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dc.contributor.author
Pertino, Mariano Walter
dc.contributor.author
Theoduloz, Cristina
dc.contributor.author
Butassi, Estefanía
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Zacchino, Susana Alicia Stella
dc.contributor.author
Schmeda Hirschmann, Guillermo
dc.date.available
2022-12-06T13:14:52Z
dc.date.issued
2015-05
dc.identifier.citation
Pertino, Mariano Walter; Theoduloz, Cristina; Butassi, Estefanía; Zacchino, Susana Alicia Stella; Schmeda Hirschmann, Guillermo; Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives; Molecular Diversity Preservation International; Molecules; 20; 5; 5-2015; 8666-8686
dc.identifier.issn
1420-3049
dc.identifier.uri
http://hdl.handle.net/11336/180362
dc.description.abstract
Abietane diterpenes exhibit an array of interesting biological activities, which have generated significant interest among the pharmacological community. Starting from the abietane diterpenes carnosic acid and carnosol, twenty four new triazole derivatives were synthesized using click chemistry. The compounds differ in the length of the linker and the substituent on the triazole moiety. The compounds were assessed as antiproliferative and antifungal agents. The antiproliferative activity was determined on normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells while the antifungal activity was assessed against Candida albicans ATCC 10231 and Cryptococcus neoformans ATCC 32264. The carnosic acid γ-lactone derivatives 1-3 were the most active antiproliferative compounds of the series, with IC50 values in the range of 43.4-46.9 μM and 39.2-48.9 μM for MRC-5 and AGS cells, respectively. Regarding antifungal activity, C. neoformans was the most sensitive fungus, with nine compounds inhibiting more than 50% of its fungal growth at concentrations ≤250 μgmL-1. Compound 22, possessing a p-Br-benzyl substituent on the triazole ring, showed the best activity (91% growth inhibition) at 250 μgmL-1 In turn, six compounds inhibited 50% C. albicans growth at concentrations lower than 250 μgmL-1.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Molecular Diversity Preservation International
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by/2.5/ar/
dc.subject
ANTIFUNGAL
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ANTIPROLIFERATIVE
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CARNOSIC ACID
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CARNOSOL
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CLICK CHEMISTRY
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-12-05T15:05:30Z
dc.journal.volume
20
dc.journal.number
5
dc.journal.pagination
8666-8686
dc.journal.pais
Suiza
dc.journal.ciudad
Basilea
dc.description.fil
Fil: Pertino, Mariano Walter. Universidad de Talca; Chile
dc.description.fil
Fil: Theoduloz, Cristina. Universidad de Talca; Chile
dc.description.fil
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; Argentina
dc.description.fil
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
dc.description.fil
Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile
dc.journal.title
Molecules
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/20/5/8666
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.3390/molecules20058666
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