Preparation, anticholinesterase activity and molecular docking of new lupane derivatives
A set of twenty one lupane derivatives (2-22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and...
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2014
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v22_n13_p3341_Castro http://hdl.handle.net/20.500.12110/paper_09680896_v22_n13_p3341_Castro |
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paper:paper_09680896_v22_n13_p3341_Castro2023-06-08T15:58:56Z Preparation, anticholinesterase activity and molecular docking of new lupane derivatives Alzheimer's disease Cholinesterase inhibitors Lupane derivatives Molecular modeling Triterpenoids 20,29 dihydrolupan 3beta,16beta diol 20s,29 epoxylupan 3beta,16beta diol 3,16 dioxo lup 20(29) en 30 al 3beta acetoxy 16beta hydroxy lup 20(29) ene 3beta hydroxy 16beta acetoxy lup 20(29) ene 3beta,16beta diacetoxy lup 20(29) en 30 al 3beta,16beta dihydroxylup 20(29) en 30 al acetylcholinesterase calenduladiol cholinesterase cholinesterase inhibitor disodium 3beta,16beta dihydroxylup 20(29) en 30 al disulfate disodium 3beta,16beta dihydroxylup 20(29) ene disulfate disodium 3beta,16beta dihydroxylup 20,29 dihydrolupane disulfate disodium 3beta,16beta dihydroxylup 20,29 epoxylupane disulfate disodium 3beta,16beta,30 trihydroxylup 20(29) ene 3,16 disulfate lup 20(29) en 3beta,16beta,30 triol lup 20(29) ene 3,16 dione lup 20(29) ene 3beta,16beta diol di 4 bromobenzoate lup 20(29) ene 3beta,16beta diol di 4 pentenoate lup 20(29) ene 3beta,16beta diol diacetate lup 20(29) ene 3beta,16beta diol dibenzoate lup 20(29) ene 3beta,16beta diol dihemiadipate lup 20(29) ene 3beta,16beta,30 triol triacetate lupane derivative physostigmine tacrine trisodium 3beta,16beta,30 trihydroxylup 20(29) ene trisulfate triterpenoid unclassified drug acetylcholinesterase cholinesterase cholinesterase inhibitor lupane triterpene article chemical modification controlled study drug potency drug selectivity drug structure drug synthesis enzyme inhibition enzyme kinetics IC 50 in vitro study molecular docking molecular model nonhuman physical chemistry structure activity relation animal blood chemical structure chemistry conformation dose response eel horse kinetics metabolism synthesis Acetylcholinesterase Animals Butyrylcholinesterase Cholinesterase Inhibitors Dose-Response Relationship, Drug Eels Horses Kinetics Models, Molecular Molecular Conformation Structure-Activity Relationship Triterpenes A set of twenty one lupane derivatives (2-22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and some structure-activity relationships were outlined with the aid of enzyme kinetic studies and docking modelization. The most active compound resulted to be 3,16,30-trioxolup-20(29)-ene (22), with an IC50 value of 21.5 μM for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme. © 2014 Elsevier Ltd. All rights reserved. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v22_n13_p3341_Castro http://hdl.handle.net/20.500.12110/paper_09680896_v22_n13_p3341_Castro |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Alzheimer's disease Cholinesterase inhibitors Lupane derivatives Molecular modeling Triterpenoids 20,29 dihydrolupan 3beta,16beta diol 20s,29 epoxylupan 3beta,16beta diol 3,16 dioxo lup 20(29) en 30 al 3beta acetoxy 16beta hydroxy lup 20(29) ene 3beta hydroxy 16beta acetoxy lup 20(29) ene 3beta,16beta diacetoxy lup 20(29) en 30 al 3beta,16beta dihydroxylup 20(29) en 30 al acetylcholinesterase calenduladiol cholinesterase cholinesterase inhibitor disodium 3beta,16beta dihydroxylup 20(29) en 30 al disulfate disodium 3beta,16beta dihydroxylup 20(29) ene disulfate disodium 3beta,16beta dihydroxylup 20,29 dihydrolupane disulfate disodium 3beta,16beta dihydroxylup 20,29 epoxylupane disulfate disodium 3beta,16beta,30 trihydroxylup 20(29) ene 3,16 disulfate lup 20(29) en 3beta,16beta,30 triol lup 20(29) ene 3,16 dione lup 20(29) ene 3beta,16beta diol di 4 bromobenzoate lup 20(29) ene 3beta,16beta diol di 4 pentenoate lup 20(29) ene 3beta,16beta diol diacetate lup 20(29) ene 3beta,16beta diol dibenzoate lup 20(29) ene 3beta,16beta diol dihemiadipate lup 20(29) ene 3beta,16beta,30 triol triacetate lupane derivative physostigmine tacrine trisodium 3beta,16beta,30 trihydroxylup 20(29) ene trisulfate triterpenoid unclassified drug acetylcholinesterase cholinesterase cholinesterase inhibitor lupane triterpene article chemical modification controlled study drug potency drug selectivity drug structure drug synthesis enzyme inhibition enzyme kinetics IC 50 in vitro study molecular docking molecular model nonhuman physical chemistry structure activity relation animal blood chemical structure chemistry conformation dose response eel horse kinetics metabolism synthesis Acetylcholinesterase Animals Butyrylcholinesterase Cholinesterase Inhibitors Dose-Response Relationship, Drug Eels Horses Kinetics Models, Molecular Molecular Conformation Structure-Activity Relationship Triterpenes |
| spellingShingle |
Alzheimer's disease Cholinesterase inhibitors Lupane derivatives Molecular modeling Triterpenoids 20,29 dihydrolupan 3beta,16beta diol 20s,29 epoxylupan 3beta,16beta diol 3,16 dioxo lup 20(29) en 30 al 3beta acetoxy 16beta hydroxy lup 20(29) ene 3beta hydroxy 16beta acetoxy lup 20(29) ene 3beta,16beta diacetoxy lup 20(29) en 30 al 3beta,16beta dihydroxylup 20(29) en 30 al acetylcholinesterase calenduladiol cholinesterase cholinesterase inhibitor disodium 3beta,16beta dihydroxylup 20(29) en 30 al disulfate disodium 3beta,16beta dihydroxylup 20(29) ene disulfate disodium 3beta,16beta dihydroxylup 20,29 dihydrolupane disulfate disodium 3beta,16beta dihydroxylup 20,29 epoxylupane disulfate disodium 3beta,16beta,30 trihydroxylup 20(29) ene 3,16 disulfate lup 20(29) en 3beta,16beta,30 triol lup 20(29) ene 3,16 dione lup 20(29) ene 3beta,16beta diol di 4 bromobenzoate lup 20(29) ene 3beta,16beta diol di 4 pentenoate lup 20(29) ene 3beta,16beta diol diacetate lup 20(29) ene 3beta,16beta diol dibenzoate lup 20(29) ene 3beta,16beta diol dihemiadipate lup 20(29) ene 3beta,16beta,30 triol triacetate lupane derivative physostigmine tacrine trisodium 3beta,16beta,30 trihydroxylup 20(29) ene trisulfate triterpenoid unclassified drug acetylcholinesterase cholinesterase cholinesterase inhibitor lupane triterpene article chemical modification controlled study drug potency drug selectivity drug structure drug synthesis enzyme inhibition enzyme kinetics IC 50 in vitro study molecular docking molecular model nonhuman physical chemistry structure activity relation animal blood chemical structure chemistry conformation dose response eel horse kinetics metabolism synthesis Acetylcholinesterase Animals Butyrylcholinesterase Cholinesterase Inhibitors Dose-Response Relationship, Drug Eels Horses Kinetics Models, Molecular Molecular Conformation Structure-Activity Relationship Triterpenes Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| topic_facet |
Alzheimer's disease Cholinesterase inhibitors Lupane derivatives Molecular modeling Triterpenoids 20,29 dihydrolupan 3beta,16beta diol 20s,29 epoxylupan 3beta,16beta diol 3,16 dioxo lup 20(29) en 30 al 3beta acetoxy 16beta hydroxy lup 20(29) ene 3beta hydroxy 16beta acetoxy lup 20(29) ene 3beta,16beta diacetoxy lup 20(29) en 30 al 3beta,16beta dihydroxylup 20(29) en 30 al acetylcholinesterase calenduladiol cholinesterase cholinesterase inhibitor disodium 3beta,16beta dihydroxylup 20(29) en 30 al disulfate disodium 3beta,16beta dihydroxylup 20(29) ene disulfate disodium 3beta,16beta dihydroxylup 20,29 dihydrolupane disulfate disodium 3beta,16beta dihydroxylup 20,29 epoxylupane disulfate disodium 3beta,16beta,30 trihydroxylup 20(29) ene 3,16 disulfate lup 20(29) en 3beta,16beta,30 triol lup 20(29) ene 3,16 dione lup 20(29) ene 3beta,16beta diol di 4 bromobenzoate lup 20(29) ene 3beta,16beta diol di 4 pentenoate lup 20(29) ene 3beta,16beta diol diacetate lup 20(29) ene 3beta,16beta diol dibenzoate lup 20(29) ene 3beta,16beta diol dihemiadipate lup 20(29) ene 3beta,16beta,30 triol triacetate lupane derivative physostigmine tacrine trisodium 3beta,16beta,30 trihydroxylup 20(29) ene trisulfate triterpenoid unclassified drug acetylcholinesterase cholinesterase cholinesterase inhibitor lupane triterpene article chemical modification controlled study drug potency drug selectivity drug structure drug synthesis enzyme inhibition enzyme kinetics IC 50 in vitro study molecular docking molecular model nonhuman physical chemistry structure activity relation animal blood chemical structure chemistry conformation dose response eel horse kinetics metabolism synthesis Acetylcholinesterase Animals Butyrylcholinesterase Cholinesterase Inhibitors Dose-Response Relationship, Drug Eels Horses Kinetics Models, Molecular Molecular Conformation Structure-Activity Relationship Triterpenes |
| description |
A set of twenty one lupane derivatives (2-22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and some structure-activity relationships were outlined with the aid of enzyme kinetic studies and docking modelization. The most active compound resulted to be 3,16,30-trioxolup-20(29)-ene (22), with an IC50 value of 21.5 μM for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme. © 2014 Elsevier Ltd. All rights reserved. |
| title |
Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| title_short |
Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| title_full |
Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| title_fullStr |
Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| title_full_unstemmed |
Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| title_sort |
preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| publishDate |
2014 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v22_n13_p3341_Castro http://hdl.handle.net/20.500.12110/paper_09680896_v22_n13_p3341_Castro |
| _version_ |
1768541947045085184 |