Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies
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- trihydr...
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todo:paper_0039128X_v78_n11_p1141_Richmond2023-10-03T14:49:31Z Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies Richmond, V. Murray, A.P. Maier, M.S. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n11_p1141_Richmond |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Richmond, V. Murray, A.P. Maier, M.S. Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Richmond, V. Murray, A.P. Maier, M.S. |
| author_facet |
Richmond, V. Murray, A.P. Maier, M.S. |
| author_sort |
Richmond, V. |
| title |
Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| title_short |
Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| title_full |
Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| title_fullStr |
Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| title_full_unstemmed |
Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies |
| title_sort |
synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: structure/activity studies |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n11_p1141_Richmond |
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