Investigating the effect of different positioning of lysine residues along the peptide chain of mastoparans for their secondary structures and biological activities

Amino Acids

Volumn 40, Issue 1, 2011, Pages 77-90

  De Souza, Bibiana Monson ^a   Dos Santos Cabrera, Marcia Perez ^a   Neto, João Ruggiero ^a   Palma, Mario Sergio ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Antibiotic peptides; Circular dichroism; Hemolysis; Lysine rich peptides; Mastoparans

Indexed keywords

ASPARAGINE 2 POLYBIA MASTOPARAN 1; ISOLEUCYLASPARAGINYLTRYPTOPHYLLEUCYLLYSYLALANYLLYSYLLYSYLVALYLALANYLGLYCYLMETHIONYLISOLEUCYLLEUCINE AMIDE; LYSINE; MASTOPARAN; MK 578; PARAPOLYBIA MASTOPARAN; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLGLYCEROL; PROTONECTARINA MASTOPARAN; UNCLASSIFIED DRUG;

ALPHA HELIX; ANIMAL CELL; ANTIBIOSIS; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BIOASSAY; BIOLOGICAL ACTIVITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG STRUCTURE; ESCHERICHIA COLI; FEMALE; HEMOLYSIS; HYDROPHOBICITY; MAST CELL DEGRANULATION; MOLECULAR DYNAMICS; MOLECULAR MODEL; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN CONTENT; PROTEIN LOCALIZATION; PROTEIN PURIFICATION; PROTEIN SECONDARY STRUCTURE; PSEUDOMONAS AERUGINOSA; RAT; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; WASP;

AMINO ACID SEQUENCE; ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; CELL LINE; CELLS, CULTURED; FEMALE; HEMOLYSIN PROTEINS; HEMOLYSIS; LYSINE; MAST CELLS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; WASP VENOMS;

PARAPOLYBIA; POLYBIA; PROTONECTARINA;

EID: 78751577565     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0481-y     Document Type: Article

References (51)

1. SF Altschul TL Madden AA Schaffer J Zhang Z Zhang W Miller DJ Lipman 1997 Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res 25 3389 3402 1:CAS:528:DyaK2sXlvFyhu7w%3D 10.1093/nar/25.17.3389 9254694
2. SE Blondelle B Forood RA Houghten E Perez-Paya 1997 Secondary structure induction in aqueous vs membrane-like environments Biopolymers 42 489 498 1:CAS:528:DyaK2sXlvFSitbo%3D 10.1002/(SICI)1097-0282(19971005)42:4<489::AID- BIP11>3.0.CO;2-B 9283295
3. TE Cheatham JL Miller T Fox TA Darden PA Kollman 1995 Molecular dynamics simulations on solvated biomolecular systems: the Particle Mesh Ewald method leads to stable trajectories of DNA, RNA and proteins J Am Chem Soc 117 4193 4194 1:CAS:528:DyaK2MXkvVaisrc%3D 10.1021/ja00119a045
4. T Darden D York L Pedersen 1993 Particle Mesh Ewald: an N-log(N) method for Ewald sums in large systems J Chem Phys 98 10089 10092 1:CAS:528: DyaK3sXks1Ohsr0%3D 10.1063/1.464397
5. M Dathe T Wiprecht 1999 Structural features of helical antimicrobial peptides: their potential to modulate activity on model membranes and biological cells Biochim Biophys Acta 1462 71 78 1:CAS:528:DyaK1MXnslymu70%3D 10.1016/S0005-2736(99)00201-1 10590303
6. M Dathe M Schumann T Wieprecht A Winkler M Beyermann E Krause K Matsuzaki O Murase M Bienert 1996 Peptide helicity and membrane surface charge modulate the balance of electrostatic and hydrophobic interactions with lipid bilayers and biological membranes Biochemistry 35 12612 12622 1:CAS:528: DyaK28XltlCqsrk%3D 10.1021/bi960835f 8823199
7. M Dathe T Wieprecht H Nikolenko L Handel WL Maloy DL MacDonald M Beyermann M Bienert 1997 Hydrophobicity, hydrophobic moment and angle subtended by charged residues modulate antibacterial and haemolytic activity of amphipathic helical peptides FEBS Lett 403 208 212 1:CAS:528:DyaK2sXht1Kgtrc%3D 10.1016/S0014-5793(97)00055-0 9042968
8. M Dathe J Meyer M Beyermann B Maul C Hoischen M Biernet 2002 General aspects of peptide selectivity towards lipid bilayers and cell membranes studied by variation of the structural parameters of amphipathic helical model peptides Biochim Byophys Acta 1558 171 186 1:CAS:528:DC%2BD38XkvFyg 10.1016/S0005- 2736(01)00429-1
9. BM De Souza MS Palma 2008 Monitoring the positioning of short polycationic peptides in model lipid bilayers by combining hydrogen/deuterium exchange and electrospray ionization mass spectrometry Biochim Biophys Acta 1778 2797 2805 10.1016/j.bbamem.2008.09.005
10. BM De Souza MR Marques DM Tomazela MN Eberlin MA Mendes MS Palma 2004 Mass spectrometric characterization of two novel inflammatory peptides from the venom of the social wasp Polybia paulista Rap Commun Mass Spectrom 18 1095 1102 10.1002/rcm.1452
11. BM De Souza MA Mendes LD Santos MR Marques LMM César RNA Almeida FC Pagnocca K Konno MS Palma 2005 Structural and functional characterization of two novel peptide toxins isolated from the venom of the social wasp Polybia paulista Peptides 26 2157 2164 1:CAS:528:DC%2BD2MXhtFylur3N 10.1016/j.peptides. 2005.04.026 16129513
12. BM De Souza AVR Silva VMF Resende HA Arcuri MP Dos Santos Cabrera J Ruggiero Neto MS Palma 2009 Characterization of two novel polyfunctional mastoparan peptides from the venom of the social wasp Polybia paulista Peptides 30 1387 1395 10.1016/j.peptides.2009.05.008 19463874
13. K Dohtsu K Hagiwara MS Palma T Nakajima 1993 Isolation and sequence analysis of peptides from the venom of Protonectarina sylveirae (Hymenoptera, Vespidae) (I) Nat Toxins 1 271 276 1:CAS:528:DyaK2cXhsFKhu70%3D 10.1002/nt.2620010503 7513243
14. MP Dos Santos Cabrera BM De Souza R Fontana K Konno MS Palma WF de Azevedo Jr J Ruggiero-Neto 2004 Conformation and lytic activity of Eumenine Mastoparan: a new antimicrobial peptide from wasp venom J Peptide Res 64 95 103 1:STN:280:DC%2BD2cvhtlCitg%3D%3D 10.1111/j.1399-3011.2004.00173.x
15. M Dos Santos Cabrera STB Costa BM de Souza MS Palma JR Ruggiero J Ruggiero Neto 2008 Selectivity in the mechanism of action of antimicrobial mastoparan peptide Polybia-MP1 Eur Biophys J 37 879 891 1:CAS:528: DC%2BD1cXnt1ars7w%3D 10.1007/s00249-008-0299-7 18414845
16. MP Dos Santos Cabrera BM De Souza J Ruggiero Neto MS Palma 2009 Interactions of mast cell degranulating peptides with model membranes: a comparative biophysical study Arch Biochem Biophys 486 1 11 10.1016/j.abb.2009. 03.009 19328184
17. D Eisenberg E Schwarz M Komaromy R Wall 1984 Analysis of membrane and surface protein sequences with the hydrophobic moment plot J Mol Biol 179 125 142 1:CAS:528:DyaL2MXnsFajuw%3D%3D 10.1016/0022-2836(84)90309-7 6502707
18. RL Gallo KM Huttner 1998 Antimicrobial peptides: an emerging concept in cutaneous biology J Investig Dermatol 111 739 743 1:CAS:528:DyaK1cXnt1Ohsrc%3D 10.1046/j.1523-1747.1998.00361.x 9804331
19. B Hess H Bekker HJC Berendsen JGEM Fraaije 1997 LINCS: a linear constraint solver for molecularsimulations J Comput Chem 18 1463 1472 1:CAS:528:DyaK2sXlvV2nu7g%3D 10.1002/(SICI)1096-987X(199709)18:12<1463::AID- JCC4>3.0.CO;2-H
20. WF Humphrey A Dalke K Schulten 1996 VMD, visual molecular dynamics J Mol Graphics 14 33 38 1:CAS:528:DyaK28Xis12nsrg%3D 10.1016/0263-7855(96)00018-5
21. MM Javadpour MM Juban WC Lo SM Bishop JB Alberty SM Cowell CL Becker ML McLaughlin 1996 De novo antimicrobial peptides with low mammalian cell toxicity J Med Chem 39 3107 3113 1:CAS:528:DyaK28Xkt1ams74%3D 10.1021/jm9509410 8759631
22. S Jones J Howl 2006 Biological applications of the receptor mimetic peptide mastoparan Curr Protein Pept Sci 7 501 508 1:CAS:528:DC%2BD28XhtFGhtbnO 10.2174/138920306779025585 17168783
23. K Konno M Hisada H Naoki Y Itagaki N Kawai A Miwa T Yasuhara Y Morimoto Y Nakata 2000 Structure and biological activities of Eumenine Mastoparan-AF (EMPAF), a new mast cell degranulating peptide in the venom of the solitary wasp (Anterhynchium flavomarginatum micado) Toxicon 38 1505 1515 1:CAS:528:DC%2BD3cXktF2rtrY%3D 10.1016/S0041-0101(00)00083-0 10775751
24. K Konno M Hisada R Fontana CCB Lorenzi H Naoki Y Itagaki A Miwa N Kawai 2001 Anoplin, a novel antimicrobial peptide from the venom of the solitary wasp Anoplius samariensis Biochim Biophys Acta 1550 70 80 1:CAS:528: DC%2BD3MXovVCis7s%3D 11738089
25. K Konno M Hisada H Naoki Y Itagaki R Fontana M Rangel JS Oliveira MP Cabrera JR Neto I Hide Y Nakata T Yasuhara T Nakajima 2006 Eumenitin, a novel antimicrobial peptide from the venom of the solitary eumenine wasp Eumenes rubronotatus Peptides 27 2624 2631 1:CAS:528:DC%2BD28XhtFSrtrjJ 10.1016/j.peptides.2006.04.013 16762455
26. R Koradi M Billeter K Wüthrich 1996 MOLMOL: a program for display and analysis of macromolecular structures J Mol Graphics 14 51 65 1:CAS:528:DyaK28Xis12nsrc%3D 10.1016/0263-7855(96)00009-4
27. V Krishnakumari P Nagaraj 1997 Antimicrobial and hemolytic activities of Crabolin, a 13-residues peptide from the venom of the European hornet, Vespa crabro, and its analogs J Peptide Res 50 88 93 1:CAS:528:DyaK2sXltlGrsLo%3D 10.1111/j.1399-3011.1997.tb01173.x
28. RA Laskowsky MW MacArthur D Moss JM Thornton 1993 PROCHECK: a program to check the stereochemical quality of protein structures J Appl Crystallogr 26 283 291 10.1107/S0021889892009944
29. SJ Ludtke K He WT Heller TA Harroun L Yang HW Huang 1996 Membrane pores induced by magainin Biochemistry 35 13723 13728 1:CAS:528:DyaK28XmtVOls7k%3D 10.1021/bi9620621 8901513
30. J Meletiadis JGM Meis JW Mouton VPE Donnelly 2000 Comparison of NCCLS and 3-(4, 5-dimethyl-2-thiazyl)-2, 5-diphenyl-2Htetrazolium bromide (MTT) methods of in vitro susceptibility testing of filamentous fungi and development of a new simplified method J Clin Microbiol 38 2949 2954 1:CAS:528:DC%2BD3cXlvFKgs70%3D 10921957
31. MA Mendes BM De Souza MR Marques MS Palma 2004 Structural and Biological characterization of two novel peptides from the venom of the neotropical social wasp Agelaia pallipes pallipes Toxicon 44 67 74 1:CAS:528:DC%2BD2cXltFOnsb0%3D 10.1016/j.toxicon.2004.04.009 15225564
32. MA Mendes BM Souza LD Santos MS Palma 2004 Structural characterization of novel chemotactic and mastoparan peptides from the venom of the social wasp Agelaia pallipes pallipes by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry Rapid Commun Mass Spectrom 18 636 642 1:CAS:528:DC%2BD2cXivVCgsLY%3D 10.1002/rcm.1382 15052574
33. MA Mendes BM Souza MS Palma 2005 Structural and biological characterization of three novel mastoparan peptides from the venom of the neotropical social wasp Protopolybia exigua (Saussure) Toxicon 45 101 106 1:CAS:528:DC%2BD2MXisFWjsA%3D%3D 10.1016/j.toxicon.2004.09.015 15581688
34. I Mitsuhara 2001 In vitro growth inhibition of human intestinal bacteria by sarcotoxin IA, an insect bactericidal peptide Biotechnol Lett 23 569 573 1:CAS:528:DC%2BD3MXjtVejt74%3D 10.1023/A:1010360828591
35. S Miyamoto PA Kollman 1992 SETTLE: an analytical version of the SHAKE and RATTLE algorithm for rigid water models J Comput Chem 13 952 962 1:CAS:528:DyaK38Xlslykt7o%3D 10.1002/jcc.540130805
36. K Murata T Shinada Y Ohfune M Hisada A Yasuda H Naoki T Nakajima 2009 Novel mastoparan and protonectin analogs isolated from a solitary wasp, Orancistrocerus drewseni drewseni Amino Acids 37 389 394 1:CAS:528: DC%2BD1MXotVKju7Y%3D 10.1007/s00726-008-0166-y 18695936
37. Nakajima T (1986) Pharmacological biochemistry of vespid venoms. In: Piek T (ed) Venom of hymenoptera, 1st edn. Academic Press, London, pp 309-327
38. T Nakajima S Uzu K Wakamatsu K Saito T Miyazawa T Yasuhara Y Tsukamoto M Fujino 1986 Amphiphilic peptides in wasp venom Biopolymers 25 115 121
39. L Oliveira AOS Cunha MR Mortari NC Coimbra WF dos Santos 2005 Cataleptic activity of the denaturad venom of the social wasp Agelaia vicina (Hymenoptera, Vespidae) in Rattus norvegicus (Rodentia, Muridae) Prog Neuro Psychopharmacol Biol Psych 30 198 203 10.1016/j.pnpbp.2005.10.016
40. T Rocha MB Leonardo BM De Souza MS Palma MA Da Cruz-Höfling 2008 Mastoparan effects in skeletal muscle damage: an ultrastructural view until now concealed Microsc Res Tech 71 220 229 10.1002/jemt.20542 18072285
41. CA Rohl RL Baldwin 1998 Deciphering rules of helix stability in peptides Methods Enzymol 295 1 26 1:CAS:528:DyaK1MXltlyg 10.1016/S0076-6879(98)95032-7 9750211
42. G Rouser S Fleischer A Yamamoto 1970 Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots Lipids 5 494 496 1:CAS:528:DyaE3cXksFarurY%3D 10.1007/BF02531316 5483450
43. A Sali TL Blundell 1993 Comparative protein modeling by satisfaction of spatial restraints J Mol Biol 234 779 815 1:CAS:528:DyaK2cXnt1ylug%3D%3D 10.1006/jmbi.1993.1626 8254673
44. MP Sansom 1991 The biophysics of peptide models of ion channels Prog Biophys Mol Biol 55 139 215 1:CAS:528:DyaK3MXlsFeiur8%3D 10.1016/0079-6107(91) 90004-C 1715999
45. AA Schäffer L Aravind TL Madden S Shavirin JL Spouge YI Wolf EV Koonin SF Altschul 2001 Improving the accuracy of PSI-BLAST protein database searches with composition-based statistics and other refinements Nucl Acids Res 29 2994 3005 10.1093/nar/29.14.2994 11452024
46. Y Shai 1999 Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by alpha-helical antimicrobial and cell non-selective membrane-lytic peptides Biochim Biophys Acta 1462 55 70 1:CAS:528:DyaK1MXnslymu78%3D 10.1016/S0005-2736(99)00200-X 10590302
47. S Taheri-Araghi BY Ha 2007 Physical basis for membrane-charge selectivity of cationic antimicrobial peptides Phys Rev Lett 98 168101-1 168101-4 10.1103/PhysRevLett.98.168101
48. Y Todokoro I Yumen K Fukushima SW Kang JS Park T Kohno K Wakamatsu H Akutsu T Fujiwara 2006 Structure of tightly membrane-bound Mastoparan-X, a G-protein-activating peptide determined by solid-state NMR Biophys J 91 1368 1379 1:CAS:528:DC%2BD28XnvF2rt78%3D 10.1529/biophysj.106.082735 16714348
49. S Turilazzi G Mastrobuoni FG Dani G Moneti G Pieraccini G La Marca G Bartolucci B Perito B Perito D Lambardi VC Cavallini L Dapporto 2006 Dominulin A and B: Two new antibacterial peptides identified on the cuticle and in the venom of the social paper wasp Polistes dominulus using MALDI-TOF, MALDI-TOF/TOF and ESI-ion trap J Am Mass Spectrom 17 376 383 10.1016/j.jasms.2005.11.017
50. AP Watt 2002 Mast cells and peptide induced histamine release Inflammopharmacol 9 421 434 1:CAS:528:DC%2BD38XlvFGrsLs%3D 10.1163/ 156856001320290679
51. X Xu J Li Q Lu H Yang Y Zhang R Lai 2006 Two families of antimicrobial peptides from wasp (Vespa magnifica) venom Toxicon 47 249 253 1:CAS:528:DC%2BD28Xnsl2itQ%3D%3D 10.1016/j.toxicon.2005.10.015 16330062