Preparation and antitrypanosomal activity of secochiliolide acid derivatives

Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochili...

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Autores: Siless, Gastón Ezequiel, Lozano, Esteban Sebastián, Sánchez, Marianela, Mazzuca, Marcia, Sosa, Miguel A., Palermo, Jorge Alejandro
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/14954
Acceso en línea:http://hdl.handle.net/11336/14954
Access Level:acceso abierto
Palabra clave:Trypanosoma Cruzi
In Vitro
Secochiliolide Acid
Antitrypanosomal Activity
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
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network_name_str Argentina
repository_id_str
dc.title.none.fl_str_mv Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title Preparation and antitrypanosomal activity of secochiliolide acid derivatives
spellingShingle Preparation and antitrypanosomal activity of secochiliolide acid derivatives
Siless, Gastón Ezequiel
Trypanosoma Cruzi
In Vitro
Secochiliolide Acid
Antitrypanosomal Activity
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
title_short Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_full Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_fullStr Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_full_unstemmed Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_sort Preparation and antitrypanosomal activity of secochiliolide acid derivatives
dc.creator.none.fl_str_mv Siless, Gastón Ezequiel
Lozano, Esteban Sebastián
Sánchez, Marianela
Mazzuca, Marcia
Sosa, Miguel A.
Palermo, Jorge Alejandro
author Siless, Gastón Ezequiel
author_facet Siless, Gastón Ezequiel
Lozano, Esteban Sebastián
Sánchez, Marianela
Mazzuca, Marcia
Sosa, Miguel A.
Palermo, Jorge Alejandro
author_role author
author2 Lozano, Esteban Sebastián
Sánchez, Marianela
Mazzuca, Marcia
Sosa, Miguel A.
Palermo, Jorge Alejandro
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Trypanosoma Cruzi
In Vitro
Secochiliolide Acid
Antitrypanosomal Activity
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
topic Trypanosoma Cruzi
In Vitro
Secochiliolide Acid
Antitrypanosomal Activity
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
description Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 lg/mL. Six of the synthesized derivatives were also active with IC50?s between 2 and 7 lg/mL which are comparable to that of the commercial drug benznidazole (2.5 lg/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule.
publishDate 2013
dc.date.none.fl_str_mv 2013-07-03
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/11336/14954
Siless, Gastón Ezequiel; Lozano, Esteban Sebastián; Sánchez, Marianela; Mazzuca, Marcia; Sosa, Miguel A.; et al.; Preparation and antitrypanosomal activity of secochiliolide acid derivatives; Elsevier; Bioorganic & Medicinal Chemistry Letters; 23; 17; 3-7-2013; 4964–4967
0960-894X
url http://hdl.handle.net/11336/14954
identifier_str_mv Siless, Gastón Ezequiel; Lozano, Esteban Sebastián; Sánchez, Marianela; Mazzuca, Marcia; Sosa, Miguel A.; et al.; Preparation and antitrypanosomal activity of secochiliolide acid derivatives; Elsevier; Bioorganic & Medicinal Chemistry Letters; 23; 17; 3-7-2013; 4964–4967
0960-894X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1016/j.bmcl.2013.06.064
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X1300797X
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
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spelling Preparation and antitrypanosomal activity of secochiliolide acid derivativesSiless, Gastón EzequielLozano, Esteban SebastiánSánchez, MarianelaMazzuca, MarciaSosa, Miguel A.Palermo, Jorge AlejandroTrypanosoma CruziIn VitroSecochiliolide AcidAntitrypanosomal Activityhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 lg/mL. Six of the synthesized derivatives were also active with IC50?s between 2 and 7 lg/mL which are comparable to that of the commercial drug benznidazole (2.5 lg/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule.Fil: Siless, Gastón Ezequiel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina; ArgentinaFil: Lozano, Esteban Sebastián. Consejo Nacional de Investigaciones Científicas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; ArgentinaFil: Sánchez, Marianela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Mazzuca, Marcia. Universidad Nacional de la Patagonia San Juan Bosco. Facultad de Ciencias Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Sosa, Miguel A.. Consejo Nacional de Investigaciones Científicas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas; Argentina. Universidad Nacional de la Patagonia San Juan Bosco. Facultad de Ciencias Naturales. Departamento de Química; ArgentinaFil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina; ArgentinaElsevier2013-07-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/14954Siless, Gastón Ezequiel; Lozano, Esteban Sebastián; Sánchez, Marianela; Mazzuca, Marcia; Sosa, Miguel A.; et al.; Preparation and antitrypanosomal activity of secochiliolide acid derivatives; Elsevier; Bioorganic & Medicinal Chemistry Letters; 23; 17; 3-7-2013; 4964–49670960-894Xenginfo:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1016/j.bmcl.2013.06.064info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X1300797Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:05:30Zoai:ri.conicet.gov.ar:11336/14954instacron: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 14:05:30.39CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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