Effect of hydrophobic modifications in antimicrobial peptides

Advances in Colloid and Interface Science

Volumn 205, Issue , 2014, Pages 265-274

  Schmidtchen, Artur ^a   Pasupuleti, Mukesh ^a   Malmsten, Martin ^b  

^a LUND UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

AMP; Antimicrobial peptide; Bacteria; Liposome; Membrane

Indexed keywords

AMP; ANTIMICROBIAL PEPTIDE; EUKARYOTIC CELLS; HYDROPHOBIC MODIFICATION; LIPID MEMBRANES; PHYSICO-CHEMICAL FACTORS; PHYSICOCHEMICAL STUDIES; TOXIC RESPONSE;

BACTERIA; CELL MEMBRANES; CYTOLOGY; HYDROPHOBICITY; LIPOSOMES; MEMBRANES;

POLYPEPTIDES;

ADENOSINE PHOSPHATE; ANTIMICROBIAL CATIONIC PEPTIDE; LIPOSOME; POLYPEPTIDE ANTIBIOTIC AGENT;

BACTERIUM; CELL MEMBRANE; CHEMICAL PHENOMENA; CHEMISTRY; CYTOLOGY; EUKARYOTIC CELL; HUMAN; MEMBRANE; REVIEW;

AMP; ANTIMICROBIAL PEPTIDE; BACTERIA; LIPOSOME; MEMBRANE;

ANTIMICROBIAL CATIONIC PEPTIDES; BACTERIA; CELL MEMBRANE; EUKARYOTIC CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS;

EID: 84903362494     PISSN: 00018686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cis.2013.06.009     Document Type: Review

References (57)

1. G.L. French Clinical impact and relevance of antibiotic resistance Adv Drug Deliv Rev 75 2005 1514 1527 (Pubitemid 40984604)
2. K.A. Brogden Antimicrobial peptides: pore formers or metabolic inhibitors in bacteria? Nat Rev Microbiol 3 2005 238 250 (Pubitemid 40298223)
3. M. Pasupuleti, A. Schmidtchen, and M. Malmsten Antimicrobial peptides: key components of the innate immune system Crit Rev Biotechnol 32 2012 143 171
4. R.E. Hancock, and H.G. Sahl Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies Nat Biotechnol 24 2006 1551 1557 (Pubitemid 44967479)
5. The antimicrobial peptide database http://aps.unmc.edu/AP/
6. M.N. Melo, R. Ferre, and M.A. Castanho Antimicrobial peptides: linking partition, activity and high membrane-bound concentrations Nat Rev Microbiol 7 2009 245 250
7. Y. Shai Mode of action of membrane active antimicrobial peptides Biopolymers 66 2002 236 248 (Pubitemid 36098316)
8. A. Pokorny, and P.F.F. Almeida Kinetics of dye efflux and lipid flip-flop induced by δ-lysin in phospholipid vesicles and the mechanism of graded release by amphipathic, α-helical peptides Biochemistry 43 2004 8846 8857 (Pubitemid 38880055)
9. A. Mecke, D.-K. Lee, A. Ramamoorthy, B.G. Orr, and M.M. Banaszak Holl Membrane thinning due to antimicrobial peptide binding: an atomic force microscopy study of MSI-78 in lipid bilayers Biophys J 89 2005 4043 4050 (Pubitemid 41725624)
10. K. Boesze-Battaglia, and R.J. Schimmel Cell membrane lipid composition and distribution: implications for cell function and lessons learned from photoreceptors and platelets J Exp Biol 200 1997 2927 2936 (Pubitemid 28029161)
11. R. El Jastimi, and M. Lafleur Nisin promotes the formation of non-lamellar inverted phases in unsaturated phosphatidylethanolamines Biochim Biophys Acta 1418 1999 97 105 (Pubitemid 29182749)
12. E.J.J. Lugtenberg, and R. Peters Distribution of lipids in cytoplasmic and outer membranes of Escherichia coli K12 Biochim Biophys Acta 441 1976 38 47
13. C.W. Haest, J. de Gier, J.A. den Kamp, P. Bartels, and L.L. van Deenen Changes in permeability of Staphylococcus aureus and derived liposomes with varying lipid composition Biochim Biophys Acta 255 1972 720 733
14. J. Seelig Thermodynamics of lipid-peptide interactions Biochim Biophys Acta 1666 2004 40 50 (Pubitemid 39425197)
15. G.J. Fleer, M.A. Cohen Stuart, J.M.H.M. Scheutjens, T. Cosgrove, and B. Vincent Polymers at interfaces 1993 Chapman & Hall London
16. L. Ringstad, A. Schmidtchen, and M. Malmsten Effect of peptide length on the interaction between consensus peptides and DOPC/DOPA bilayers Langmuir 22 2006 5042 5050 (Pubitemid 44012069)
17. L. Ringstad, L. Kacprzyk, A. Schmidtchen, and M. Malmsten Effects of topology, length, and charge on the activity of a kininogen-derived peptide on lipid membranes and bacteria Biochim Biophys Acta 1768 2007 715 727 (Pubitemid 46275597)
18. B. Deslouches, S.M. Phadke, V. Lazarevic, M. Cascio, K. Islam, and R.C. Montelaro et al. De novo generation of cationic antimicrobial peptides: influence of length and tryptophan substitution on antimicrobial activity Antimicrob Agents Chemother 49 2005 316 322 (Pubitemid 40065808)
19. U.H. Durr, U.S. Sudheendra, and A. Ramamoorthy LL-37, the only human member of the cathelicidin family of antimicrobial peptides Biochim Biophys Acta 1758 2006 1408 1425 (Pubitemid 44436081)
20. T. Sigurdadottir, P. Andersson, M. Davoudi, M. Malmsten, A. Schmidtchen, and M. Bodelsson In silico identification and biological evaluation of antimicrobial peptides based on human cathelicidin LL-37 Antimicrob Agents Chemother 50 2006 2983 2989 (Pubitemid 44396402)
21. A.A. Strömstedt, M. Pasupuleti, A. Schmidtchen, and M. Malmsten Evaluation of strategies for improving proteolytic resistance of antimicrobial peptides by using variants of EFK17, an internal segment of LL-37 Antimicrob Agents Chemother 53 2009 593 602
22. L. Ringstad, E. Andersson Nordahl, A. Schmidtchen, and M. Malmsten Composition effect on peptide interaction with lipids and bacteria: variants of C3a peptide CNY21 Biophys J 92 2007 87 98 (Pubitemid 46048419)
23. A. Marquett, A.J. Mason, and B. Bechinger Aggregation and membrane permeabilizing properties of designed histidine-containing cationic linear peptide antibiotics J Pept Sci 14 2008 488 495 (Pubitemid 351540911)
24. M.L. Sforça, A. Machado, R.C.R. Figueredo, S. Oyama, F.D. Silva, and A. Miranda et al. The micelle-bound structure of an antimicrobial peptide derived from the α-chain of bovine hemoglobin isolated from the tick Boophilus microplus Biochemistry 44 2005 6440 6451 (Pubitemid 40593795)
25. L. Kacprzyk, V. Rydengård, M. Mörgelin, M. Davoudi, M. Pasupuleti, and M. Malmsten et al. Antimicrobial activity of histidine-rich peptides is dependent on acidic conditions Biophys Biochim Acta 1768 2007 2667 2680 (Pubitemid 350060862)
26. A. Makovitzki, and Y. Shai pH-Dependent antifungal lipopeptides and their plausible mode of action Biochemistry 44 2005 9775 9784 (Pubitemid 40994371)
27. A. Giangaspero, L. Sandri, and A. Tossi Amphipatic α helical antimicrobial peptides: a systematic study of the effects of structural and physical properties on biological activity Eur J Biochem 268 2001 5589 5600 (Pubitemid 34183324)
28. L. Ringstad, E. Protopapa, B. Lindholm-Sethson, A. Schmidtchen, A. Nelson, and M. Malmsten An electrochemical study into the interaction between complement-derived peptides and DOPC mono- and bilayers Langmuir 24 2008 208 216
29. A.A. Strömstedt, P. Wessman, L. Ringstad, K. Edwards, and M. Malmsten Effect of lipid headgroup composition on the interaction between melittin and lipid bilayers J Colloid Interface Sci 311 2007 56 69
30. L. Ringstad, A. Schmidtchen, and M. Malmsten Effects of single amino acid substitutions on peptide interaction with lipid membranes and bacteria - variants of GKE21, an internal sequence from human LL-37 Colloids Surf A 354 2010 65 71
31. V.V. Andrushchenko, H.J. Vogel, and E.J. Prenner Interactions of tryptophan-rich cathelicidin antimicrobial peptides with model membranes studied by differential scanning calorimetry Biochim Biophys Acta 1768 2007 2447 2458 (Pubitemid 47532026)
32. I. Zelezetsky, S. Pacor, U. Pag, N. Papo, Y. Shai, and H.G. Sahl et al. Controlled alteration of the shape and conformational stability of α-helical cell-lytic peptides: effect on mode of action and cell specificity Biochem J 390 2005 177 188 (Pubitemid 41192243)
33. M. Pasupuleti, B. Walse, B. Svensson, M. Malmsten, and A. Schmidtchen Rational design of antimicrobial C3a analogues with enhanced effects against Staphylococci using an integrated structure and function-based approach Biochemistry 47 2008 9057 9070
34. V. Nizet Antimicrobial peptide resistance mechanisms of human bacterial pathogens Curr Issues Mol Biol 8 2006 11 26 (Pubitemid 43141388)
35. I. Cornut, K. Büttner, J.-L. Dasseaux, and J. Dufourcq The amphipathic α-helix concept: application to the de novo design of ideally amphipathic Leu, Lys peptides with hemolytic activity higher than melittin FEBS Lett 349 1994 29 33
36. M. Dathe, T. Wieprecht, H. Nikolenko, L. Handel, W.L. Maloy, and D.L. MacDonald et al. Hydrophobicity, hydrophobic moment and angle subtended by charged residues modulate antibacterial and haemolytic activity of amphipathic helical peptides FEBS Lett 403 1997 208 212 (Pubitemid 27081496)
37. R. Jerala Synthetic lipopeptides: a novel class of anti-infectives Expert Opin Investig Drugs 16 2007 1159 1169 (Pubitemid 47317009)
38. D. Avrahami, and Y. Shai Conjugation of a magainin analogue with lipophilic acids controls hydrophobicity, solution assembly, and cell selectivity Biochemistry 41 2002 2254 2263 (Pubitemid 34160886)
39. D. Avrahami, and Y. Shai A new group of antifungal and antibacterial lipopeptides derived from non-membrane peptides conjugated to palmitic acid J Biol Chem 279 2004 12277 12285 (Pubitemid 38445793)
40. D. Jia, K. Tao, J. Wang, C. Wang, W. Zhao, and M. Yaseen et al. Dynamic adsorption and structure of interfacial bilayers adsorbed from lipopeptide surfactants at the hydrophilic silicon/water interface: effects of the headgroup length Langmuir 2011 8798 8809
41. A. Makovitzki, D. Avrahami, and Y. Shai Ultrashort antibacterial and antifungal lipopeptides Proc Natl Acad Sci 103 2006 15997 16002 (Pubitemid 44657581)
42. A.F. Chu-Kung, R. Nguyen, K.N. Bozelli, and M. Tirrell Chain length dependence of antimicrobial peptide-fatty acid conjugate activity J Colloid Interface Sci 345 2010 160 167
43. M. Eeman, G. Francius, Y.F. Dufrene, K. Nott, M. Paquot, and M. Deleu Effect of cholesterol and fatty acids on the molecular interactions of fengycin with stratum corneum mimicking lipid monolayers Langmuir 25 2009 3029 3039
44. A. Malina, and Y. Shai Conjugation of fatty acids with different lengths modulates the antibacterial and antifungal activity of a cationic biologically inactive peptide Biochem J 390 2005 695 702 (Pubitemid 41395352)
45. A. Schmidtchen, M. Pasupuleti, M. Mörgelin, M. Davoudi, J. Alenfall, and A. Chalupka et al. Boosting antimicrobial peptides by hydrophobic oligopeptide end-tags J Biol Chem 284 2009 17584 17594
46. E. Glukhov, M. Stark, L.L. Burrow, and C.M. Deber Basis for selectivity of cationic antimicrobial peptides for bacterial versus mammalian membranes J Biol Chem 280 2005 33960 33967 (Pubitemid 41443116)
47. X. Li, Y. Li, A. Peterkofsky, and G. Wang NMR studies of aurein 1.2 analogs Biochim Biophys Acta 1758 2006 1203 1214 (Pubitemid 44436082)
48. A. Schmidtchen, L. Ringstad, G. Kasetty, H. Mizuno, M.W. Rutland, and M. Malmsten Membrane selectivity by W-tagging of antimicrobial peptides Biochim Biophys Acta 1808 2011 1081 1091
49. O.G. Mouritsen, and M.J. Zuckermann What's so special about cholesterol? Lipids 39 2004 1101 1113 (Pubitemid 40136615)
50. M. Pasupuleti, A. Schmidtchen, A. Chalupka, L. Ringstad, and M. Malmsten End-tagging of ultra-short antimicrobial peptides by W/F stretches to facilitate bacterial killing PLoS One 4 e5285 2009 1 9
51. M. Pasupuleti, A. Chalupka, M. Mörgelin, A. Schmidtchen, and M. Malmsten Tryptophan end-tagging of antimicrobial peptides for increased potency against Pseudomonas aeruginosa Biochim Biophys Acta 1790 2009 800 808
52. M. Malmsten, G. Kasetty, M. Pasupuleti, J. Alenfall, and A. Schmidtchen Highly selective end-tagged antimicrobial peptides derived from PRELP PLoS One 6 e16400 2011 1 13
53. A.J. Mason, A. Marquette, and B. Bechinger Zwitterionic phospholipids and sterols modulate antimicrobial peptide-induced membrane destabilization Biophys J 93 2007 4289 4299 (Pubitemid 350294476)
54. 2H solid-state NMR spectroscopy Biochimie 91 2009 734 743
55. J. Henriksen, A.C. Rowat, E. Brief, Y.W. Hsueh, J.L. Thewalt, and M.J. Zuckermann et al. Universal behavior of membranes with sterols Biophys J 90 2006 1639 1649
56. J.A. Ember, N.L. Johansen, and T.E. Hugli Designing synthetic superagonists of C3a anaphylatoxin Biochemistry 30 1991 3103 3612
57. A.A. Strömstedt, M. Pasupuleti, A. Schmidtchen, and M. Malmsten Oligotryptophan-tagged antimicrobial peptides and the role of the cationic sequence Biophys Biochim Acta 1788 2009 1916 1923