Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives
- Autores
- Pertino, Mariano Walter; Theoduloz, Cristina; Butassi, Estefanía; Zacchino, Susana Alicia Stella; Schmeda Hirschmann, Guillermo
- Año de publicación
- 2015
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- 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.
Fil: Pertino, Mariano Walter. Universidad de Talca; Chile
Fil: Theoduloz, Cristina. Universidad de Talca; 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; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile - Materia
-
ANTIFUNGAL
ANTIPROLIFERATIVE
CARNOSIC ACID
CARNOSOL
CLICK CHEMISTRY - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/180362
Ver los metadatos del registro completo
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Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivativesPertino, Mariano WalterTheoduloz, CristinaButassi, EstefaníaZacchino, Susana Alicia StellaSchmeda Hirschmann, GuillermoANTIFUNGALANTIPROLIFERATIVECARNOSIC ACIDCARNOSOLCLICK CHEMISTRYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Abietane 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.Fil: Pertino, Mariano Walter. Universidad de Talca; ChileFil: Theoduloz, Cristina. Universidad de Talca; 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; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Schmeda Hirschmann, Guillermo. Universidad de Talca; ChileMolecular Diversity Preservation International2015-05info: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/11336/180362Pertino, 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; 8666-86861420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/20/5/8666info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules20058666info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:06:17Zoai:ri.conicet.gov.ar:11336/180362instacron: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 10:06:17.842CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| title |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| spellingShingle |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives Pertino, Mariano Walter ANTIFUNGAL ANTIPROLIFERATIVE CARNOSIC ACID CARNOSOL CLICK CHEMISTRY |
| title_short |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| title_full |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| title_fullStr |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| title_full_unstemmed |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| title_sort |
Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives |
| dc.creator.none.fl_str_mv |
Pertino, Mariano Walter Theoduloz, Cristina Butassi, Estefanía Zacchino, Susana Alicia Stella Schmeda Hirschmann, Guillermo |
| author |
Pertino, Mariano Walter |
| author_facet |
Pertino, Mariano Walter Theoduloz, Cristina Butassi, Estefanía Zacchino, Susana Alicia Stella Schmeda Hirschmann, Guillermo |
| author_role |
author |
| author2 |
Theoduloz, Cristina Butassi, Estefanía Zacchino, Susana Alicia Stella Schmeda Hirschmann, Guillermo |
| author2_role |
author author author author |
| dc.subject.none.fl_str_mv |
ANTIFUNGAL ANTIPROLIFERATIVE CARNOSIC ACID CARNOSOL CLICK CHEMISTRY |
| topic |
ANTIFUNGAL ANTIPROLIFERATIVE CARNOSIC ACID CARNOSOL CLICK CHEMISTRY |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
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. Fil: Pertino, Mariano Walter. Universidad de Talca; Chile Fil: Theoduloz, Cristina. Universidad de Talca; 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; Argentina Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile |
| description |
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. |
| publishDate |
2015 |
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2015-05 |
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info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
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article |
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publishedVersion |
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http://hdl.handle.net/11336/180362 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 1420-3049 CONICET Digital CONICET |
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http://hdl.handle.net/11336/180362 |
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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 1420-3049 CONICET Digital CONICET |
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eng |
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eng |
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Molecular Diversity Preservation International |
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Molecular Diversity Preservation International |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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