Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora

Free-living amoebae of Acanthamoeba spp. are causative agents of human infections such as granulomatous amoebic encephalitis (GAE) and Acanthamoeba keratitis (AK). The exploration of innovative chemical entities from natural sources that induce intrinsic apoptotic pathway or a Programmed Cell Death...

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Authors: Rodríguez-Expósito, Rubén L., Sosa-Rueda, Javier, Reyes-Batlle, María, Sifaoui, Inés, Cen-Pacheco, Francisco, Hernández Daranas, Antonio, Díaz-Marrero, Ana Raquel, Piñero, José E., Fernández, José J., Lorenzo-Morales, Jacob
Format: article
Status:Published version
Publication Date:2021
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/255621
Online Access:http://hdl.handle.net/10261/255621
Access Level:Open access
Keyword:Squamin
Cyclopeptide
Acanthamoeba
Annona
Antiamoeboid
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spelling Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globiforaRodríguez-Expósito, Rubén L.Sosa-Rueda, JavierReyes-Batlle, MaríaSifaoui, InésCen-Pacheco, FranciscoHernández Daranas, AntonioDíaz-Marrero, Ana RaquelPiñero, José E.Fernández, José J.Lorenzo-Morales, JacobSquaminCyclopeptideAcanthamoebaAnnonaAntiamoeboidFree-living amoebae of Acanthamoeba spp. are causative agents of human infections such as granulomatous amoebic encephalitis (GAE) and Acanthamoeba keratitis (AK). The exploration of innovative chemical entities from natural sources that induce intrinsic apoptotic pathway or a Programmed Cell Death (PCD) in Acanthamoeba protozoa is essential to develop new therapeutic strategies. In this work, the antiamoeboid activity of squamins C–F (1–4), four cyclooctapeptides isolated from Annona globiflora was tested in vitro against Acanthamoeba castellanii Neff, A. polyphaga, A. quina, and A. griffini, and a structure–activity relationship was also established. The most sensitive strain against all tested cyclooctapeptides was A. castellanii Neff being the R conformers of the S-oxo-methionine residue, squamins D (2) and F (4), the most active against the trophozoite stage. It is remarkable that all four peptides showed no cytotoxic effects against murine macrophages cell line J774A.1. The analysis of the mode of action of squamins C–F against A. castellanii indicate that these cyclopeptides induced the mechanisms of programmed cell death (PCD). All peptides trigger mitochondrial damages, significant inhibition of ATP production compared to the negative control, chromatin condensation and slight damages in membrane that affects its permeability despite it conserves integrity at the IC90 for 24 h. An increase in reactive oxygen species (ROS) was observed in all cases.This study was supported by This study was supported by the Government of the State of Veracruz de Ignacio de la Llave, Veracruz Council for Scientific Research and Technological Development [COVEICyDET, grant number 14 1953/2021],.; PI18/01380 (Fondo Europeo de Desarrollo Regional, FEDER) and RICET (project no. RD16/0027/0001 of the programme of Redes Temáticas de Investigación Cooperativa, FIS), and Project PID2019-109476RB-C21 (BIOALGRI) (Spanish Ministry of Science, Madrid, Spain). ARDM was funded by Agustín de Betancourt Programme, Cabildo de Tenerife, Tenerife 2030, FDCAN, MEDI. RLRE was funded by a grant from Agencia Canaria de Investigación, Innovación y Sociedad de la Información (ACIISI) cofunded by Fondo Social Europeo (FSE) y FEDER, (TESIS2020010117).Peer reviewedElsevierAustralian Society for ParasitologyGobierno del Estado de Veracruz de Ignacio de la LlaveConsejo Veracruzano de Investigación Científica y Desarrollo TecnológicoRed de Investigación Cooperativa en Enfermedades Tropicales (España)Redes Temáticas de Investigación Cooperativa en Salud (España)Ministerio de Ciencia e Innovación (España)Cabildo de TenerifeAgencia Canaria de Investigación, Innovación y Sociedad de la InformaciónConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202120212021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/255621reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#MICINN/PID2019/109476RB-C21https://doi.org/10.1016/j.ijpddr.2021.08.003Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2556212026-05-22T06:33:51Z
dc.title.none.fl_str_mv Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
title Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
spellingShingle Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
Rodríguez-Expósito, Rubén L.
Squamin
Cyclopeptide
Acanthamoeba
Annona
Antiamoeboid
title_short Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
title_full Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
title_fullStr Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
title_full_unstemmed Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
title_sort Antiamoeboid activity of squamins C–F, cyclooctapeptides from Annona globifora
dc.creator.none.fl_str_mv Rodríguez-Expósito, Rubén L.
Sosa-Rueda, Javier
Reyes-Batlle, María
Sifaoui, Inés
Cen-Pacheco, Francisco
Hernández Daranas, Antonio
Díaz-Marrero, Ana Raquel
Piñero, José E.
Fernández, José J.
Lorenzo-Morales, Jacob
author Rodríguez-Expósito, Rubén L.
author_facet Rodríguez-Expósito, Rubén L.
Sosa-Rueda, Javier
Reyes-Batlle, María
Sifaoui, Inés
Cen-Pacheco, Francisco
Hernández Daranas, Antonio
Díaz-Marrero, Ana Raquel
Piñero, José E.
Fernández, José J.
Lorenzo-Morales, Jacob
author_role author
author2 Sosa-Rueda, Javier
Reyes-Batlle, María
Sifaoui, Inés
Cen-Pacheco, Francisco
Hernández Daranas, Antonio
Díaz-Marrero, Ana Raquel
Piñero, José E.
Fernández, José J.
Lorenzo-Morales, Jacob
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Gobierno del Estado de Veracruz de Ignacio de la Llave
Consejo Veracruzano de Investigación Científica y Desarrollo Tecnológico
Red de Investigación Cooperativa en Enfermedades Tropicales (España)
Redes Temáticas de Investigación Cooperativa en Salud (España)
Ministerio de Ciencia e Innovación (España)
Cabildo de Tenerife
Agencia Canaria de Investigación, Innovación y Sociedad de la Información
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Squamin
Cyclopeptide
Acanthamoeba
Annona
Antiamoeboid
topic Squamin
Cyclopeptide
Acanthamoeba
Annona
Antiamoeboid
description Free-living amoebae of Acanthamoeba spp. are causative agents of human infections such as granulomatous amoebic encephalitis (GAE) and Acanthamoeba keratitis (AK). The exploration of innovative chemical entities from natural sources that induce intrinsic apoptotic pathway or a Programmed Cell Death (PCD) in Acanthamoeba protozoa is essential to develop new therapeutic strategies. In this work, the antiamoeboid activity of squamins C–F (1–4), four cyclooctapeptides isolated from Annona globiflora was tested in vitro against Acanthamoeba castellanii Neff, A. polyphaga, A. quina, and A. griffini, and a structure–activity relationship was also established. The most sensitive strain against all tested cyclooctapeptides was A. castellanii Neff being the R conformers of the S-oxo-methionine residue, squamins D (2) and F (4), the most active against the trophozoite stage. It is remarkable that all four peptides showed no cytotoxic effects against murine macrophages cell line J774A.1. The analysis of the mode of action of squamins C–F against A. castellanii indicate that these cyclopeptides induced the mechanisms of programmed cell death (PCD). All peptides trigger mitochondrial damages, significant inhibition of ATP production compared to the negative control, chromatin condensation and slight damages in membrane that affects its permeability despite it conserves integrity at the IC90 for 24 h. An increase in reactive oxygen species (ROS) was observed in all cases.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/255621
url http://hdl.handle.net/10261/255621
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
MICINN/PID2019/109476RB-C21
https://doi.org/10.1016/j.ijpddr.2021.08.003
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
Australian Society for Parasitology
publisher.none.fl_str_mv Elsevier
Australian Society for Parasitology
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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