, Daniel ^c  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b PAUL SCHERRER INSTITUTE   (Switzerland)

^c Polyphor AG   (Switzerland)

Author keywords

Antibiotic; Haemolysis; Protein epitope mimetic; Secondary structure

Indexed keywords

ANTIINFECTIVE AGENT; CYCLO(LEUCYLARGINYLLEUCYLLYSYLLYSYLARGINYLARGINYLTRYPTOPHYLLYSYLTYROSYL ARGINYLVALYL DEXTRO PROLYLPROLINE); DYE; LIPOSOME; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLGLYCEROL; POLYPEPTIDE; PROTEGRIN 1; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANTIBACTERIAL ACTIVITY; ARTICLE; CELL MEMBRANE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG RELEASE; DRUG SYNTHESIS; DRUG TOLERABILITY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HEMOLYSIS; HUMAN; HUMAN CELL; NONHUMAN; SEQUENCE ANALYSIS; STRUCTURE ACTIVITY RELATION;

POSIBACTERIA; SUIDAE;

EID: 13944259333     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.01.009     Document Type: Article

References (68)

1. P. Sima, I. Trebichavsky, and K. Sigler Folia Microbiol. 48 2003 123 137
2. P. Bulet, R. Stocklin, and L. Menin Immunol. Revs. 198 2004 169 184
3. H.G. Boman J. Int. Med. 254 2003 197 215
4. E. Andres, and J.L. Dimarcq J. Int. Med. 255 2004 519 520
5. L.J. Zhang, and T.J. Falla Exp. Opin. Invest. Drugs 13 2004 97 106
6. R.E.W. Hancock Exp. Opin. Invest. Drugs 9 2000 1723 1729
7. J.P.S. Powers, and R.E.W. Hancock Peptides 24 2003 1681 1691
8. W. van't Hof, E.C.I. Veerman, E.J. Helmerhorst, and A.V.N. Amerongen Biol. Chem. 382 2001 597 619
9. Y. Shai Biopolymers 66 2002 236 248
10. M. Wu, E. Maier, R. Benz, and R.E.W. Hancock Biochemistry 38 1999 7235 7242
11. R.E.W. Hancock, and A. Rozek FEMS Microbiol. Lett. 206 2002 143 149
12. M. Zanetti J. Leukocyte Biol. 75 2004 39 48
13. V.N. Kokryakov, S.S.L. Harwig, E.A. Panyutich, A.A. Shevchenko, G.M. Aleshina, O.V. Shamova, H.A. Korneva, and R.I. Lehrer FEBS Lett. 1993 1993 231 236
14. C.Q. Zhao, T. Ganz, and R.I. Lehrer FEBS Lett. 368 1995 197 202
15. C. Roumestand, V. Louis, A. Aumelas, G. Grassy, B. Calas, and A. Chavanieu FEBS Lett. 421 1998 263 267
16. A. Aumelas, M. Mangoni, C. Roumestand, L. Chiche, E. Despaux, G. Grassy, B. Calas, and A. Chavanieu Eur. J. Biochem. 237 1996 575 583
17. R.L. Fahrner, T. Dieckmann, S.S.L. Harwig, R.I. Lehrer, D. Eisenberg, and J. Feigon Chem. Biol. 3 1996 543 550
18. A. Laederach, A.H. Andreotti, and D.B. Fulton Biochemistry 41 2002 12359 12368
19. H. Tamamura, M. Kuroda, M. Masada, A. Otaka, S. Funakoshi, H. Nakashima, N. Yamamoto, M. Waki, A. Matsumoto, J.M. Lancelin, D. Kohda, S. Tate, F. Inagaki, and N. Fujii Biochim. Biophys. Acta 1163 1993 209 216
20. K. Kawano, T. Yoneya, T. Miyata, K. Yoshikawa, F. Tokunaga, Y. Terada, and S. Iwanaga J. Biol. Chem. 265 1990 15365 15367
21. T. Nakamura, H. Furunaka, T. Miyata, F. Tokunaga, T. Muta, S. Iwanaga, M. Niwa, T. Takao, and Y. Shimonishi J. Biol. Chem. 263 1988 16709 16713
22. T. Miyata, F. Tokunaga, T. Yoneya, K. Yoshikawa, S. Iwanaga, M. Niwa, T. Takao, and Y. Shimonishi J. Biochem. 106 1989 663 668
23. N. Mandard, D. Sy, C. Maufrais, J.-M. Bonmatin, P. Bulet, C. Hetru, and F. Vovelle J. Biomol. Struct. Dyn. 17 1999 367 380
24. L. Ehret-Sabatier, D. Loew, M. Goyffon, P. Fehlbaum, J.A. Hoffmann, A.v. Dorsselaer, and P. Bulet J. Biol. Chem. 271 1996 29537 29544
25. N. Mandard, P. Sodano, H. Labbe, J.-M. Bonmatin, P. Bulet, C. Hetru, M. Ptak, and F. Vovelle Eur. J. Biochem. 256 1998 404 410
26. P.M. Hwang, N. Zhou, X. Shan, C.H. Arrowsmith, and H.J. Vogel Biochemistry 37 1998 4288 4298
27. H.N. Hunter, D.B. Fulton, T. Ganz, and H.J. Vogel J. Biol. Chem. 277 2002 37597 37603
28. S.U. Patel, R. Osborn, S. Rees, and J.M. Thornton Biochemistry 37 1998 983 990
29. N. Mandard, P. Bulet, A. Caille, S. Daffre, and F. Vovelle Eur. J. Biochem. 269 2002 1190 1198
30. P.I.J. Silva, S. Daffre, and P. Bulet J. Biol. Chem. 275 2000 33464 33470
31. S.E. Hull, R. Karlsson, P. Main, M.M. Woolfson, and E.J. Dodson Nature 275 1978 206 207
32. M.C. Kuo, and W.A. Gibbons Biophys. J. 32 1980 807 836
33. M. Trabi, H.J. Schirra, and D.J. Craik Biochemistry 40 2001 4211 4221
34. Y.-Q. Tang, J. Yuan, G. Ösapay, K. Ösapay, D. Tran, C.J. Miller, A.J. Ouellette, and M.E. Selsted Science 286 1999 498 502
35. D.A. Steinberg, M.A. Hurst, C.A. Fujil, A.H.C. Kung, J.F. Ho, F.-C. Cheng, D.J. Loury, and J.C. Fiddes Antimicrob. Agents Chemother. 41 1997 1738 1742
36. X.-D. Qu, S.S.L. Harwig, A. Oren, W.M. Shafer, and R.I. Lehrer Infect. Immun. 64 1996 1240 1245
37. Y. Cho, J.S. Turner, N.-N. Dinh, and R.I. Lehrer Infect. Immun. 66 1998 2486 2493
38. H. Tamamura, T. Murakami, S. Horiuchi, K. Sugihara, A. Otaka, W. Takada, T. Ibuka, M. Waki, N. Yamamoto, and N. Fujii Chem. Pharm. Bull. 43 1995 853 858
39. B. Yasin, R.I. Lehrer, S.S.L. Harwig, and E.A. Wagar Infect. Immun. 64 1996 4863 4866
40. B. Yasin, S.S.L. Harwig, R.I. Lehrer, and E.A. Wagar Infect. Immun. 64 1996 709 713
41. P. Juvvadi, S. Vunnam, and R.B. Merrifield J. Am. Chem. Soc. 118 1996 8989 8997
42. R. Bessalle, A. Kapitkovsky, A. Gorea, I. Shalit, and M. Fridkin FEBS Lett. 274 1990 151 155
43. D. Wade, A. Boman, B. Wåhlin, C.M. Drain, D. Andreu, H.G. Boman, and R.B. Merrifield Proc. Natl. Acad. Sci. U.S.A. 87 1990 4761 4765
44. M.T. Albrecht, W. Wang, O.V. Shamova, R.I. Lehrer, and N.L. Schiller Respir. Res. 3 2002 18 28
45. W.T. Heller, A. Waring, R.I. Lehrer, and H.W. Huang Biochemistry 37 1998 17331 17338
46. S. Yamaguchi, T. Hong, A. Waring, R.I. Lehrer, and M. Hong Biochemistry 41 2002 9852 9862
47. D. Gidalevitz, Y.J. Ishitsuka, A.S. Muresan, O. Konovalov, A.J. Waring, R.I. Lehrer, and K.Y.C. Lee Proc. Natl. Acad. Sci. U.S.A. 100 2003 6302 6307
48. J.J. Buffy, A.J. Waring, R.I. Lehrer, and M. Hong Biochemistry 42 2003 13725 13734
49. J.J. Buffy, T. Hong, S. Yamaguchi, A.J. Waring, R.I. Lehrer, and M. Hong Biophys. J. 85 2003 2363 2373
50. W.T. Heller, A.J. Waring, R.I. Lehrer, T.A. Harroun, T.M. Weiss, L. Yang, and H.W. Huang Biochemistry 39 2000 139 145
51. J.R. Lai, B.R. Huck, B. Weisblum, and S.H. Gellman Biochemistry 41 2002 12835 12842
52. J. Chen, T.J. Falla, H. Liu, M.A. Hurst, C.A. Fujii, D.A. Mosca, J.R. Embree, D.J. Loury, P.A. Radel, C.C. Chang, L. Gu, and J.C. Fiddes Bioploymers 55 2000 88 98
53. S.S.L. Harwig, A. Waring, H.J. Tang, Y. Cho, L. Tan, and R.I. Lehrer Eur. J. Biochem. 240 1996 352 357
54. M. Mangoni, A. Aumelas, P. Charnet, C. Roumestand, L. Chiche, E. Despaux, G. Grassy, B. Calas, and A. Chavanieu FEBS Lett. 383 1996 93 98
55. J.P. Tam, C. Wu, and J.-L. Yang Eur. J. Biochem. 267 2000 3289 3300
56. S.C. Shankaramma, Z. Athanassiou, O. Zerbe, K. Moehle, C. Mouton, F. Bernardini, J.W. Vrijbloed, D. Obrecht, and J.A. Robinson ChemBioChem 3 2002 1126 1133
57. S.C. Shankaramma, K. Moehle, S. James, J.W. Vrijbloed, D. Obrecht, and J.A. Robinson Chem. Commun. 2003 1842 1843
58. M. Favre, K. Moehle, L. Jiang, B. Pfeiffer, and J.A. Robinson J. Am. Chem. Soc. 121 1999 2679 2685
59. A. Descours, K. Moehle, A. Renard, and J.A. Robinson ChemBioChem 3 2002 318 323
60. Z. Athanassiou, R.L.A. Dias, K. Moehle, N. Dobson, G. Varani, and J.A. Robinson J. Am. Chem. Soc. 126 2004 6906 6913
61. R. Fasan, R.L.A. Dias, K. Moehle, O. Zerbe, J.W. Vrijbloed, D. Obrecht, and J.A. Robinson Angew. Chem., Int. Ed. 43 2004 2109 2112
62. A. Waring, S.S.L. Harwig, and R.I. Lehrer Prot. Pept. Lett. 3 1996 177 184
63. G. Drin, and J. Temsamani Biochim. Biophys. Acta 1559 2002 160 170
64. L. Zhang, A. Rozek, and R.E.W. Hancock J. Biol. Chem. 276 2001 35714 35722
65. P. Remuzon Tetrahedron 52 1996 13803 13835
66. L.D. Mayer, M.J. Hope, and P.R. Cullis Biochim. Biophys. Acta 858 1986 161 168
67. M.J. Hope, M.B. Bally, G. Webb, and P.R. Cullis Biochim. Biophys. Acta 812 1985 55 65
68. G.R. Bartlett J. Biol. Chem. 234 1959 466 468