Synthesis, antiproliferative and antifungal activities of 1,2,3-triazole-substituted carnosic acid and carnosol derivatives

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dc.citation.titleMoleculeses
dc.citation.volume20(5)es
dc.creatorPertino, Mariano Walter
dc.creatorTheoduloz, Cristina
dc.creatorButassi, Estefanía
dc.creatorZacchino, Susana
dc.creatorSchmeda-Hirschmann, Guillermo
dc.date.accessioned2020-12-19T01:26:37Z
dc.date.available2020-12-19T01:26:37Z
dc.date.issued2015-05-14
dc.descriptionAbietane 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 µg·mL−1 . Compound 22, possessing a p-Br-benzyl substituent on the triazole ring,showed the best activity (91% growth inhibition) at 250 µg·mL−1 In turn, six compounds inhibited 50% C. albicans growth at concentrations lower than 250 µg·mL−1.es
dc.descriptionPara citar este articulo: Pertino, M.W.; Theoduloz, C.; Butassi, E.; Zacchino, S.; Schmeda-Hirschmann, G. Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives. Molecules 2015, 20, 8666-8686.
dc.description.filFil: Pertino, Mariano Walter. Universidad de Talca. Instituto de Química de Recursos Naturales; Chile.es
dc.description.filFil: Theoduloz, Cristina. Universidad de Talca. Facultad de Ciencias de la Salud; Chile.es
dc.description.filFil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.es
dc.description.filFil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.es
dc.description.filFil: Schmeda-Hirschmann, Guillermo. Universidad de Talca. Instituto de Química de Recursos Naturales; Chile.es
dc.description.sponsorshipPrograma de Investigación de Excelencia Interdisciplinaria (PIEI-QUIM-BIO)es
dc.description.sponsorshipUniversidad de Talcaes
dc.description.sponsorshipFondo Nacional de Desarrollo Científico y Tecnológico ( FONDECYT): Project 11100046es
dc.formatapplication/pdf
dc.format.extent8666-8686es
dc.identifier.issn1420-3049es
dc.identifier.urihttp://hdl.handle.net/2133/19515
dc.language.isoenges
dc.publisherMDPIes
dc.relation.publisherversionhttps://doi.org/10.3390/molecules20058666es
dc.relation.publisherversionhttps://www.mdpi.com/1420-3049/20/5/8666es
dc.rightsopenAccesses
dc.rights.holderUniversidad Nacional de Rosarioes
dc.rights.holderPertino, Mariano Walteres
dc.rights.holderTheoduloz, Cristinaes
dc.rights.holderButassi, Estefaníaes
dc.rights.holderZacchino, Susanaes
dc.rights.holderSchmeda-Hirschmann, Guillermoes
dc.rights.textAttribution 4.0 International (CC BY 4.0)es
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subjectCarnosic Acides
dc.subjectCarnosoles
dc.subjectClick Chemistryes
dc.subjectAntifungal Activityes
dc.subjectAntiproliferative Activityes
dc.titleSynthesis, antiproliferative and antifungal activities of 1,2,3-triazole-substituted carnosic acid and carnosol derivativeses
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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