Indolicidin-derived antimicrobial peptide analogs with greater bacterial selectivity and requirements for antibacterial and hemolytic activities

Sung-Min Kim1, Joung-Min Kim1, Bishnu Prasad Joshi1, Hyeongjin Cho1, Keun-Hyeung Lee1
1Bioorganic Chemistry Lab., Department of Chemistry, Inha University, 253 Younghyun-Dong, Nam-Gu, Inchon-City, 402-751, South Korea

Tài liệu tham khảo

Zasloff, 2002, Antimicrobial peptides of multicellular organisms, Nature, 415, 389, 10.1038/415389a Selsted, 1992, Indolicidin, a novel bactericidal tridecapeptide amide from neutrophils, J. Biol. Chem., 267, 4292, 10.1016/S0021-9258(18)42830-X Lee, 2003, Fungicidal effect of indolicidin and its interaction with phospholipid membranes, Biochem. Biophys. Res. Commun., 305, 305, 10.1016/S0006-291X(03)00755-1 Aley, 1994, Killing of giardia lamblia by cryptdins and cationic neutrophil peptides, Infect. Immun., 62, 5397, 10.1128/IAI.62.12.5397-5403.1994 Robinson Jr, 1998, Anti-HIV-1 activity of indolicidin, an antimicrobial peptide from neutrophils, J. Leukocyte Biol., 63, 94, 10.1002/jlb.63.1.94 Schluesener, 1993, Leukocytic antimicrobial peptides kill autoimmune T cells, J. Neuroimmunol., 47, 199, 10.1016/0165-5728(93)90030-3 Chan, 2006, Tryptophan- and arginine-rich antimicrobial peptides: Structures and mechanisms of action, Biochim. Biophys. Acta., 1758, 1184, 10.1016/j.bbamem.2006.04.006 Marchand, 2006, Covalent binding of the natural antimicrobial peptide indolicidin to DNA abasic sites, Nucleic Acids Res., 34, 5157, 10.1093/nar/gkl667 Hsu, 2005, Structural and DNA-binding studies on the bovine antimicrobial peptide, indolicidin: evidence for multiple conformations involved in binding to membranes and DNA, Nucleic Acids Res., 33, 4053, 10.1093/nar/gki725 Ladokhin, 1999, CD spectra of indolicidin antimicrobial peptides suggest turns, not polyproline helix, Biochemistry, 38, 12313, 10.1021/bi9907936 Andrushchenko, 2006, Solvent-dependent structure of two tryptophan-rich antimicrobial peptides and their analogs studied by FTIR and CD spectroscopy, Biochim. Biophys. Acta., 1758, 1596, 10.1016/j.bbamem.2006.07.013 Falla, 1996, Mode of action of the antimicrobial peptide indolicidin, J. Biol. Chem., 271, 19298, 10.1074/jbc.271.32.19298 Ryge, 2004, New indolicidin analogues with potent antibacterial activity, J. Pept. Res., 64, 171, 10.1111/j.1399-3011.2004.00177.x Staubitz, 2001, Structure–function relationships in the tryptophan-rich, antimicrobial peptide indolicidin, J. Pept. Sci., 7, 552, 10.1002/psc.351 Subbalakshmi, 2000, Antibacterial and hemolytic activities of single tryptophan analogs of indolicidin, Biochem. Biophys. Res. Commun., 274, 714, 10.1006/bbrc.2000.3214 Friedrich, 2001, Structure and mechanism of action of an indolicidin peptide derivative with improved activity against gram-positive bacteria, J. Biol. Chem., 276, 24015, 10.1074/jbc.M009691200 Ösapay, 2000, Formation and characterization of a single Trp–Trp cross-link in indolicidin that confers protease stability without altering antimicrobial activity, J. Biol. Chem., 275, 12017, 10.1074/jbc.275.16.12017 Rozek, 2003, Structure-based design of an indolicidin peptide analogue with increased protease stability, Biochemistry, 42, 14130, 10.1021/bi035643g Fields, 1990, Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids, Int. J. Pept. Protein Res., 35, 161, 10.1111/j.1399-3011.1990.tb00939.x Park, 2007, Microwave-assisted solid-phase synthesis of pseudopeptides containing reduced amide bond, Tetrahedron Lett., 48, 1053, 10.1016/j.tetlet.2006.11.151 Mayer, 1986, Vesicles of variable sizes produced by a rapid extrusion procedure, Biochim. Biophys. Acta, 858, 161, 10.1016/0005-2736(86)90302-0 Harwick, 1973, In vitro activity of ampicillin or vancomycin combined with gentamicin or streptomycin against enterococci, Antimicrob. Agents Chemother., 4, 383, 10.1128/AAC.4.4.383 Cheron, 1988, Quantitative structure–activity relationships in amphotericin B derivatives, Biochem. Pharmacol., 37, 827, 10.1016/0006-2952(88)90168-2 Frecer, 2006, QSAR Analysis of antimicrobial and haemolytic effects of cyclic cationic antimicrobial peptides derived from protegrin-1, Bioorg. Med. Chem., 14, 6065, 10.1016/j.bmc.2006.05.005 Dathe, 1997, Hydrophobicity, hydrophobic moment and angle subtended by charged Residues modulate antibacterial and haemolytic activity of amphipathic helical peptides, FEBS Lett., 403, 208, 10.1016/S0014-5793(97)00055-0 Kwon, 1998, Structure–activity analysis of brevinin 1E amide, an antimicrobial peptide from Rana esculenta, Biochim. Biophys. Acta, 1387, 239, 10.1016/S0167-4838(98)00123-X Oren, 1997, A repertoire of novel antibacterial diastereomeric peptides with selective cytolytic activity, J. Biol. Chem., 272, 14643, 10.1074/jbc.272.23.14643 Vanderesse, 1998, Structural comparison of homologous reduced peptide, reduced azapeptide, iminoazapeptide, and methyleneoxypeptide analogues, J. Am. Chem. Soc., 120, 9444, 10.1021/ja980937o Oh, 2000, Characterization of the unique function of a reduced amide cytolytic peptide that acts on phospholipid membranes, Biochem. J., 352, 659, 10.1042/0264-6021:3520659 Krause, 1995, Location of an amphipathic alpha-helix in peptides using reversed-phase HPLC retention behavior of d-amino acid analogs, Anal. Chem., 67, 252, 10.1021/ac00098a003 Wu, 1981, Ordered conformation of polypeptides and proteins in acidic dodecyl sulfate solution, Biochemistry, 20, 566, 10.1021/bi00506a019 Berova, 2000, Chapter 21, 601 Grishina, 1994, Contributions of tryptophan side chains to the circular dichroism of globular proteins: exciton couplets and coupled oscillators, Faraday Discuss, 99, 245, 10.1039/fd9949900245 Rozek, 2000, Structure of the bovine antimicrobial peptide indolicidin bound to dodecylphosphocholine and sodium dodecyl sulfate micelles, Biochemistry, 39, 15744, 10.1021/bi000714m Hristova, 1997, Critical role of lipid composition in membrane permeabilization by rabbit neutrophil defensins, J. Biol. Chem., 272, 24224, 10.1074/jbc.272.39.24224 Guidotti, 1972, Membrane proteins, Annu. Rev. Biochem., 41, 731, 10.1146/annurev.bi.41.070172.003503 Vogel, 1981, Incorporation of melittin into phosphatidylcholine bilayers. Study of binding and conformational changes, FEBS Lett., 134, 37, 10.1016/0014-5793(81)80545-5 Kiyota, 1996, Design and synthesis of amphiphilic alpha-helical model peptides with systematically varied hydrophobic–hydrophilic balance and their interaction with lipid- and bio-membranes, Biochemistry, 35, 13196, 10.1021/bi961289t Oren, 1997, Selective lysis of bacteria but not mammalian cells by diastereomers of melittin: structure–function study, Biochemistry, 36, 1826, 10.1021/bi962507l Matsuzaki, 1999, Why and how are peptide–lipid interactions utilized for self-defense? Magainins and tachyplesins as archetypes, Biochim. Biophys. Acta, 1462, 1, 10.1016/S0005-2736(99)00197-2 Shai, 2002, From innate immunity to de-novo designed antimicrobial peptides, Curr. Pharm. Design, 8, 715, 10.2174/1381612023395367 Bruehlmeier, 2002, Stabilization neurotensin analogues: effect on peptide catabolism, biodistribution and tumor binding, Nucl. Med. Biol., 29, 321, 10.1016/S0969-8051(01)00304-3 Oh, 1999, A Comparison of characteristics between membrane-active antifungal peptide and its pseudopeptides, Bioorg. Med. Chem., 11, 2509, 10.1016/S0968-0896(99)00176-5 Chen, 2002, Bioactive pseudopeptidic analogues and cyclostereoisomers of osteogenic growth peptide c-terminal pentapeptide, OGP(10–14) J, Med. Chem., 44, 1624, 10.1021/jm010479l