Deletion of two C-terminal Gln residues of 12-26-residue fragment of melittin improves its antimicrobial activity

Peptides

Volumn 26, Issue 3, 2005, Pages 369-375

  Sun, Xuejun ^a   Chen, Suxia ^a   Li, Shunzi ^a   Yan, Husheng ^a   Fan, Yunge ^a   Mi, Huaifeng ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Antibiotic; Antimicrobial peptide; Hemolysis; Melittin

Indexed keywords

GLYCINE; GLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYL ARGINYLLYSYLARGININAMIDE; GLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYL ARGINYLLYSYLARGINYLGLUTAMINAMIDE; GLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYL ARGINYLLYSYLARGINYLGLUTAMINYLGLUTAMINAMIDE; GLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYL ARGINYLLYSYLARGINYLGLYCYLGLYCINAMIDE; GLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYL ARGINYLLYSYLARGINYLLEUCINAMIDE; LEUCINE; MELITTIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL MEMBRANE; BINDING AFFINITY; CARBOXY TERMINAL SEQUENCE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG BINDING; DRUG CONFORMATION; DRUG SYNTHESIS; ENTROPY; HYDROPHOBICITY; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; SUBSTITUTION REACTION;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; BEE VENOMS; BEES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DOSE-RESPONSE RELATIONSHIP, DRUG; GENE DELETION; GLUTAMINE; LIPIDS; MELITTEN; MICROSCOPY, FLUORESCENCE; PEPTIDES; PROPANOLS; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; TRYPTOPHAN; WATER;

BACTERIA (MICROORGANISMS);

EID: 12344271181     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2004.10.004     Document Type: Article

References (49)

1. G.R. Bartlett Phosphorus assay in column chromatography J Biol Chem 234 1959 466 468
2. R. Bazzo, M.J. Tappin, A. Pastore, T.S. Harvey, J.A. Carver, and I.D. Campbell The structure of melittin a 1H-NMR study in methanol Eur J Biochem 173 1988 139 146
3. S.E. Blondelle, and R.A. Houghten Hemolytic and antimicrobial activities of the twenty-four individual omission analogues of melittin Biochemistry 30 1991 4671 4678
4. P. Bulet, C. Hetru, J.L. Dimarcq, and D. Hoffmann Antimicrobial peptides in insects; structure and function Dev Comp Immunol 23 1999 329 344
5. H.C. Chen, J.H. Brown, J.L. Morell, and C.M. Huang Synthetic magainin analogues with improved antimicrobial activity FEBS Lett 236 1988 462 466
6. Y.H. Chen, J.T. Yang, and K.H. Chau Determination of the helix and beta form of proteins in aqueous solution by circular dichroism Biochemistry 13 1974 3350 3359
7. M. Dathe, and T. Wieprecht Structural features of helical antimicrobial peptides: their potential to modulate activity on model membranes and biological cells Biochim Biophys Acta 1462 1999 71 87
8. C.E. Dempsey The actions of melittin on membrances Biochim Biophys Acta 1031 1990 143 161
9. D. Eisenberg Three-dimensional structure of membrane and surface proteins Annu Rev Biochem 53 1984 595 623
10. R. Feder, A. Dagan, and A. Mor SAR study of antimicrobial dermaseptin S4 showing the consequences of peptide oligomerization on selective cytotoxicity J Biol Chem 275 2000 4230 4238
11. T. Ganz, and R. Lehrer Antibiotic peptides from higher eukaryotes: biology and applications Mol Med Today 5 1999 292 297
12. E. Gazit, A. Boman, H.G. Boman, and Y. Shai Interaction of the mammalian antibacterial peptide cecropin P1 with phospholipid vesicles Biochemistry 34 1995 11479 11488
13. Y. Goto, and Y. Hagihara Mechanism of the conformational transition of melittin Biochemistry 31 1992 732 738
14. R.E. Hancock, and G. Diamond The role of cationic antimicrobial peptides in innate host defenses Trends Microbiol 8 2000 402 410
15. S. Hara, A. Asaoka, and M. Yamakawa Effect of moricin, a novel antibacterial peptide of Bombyx mori (Lepidoptera bombycidae) on the growth of methicillin-resistant Staphylococcus aureus (MRSA) Appl Entomol Zool 31 1996 465 466
16. F. Inagaki, I. Shimada, K. Kawaguchi, M. Hirano, I. Terasawa, and T. Ikura Structure of melittin bound to perdeuterated dodecylphosphocholine micelles as studied by two-dimensional NMR and distance geometry calculations Biochemistry 28 1989 5985 5991
17. P. Juvvadi, S. Vunnam, and R.B. Merrifield Synthetic melittin, its enantio, retro, and retroenantio isomers, and selected chimeric analogs: their antibacterial, hemolytic, and lipid bilayer action J Am Chem Soc 118 1996 8989 8997
18. J.W. Larrick, M. Hirata, J. Zhong, and S.C. Wright Antimicrobial activity of human CAP18 peptides Immunotechnology 1 1995 65 72
19. S.Z. Li, H.S. Yan, G.D. Liu, L. Jiang, and B.L. He Studies on synthesis and biological activities of analogues of melittin Chem J Chin Univ 24 2003 449 453
20. L.P. Liu, Z.D. Xie, H.S. Yan, X.H. Cheng, and B.L. He Hemolytic and antibacterial activity of synthetic deletion peptides of melittin G.S. Lu J.P. Tam Y.C. Du Peptides: biology and chemistry 1995 ESCOM Leiden p. 20-22
21. L.P. Liu, H.S. Yan, A.G. Ni, X.H. Cheng, and B.L. He Interaction of calmodulin with synthetic deletion peptides of melittin Int J Pept Protein Res 43 1994 107 112
22. J.F. Macros, R.N. Beachy, R.A. Houghten, S.E. Blondelle, and E. Perez-Paya Inhibition of a plant virus infection by analogs of melittin Proc Natl Acad Sci USA 92 1995 12466 12469
23. K. Matsuzaki Why and how are peptide-lipid interactions utilized for self-defense? Magainins and tachyplesins as archetypes Biochim Biophys Acta 1462 1999 1 10
24. A. Miyanoshita, S. Hara, M. Sugiyama, A. Asaoka, K. Taniai, and F. Yukuhiro Isolation and characterization of a new member of insect defensin family from a beetle Allomyrina dichotoma Biochem Biophys Res Commun 220 1996 526 531
25. 2-terminal helical domain 1-18 of dermaseptin is responsible for antimicrobial activity J Biol Chem 269 1994 1934 1939
26. S. Nagpal, V. Gupta, J.K. Kaur, and D.M. Salunke Structure-function analysis of tritrypticin, an antibacterial peptide of innate immune origin J Biol Chem 274 1999 23296 23304
27. H. Neu The crisis in antibiotic resistance Science 257 1992 1064 1073
28. A. Okada, K. Wakamatsu, T. Miyazawa, and T. Higashijima Vesicle-bound conformation of melittin: transferred nuclear overhauser enhancement analysis in the presence of perdeuterated phosphatidylcholinevesiclest Biochemistry 33 1994 9438 9446
29. Z. Oren, and Y. Shai Selective lysis of bacteria but not mammalian cells by diastereomers of melittin: structure-function study Biochemistry 36 1997 1826 1835
30. A. Pellegrini, U. Thomas, N. Bramaz, S. Klauser, P. Hunziker, and R. von Fellenberg Identification and isolation of the bactericidal domains in the proteinase inhibitor aprotinin Biochem Biophys Res Commun 222 1996 559 565
31. E. Perez-Paya, R.A. Houghten, and S.E. Blondelle Determination of the secondary structure of selected melittin analogues with different hemolytic activities Biochem J 299 1994 587 591
32. E. Perez-Paya, R.A. Houghten, and S.E. Blondelle The role of amphipathicity in the folding, self-association and biological activity of multiple subunit small proteins J Biol Chem 270 1995 1048 1056
33. O. Rekdal, J. Andersen, L.H. Vorland, and J.S. Svendsen Construction and synthesis of lactoferricin derivatives with enhanced antibacterial activity J Pept Sci 5 1999 32 45
34. D.E. Revitt, A. Kirkpatrick, D.R. Hewish, W. Reilly, and J.A. Werkmeister Dimerization of truncated melittin analogues results in cytolytic peptides Biochem J 316 1996 525 529
35. D.M. Rothstein, P. Spacciapoli, L.T. Tran, T. Xu, F.D. Roberts, and M. Dalla Serra Anticandida activity is retained in P-113, a 12-amino-acid fragment of histatin 5 Antimicrob Agents Chemother 45 2001 1367 1373
36. M.S. Searle, D.H. Williams, and U. Gerhard Partitioning of free energy contributions in the estimation of binding constants: residual motion and consequences for amide-amide hydrogen bond strengths J Am Chem Soc 114 1992 10697 10704
37. Y. Shai, and Z. Oren From "carpet" mechanism to de-novo designed diastereomeric cell-selective antimicrobial peptides Peptides 22 2001 1629 1641
38. D.A. Steinberg, M.A. Hurst, C.A. Fujii, A.H.C. Kung, J.F. Ho, and F.C. Cheng Protegrin-l: a broad-spectrum, rapidly microbicidal peptide with in vivo activity Antimicrob Agents Chemother 41 1997 1738 1742
39. T.C. Terwilliger, and D. Eisenberg The structure of melittin II Interpretation of the structure J Biol Chem 257 1982 6016 6022
40. S. Thennarasu, and R. Nagaraj Specific antimicrobial and hemolytic activities of 18-residue peptides derived from the amino terminal region of the toxin pardaxin Protein Eng 9 1996 1219 1224
41. A. Tossi, L. Sandri, and A. Giangaspero Amphipathic α-helical antimicrobial peptides Biopolymers 55 2000 4 30
42. J. Travis Reviving the antibiotic miracle Science 264 1994 360 362
43. K. Yamada, and S. Natori Purification, sequence and antibacterial activity of two novel sapecin homologues from sacrophaga embryonic cells: similarity of sapecin B to charybdotoxin Biochim J 291 1993 275 279
44. H.S. Yan, and B.L. He The effect of the basicity and hydrophobicity of peptides on their affinities for calmodulin Chin J Biochem Biophys 24 1992 295 300
45. H.S. Yan, S.Z. Li, X.J. Sun, H.F. Mi, and B.L. He Individual substitution analogs of Mel(12-26), melittin's C-terminal 15-residue peptide: their antimicrobial and hemolytic actions FEBS Lett 554 2003 100 104
46. H.S. Yan, A.G. Ni, L.P. Liu, X.H. Cheng, and B.L. He Prediction of affinities of peptides for calmodulin Sci. China Ser B 39 1996 113 122
47. W.S. Young, and C.L. Brooks III A microscopic view of helix propagation: N- and C-terminal helix growth in alanine helices J Mol Biol 259 1996 560 572
48. M. Zasloff Antimicrobial peptides of multicelullar organisms Nature 415 2002 389 395
49. B.H. Zimm, and J.K. Bragg Theory of phase transition between helix and random coil in polypeptide chains J Chem Phys 31 1959 526 535