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dc.contributor.author
Garcia Liñares, Guadalupe Eugenia  
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Zígolo, M. Antonela  
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Simonetti, Leandro  
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Longhi, Silvia Andrea  
dc.contributor.author
Baldessari, Alicia  
dc.date.available
2016-02-01T20:31:34Z  
dc.date.issued
2015-05-30  
dc.identifier.citation
Garcia Liñares, Guadalupe Eugenia; Zígolo, M. Antonela; Simonetti, Leandro; Longhi, Silvia Andrea; Baldessari, Alicia; Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi; Elsevier; Bioorganic & Medicinal Chemistry; 23; 15; 30-5-2015; 4804–4814  
dc.identifier.issn
0968-0896  
dc.identifier.uri
http://hdl.handle.net/11336/3947  
dc.description.abstract
Enzyme catalysis was applied to synthesize derivatives of three bile acids and their biological activity was evaluated as growth inhibitors of the protozoan Trypanosoma cruzi. Twelve mono-, diacetyl and ester derivatives of deoxycholic, chenodeoxycholic and lithocholic acid, seven of them new compounds, were obtained through lipase-catalyzed acetylation, esterification and alcoholysis reactions in very good to excellent yield and a highly regioselective way. Among them, acetylated ester products, in which the lipase catalyzed both reactions in one-pot, were obtained. The influence of various reaction parameters in the enzymatic reactions, such as enzyme source, acylating agent/substrate ratio, enzyme/substrate ratio, solvent and temperature, was studied. Some of the evaluated compounds showed a remarkable activity as Trypanosoma cruzi growth inhibitors, obtaining the best results with ethyl chenodeoxycholate 3-acetate and chenodeoxycholic acid 3,7-diacetate, which showed IC50: 8.6 and 22.8μM, respectively. In addition, in order to shed light to bile acids behavior in enzymatic reactions, molecular modeling was applied to some derivatives. The advantages showed by the enzymatic methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to synthesize these bile acid derivatives with application as potential antiparasitic agents.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Elsevier  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/  
dc.subject
Bile Acids  
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Lipase-Catalyzed  
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Molecular Modeling  
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Chagas Disease  
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Química Orgánica  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
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Enfermedades Infecciosas  
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Ciencias de la Salud  
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CIENCIAS MÉDICAS Y DE LA SALUD  
dc.title
Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
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info:eu-repo/semantics/publishedVersion  
dc.date.updated
2016-03-30 10:35:44.97925-03  
dc.journal.volume
23  
dc.journal.number
15  
dc.journal.pagination
4804–4814  
dc.journal.pais
Países Bajos  
dc.journal.ciudad
Amsterdam  
dc.description.fil
Fil: Garcia Liñares, Guadalupe Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina  
dc.description.fil
Fil: Zígolo, M. Antonela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina  
dc.description.fil
Fil: Simonetti, Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular; Argentina  
dc.description.fil
Fil: Longhi, Silvia Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular; Argentina  
dc.description.fil
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina  
dc.journal.title
Bioorganic & Medicinal Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089615004459  
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info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.bmc.2015.05.035  
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info:eu-repo/semantics/altIdentifier/issn/0968-0896