Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study
We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various pa...
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2018
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paper:paper_00452068_v78_n_p210_Zigolo2023-06-08T15:05:12Z Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study Antivirals Glycyrrhetinic acid Lipase-catalyzed Molecular modeling 3 acetylglycyrrhetinic acid glycyrrhetinic acid derivative n (3 acetylglycyrrhetinoyl) 1 amino 2 propanol n (3 acetylglycyrrhetinoyl) 2 amino 1 propanol n (3 acetylglycyrrhetinoyl) 4 hydroxy 1 butanol n (3 acetylglycyrrhetinoyl)butanolamine n (3 acetylglycyrrhetinoyl)ethanolamine solvent triacylglycerol lipase unclassified drug aciclovir antivirus agent glycyrrhetinic acid Lipozyme triacylglycerol lipase acetylation animal cell antiviral activity Article catalysis controlled study drug synthesis enzyme substrate enzyme synthesis Human alphaherpesvirus 1 molecular docking molecular model nonhuman priority journal Rhizomucor miehei temperature sensitivity biocatalysis Candida Carica chemical structure chemistry dose response drug effect enzymology Eurotiales metabolism microbial sensitivity test Rhizomucor Rhizopus structure activity relation Acyclovir Antiviral Agents Biocatalysis Candida Carica Dose-Response Relationship, Drug Eurotiales Glycyrrhetinic Acid Herpesvirus 1, Human Lipase Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Rhizomucor Rhizopus Structure-Activity Relationship We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. Moreover, in order to explain the reactivity of glycyrrhetinic acid and the acetylated derivative to different nucleophiles in the enzymatic reactions, molecular docking studies were carried out. In addition, one of the synthesized compounds exhibited remarkable antiviral activity against TK + and TK- strains of Herpes simplex virus type 1 (HSV-1), sensitive and resistant to acyclovir (ACV) treatment. © 2018 Elsevier Inc. 2018 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00452068_v78_n_p210_Zigolo http://hdl.handle.net/20.500.12110/paper_00452068_v78_n_p210_Zigolo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antivirals Glycyrrhetinic acid Lipase-catalyzed Molecular modeling 3 acetylglycyrrhetinic acid glycyrrhetinic acid derivative n (3 acetylglycyrrhetinoyl) 1 amino 2 propanol n (3 acetylglycyrrhetinoyl) 2 amino 1 propanol n (3 acetylglycyrrhetinoyl) 4 hydroxy 1 butanol n (3 acetylglycyrrhetinoyl)butanolamine n (3 acetylglycyrrhetinoyl)ethanolamine solvent triacylglycerol lipase unclassified drug aciclovir antivirus agent glycyrrhetinic acid Lipozyme triacylglycerol lipase acetylation animal cell antiviral activity Article catalysis controlled study drug synthesis enzyme substrate enzyme synthesis Human alphaherpesvirus 1 molecular docking molecular model nonhuman priority journal Rhizomucor miehei temperature sensitivity biocatalysis Candida Carica chemical structure chemistry dose response drug effect enzymology Eurotiales metabolism microbial sensitivity test Rhizomucor Rhizopus structure activity relation Acyclovir Antiviral Agents Biocatalysis Candida Carica Dose-Response Relationship, Drug Eurotiales Glycyrrhetinic Acid Herpesvirus 1, Human Lipase Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Rhizomucor Rhizopus Structure-Activity Relationship |
| spellingShingle |
Antivirals Glycyrrhetinic acid Lipase-catalyzed Molecular modeling 3 acetylglycyrrhetinic acid glycyrrhetinic acid derivative n (3 acetylglycyrrhetinoyl) 1 amino 2 propanol n (3 acetylglycyrrhetinoyl) 2 amino 1 propanol n (3 acetylglycyrrhetinoyl) 4 hydroxy 1 butanol n (3 acetylglycyrrhetinoyl)butanolamine n (3 acetylglycyrrhetinoyl)ethanolamine solvent triacylglycerol lipase unclassified drug aciclovir antivirus agent glycyrrhetinic acid Lipozyme triacylglycerol lipase acetylation animal cell antiviral activity Article catalysis controlled study drug synthesis enzyme substrate enzyme synthesis Human alphaherpesvirus 1 molecular docking molecular model nonhuman priority journal Rhizomucor miehei temperature sensitivity biocatalysis Candida Carica chemical structure chemistry dose response drug effect enzymology Eurotiales metabolism microbial sensitivity test Rhizomucor Rhizopus structure activity relation Acyclovir Antiviral Agents Biocatalysis Candida Carica Dose-Response Relationship, Drug Eurotiales Glycyrrhetinic Acid Herpesvirus 1, Human Lipase Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Rhizomucor Rhizopus Structure-Activity Relationship Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| topic_facet |
Antivirals Glycyrrhetinic acid Lipase-catalyzed Molecular modeling 3 acetylglycyrrhetinic acid glycyrrhetinic acid derivative n (3 acetylglycyrrhetinoyl) 1 amino 2 propanol n (3 acetylglycyrrhetinoyl) 2 amino 1 propanol n (3 acetylglycyrrhetinoyl) 4 hydroxy 1 butanol n (3 acetylglycyrrhetinoyl)butanolamine n (3 acetylglycyrrhetinoyl)ethanolamine solvent triacylglycerol lipase unclassified drug aciclovir antivirus agent glycyrrhetinic acid Lipozyme triacylglycerol lipase acetylation animal cell antiviral activity Article catalysis controlled study drug synthesis enzyme substrate enzyme synthesis Human alphaherpesvirus 1 molecular docking molecular model nonhuman priority journal Rhizomucor miehei temperature sensitivity biocatalysis Candida Carica chemical structure chemistry dose response drug effect enzymology Eurotiales metabolism microbial sensitivity test Rhizomucor Rhizopus structure activity relation Acyclovir Antiviral Agents Biocatalysis Candida Carica Dose-Response Relationship, Drug Eurotiales Glycyrrhetinic Acid Herpesvirus 1, Human Lipase Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Rhizomucor Rhizopus Structure-Activity Relationship |
| description |
We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. Moreover, in order to explain the reactivity of glycyrrhetinic acid and the acetylated derivative to different nucleophiles in the enzymatic reactions, molecular docking studies were carried out. In addition, one of the synthesized compounds exhibited remarkable antiviral activity against TK + and TK- strains of Herpes simplex virus type 1 (HSV-1), sensitive and resistant to acyclovir (ACV) treatment. © 2018 Elsevier Inc. |
| title |
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| title_short |
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| title_full |
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| title_fullStr |
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| title_full_unstemmed |
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study |
| title_sort |
chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. molecular docking study |
| publishDate |
2018 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00452068_v78_n_p210_Zigolo http://hdl.handle.net/20.500.12110/paper_00452068_v78_n_p210_Zigolo |
| _version_ |
1768542729645588480 |