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 a...

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Autores: Vilà Roura, Sílvia, Badosa Romañó, Esther, Montesinos Seguí, Emilio, Planas i Grabuleda, Marta, Feliu Soley, Lidia
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2016
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/12304
Acesso em linha:http://hdl.handle.net/10256/12304
Access Level:Acceso aberto
Palavra-chave:Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
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spelling Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or HistidineVilà Roura, SílviaBadosa Romañó, EstherMontesinos Seguí, EmilioPlanas i Grabuleda, MartaFeliu Soley, LidiaPèptids -- SíntesiPeptides -- SynthesisCompostos orgànics -- SíntesiOrganic compounds -- SynthesisCyclolipopeptides 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 fieldsFunding 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 SpainPublic Library of Science (PLoS)Ministerio de Ciencia e Innovación (Espanya)2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/12304PLoS One, 2016, vol. 11, núm. 3, p. e0151639Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1371/journal.pone.0151639info:eu-repo/semantics/altIdentifier/eissn/1932-6203info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02Attribution 3.0 Spainhttp://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/123042026-05-29T05:05:01Z
dc.title.none.fl_str_mv Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
title Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
spellingShingle Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
Vilà Roura, Sílvia
Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
title_short Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
title_full Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
title_fullStr Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
title_full_unstemmed Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
title_sort Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine
dc.creator.none.fl_str_mv Vilà Roura, Sílvia
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author Vilà Roura, Sílvia
author_facet Vilà Roura, Sílvia
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author_role author
author2 Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
dc.subject.none.fl_str_mv Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
topic Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
description 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
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/12304
url http://hdl.handle.net/10256/12304
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1371/journal.pone.0151639
info:eu-repo/semantics/altIdentifier/eissn/1932-6203
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02
info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02
dc.rights.none.fl_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Public Library of Science (PLoS)
publisher.none.fl_str_mv Public Library of Science (PLoS)
dc.source.none.fl_str_mv PLoS One, 2016, vol. 11, núm. 3, p. e0151639
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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