Design and synthesis of novel antimicrobial peptides on the basis of α helical domain of Tenecin 1, an insect defensin protein, and structure-activity relationship study

Peptides

Volumn 27, Issue 4, 2006, Pages 640-648

  Ahn, Hye Sun ^a   Cho, Wonmi ^a   Kang, Sun Hee ^a   Ko, Sung Sin ^a   Park, Mi Sun ^a   Cho, Hyeongjin ^a   Lee, Keun Hyeung ^a  

^a Inha University   (South Korea)

Author keywords

Helicity; Antimicrobial peptide; Defensin; Isoelectric point; Net positive charge

Indexed keywords

DEFENSIN; MAGAININ 2; MELITTIN; POLYPEPTIDE ANTIBIOTIC AGENT; TENECIN 1; UNCLASSIFIED DRUG;

ALPHA HELIX; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HEMOLYSIS; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; ANTI-INFECTIVE AGENTS; DRUG DESIGN; INSECT PROTEINS; INSECTS; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE-ACTIVE AGENTS;

INSECTA; POSIBACTERIA;

EID: 33645388381     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2005.08.016     Document Type: Article

References (36)

1. J.M. Bonmatin, J.L. Bonnat, X. Gallet, F. Vovelle, M. Ptak, and J.M. Reichhart Two-dimensional 1H NMR study of recombinant insect defensin A in water: resonance assignments, secondary structure and global folding J Biomol NMR 2 1992 235 256
2. D.J. Campopiano, D.J. Clarke, PolferNC, P.E. Barran, R.J. Langley, and J.R. Govan Structure-activity relationships in defensin dimers: a novel link between beta-defensin tertiary structure and antimicrobial activity J Biol Chem 279 2004 48671 48679
3. 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 3335 3350
4. M. Cheron, B. Cybulska, J. Mazerski, J. Grzybowska, A. Czerwinski, and E. Borowski Quantitative structure-activity relationships in amphotericin B derivatives Biochem Pharmacol 37 1998 827 836
5. M. Dathe, M. Schumann, T. Wieprecht, A. Winkler, M. Beyermann, and E. Krause Peptide helicity and membrane surface charge modulate the balance of electrostatic and hydrophobic interactions with lipid bilayers and biological membranes Biochemistry 35 1996 12612 12622
6. 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
7. C.E. Dempsey, S. Ueno, and M.B. Avison Enhanced membrane permeabilization and antibacterial activity of a disulfide-dimerized magainin analogue Biochemistry 42 2003 402 409
8. D.E. Eisenberg, M. Schwarz, and R.W. Komaronmy Analysis of membrane and surface protein sequences with the hydrophobic moment plot J Mol Biol 179 1984 125 142
9. G.L. Ellman Tissue sulfhydryl groups Arch Biochem Biophys 82 1959 70 77
10. R.M. Epand, and H.J. Vogel Diversity of antimicrobial peptides and their mechanisms of action Biochim Biophys Acta 1462 1999 11 28
11. G.B. Fields, and R.L. Noble Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids Int J Pept Protein Res 35 1990 161 214
12. K.S. Hoek, J.M. Milen, P.A. Grieve, D.A. Donysius, and R. Smith Antibacterial activity in bovine lactoferrin-derived peptides Antimicrob Agents Chemother 41 1997 54 59
13. R.A. Houghten, and S.T. Degraw Effect of positional environmental domains on the variation of high-performance liquid chromatographic peptide retention coefficients J Chromatogr 386 1987 223 228
14. K. Hristova, M.E. Selsted, and S.H. White Critical role of lipid composition in membrane permeabilization by rabbit neutrophil defensins J Biol Chem 272 1997 24224 24233
15. T. Kuzuhara, Y. Nakajima, K. Matsuyama, and S. Natori Determination of the disulfide array in sapecin, an antibacterial peptide of Sarcophaga peregrina (flesh fly) J Biochem (Tokyo) 107 1990 514 518
16. M. Lamberty, A. Caille, C. Landon, S. Tassin-Moindrot, C. Hetru, and P. Bulet Solution structures of the antifungal heliomicin and a selected variant with both antibacterial and antifungal activities Biochemistry 40 2001 11995 12003
17. K.H. Lee Development of short antimicrobial peptides derived from host defense peptides or by combinatorial libraries Curr Pharm Design 8 2002 795 813
18. K.H. Lee, S.Y. Hong, J.E. Oh, M.Y. Kwon, J.H. Yoon, and J. Lee Identification and characterization of the antimicrobial peptide corresponding to C-terminal beta-sheet domain of tenecin 1, an antibacterial protein of larvae of Tenebrio molitor Biochem J 334 1998 99 105
19. G.R. Little, D.N. Kelner, E. Lim, D.J. Burke, and P. Conlon Functional domains of recombinant bactericidal/permeability increasing protein (rBPI23) J Biol Chem 269 1994 1865 1872
20. R. Maget-Dana, and M. Ptak Penetration of the insect defensin A into phospholipid monolayers and formation of defensin A-lipid complexes Biophys J 73 1997 2527 2533
21. W.L. Maloy, and U.P. Kari Structure-activity studies on magainins and other host defense peptides Biopolymers 37 1995 105 122
22. 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
23. L.D. Mayer, M.J. Hope, and P.R. Cullis Vesicles of variable sizes produced by a rapid extrusion procedure Biochim Biophys Acta 858 1986 161 168
24. M. Michel, and L. Gutmann Methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci: therapeutic realities and possibilities Lancet 349 1997 1901 1906
25. Y. Nakajima, J. Alvarez-Bravo, J. Cho, K. Homma, S. Kanegasaki, and S. Natori Chemotherapeutic activity of synthetic antimicrobial peptides: correlation between chemotherapeutic activity and neutrophil-activating activity FEBS Lett 415 1997 64 66
26. J.L. Rodriguez-Tudela, J. Berenguer, J.V. Martinez-Sugarez, and R. Sanchez Comparison of a spectrophotometric microdilution method with RPMI-2% glucose with the national committee for clinical laboratory standards reference macrodilution method M27-P for in vitro susceptibility testing of amphotericin B, flucytosine, and fluconazole against Candida albicans Antimicrob Agents Chemother 40 1996 1998 2003
27. B. Romestand, F. Molina, V. Richard, P. Roch, and C. Granier Key role of the loop connecting the two beta strands of mussel defensin in its antimicrobial activity Eur J Biochem 270 2003 2805 2813
28. H. Saido-Sakanaka, J. Ishibashi, A. Sagisaka, E. Momotani, and M. Yamakawa Synthesis and characterization of bactericidal oligopeptides designed on the basis of an insect anti-bacterial peptide Biochem J 338 1999 29 33
29. H. Saido-Sakanaka, J. Ishibashi, E. Momotani, F. Amano, and M. Yamakawa In vitro and in vivo activity of antimicrobial peptides synthesized based on the insect defensin Peptides 25 2004 19 27
30. Y. Shai Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by α-helical antimicrobial and cell non-selective membrane-lytic peptides Biochim Biophys Acta 1462 1999 55 70
31. N. Sitaram, and R. Nagaraj Interaction of antimicrobial peptides with biological and model membranes: structural and charge requirements for activity Biochim Biophys Acta 1462 1999 29 54
32. K. Takeuchi, H. Takahashi, M. Sugai, H. Iwai, T. Kohno, and K. Sekimizu Channel-forming membrane permeabilization by an antibacterial protein, sapecin: determination of membrane-buried and oligomerization surfaces by NMR J Biol Chem 279 2004 4981 4987
33. C. Tanford The hydrophobic effect 1990 Wiley p. 109
34. A. Tossi, L. Sandri, and A. Giangaspero Biopolymers. Amphipathic, alpha-helical antimicrobial peptides Biopolymers 55 2000 4 30
35. V.E. Vaskovsky, E.Y. Kostetsky, and I.M. Vasendin A universal reagent for phospholipid analysis J Chromatogr 114 1975 129 141
36. K. Yamada, and S. Natori Characterization of the antimicrobial peptide derived from sapecin B, an antibacterial protein of Sarcophaga peregrina (flesh fly) Biochem J 298 1994 623 628