Improved Enzymatic Procedure for the Synthesis of Anandamide and N‐Fatty Acylalkanolamine Analogues: A Combination Strategy to Antitumor Activity
Abstract 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 achiev...
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Online Access: | http://dx.doi.org/10.1002/ejoc.201501263 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201501263 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201501263/fullpdf |
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crwiley:10.1002/ejoc.201501263 2024-06-02T07:57:04+00:00 Improved Enzymatic Procedure for the Synthesis of Anandamide and N‐Fatty Acylalkanolamine Analogues: A Combination Strategy to Antitumor Activity Quintana, Paula G. García Liñares, Guadalupe Chanquia, Santiago N. Gorojod, Roxana M. Kotler, Mónica L. Baldessari, Alicia 2015 http://dx.doi.org/10.1002/ejoc.201501263 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201501263 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201501263/fullpdf en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Organic Chemistry volume 2016, issue 3, page 518-528 ISSN 1434-193X 1099-0690 journal-article 2015 crwiley https://doi.org/10.1002/ejoc.201501263 2024-05-03T10:48:58Z Abstract 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Organic Chemistry 2016 3 518 528 |
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Wiley Online Library |
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crwiley |
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English |
description |
Abstract 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. |
format |
Article in Journal/Newspaper |
author |
Quintana, Paula G. García Liñares, Guadalupe Chanquia, Santiago N. Gorojod, Roxana M. Kotler, Mónica L. Baldessari, Alicia |
spellingShingle |
Quintana, Paula G. García Liñares, Guadalupe Chanquia, Santiago N. Gorojod, Roxana M. Kotler, Mónica L. Baldessari, Alicia Improved Enzymatic Procedure for the Synthesis of Anandamide and N‐Fatty Acylalkanolamine Analogues: A Combination Strategy to Antitumor Activity |
author_facet |
Quintana, Paula G. García Liñares, Guadalupe Chanquia, Santiago N. Gorojod, Roxana M. Kotler, Mónica L. Baldessari, Alicia |
author_sort |
Quintana, Paula G. |
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 |
publisher |
Wiley |
publishDate |
2015 |
url |
http://dx.doi.org/10.1002/ejoc.201501263 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201501263 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201501263/fullpdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Organic Chemistry volume 2016, issue 3, page 518-528 ISSN 1434-193X 1099-0690 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejoc.201501263 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2016 |
container_issue |
3 |
container_start_page |
518 |
op_container_end_page |
528 |
_version_ |
1800738397640196096 |