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Abstract:

Disulfated and trisulfated steroids have been synthesized from cholesterol and their acetylcholinesterase inhibitory activity has been evaluated. In our studies we have found that the activity was not only dependent on the location of the sulfate groups but on their configurations. 2β,3α,6α- trihydroxy-5α-cholestan-6-one trisulfate (18) was the most active steroid with an IC50 value of 15.48 μM comparable to that of 2β,3α-dihydroxy-5α-cholestan-6-one disulfate (1). Both compounds were found to be less active than the reference compound eserine. The butyrylcholinesterase activity of 1 and 18 was one magnitude lower than that against acetylcholinesterase revealing a selective inhibitor profile. © 2013 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies
Autor:Richmond, V.; Murray, A.P.; Maier, M.S.
Filiación:UMYMFOR (CONICET-UBA), Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
INQUISUR, Departamento de Química, Universidad Nacional Del sur, Avda. Alem 1253, 8000 Bahía Blanca, Buenos Aires, Argentina
Palabras clave:Acetylcholinesterase activity; Sulfated steroids; Synthesis; 2 alpha,3 alpha dihydroxy 5 alpha cholestan 6 one; 2 alpha,3 alpha epoxy 5 alpha cholestan 6 alpha ol; 2 beta,3 alpha dihydroxy 5 alpha cholestan 6 one; 2 beta,3 alpha dihydroxy 5 alpha cholestan 6 one disulfate; 2 beta,3 alpha dihydroxy 5 beta cholestan 6 one; 2 beta,3 alpha,6 alpha trihydroxy 5 alpha cholestane; 2 beta,3 alpha,6 beta trihydroxy 5 alpha cholestane; 2 beta,3 beta dihydroxy 5 alpha cholestan 6 one; 5 alpha cholest 2 en 6 alpha ol; cholinesterase; cholinesterase inhibitor; disodium 2 alpha,3 alpha dihydroxy 5 alpha cholestan 6 one disulfate; disodium 2 beta,3 alpha dihydroxycholest 5 ene disulfate; disodium 2 beta,3 alpha,6 beta trihydroxy 5 alpha cholestan 2 beta,3 alpha disulfate; disodium 2 beta,3 beta dihydroxy 5 alpha cholestan 6 one disulfate; physostigmine; steroid; trisodium 2 beta,3 alpha,6 alpha trihydroxy 5 alpha cholestane trisulfate; trisodium 2 beta,3 alpha,6 beta trihydroxy 5 alpha cholestane triisulfate; unclassified drug; article; cholinesterase inhibition; drug screening; drug synthesis; IC 50; in vitro study; structure activity relation; Acetylcholinesterase activity; Sulfated steroids; Synthesis; Acetylcholinesterase; Animals; Chemistry Techniques, Synthetic; Cholinesterase Inhibitors; Hydroxylation; Inhibitory Concentration 50; Steroids; Structure-Activity Relationship; Sulfates; Torpedo
Año:2013
Volumen:78
Número:11
Página de inicio:1141
Página de fin:1147
DOI: http://dx.doi.org/10.1016/j.steroids.2013.08.003
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:cholinesterase, 9001-08-5; physostigmine, 57-47-6, 64-47-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n11_p1141_Richmond

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Citas:

---------- APA ----------
Richmond, V., Murray, A.P. & Maier, M.S. (2013) . Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies. Steroids, 78(11), 1141-1147.
http://dx.doi.org/10.1016/j.steroids.2013.08.003
---------- CHICAGO ----------
Richmond, V., Murray, A.P., Maier, M.S. "Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies" . Steroids 78, no. 11 (2013) : 1141-1147.
http://dx.doi.org/10.1016/j.steroids.2013.08.003
---------- MLA ----------
Richmond, V., Murray, A.P., Maier, M.S. "Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies" . Steroids, vol. 78, no. 11, 2013, pp. 1141-1147.
http://dx.doi.org/10.1016/j.steroids.2013.08.003
---------- VANCOUVER ----------
Richmond, V., Murray, A.P., Maier, M.S. Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies. Steroids. 2013;78(11):1141-1147.
http://dx.doi.org/10.1016/j.steroids.2013.08.003