Antimicrobial HPA3NT3 peptide analogs: Placement of aromatic rings and positive charges are key determinants for cell selectivity and mechanism of action

Biochimica et Biophysica Acta - Biomembranes

Volumn 1828, Issue 2, 2013, Pages 443-454

  Lee, Jong Kook ^a   Park, Seong Cheol ^a   Hahm, Kyung Soo ^b   Park, Yoonkyung ^a  

^a Chosun University   (South Korea)

^b Bioleaders Corporation   (South Korea)

Author keywords

Antimicrobial action; Determinants of cell selectivity; Resistance

Indexed keywords

ALANINE; AMPICILLIN; ANTIMICROBIAL PEPTIDE HPA3NT3; CALCEIN; CIPROFLOXACIN; ERYTHROMYCIN; GREEN FLUORESCENT PROTEIN; PHENYLALANINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLGLYCEROL; POLYPEPTIDE ANTIBIOTIC AGENT; RIFAMPICIN; SPHINGOMYELIN; UNCLASSIFIED DRUG; VANCOMYCIN;

AMINO ACID SUBSTITUTION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS AWAMORI; ASPERGILLUS FLAVUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS PARASITICUS; BACILLUS SUBTILIS; BACTERIAL MEMBRANE; BACTERICIDAL ACTIVITY; CANDIDA ALBICANS; CELL MEMBRANE PERMEABILITY; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CYTOPLASM; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; ERYTHROCYTE; ESCHERICHIA COLI; FUNGAL MEMBRANE; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; KERATINOCYTE; LIPID BILAYER; LISTERIA MONOCYTOGENES; MEMBRANE BINDING; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DNA BINDING; PROTEIN RNA BINDING; PROTEIN SYNTHESIS INHIBITION; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; TRICHOSPORON BEIGELII;

AMINO ACIDS; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; CATIONS; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG RESISTANCE, MULTIPLE, FUNGAL; FLUORESCENT DYES; HUMANS; KINETICS; LIPOSOMES; MICROBIAL SENSITIVITY TESTS; MICROSCOPY, CONFOCAL; MICROSCOPY, ELECTRON, TRANSMISSION; MODELS, CHEMICAL; ORGANIC CHEMICALS; PEPTIDES; RIFAMPIN; SPHINGOMYELINS; STAPHYLOCOCCUS AUREUS; TRYPTOPHAN;

BACTERIA (MICROORGANISMS); HELICOBACTER PYLORI; MAMMALIA; STAPHYLOCOCCUS AUREUS;

EID: 84870234194     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2012.09.005     Document Type: Article

References (43)

1. K.A. Brogden Antimicrobial peptides: pore formers or metabolic inhibitors in bacteria? Nature 3 2005 238 250
2. M. Zasloff Antimicrobial peptides of multicellular organisms Nature 415 2002 389 395
3. R.E.W. Hancock, and R. Lehrer Cationic peptides: a new source of antibiotics Trends Biotechnol. 16 1998 82 88
4. L.A. Allen Modulating phagocyte activation: the pros and cons of Helicobacter pylori virulence factors J. Exp. Med. 191 2000 1451 1454
5. K. Pütsep, C.I. Bränden, H.G. Boman, and S. Normark Antibacterial peptide from H. pylori Nature 398 1999 671 672
6. J. Bylund, T. Christophe, F. Boulay, T. Nyström, A. Karlsson, and C. Dahlgren Proinflammatory activity of a cecropin-like antibacterial peptide from Helicobacter pylori Antimicrob. Agents Chemother. 45 2001 1700 1704
7. S.C. Park, M.H. Kim, M.A. Hossain, S.Y. Shin, Y. Kim, L. Stella, J.D. Wade, Y. Park, and K.S. Hahm Amphipathic alpha-helical peptide, HP (2 20), and its analogues derived from Helicobacter pylori: pore formation mechanism in various lipid compositions Biochim. Biophys. Acta Biomembr. 1778 2008 229 241
8. J.K. Ghosh, D. Shaool, P. Guillaud, L. Cicéron, D. Mazier, I. Kustanovich, Y. Shai, and A. Mor Selective cytotoxicity of dermaseptin S3 toward intraerythrocytic Plasmodium falciparum and the underlying molecular basis J. Biol. Chem. 272 1997 31609 31616
9. D. Rapaport, and Y. Shai Aggregation and organization of pardaxin in phospholipid membranes J. Biol. Chem. 267 1992 6502 6509
10. S.C. Park, J.R. Lee, S.O. Shin, Y. Park, S.Y. Lee, and K.S. Hahm Characterization of a heat-stable protein with antimicrobial activity from Arabidopsis thaliana Biochem. Biophys. Res. Commun. 362 2007 562 567
11. Y. Park, S.C. Park, H.K. Park, S.Y. Shin, Y. Kim, and K.S. Hahm Structure-activity relationship of HP (2 20) analog peptide: enhanced antimicrobial activity by N-terminal random coil region deletion Biopolymers 88 2007 199 207
12. 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
13. K. Marynka, S. Rotem, I. Portnaya, U. Cogan, and A. Mor In vitro discriminative antipseudomonal properties resulting from acyl substitution of N-terminal sequence of dermaseptin S4 derivatives Chem. Biol. 14 2007 75 85
14. M.L. Mangoni, N. Papo, D. Barra, M. Simmaco, A. Bozzi, A. Di Giulio, and A.C. Rinaldi Effects of the antimicrobial peptide temporin L on cell morphology, membrane permeability and viability of Escherichia coli Biochem. J. 380 2004 859 865
15. S.C. Park, J.R. Lee, S.O. Shin, J.H. Jung, Y.M. Lee, H. Son, Y. Park, S.Y. Lee, and K.S. Hahm Purification and characterization of an antifungal protein, C-FKBP, from Chinese cabbage J. Agric. Food Chem. 55 2007 5277 5281
16. D.G. Lee, H.N. Kim, Y. Park, H.K. Kim, B.H. Choi, C.H. Choi, and K.S. Hahm Design of novel analogue peptides with potent antibiotic activity based on the antimicrobial peptide, HP (2 20), derived from N-terminus of Helicobacter pylori ribosomal protein L1 Biochim. Biophys. Acta 1598 2002 185 194
17. 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
18. J.C.M. Stewart Colorimetric determination of phospholipids with ammonium ferrothiocyanate Anal. Biochem. 104 1980 10 14
19. J.K. Ghosh, S.G. Peisajovich, M. Ovadia, and Y. Shai Serum-induced leakage of liposome contents J. Biol. Chem. 273 1998 27182 27190
20. C.H. Hsu, C. Chen, M.L. Jou, A.Y. Lee, Y.C. Lin, Y.P. Yu, W.T. Huang, and S.H. Wu 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 2005 4053 4064
21. J.R. Lee, S.S. Lee, H.H. Jang, Y.M. Lee, J.H. Park, S.C. Park, J.C. Moon, S.K. Park, S.Y. Kim, S.Y. Lee, H.B. Chae, Y.J. Jung, W.Y. Kim, M.R. Shin, G.W. Cheong, M.G. Kim, K.R. Kang, K.O. Lee, D.J. Yun, and S.Y. Lee Heat-shock dependent oligomeric status alters the function of a plant-specific thioredoxin-like protein, AtTDX Proc. Natl. Acad. Sci. U. S. A. 106 14 2009 5978 5983
22. V. Dartois, J. Sanchez-Quesada, E. Cabezas, E. Chi, C. Dubbelde, C. Dunn, J. Granja, C. Gritzen, D. Weinberger, M.R. Ghadiri, and T.R. Parr Jr. Systemic antibacterial activity of novel synthetic cyclic peptides Antimicrob. Agents Chemother. 49 2005 3302 3310
23. E.A. Burstein, N.S. Vedenkina, and M.N. Ivkova Fluorescence and the location of tryptophan residues in protein molecules Photochem. Photobiol. 18 4 1973 263 279
24. C. Subbalakshmi, and N. Sitaram Mechanism of antimicrobial action of indolicidin FEMS Microbiol. Lett. 160 1998 91 96
25. W. Zheng, Z. Li, K. Skarstad, and E. Crooke Mutations in DnaA protein suppress the growth arrest of acidic phospholipid-deficient Escherichia coli cells EMBO J. 20 5 2001 1164 1172
26. L. Yang, T.A. Harroun, T.M. Weiss, L. Ding, and H.W. Huang Barrel-stave model or toroidal model? A case study on melittin pores Biophys. J. 81 2001 1475 1485
27. R.S. Cantor Size distribution of barrel-stave aggregates of membrane peptides: influence of the bilayer lateral pressure profile Biophys. J. 82 2002 2520 2525
28. E. Gazit, W.J. Lee, P.T. Brey, and Y. Shai Mode of action of the antibacterial cecropin B2: a spectrofluorometric study Biochemistry 33 1994 10681 10692
29. A.S. Ladokhin, M.E. Selsted, and S.H. White Sizing membrane pores in lipid vesicles by leakage of co-encapsulated markers: pore formation by melittin Biophys. J. 72 1997 1762 1766
30. K. Takeshima, A. Chikushi, K.K. Lee, S. Yonehara, and K. Matsuzaki Translocation of analogues of the antimicrobial peptides magainin and buforin across human cell membranes J. Biol. Chem. 278 2 2003 1310 1315
31. J.A. Killian, and G. von Heijne How proteins adapt to a membrane-water interface Trends Biochem. Sci. 25 2000 429 434
32. E. Wallin, T. Tsukihara, S. Yoshikawa, G. von Heijne, and A. Elofsson Architecture of helix bundle membrane proteins: an analysis of cytochrome c oxidase from bovine mitochondria Protein Sci. 6 1997 808 815
33. J.P. Segrest, H. De Loof, J.G. Dohlman, C.G. Brouillette, and G.M. Anantharamaiah Amphipathic helix motif: classes and properties Proteins 8 1990 103 117
34. M.R. de Planque, J.A. Kruijtzer, R.M. Liskamp, D. Marsh, D.V. Greathouse, R.E. Koeppe II, B. de Kruijff, and J.A. Killian Different membrane anchoring positions of tryptophan and lysine in synthetic transmembrane alpha-helical peptides J. Biol. Chem. 274 1999 20839 20846
35. Ø. Rekdal, B.E. Haug, M. Kalaaji, H.N. Hunter, I. Lindin, I. Israelsson, T. Solstad, N. Yang, M. Brandl, D. Mantzilas, and H.J. Vogel Relative spatial positions of tryptophan and cationic residues in helical membrane-active peptides determine their cytotoxicity J. Biol. Chem. 287 2012 233 244
36. 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
37. A. Giangaspero, L. Sandri, and A. Tossi Amphipathic alpha helical antimicrobial peptides Eur. J. Biochem. 268 2001 5589 5600
38. D.J. Schibli, R.F. Epand, H.J. Vogel, and R.M. Epand Tryptophan-rich antimicrobial peptides: comparative properties and membrane interactions Biochem. Cell Biol. 80 2002 667 677
39. R. Gopal, Y.J. Kim, C.H. Seo, K.S. Hahm, and Y. Park Reversed sequence enhances antimicrobial activity of a synthetic peptide J. Pept. Sci. 17 5 2011 329 334
40. C.B. Park, H.S. Kim, and S.C. Kim Mechanism of action of the antimicrobial peptide buforin II: buforin II kills microorganisms by penetrating the cell membrane and inhibiting cellular functions Biochem. Biophys. Res. Commun. 244 1998 253 257
41. Y. Park, D.G. Lee, S.H. Jang, E.R. Woo, H.G. Jeong, C.H. Choi, and K.S. Hahm A Leu-Lys-rich antimicrobial peptide: activity and mechanism Biochim. Biophys. Acta 1645 2 2003 172 182
42. A. Yonezawa, J. Kuwahara, N. Fujii, and Y. Sugiura Binding of tachyplesin I to DNA revealed by footprinting analysis: significant contribution of secondary structure to DNA binding and implication for biological action Biochemistry 31 1992 2998 3004
43. H. Ulvatne, O. Samuelsen, H.H. Haukland, M. Kramer, and L.H. Vorland Lactoferricin B inhibits bacterial macromolecular synthesis in Escherichia coli and Bacillus subtilis FEMS Microbiol. Lett. 237 2004 377 384