Hydrophobic effects on antibacterial and channel-forming properties of cecropin A-melittin hybrids

Journal of Peptide Science

Volumn 2, Issue 4, 1996, Pages 223-232

  Juvvadi, Padmaja ^a   Vunnam, Satyanarayana ^a   Merrifield, Elizabeth L ^a   Boman, Hans G ^b   Merrifield, R B ^a  

^a ROCKEFELLER UNIVERSITY   (United States)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Antimicrobial peptides; Hydrophobic residue; Ion channels; Pores; helix

Indexed keywords

STAPHYLOCOCCUS AUREUS;

ANTIINFECTIVE AGENT; ANTIMICROBIAL CATIONIC PEPTIDE; CECROPIN A; DRUG DERIVATIVE; INSECT HORMONE; ION CHANNEL; MELITTIN; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; ELECTRIC CONDUCTIVITY; MICROBIOLOGICAL EXAMINATION; MOLECULAR GENETICS; PROTEIN CONFORMATION; PROTEIN ENGINEERING; SYNTHESIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; ELECTRIC CONDUCTIVITY; INSECT HORMONES; ION CHANNELS; MELITTEN; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN CONFORMATION; PROTEIN ENGINEERING;

EID: 0030178188     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199607)2:4<223::AID-PSC63>3.0.CO;2-C     Document Type: Article

References (47)

1. H. Steiner, D. Hultmark, A. Engstrom, H. Bennich and H. G. Boman (1981). Sequence and specificity of two antibacterial proteins involved in insect immunity. Nature 292, 246-248.
2. H. G. Boman and D. Hultmark (1987). Cell-free immunity in insects. Annu. Rev. Microbiol. 41, 103-126.
3. H. G. Boman in: Phylogenetic Perspectives in Immunity: The Insect-Host Defense. J. Hoffmann, S. Natori and C. Janeway, Eds., p. 24-37, R. G. Landes Biomedical Publishers, Texas 1994.
4. H. G. Boman (1995). Peptide antibiotics and their role in innate immunity. Annu. Rev. Immunol. 13, 61-92.
5. H. G. Boman, I. A. Boman, D. Andreu, Z-Qu. Li, R. B. Merrifield, G. Schlenstedt and R. Zimmermann (1989). Chemical synthesis and enzyme processing of precursor forms of cecropin A and B. J. Biol. Chem. 264, 5852-5860.
6. R. B. Merrifield, L. D. Vizioli and H. G. Boman (1982). Synthesis of the antibacterial peptide cecropin A (1-33). Biochemistry 21, 5020-5031.
7. D. Andreu, R. B. Merrifield, H. Steiner and H. G. Boman (1983). Solid-phase synthesis of cecropin and related peptides. Proc. Natl. Acad. Sci. USA 80, 6475-6479.
8. D. Andreu, R. B. Merrifield, H. Steiner and H. G. Boman (1985). N-terminal analogues of cecropin A: Synthesis, antibacterial activity and conformational properties. Biochemistry 24, 1683-1688.
9. J. P. Segrest, R. L. Jackson, J. P. Morrisett and A. M. Jr. Gotto (1974). A molecular theory of lipid-protein interactions in the plasma lipo proteins. FEBS Lett. 38, 247-253.
10. E. T. Kaiser and F. J. Kezdy (1983). Secondary structures of proteins and peptides in amphiphilic environments. Proc. Natl. Acad. Sci. USA 80, 1137-1143.
11. H. Steiner (1982). Secondary structure of the cecropins: antibacterial peptides from the moth Hyalophora cecropia. FEBS Lett. 137, 283-287.
12. T. A. Holak, A. Engstrom, P. J. Kraulis, G. Lindeberg, H. Bennich, T. A. Jones, A. M. Gronenborn and G. M. Clore (1988). The solution conformation of the antibacterial peptide cecropin A: a nuclear magnetic resonance and dynamical simulated annealing study. Biochemistry 27, 7620-7629.
13. B. Christensen, J. Fink, R. B. Merrifield and D. Mauzerall (1988). Channel-forming properties of cecropins and related model compounds incorporated into planar lipid membranes. Proc. Natl. Acad. Sci. USA 85, 5072-5076.
14. J. Fink, R. B. Merrifield, A. Boman and H. G. Boman (1989). The chemical synthesis of cecropin D and an analog with enhanced antibacterial activity. J. Biol Chem. 264, 6260-6267.
15. E. Habermann and J. Jentsch (1967). Sequence analysis of melittin from tryptlc and peptic degradation. Hoppe-Seylers Z. Physiol. Chem. 348, 37-50.
16. T. C. Terwilliger and D. Eisenberg (1982). The structure of melittin. II. Interpretation of the structure. J. Biol. Chem. 257, 6016-6022.
17. H. G. Boman (1982). Humoral immunity in insects and the counter defense of some pathogens. Fortschr. Zool. 27, 211-222.
18. E. Habermann (1972). Bee and wasp venoms. Science 177, 314-322.
19. H. G. Boman, D. Wade, I. A. Boman, B. Wahlin and R. B. Merrifield (1989). Antibacterial and antimalarial properties of peptides that are cecropin-melittin hybrids. FEBS Lett. 259, 103-106.
20. P. V. Hofsten, I. Faye, K. Kockum, J-Y. Lee, K. G. Xanthopoulos, I. A. Boman, H. G. Boman, A. Engstrom, D. Andreu and R. B. Merrifield (1985). Molecular cloning, cDNA sequencing and chemical synthesis of cecropin B from Hyalophora cecropia. Proc. Natl. Acad. Sci. USA 82, 2240-2243.
21. J. Fink, A. Boman, H. G. Boman and R. B. Merrifield (1989). Design, synthesis and antibacterial activity of cecropin-like model peptides. Int J. Peptide Protein Res. 33, 412-421.
22. R. B. Merrifield, P. Juwadi, D. Andreu, J. Ubach, A. Boman and H. G. Boman (1995). Retro and retroenantio analogs of cecropin-melittin hybrids. Proc. Natl. Acad. Sci. USA 92, 3449-3453.
23. D. Andreu, J. Ubach, A. Boman, B. Wahlin, D. Wade, R B. Merrifield and H. G. Boman (1992). Shortened cecropin A-melittin hybrids: Significant size reduction retains potent antibiotic activity. FEBS Lett. 296, 190-194.
24. R. B. Merrifield, D. Andreu, H. G. Boman and H. Steiner in: Progress in Bioorganic Chemistry and Molecular Biology, Yu. A. Ovshinnikov, Ed., p. 101-108, Elsevier, Amsterdam 1984.
25. R. B. Merrifield (1963). Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149-2154.
26. G. R. Matseuda and J. M. Stewart (1981). A p-methylbenzhydrylamine resin for improved solid-phase synthesis of peptide amides. Peptides 2, 45-50.
27. V. K. Sarin, S. B. H. Kent. J. P. Tam and R. B. Merrifield (1981). Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal. Biochem. 117, 147-157.
28. N2 deprotection of synthetic peptides with a low concentration of HF in dimethyl sulfide: Evidence and application in peptide synthesis. J. Am. Chem. Soc. 105, 6442-6455.
29. F. C. Westall, J. Scotchler and A. B. Robinson (1972). The use of propionic acid-hydrochloric acid hydrolysis in Merrifield solid-phase synthesis. J. Org. Chem. 37, 3363-3365.
30. S. K. Chowdhury, V. Katta and B. T. Chait (1990). An electrospray-ionization mass spectrometer with new features. Rapid Commun. Mass Spectrometery 4, 81-87.
31. D. Hultmark, A. Engstrom, H. Bennich, R. Kapur and H. G. Boman (1982). Insect immunity: Isolation and structure of cecropin D and four minor components from Cecropia pupae. Eur. J. Biochem. 127, 207-217.
32. D. Hultmark, A. Engstrom, K. Andersson, H. Steiner, H. Bennich and H. G. Boman (1983). Insect immunity. Attacins, a family of antibacterial proteins from Hyalophora cecropia. EMBO J. 2, 571-576.
33. Y.-H. Chen, J. T. Yang and K. H. Chau (1974). Determination of the helix and beta form of proteins In aqueous solution by circular dichroism. Biochemistry 13, 3350-3359.
34. C. M. Drain, B. Christensen and D. Mauzerall (1989). Photogating of Ionic currents across a lipid bilayer. Proc. Natl. Acad. Sci. USA 86, 6959-6962.
35. P. Mueller, D. O. Rudin, H. T. Tien and W. C. Wescott (1963). Reconstitution of excitable cell membrane structure in vitro circulation. J. Phys. Chem. 67, 534-535.
36. M. Montal and P. Mueller (1972). Formation of biomolecular membranes from lipid monolayers and a study of their electrical properties. Proc. Natl. Acad. Sci. USA 69, 3561-3566.
37. R Fettiplace, D. M. Andrews and D. A. Haydon (1971). The thickness, composition and structure of some lipid bilayers and natural membranes. J. Membr. Biol. 5, 277-296.
38. O. D. Monera, T. J. Sereda, N. E. Zhou, C. M. Kayt and R. S. Hodges (1995). Relationship of side-chain hydrophobicity and α-helical propensity on the stability of the single-stranded amphipathic α-helix. J. Peptide Science 1, 319-329.
39. R V. Wolfenden, P. M. Cullis and C. C. Southgate (1979). Water, protein folding and genetic code. Science 206, 575-577.
40. C. Chothia (1976). The nature of the accessible and buried surfaces in proteins. J. Mol. Biol. 105, 1-14.
41. D. Wade, A. Boman, B. Wahlin, C. M. Drain, D. Andreu, H. G. Boman and R. B. Merrifield (1990). All-D amino acid-containing channel-forming antibiotic peptides. Proc. Natl. Acad. Sci. USA 87, 4761-4765.
42. E. L. Merrifield, S. A. Mitchell, J. Ubach, H. G. Boman. D. Andreu and R. B. Merrifield (1995). D-enantiomers of 15-residue cecropin A-melittin hybrids. Int. J. Peptide Protein Res. 46, 214-220.
43. F. Jahnig (1983). Thermodynamics and kinetics of protein incorporation Into membranes. Proc. Natl. Acad. Sci. USA 80, 3691-3695.
44. M. K. Mathew and P. Balaram (1983). A helix dipole model for alamethicin and related transmembrane channels. FEBS Lett. 157, 1-5.
45. P. Schoch and D. F. Sargent (1980). Quantitative analysis of the binding of melittin to planar lipid bilayers allowing for the discrete-charge effect. Biochim Biophys. Acta 602, 234-247.
46. R. Latorre and O. Alvarez (1981). Voltage-dependent channels in planar lipid bilayer membranes. Physiol Rev. 61, 77-150.
47. G. Menestrina, K.-P. Voges, G. Jung and G. Boheim (1986). Voltage-dependent channel formation by rods of helical polypeptides. J. Membr. Biol. 93, 111-132.