Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity

Twenty N-fatty acylamines from linolenic and arachidonic acids, fifteen of them new compounds, were obtained through Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields and with high chemoselectivity. The optimal reaction conditions were achieved by stud...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Quintana, Paula Gabriela, García Liñares, Guadalupe E., Kotler, Mónica Lidia, Baldessari, Alicia
Publicado:	2016
Materias:	Aminolysis Antitumor agents Chemoselectivity Enzyme catalysis Medicinal chemistry
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v2016_n3_p518_Quintana http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n3_p518_Quintana
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_1434193X_v2016_n3_p518_Quintana
record_format	dspace
spelling	paper:paper_1434193X_v2016_n3_p518_Quintana2023-06-08T16:14:21Z Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity Quintana, Paula Gabriela García Liñares, Guadalupe E. Kotler, Mónica Lidia Baldessari, Alicia Aminolysis Antitumor agents Chemoselectivity Enzyme catalysis Medicinal chemistry Twenty N-fatty acylamines from linolenic and arachidonic acids, fifteen of them new compounds, were obtained through Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields and with high chemoselectivity. The optimal reaction conditions were achieved by studying the reaction parameters (temperature, E/S ratio, alcohol and alkanolamine/fatty acid ratio, time, solvent, free-solvent system, etc.). To identify ideal enzymatic methods for generating the alkanolamides we evaluated enzyme performance in three procedures: i) aminolysis of ethyl ester, ii) direct condensation between the fatty acid and the alkanolamine, and iii) a one-pot/two-step conversion of fatty acids into alkanolamides via in situ formation of the ethyl ester and subsequent aminolysis by the alkanolamine. The advantages noted with the enzymatic methodology, such as mild reaction conditions and low environmental impact, underscore biocatalysis as a convenient way to prepare the reported compounds. The cytotoxic activities of all compounds and mixtures of anandamide and its analogues were evaluated in rat glioma C6 cells. These studies reveal that some anandamide analogues enhance the antitumor effects of anandamide, suggesting their possible application as therapeutic tools in cancer treatment. Twenty N-fatty acylamines from linolenic and arachidonic acids were obtained by one-pot/two-step Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields with high chemoselectivity. Cytotoxicity assays using rat glioma C6 cells revealed that some analogues enhanced the antitumor effects of anandamide (AEA), suggesting possible anticancer applications. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Fil:Quintana, P.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:García Liñares, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Kotler, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2016 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v2016_n3_p518_Quintana http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n3_p518_Quintana
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Aminolysis Antitumor agents Chemoselectivity Enzyme catalysis Medicinal chemistry
spellingShingle	Aminolysis Antitumor agents Chemoselectivity Enzyme catalysis Medicinal chemistry Quintana, Paula Gabriela García Liñares, Guadalupe E. Kotler, Mónica Lidia Baldessari, Alicia Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
topic_facet	Aminolysis Antitumor agents Chemoselectivity Enzyme catalysis Medicinal chemistry
description	Twenty N-fatty acylamines from linolenic and arachidonic acids, fifteen of them new compounds, were obtained through Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields and with high chemoselectivity. The optimal reaction conditions were achieved by studying the reaction parameters (temperature, E/S ratio, alcohol and alkanolamine/fatty acid ratio, time, solvent, free-solvent system, etc.). To identify ideal enzymatic methods for generating the alkanolamides we evaluated enzyme performance in three procedures: i) aminolysis of ethyl ester, ii) direct condensation between the fatty acid and the alkanolamine, and iii) a one-pot/two-step conversion of fatty acids into alkanolamides via in situ formation of the ethyl ester and subsequent aminolysis by the alkanolamine. The advantages noted with the enzymatic methodology, such as mild reaction conditions and low environmental impact, underscore biocatalysis as a convenient way to prepare the reported compounds. The cytotoxic activities of all compounds and mixtures of anandamide and its analogues were evaluated in rat glioma C6 cells. These studies reveal that some anandamide analogues enhance the antitumor effects of anandamide, suggesting their possible application as therapeutic tools in cancer treatment. Twenty N-fatty acylamines from linolenic and arachidonic acids were obtained by one-pot/two-step Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields with high chemoselectivity. Cytotoxicity assays using rat glioma C6 cells revealed that some analogues enhanced the antitumor effects of anandamide (AEA), suggesting possible anticancer applications. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
author	Quintana, Paula Gabriela García Liñares, Guadalupe E. Kotler, Mónica Lidia Baldessari, Alicia
author_facet	Quintana, Paula Gabriela García Liñares, Guadalupe E. Kotler, Mónica Lidia Baldessari, Alicia
author_sort	Quintana, Paula Gabriela
title	Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
title_short	Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
title_full	Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
title_fullStr	Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
title_full_unstemmed	Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
title_sort	improved enzymatic procedure for the synthesis of anandamide and n-fatty acylalkanolamine analogues: a combination strategy to antitumor activity
publishDate	2016
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v2016_n3_p518_Quintana http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n3_p518_Quintana
work_keys_str_mv	AT quintanapaulagabriela improvedenzymaticprocedureforthesynthesisofanandamideandnfattyacylalkanolamineanaloguesacombinationstrategytoantitumoractivity AT garcialinaresguadalupee improvedenzymaticprocedureforthesynthesisofanandamideandnfattyacylalkanolamineanaloguesacombinationstrategytoantitumoractivity AT kotlermonicalidia improvedenzymaticprocedureforthesynthesisofanandamideandnfattyacylalkanolamineanaloguesacombinationstrategytoantitumoractivity AT baldessarialicia improvedenzymaticprocedureforthesynthesisofanandamideandnfattyacylalkanolamineanaloguesacombinationstrategytoantitumoractivity
_version_	1768543050745774080

Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity

Ejemplares similares