Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents

Autores
Taborga, Lautaro; Sortino, Maximiliano Andrés; Carrasco, Héctor; Butassi, Estefanía; Zacchino, Susana Alicia Stella; Espinoza, Luis
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Twenty four linear geranylphenols were evaluated for their antifungal properties against ATCC and clinical isolates of Candida albicans and Cryptococcus neoformans. For the analysis of their antifungal behavior the compounds were grouped into two series: (i) compounds with only one geranyl substituent on the benzene ring and (ii) compounds with two geranyl moieties on the benzene ring. Results showed that compounds of series (i) present better antifungal activities than those of series (ii). In addition, within group (i) all compounds showed better activities against C. neoformans than against C. albicans which can be easily verified by comparing MIC100 or MIC50 of each compound against both fungi. Di- (10 and 11) and tri-hydroxy (3 and 4) compounds showed significant anti-cryptoccocal activity, being 3, 10 and 11 highly active with MIC100 or MIC50 = 3.9 μg/mL similar to the standard drug amphotericin B. Moreover, when evaluating the toxicity of compounds 6, 10 and 11 on the HDF cell line (human dermal fibroblasts), results were obtained with IC50 values > 100 μM, considered as non-toxic for the cell. This indicates that the toxicity of the analyzed compounds is selective towards fungi, which makes them a very attractive family for the development of future drugs.
Fil: Taborga, Lautaro. Universidad Técnica Federico Santa María; Chile
Fil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Carrasco, Héctor. Universidad Autónoma de Chile; Chile
Fil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Espinoza, Luis. Universidad Técnica Federico Santa María; Chile
Materia
Antifungal Activity
Candida Albicans
Cryptococcus Neoformans.
Linear Geranylphenols
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:11336/50214
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50214
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituentsTaborga, LautaroSortino, Maximiliano AndrésCarrasco, HéctorButassi, EstefaníaZacchino, Susana Alicia StellaEspinoza, LuisAntifungal ActivityCandida AlbicansCryptococcus Neoformans.Linear Geranylphenolshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Twenty four linear geranylphenols were evaluated for their antifungal properties against ATCC and clinical isolates of Candida albicans and Cryptococcus neoformans. For the analysis of their antifungal behavior the compounds were grouped into two series: (i) compounds with only one geranyl substituent on the benzene ring and (ii) compounds with two geranyl moieties on the benzene ring. Results showed that compounds of series (i) present better antifungal activities than those of series (ii). In addition, within group (i) all compounds showed better activities against C. neoformans than against C. albicans which can be easily verified by comparing MIC100 or MIC50 of each compound against both fungi. Di- (10 and 11) and tri-hydroxy (3 and 4) compounds showed significant anti-cryptoccocal activity, being 3, 10 and 11 highly active with MIC100 or MIC50 = 3.9 μg/mL similar to the standard drug amphotericin B. Moreover, when evaluating the toxicity of compounds 6, 10 and 11 on the HDF cell line (human dermal fibroblasts), results were obtained with IC50 values > 100 μM, considered as non-toxic for the cell. This indicates that the toxicity of the analyzed compounds is selective towards fungi, which makes them a very attractive family for the development of future drugs.Fil: Taborga, Lautaro. Universidad Técnica Federico Santa María; ChileFil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Carrasco, Héctor. Universidad Autónoma de Chile; ChileFil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Espinoza, Luis. Universidad Técnica Federico Santa María; ChilePergamon-Elsevier Science Ltd2017-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/50214Taborga, Lautaro; Sortino, Maximiliano Andrés; Carrasco, Héctor; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents; Pergamon-Elsevier Science Ltd; Food And Chemical Toxicology; 109; Parte 2; 11-2017; 827-8350278-6915CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.fct.2017.05.027info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0278691517302557info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:20:52Zoai:ri.conicet.gov.ar:11336/50214instacron: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:34982025-10-22 11:20:52.597CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
title Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
spellingShingle Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
Taborga, Lautaro
Antifungal Activity
Candida Albicans
Cryptococcus Neoformans.
Linear Geranylphenols
title_short Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
title_full Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
title_fullStr Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
title_full_unstemmed Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
title_sort Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
dc.creator.none.fl_str_mv Taborga, Lautaro
Sortino, Maximiliano Andrés
Carrasco, Héctor
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Espinoza, Luis
author Taborga, Lautaro
author_facet Taborga, Lautaro
Sortino, Maximiliano Andrés
Carrasco, Héctor
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Espinoza, Luis
author_role author
author2 Sortino, Maximiliano Andrés
Carrasco, Héctor
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Espinoza, Luis
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Antifungal Activity
Candida Albicans
Cryptococcus Neoformans.
Linear Geranylphenols
topic Antifungal Activity
Candida Albicans
Cryptococcus Neoformans.
Linear Geranylphenols
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Twenty four linear geranylphenols were evaluated for their antifungal properties against ATCC and clinical isolates of Candida albicans and Cryptococcus neoformans. For the analysis of their antifungal behavior the compounds were grouped into two series: (i) compounds with only one geranyl substituent on the benzene ring and (ii) compounds with two geranyl moieties on the benzene ring. Results showed that compounds of series (i) present better antifungal activities than those of series (ii). In addition, within group (i) all compounds showed better activities against C. neoformans than against C. albicans which can be easily verified by comparing MIC100 or MIC50 of each compound against both fungi. Di- (10 and 11) and tri-hydroxy (3 and 4) compounds showed significant anti-cryptoccocal activity, being 3, 10 and 11 highly active with MIC100 or MIC50 = 3.9 μg/mL similar to the standard drug amphotericin B. Moreover, when evaluating the toxicity of compounds 6, 10 and 11 on the HDF cell line (human dermal fibroblasts), results were obtained with IC50 values > 100 μM, considered as non-toxic for the cell. This indicates that the toxicity of the analyzed compounds is selective towards fungi, which makes them a very attractive family for the development of future drugs.
Fil: Taborga, Lautaro. Universidad Técnica Federico Santa María; Chile
Fil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Carrasco, Héctor. Universidad Autónoma de Chile; Chile
Fil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Espinoza, Luis. Universidad Técnica Federico Santa María; Chile
description Twenty four linear geranylphenols were evaluated for their antifungal properties against ATCC and clinical isolates of Candida albicans and Cryptococcus neoformans. For the analysis of their antifungal behavior the compounds were grouped into two series: (i) compounds with only one geranyl substituent on the benzene ring and (ii) compounds with two geranyl moieties on the benzene ring. Results showed that compounds of series (i) present better antifungal activities than those of series (ii). In addition, within group (i) all compounds showed better activities against C. neoformans than against C. albicans which can be easily verified by comparing MIC100 or MIC50 of each compound against both fungi. Di- (10 and 11) and tri-hydroxy (3 and 4) compounds showed significant anti-cryptoccocal activity, being 3, 10 and 11 highly active with MIC100 or MIC50 = 3.9 μg/mL similar to the standard drug amphotericin B. Moreover, when evaluating the toxicity of compounds 6, 10 and 11 on the HDF cell line (human dermal fibroblasts), results were obtained with IC50 values > 100 μM, considered as non-toxic for the cell. This indicates that the toxicity of the analyzed compounds is selective towards fungi, which makes them a very attractive family for the development of future drugs.
publishDate 2017
dc.date.none.fl_str_mv 2017-11
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/11336/50214
Taborga, Lautaro; Sortino, Maximiliano Andrés; Carrasco, Héctor; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents; Pergamon-Elsevier Science Ltd; Food And Chemical Toxicology; 109; Parte 2; 11-2017; 827-835
0278-6915
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50214
identifier_str_mv Taborga, Lautaro; Sortino, Maximiliano Andrés; Carrasco, Héctor; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents; Pergamon-Elsevier Science Ltd; Food And Chemical Toxicology; 109; Parte 2; 11-2017; 827-835
0278-6915
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.fct.2017.05.027
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0278691517302557
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 12.982451

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