Antiparasitic hybrids of Cinchona alkaloids and bile acids
- Autores
- Leverrier, Aurélie; Bero, Joanne; Frédérich, Michel; Quetin Leclercq, Joelle; Palermo, Jorge Alejandro
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A series of 16 hybrids of Cinchona alkaloids and bile acids (4a–h, 5a–h) was prepared by means of a Barton–Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6–15.7.
Fil: Leverrier, Aurélie. 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; Argentina
Fil: Bero, Joanne. Universite Catholique de Louvain; Bélgica
Fil: Frédérich, Michel. Universite de Liege; Bélgica
Fil: Quetin Leclercq, Joelle. Universite Catholique de Louvain; Bélgica
Fil: Palermo, Jorge Alejandro. 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; Argentina - Materia
-
Cinchona Alkaloids
Bile Acids
Barton-Zard Reaction
Antiparasitic Activity - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/18703
Ver los metadatos del registro completo
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Antiparasitic hybrids of Cinchona alkaloids and bile acidsLeverrier, AurélieBero, JoanneFrédérich, MichelQuetin Leclercq, JoellePalermo, Jorge AlejandroCinchona AlkaloidsBile AcidsBarton-Zard ReactionAntiparasitic Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of 16 hybrids of Cinchona alkaloids and bile acids (4a–h, 5a–h) was prepared by means of a Barton–Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6–15.7.Fil: Leverrier, Aurélie. 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: Bero, Joanne. Universite Catholique de Louvain; BélgicaFil: Frédérich, Michel. Universite de Liege; BélgicaFil: Quetin Leclercq, Joelle. Universite Catholique de Louvain; BélgicaFil: Palermo, Jorge Alejandro. 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; ArgentinaElsevier Masson2013-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/18703Leverrier, Aurélie; Bero, Joanne; Frédérich, Michel; Quetin Leclercq, Joelle; Palermo, Jorge Alejandro; Antiparasitic hybrids of Cinchona alkaloids and bile acids; Elsevier Masson; European Journal of Medical Chemistry; 66; 8-2013; 355-3630223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2013.06.004info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523413003693info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:38:25Zoai:ri.conicet.gov.ar:11336/18703instacron: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:34982025-09-29 10:38:25.341CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
title |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
spellingShingle |
Antiparasitic hybrids of Cinchona alkaloids and bile acids Leverrier, Aurélie Cinchona Alkaloids Bile Acids Barton-Zard Reaction Antiparasitic Activity |
title_short |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
title_full |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
title_fullStr |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
title_full_unstemmed |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
title_sort |
Antiparasitic hybrids of Cinchona alkaloids and bile acids |
dc.creator.none.fl_str_mv |
Leverrier, Aurélie Bero, Joanne Frédérich, Michel Quetin Leclercq, Joelle Palermo, Jorge Alejandro |
author |
Leverrier, Aurélie |
author_facet |
Leverrier, Aurélie Bero, Joanne Frédérich, Michel Quetin Leclercq, Joelle Palermo, Jorge Alejandro |
author_role |
author |
author2 |
Bero, Joanne Frédérich, Michel Quetin Leclercq, Joelle Palermo, Jorge Alejandro |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
Cinchona Alkaloids Bile Acids Barton-Zard Reaction Antiparasitic Activity |
topic |
Cinchona Alkaloids Bile Acids Barton-Zard Reaction Antiparasitic Activity |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
A series of 16 hybrids of Cinchona alkaloids and bile acids (4a–h, 5a–h) was prepared by means of a Barton–Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6–15.7. Fil: Leverrier, Aurélie. 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; Argentina Fil: Bero, Joanne. Universite Catholique de Louvain; Bélgica Fil: Frédérich, Michel. Universite de Liege; Bélgica Fil: Quetin Leclercq, Joelle. Universite Catholique de Louvain; Bélgica Fil: Palermo, Jorge Alejandro. 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; Argentina |
description |
A series of 16 hybrids of Cinchona alkaloids and bile acids (4a–h, 5a–h) was prepared by means of a Barton–Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6–15.7. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-08 |
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/11336/18703 Leverrier, Aurélie; Bero, Joanne; Frédérich, Michel; Quetin Leclercq, Joelle; Palermo, Jorge Alejandro; Antiparasitic hybrids of Cinchona alkaloids and bile acids; Elsevier Masson; European Journal of Medical Chemistry; 66; 8-2013; 355-363 0223-5234 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/18703 |
identifier_str_mv |
Leverrier, Aurélie; Bero, Joanne; Frédérich, Michel; Quetin Leclercq, Joelle; Palermo, Jorge Alejandro; Antiparasitic hybrids of Cinchona alkaloids and bile acids; Elsevier Masson; European Journal of Medical Chemistry; 66; 8-2013; 355-363 0223-5234 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2013.06.004 info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523413003693 |
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/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier Masson |
publisher.none.fl_str_mv |
Elsevier Masson |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
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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1844614406963462144 |
score |
13.070432 |