Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry

Autores
Pertino, Mariano Walter; Petrera, Erina; Alche, Laura Edith; Schmeda Hirschmann, Guillermo
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.
Fil: Pertino, Mariano Walter. Universidad de Talca; Chile
Fil: Petrera, Erina. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Alche, Laura Edith. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile
Materia
ANTIVIRAL
CLICK CHEMISTRY
CYTOTOXICITY
HYBRID MOLECULES
TERPENES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/93999
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/93999
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistryPertino, Mariano WalterPetrera, ErinaAlche, Laura EdithSchmeda Hirschmann, GuillermoANTIVIRALCLICK CHEMISTRYCYTOTOXICITYHYBRID MOLECULESTERPENEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.Fil: Pertino, Mariano Walter. Universidad de Talca; ChileFil: Petrera, Erina. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Alche, Laura Edith. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Schmeda Hirschmann, Guillermo. Universidad de Talca; ChileMolecular Diversity Preservation International2018-06info: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/11336/93999Pertino, Mariano Walter; Petrera, Erina; Alche, Laura Edith; Schmeda Hirschmann, Guillermo; Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry; Molecular Diversity Preservation International; Molecules; 23; 6; 6-2018; 1-121420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/molecules23061343info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/23/6/1343info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:53:54Zoai:ri.conicet.gov.ar:11336/93999instacron: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:34982025-09-03 09:53:54.696CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
title Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
spellingShingle Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
Pertino, Mariano Walter
ANTIVIRAL
CLICK CHEMISTRY
CYTOTOXICITY
HYBRID MOLECULES
TERPENES
title_short Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
title_full Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
title_fullStr Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
title_full_unstemmed Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
title_sort Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
dc.creator.none.fl_str_mv Pertino, Mariano Walter
Petrera, Erina
Alche, Laura Edith
Schmeda Hirschmann, Guillermo
author Pertino, Mariano Walter
author_facet Pertino, Mariano Walter
Petrera, Erina
Alche, Laura Edith
Schmeda Hirschmann, Guillermo
author_role author
author2 Petrera, Erina
Alche, Laura Edith
Schmeda Hirschmann, Guillermo
author2_role author
author
author
dc.subject.none.fl_str_mv ANTIVIRAL
CLICK CHEMISTRY
CYTOTOXICITY
HYBRID MOLECULES
TERPENES
topic ANTIVIRAL
CLICK CHEMISTRY
CYTOTOXICITY
HYBRID MOLECULES
TERPENES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.
Fil: Pertino, Mariano Walter. Universidad de Talca; Chile
Fil: Petrera, Erina. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Alche, Laura Edith. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile
description Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.
publishDate 2018
dc.date.none.fl_str_mv 2018-06
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/11336/93999
Pertino, Mariano Walter; Petrera, Erina; Alche, Laura Edith; Schmeda Hirschmann, Guillermo; Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry; Molecular Diversity Preservation International; Molecules; 23; 6; 6-2018; 1-12
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/93999
identifier_str_mv Pertino, Mariano Walter; Petrera, Erina; Alche, Laura Edith; Schmeda Hirschmann, Guillermo; Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry; Molecular Diversity Preservation International; Molecules; 23; 6; 6-2018; 1-12
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules23061343
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/23/6/1343
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 Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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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score 13.13397

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