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Solution NMR structures of the antimicrobial peptides phylloseptin-1, -2, and -3 and biological activity: the role of charges and hydrogen bonding interactions in stabilizing helix conformations.

Resende JM, Moraes CM, Prates MV, Cesar A, Almeida FC, Mundim NC, Valente AP, Bemquerer MP, Piló-Veloso D, Bechinger B
Peptides 29 1633-44 (2008)
Related entries: 2jq0, 2jq1

Cited: 32 times
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Abstract

Phylloseptins are antimicrobial peptides of 19-20 residues which are found in the skin secretions of the Phyllomedusa frogs that inhabit the tropical forests of South and Central Americas. The peptide sequences of PS-1, -2, and -3 carry an amidated C-terminus and they exhibit 74% sequence homology with major variations of only four residues close to the C-terminus. Here we investigated and compared the structures of the three phylloseptins in detail by CD- and two-dimensional NMR spectroscopies in the presence of phospholipid vesicles or in membrane-mimetic environments. Both CD and NMR spectroscopies reveal a high degree of helicity in the order PS-2> or =PS-1>PS-3, where the differences accumulate at the C-terminus. The conformational variations can be explained by taking into consideration electrostatic interactions of the negative ends of the helix dipoles with potentially cationic residues at positions 17 and 18. Whereas two are present in the sequence of PS-1 and -2 only one is present in PS-3. In conclusion, the antimicrobial phylloseptin peptides adopt alpha-helical conformations in membrane environments which are stabilized by electrostatic interactions of the helix dipole as well as other contributions such hydrophobic and capping interactions.

Articles - 2jpy mentioned but not cited (2)

  1. Membrane interactions of phylloseptin-1, -2, and -3 peptides by oriented solid-state NMR spectroscopy. Resende JM, Verly RM, Aisenbrey C, Cesar A, Bertani P, Piló-Veloso D, Bechinger B. Biophys J 107 901-911 (2014)
  2. An N-capping asparagine-lysine-proline (NKP) motif contributes to a hybrid flexible/stable multifunctional peptide scaffold. Cardoso MH, Chan LY, Cândido ES, Buccini DF, Rezende SB, Torres MDT, Oshiro KGN, Silva ÍC, Gonçalves S, Lu TK, Santos NC, de la Fuente-Nunez C, Craik DJ, Franco OL. Chem Sci 13 9410-9424 (2022)


Reviews citing this publication (4)

  1. Antimicrobial peptides from Phyllomedusa frogs: from biomolecular diversity to potential nanotechnologic medical applications. Azevedo Calderon Ld, Silva Ade A, Ciancaglini P, Stábeli RG. Amino Acids 40 29-49 (2011)
  2. ATP synthase: a molecular therapeutic drug target for antimicrobial and antitumor peptides. Ahmad Z, Okafor F, Azim S, Laughlin TF. Curr Med Chem 20 1956-1973 (2013)
  3. The Amazonian kambô frog Phyllomedusa bicolor (Amphibia: Phyllomedusidae): Current knowledge on biology, phylogeography, toxinology, ethnopharmacology and medical aspects. Nogueira TAC, Kaefer IL, Sartim MA, Pucca MB, Sachett J, Barros AL, Júnior MBA, Baía-da-Silva DC, Bernarde PS, Koolen HHF, Monteiro WM. Front Pharmacol 13 997318 (2022)
  4. Thinking on the Construction of Antimicrobial Peptide Databases: Powerful Tools for the Molecular Design and Screening. Zhang K, Teng D, Mao R, Yang N, Hao Y, Wang J. Int J Mol Sci 24 3134 (2023)

Articles citing this publication (26)

  1. DADP: the database of anuran defense peptides. Novković M, Simunić J, Bojović V, Tossi A, Juretić D. Bioinformatics 28 1406-1407 (2012)
  2. Structure and topology of the huntingtin 1-17 membrane anchor by a combined solution and solid-state NMR approach. Michalek M, Salnikov ES, Bechinger B. Biophys J 105 699-710 (2013)
  3. Antiplasmodial and antileishmanial activities of phylloseptin-1, an antimicrobial peptide from the skin secretion of Phyllomedusa azurea (Amphibia). Kückelhaus SA, Leite JR, Muniz-Junqueira MI, Sampaio RN, Bloch C, Tosta CE. Exp Parasitol 123 11-16 (2009)
  4. Identification and Characterisation of the Antimicrobial Peptide, Phylloseptin-PT, from the Skin Secretion of Phyllomedusa tarsius, and Comparison of Activity with Designed, Cationicity-Enhanced Analogues and Diastereomers. Gao Y, Wu D, Xi X, Wu Y, Ma C, Zhou M, Wang L, Yang M, Chen T, Shaw C. Molecules 21 E1667 (2016)
  5. NMR structures of the histidine-rich peptide LAH4 in micellar environments: membrane insertion, pH-dependent mode of antimicrobial action, and DNA transfection. Georgescu J, Munhoz VH, Bechinger B. Biophys J 99 2507-2515 (2010)
  6. Structure and membrane interactions of the antibiotic peptide dermadistinctin K by multidimensional solution and oriented 15N and 31P solid-state NMR spectroscopy. Verly RM, de Moraes CM, Resende JM, Aisenbrey C, Bemquerer MP, Piló-Veloso D, Valente AP, Almeida FC, Bechinger B. Biophys J 96 2194-2203 (2009)
  7. A peptide of the phylloseptin family from the skin of the frog Hylomantis lemur (Phyllomedusinae) with potent in vitro and in vivo insulin-releasing activity. Abdel-Wahab YH, Power GJ, Flatt PR, Woodhams DC, Rollins-Smith LA, Conlon JM. Peptides 29 2136-2143 (2008)
  8. LyeTxI-b, a Synthetic Peptide Derived From Lycosa erythrognatha Spider Venom, Shows Potent Antibiotic Activity in Vitro and in Vivo. Reis PVM, Boff D, Verly RM, Melo-Braga MN, Cortés ME, Santos DM, Pimenta AMC, Amaral FA, Resende JM, de Lima ME. Front Microbiol 9 667 (2018)
  9. Structure, antimicrobial activities and mode of interaction with membranes of novel [corrected] phylloseptins from the painted-belly leaf frog, Phyllomedusa sauvagii. Raja Z, André S, Piesse C, Sereno D, Nicolas P, Foulon T, Oury B, Ladram A. PLoS One 8 e70782 (2013)
  10. Antiplasmodial activity study of angiotensin II via Ala scan analogs. Silva AF, Bastos EL, Torres MD, Costa-da-Silva AL, Ioshino RS, Capurro ML, Alves FL, Miranda A, Vieira Rde F, Oliveira VX. J Pept Sci 20 640-648 (2014)
  11. Peptidomic dissection of the skin secretion of Phasmahyla jandaia (Bokermann and Sazima, 1978) (Anura, Hylidae, Phyllomedusinae). Rates B, Silva LP, Ireno IC, Leite FS, Borges MH, Bloch C, De Lima ME, Pimenta AM. Toxicon 57 35-52 (2011)
  12. Structure and membrane interactions of the homodimeric antibiotic peptide homotarsinin. Verly RM, Resende JM, Junior EF, de Magalhães MT, Guimarães CF, Munhoz VH, Bemquerer MP, Almeida FC, Santoro MM, Piló-Veloso D, Bechinger B. Sci Rep 7 40854 (2017)
  13. Structure-activity relationship of an antimicrobial peptide, Phylloseptin-PHa: balance of hydrophobicity and charge determines the selectivity of bioactivities. Liu Y, Du Q, Ma C, Xi X, Wang L, Zhou M, Burrows JF, Chen T, Wang H. Drug Des Devel Ther 13 447-458 (2019)
  14. A Novel Amphibian Antimicrobial Peptide, Phylloseptin-PV1, Exhibits Effective Anti-staphylococcal Activity Without Inducing Either Hepatic or Renal Toxicity in Mice. Liu Y, Shi D, Wang J, Chen X, Zhou M, Xi X, Cheng J, Ma C, Chen T, Shaw C, Wang L. Front Microbiol 11 565158 (2020)
  15. Ocellatin peptides from the skin secretion of the South American frog Leptodactylus labyrinthicus (Leptodactylidae): characterization, antimicrobial activities and membrane interactions. Gusmão KAG, Dos Santos DM, Santos VM, Cortés ME, Reis PVM, Santos VL, Piló-Veloso D, Verly RM, de Lima ME, Resende JM. J Venom Anim Toxins Incl Trop Dis 23 4 (2017)
  16. PEGylation of the antimicrobial peptide LyeTx I-b maintains structure-related biological properties and improves selectivity. Moreira Brito JC, Carvalho LR, Neves de Souza A, Carneiro G, Magalhães PP, Farias LM, Guimarães NR, Verly RM, Resende JM, Elena de Lima M. Front Mol Biosci 9 1001508 (2022)
  17. Evidences for the action mechanism of angiotensin II and its analogs on Plasmodium sporozoite membranes. Torres MD, Silva AF, Alves FL, Capurro ML, Miranda A, Cordeiro RM, Oliveira Junior VX. J Pept Sci 22 132-142 (2016)
  18. Highly potential antiplasmodial restricted peptides. Marcelo Der Torossian T, Silva AF, Alves FL, Capurro ML, Miranda A, Vani Xavier O. Chem Biol Drug Des 85 163-171 (2015)
  19. Phylloseptin-1 is Leishmanicidal for Amastigotes of Leishmaniaamazonensis Inside Infected Macrophages. Kückelhaus SAS, Aquino DS, Borges TK, Moreira DC, Leite LM, Muniz-Junqueira MI, Kückelhaus CS, Romero GAS, Prates MV, Bloch C, Leite JRSA. Int J Environ Res Public Health 17 E4856 (2020)
  20. In Silico Structural Evaluation of Short Cationic Antimicrobial Peptides. Passarini I, Rossiter S, Malkinson J, Zloh M. Pharmaceutics 10 E72 (2018)
  21. Discovery of Novel Bacterial Cell-Penetrating Phylloseptins in Defensive Skin Secretions of the South American Hylid Frogs, Phyllomedusa duellmani and Phyllomedusa coelestis. Yang N, Li L, Wu D, Gao Y, Xi X, Zhou M, Wang L, Chen T, Shaw C. Toxins (Basel) 8 E255 (2016)
  22. MD simulations and multivariate studies for modeling the antileishmanial activity of peptides. Guerra MER, Fadel V, Maltarollo VG, Baldissera G, Honorio KM, Ruggiero JR, Dos Santos Cabrera MP. Chem Biol Drug Des 90 501-510 (2017)
  23. Immunomodulatory, insulinotropic, and cytotoxic activities of phylloseptins and plasticin-TR from the Trinidanian leaf frog Phyllomedusa trinitatis. Pantic J, Guilhaudis L, Musale V, Attoub S, Lukic ML, Mechkarska M, Conlon JM. J Pept Sci 25 e3153 (2019)
  24. NMR structures and molecular dynamics simulation of hylin-a1 peptide analogs interacting with micelles. Crusca E, Câmara AS, Matos CO, Marchetto R, Cilli EM, Lião LM, Lima de Oliveira A. J Pept Sci 23 421-430 (2017)
  25. Design and modification of frog skin peptide brevinin-1GHa with enhanced antimicrobial activity on Gram-positive bacterial strains. Kara Ş, Kürekci C, Akcan M. Amino Acids 54 1327-1336 (2022)
  26. Optimizing the synthesis of dimeric peptides: influence of the reaction medium and effects that modulate kinetics and reaction yield. Guimarães CFRC, Félix AS, Brandão TAS, Bemquerer MP, Piló-Veloso D, Verly RM, Resende JM. Amino Acids 55 1201-1212 (2023)


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