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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Detalles Bibliográficos
Autores principales: Castro, M.J., Richmond, V., Romero, C., Maier, M.S., Estévez-Braun, A., Ravelo, Á.G., Faraoni, M.B., Murray, A.P.
Formato: JOUR
Materias:
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
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_09680896_v22_n13_p3341_Castro
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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