Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii

As a part of our project aimed at searching new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesized and evaluat...

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Detalhes bibliográficos
Autores: Chao, Maria Noelia, Exeni Matiuzzi, Carolina, Storey, Melissa, Li, Catherine, Szajnman, Sergio Hernan, Docampo, Roberto, Moreno, Silvia N. J., Rodriguez, Juan Bautista
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/31544
Acesso em linha:http://hdl.handle.net/11336/31544
Access Level:acceso abierto
Palavra-chave:Trypanosoma cruzi
Toxoplasma gondii
Chagas disease
Squalene synthase
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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oai_identifier_str oai:ri.conicet.gov.ar:11336/31544
network_acronym_str AR
network_name_str Argentina
repository_id_str
dc.title.none.fl_str_mv Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
title Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
spellingShingle Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
Chao, Maria Noelia
Trypanosoma cruzi
Toxoplasma gondii
Chagas disease
Squalene synthase
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
title_full Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
title_fullStr Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
title_full_unstemmed Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
title_sort Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
dc.creator.none.fl_str_mv Chao, Maria Noelia
Exeni Matiuzzi, Carolina
Storey, Melissa
Li, Catherine
Szajnman, Sergio Hernan
Docampo, Roberto
Moreno, Silvia N. J.
Rodriguez, Juan Bautista
author Chao, Maria Noelia
author_facet Chao, Maria Noelia
Exeni Matiuzzi, Carolina
Storey, Melissa
Li, Catherine
Szajnman, Sergio Hernan
Docampo, Roberto
Moreno, Silvia N. J.
Rodriguez, Juan Bautista
author_role author
author2 Exeni Matiuzzi, Carolina
Storey, Melissa
Li, Catherine
Szajnman, Sergio Hernan
Docampo, Roberto
Moreno, Silvia N. J.
Rodriguez, Juan Bautista
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Trypanosoma cruzi
Toxoplasma gondii
Chagas disease
Squalene synthase
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Trypanosoma cruzi
Toxoplasma gondii
Chagas disease
Squalene synthase
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description As a part of our project aimed at searching new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesized and evaluated as growth inhibitors against Trypanosoma cruzi, the etiological agent of Chagas disease and Toxoplasma gondii, the parasite responsible of toxoplasmosis. Most of the synthetic analogues exhibited similar antiparasitic activity being slightly more potent than our lead WC-9. For example, the trifluoromethyl derivatives 15 and 16 exhibited ED50 values of 10.0 uM and 9.2 uM, respectively, against intracellular T. cruzi, whereas they showed potent action against tachyzoites of T. gondii (ED50 values 1.6 uM and 1.9 uM against T. gondii, respectively). In addition, the WC-9 analogues 48 and 61, in which the terminal aryl group was meta with respect to the alkyl chain bearing the thiocyanate group, showed potent inhibitory action against both T. cruzi and T. gondii at the very low micromolar range suggesting that para-phenyl substitution pattern is not necessarily required for biological activity.
publishDate 2015
dc.date.none.fl_str_mv 2015-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/31544
Rodriguez, Juan Bautista; Moreno, Silvia N. J.; Docampo, Roberto; Szajnman, Sergio Hernan; Li, Catherine; Storey, Melissa; et al.; Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii; Wiley VCH Verlag; Chemmedchem; 10; 6; 3-2015; 1094-1108
1860-7179
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31544
identifier_str_mv Rodriguez, Juan Bautista; Moreno, Silvia N. J.; Docampo, Roberto; Szajnman, Sergio Hernan; Li, Catherine; Storey, Melissa; et al.; Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii; Wiley VCH Verlag; Chemmedchem; 10; 6; 3-2015; 1094-1108
1860-7179
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/cmdc.201500100
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201500100/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1799195763710885888
spelling Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondiiChao, Maria NoeliaExeni Matiuzzi, CarolinaStorey, MelissaLi, CatherineSzajnman, Sergio HernanDocampo, RobertoMoreno, Silvia N. J.Rodriguez, Juan BautistaTrypanosoma cruziToxoplasma gondiiChagas diseaseSqualene synthasehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1As a part of our project aimed at searching new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesized and evaluated as growth inhibitors against Trypanosoma cruzi, the etiological agent of Chagas disease and Toxoplasma gondii, the parasite responsible of toxoplasmosis. Most of the synthetic analogues exhibited similar antiparasitic activity being slightly more potent than our lead WC-9. For example, the trifluoromethyl derivatives 15 and 16 exhibited ED50 values of 10.0 uM and 9.2 uM, respectively, against intracellular T. cruzi, whereas they showed potent action against tachyzoites of T. gondii (ED50 values 1.6 uM and 1.9 uM against T. gondii, respectively). In addition, the WC-9 analogues 48 and 61, in which the terminal aryl group was meta with respect to the alkyl chain bearing the thiocyanate group, showed potent inhibitory action against both T. cruzi and T. gondii at the very low micromolar range suggesting that para-phenyl substitution pattern is not necessarily required for biological activity.Fil: Chao, Maria Noelia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Exeni Matiuzzi, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Storey, Melissa. University of Georgia; Estados UnidosFil: Li, Catherine. University of Georgia; Estados UnidosFil: Szajnman, Sergio Hernan. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Docampo, Roberto. University of Georgia; Estados UnidosFil: Moreno, Silvia N. J.. University of Georgia; Estados UnidosFil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaWiley VCH Verlag2015-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfhttp://hdl.handle.net/11336/31544Rodriguez, Juan Bautista; Moreno, Silvia N. J.; Docampo, Roberto; Szajnman, Sergio Hernan; Li, Catherine; Storey, Melissa; et al.; Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii; Wiley VCH Verlag; Chemmedchem; 10; 6; 3-2015; 1094-11081860-7179CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/cmdc.201500100info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201500100/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:02:44Zoai:ri.conicet.gov.ar:11336/31544instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 14:02:44.802CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
score 15,228081

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