Artículo
Castro, M.J.; Richmond, V.; Romero, C.; Maier, M.S.; Estévez-Braun, A.; Ravelo, Á.G.; Faraoni, M.B.; Murray, A.P. "Preparation, anticholinesterase activity and molecular docking of new lupane derivatives" (2014) Bioorganic and Medicinal Chemistry. 22(13):3341-3350
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Abstract:
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.
Registro:
| Documento: | Artículo |
| Título: | Preparation, anticholinesterase activity and molecular docking of new lupane derivatives |
| Autor: | Castro, M.J.; Richmond, V.; Romero, C.; Maier, M.S.; Estévez-Braun, A.; Ravelo, Á.G.; Faraoni, M.B.; Murray, A.P. |
| Filiación: | INQUISUR-CONICET, Departamento de Química, Universidad Nacional Del sur, Av. Alem 1253, B8000CPB Bahía Blanca, Argentina UMYMFOR (CONICET-UBA), Departamento de Química Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina Instituto Universitario de Bio-Orgánica (CIBICAN), Departamento de Química Orgánica, Universidad de la Laguna, Av. Astrofísico Francisco Sánchez 2, 38206, Tenerife, Spain |
| Palabras clave: | 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 |
| Año: | 2014 |
| Volumen: | 22 |
| Número: | 13 |
| Página de inicio: | 3341 |
| Página de fin: | 3350 |
| DOI: | http://dx.doi.org/10.1016/j.bmc.2014.04.050 |
| Título revista: | Bioorganic and Medicinal Chemistry |
| Título revista abreviado: | Bioorg. Med. Chem. |
| ISSN: | 09680896 |
| CODEN: | BMECE |
| CAS: | acetylcholinesterase, 9000-81-1; cholinesterase, 9001-08-5; physostigmine, 57-47-6, 64-47-1; tacrine, 1684-40-8, 3198-41-2, 321-64-2; Acetylcholinesterase; Butyrylcholinesterase; Cholinesterase Inhibitors; lupane; Triterpenes |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v22_n13_p3341_Castro |
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Citas:
---------- APA ----------
Castro, M.J., Richmond, V., Romero, C., Maier, M.S., Estévez-Braun, A., Ravelo, Á.G., Faraoni, M.B.,..., Murray, A.P. (2014) . Preparation, anticholinesterase activity and molecular docking of new lupane derivatives. Bioorganic and Medicinal Chemistry, 22(13), 3341-3350.http://dx.doi.org/10.1016/j.bmc.2014.04.050
---------- CHICAGO ----------
Castro, M.J., Richmond, V., Romero, C., Maier, M.S., Estévez-Braun, A., Ravelo, Á.G., et al. "Preparation, anticholinesterase activity and molecular docking of new lupane derivatives" . Bioorganic and Medicinal Chemistry 22, no. 13 (2014) : 3341-3350.http://dx.doi.org/10.1016/j.bmc.2014.04.050
---------- MLA ----------
Castro, M.J., Richmond, V., Romero, C., Maier, M.S., Estévez-Braun, A., Ravelo, Á.G., et al. "Preparation, anticholinesterase activity and molecular docking of new lupane derivatives" . Bioorganic and Medicinal Chemistry, vol. 22, no. 13, 2014, pp. 3341-3350.http://dx.doi.org/10.1016/j.bmc.2014.04.050
---------- VANCOUVER ----------
Castro, M.J., Richmond, V., Romero, C., Maier, M.S., Estévez-Braun, A., Ravelo, Á.G., et al. Preparation, anticholinesterase activity and molecular docking of new lupane derivatives. Bioorg. Med. Chem. 2014;22(13):3341-3350.http://dx.doi.org/10.1016/j.bmc.2014.04.050
