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Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine

Cyclolipopeptides derived from the antimicrobial peptide c(Lys-Lys-Leu-Lys-Lys-Phe-Lys-Lys-Leu-Gln) (BPC194) were prepared on solid-phase and screened against four plant pathogens. The incorporation at Lys5 of fatty acids of 4 to 9 carbon atoms led to active cyclolipopeptides. The influence on the antimicrobial activity of the Lys residue that is derivatized was also evaluated. In general, acylation of Lys1, Lys2 or Lys5 rendered the sequences with the highest activity. Incorporation of a D-amino acid maintained the antimicrobial activity while significantly reduced the hemolysis. Replacement of Phe with a His also yielded cyclolipopeptides with low hemolytic activity. Derivatives exhibiting low phytotoxicity in tobacco leaves were also found. Interestingly, sequences with or without significant activity against phytopathogenic bacteria and fungi, but with differential hemolysis and phytotoxicity were identified. Therefore, this study represents an approach to the development of bioactive peptides with selective activity against microbial, plant and animal cell targets. These selective cyclolipopeptides are candidates useful not only to combat plant pathogens but also to be applied in other fields

Funding provided by grant numbers: AGL2009-13255-C02-02/AGR (SV, MP, LF) and AGL2012-39880-C02-02 (SV, MP, LF). These grants were obtained from the Ministerio de Economía y Competitividad of Spain

PLoS One, 2016, vol. 11, núm. 3, p. e0151639

Public Library of Science (PLoS)

Author: Vilà Roura, Sílvia
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lídia
Date: 2016
Abstract: Cyclolipopeptides derived from the antimicrobial peptide c(Lys-Lys-Leu-Lys-Lys-Phe-Lys-Lys-Leu-Gln) (BPC194) were prepared on solid-phase and screened against four plant pathogens. The incorporation at Lys5 of fatty acids of 4 to 9 carbon atoms led to active cyclolipopeptides. The influence on the antimicrobial activity of the Lys residue that is derivatized was also evaluated. In general, acylation of Lys1, Lys2 or Lys5 rendered the sequences with the highest activity. Incorporation of a D-amino acid maintained the antimicrobial activity while significantly reduced the hemolysis. Replacement of Phe with a His also yielded cyclolipopeptides with low hemolytic activity. Derivatives exhibiting low phytotoxicity in tobacco leaves were also found. Interestingly, sequences with or without significant activity against phytopathogenic bacteria and fungi, but with differential hemolysis and phytotoxicity were identified. Therefore, this study represents an approach to the development of bioactive peptides with selective activity against microbial, plant and animal cell targets. These selective cyclolipopeptides are candidates useful not only to combat plant pathogens but also to be applied in other fields
Funding provided by grant numbers: AGL2009-13255-C02-02/AGR (SV, MP, LF) and AGL2012-39880-C02-02 (SV, MP, LF). These grants were obtained from the Ministerio de Economía y Competitividad of Spain
Format: application/pdf
ISSN: 1932-6203
Document access: http://hdl.handle.net/10256/12304
Language: eng
Publisher: Public Library of Science (PLoS)
Collection: MICINN/PN 2010-2012/ AGL2009-13255-C02-02
MICINN/PN 2013-2015/AGL2012-39880-C02-02
Reproducció digital del document publicat a: http://dx.doi.org/10.1371/journal.pone.0151639
Articles publicats (D-Q)
Is part of: PLoS One, 2016, vol. 11, núm. 3, p. e0151639
Rights: Attribution 3.0 Spain
Rights URI: http://creativecommons.org/licenses/by/3.0/es/
Subject: Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
Title: Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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