Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies
[Display omitted] •Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions wi...
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Veröffentlicht in: | Steroids 2015-12, Vol.104, p.95-110 |
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creator | García, Manuela E. Borioni, José L. Cavallaro, Valeria Puiatti, Marcelo Pierini, Adriana B. Murray, Ana P. Peñéñory, Alicia B. |
description | [Display omitted]
•Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions with the enzyme and binding conformations were evaluated.
The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. Through this study valuable information was obtained of steroidal alkaloid-type compounds as a starting point for the synthesis of AChE inhibitors. |
doi_str_mv | 10.1016/j.steroids.2015.09.001 |
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•Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions with the enzyme and binding conformations were evaluated.
The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. Through this study valuable information was obtained of steroidal alkaloid-type compounds as a starting point for the synthesis of AChE inhibitors.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2015.09.001</identifier><identifier>PMID: 26362598</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Acetylcholinesterase - metabolism ; Acetylcholinesterase inhibitors ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Alkaloids - pharmacology ; Animals ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - chemistry ; Cholinesterase Inhibitors - pharmacology ; Dose-Response Relationship, Drug ; Electrophorus ; Molecular Docking Simulation ; Molecular Structure ; Solanocapsine derivatives ; Solanum pseudocapsicum ; Steroidal alkaloids ; Steroids - chemical synthesis ; Steroids - chemistry ; Steroids - pharmacology ; Structure-Activity Relationship</subject><ispartof>Steroids, 2015-12, Vol.104, p.95-110</ispartof><rights>2015 Elsevier Inc.</rights><rights>Copyright © 2015 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-d934e4d942104f58566ceeedbcc80605d6ca810d9e7510ff3f1f7066c05b75903</citedby><cites>FETCH-LOGICAL-c368t-d934e4d942104f58566ceeedbcc80605d6ca810d9e7510ff3f1f7066c05b75903</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2015.09.001$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3552,27931,27932,46002</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26362598$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>García, Manuela E.</creatorcontrib><creatorcontrib>Borioni, José L.</creatorcontrib><creatorcontrib>Cavallaro, Valeria</creatorcontrib><creatorcontrib>Puiatti, Marcelo</creatorcontrib><creatorcontrib>Pierini, Adriana B.</creatorcontrib><creatorcontrib>Murray, Ana P.</creatorcontrib><creatorcontrib>Peñéñory, Alicia B.</creatorcontrib><title>Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies</title><title>Steroids</title><addtitle>Steroids</addtitle><description>[Display omitted]
•Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions with the enzyme and binding conformations were evaluated.
The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. Through this study valuable information was obtained of steroidal alkaloid-type compounds as a starting point for the synthesis of AChE inhibitors.</description><subject>Acetylcholinesterase - metabolism</subject><subject>Acetylcholinesterase inhibitors</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Electrophorus</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Solanocapsine derivatives</subject><subject>Solanum pseudocapsicum</subject><subject>Steroidal alkaloids</subject><subject>Steroids - chemical synthesis</subject><subject>Steroids - chemistry</subject><subject>Steroids - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFu1DAQhi1ERZfCK1Q-ciBhnMROwglUAa1UqYdSiZvl2JPuLNl4sZ2V9sKz16ttuXKay_f_M_MxdimgFCDUp00ZEwZPLpYVCFlCXwKIV2wlurYrZKfa12wFUPeFqLpf5-xtjBsAUHVfvWHnlapVJftuxf7e-8nM3ppdpBm5w0B7k2iPkZvIdz7hnMhMnOY1DZR8iNyP3FhMh8mu_ZRDx0NMxM_8_jCnNUaKH_nWT2iXyQTuvP1N8yM3s-MD-ck_ks19MS2OML5jZ6OZIr5_nhfs4fu3n1fXxe3dj5urr7eFrVWXCtfXDTaubyoBzSg7qZRFRDdY24EC6ZQ1nQDXYysFjGM9irGFDIEcWtlDfcE-nHp3wf9Z8sl6S9HilH9Hv0Qt2lo1Qqqmyqg6oTb4GAOOehdoa8JBC9BH93qjX9zro3sNvc7uc_DyeccybNH9i73IzsCXE4D50z1h0NESzhYdBbRJO0__2_EEUauc7g</recordid><startdate>201512</startdate><enddate>201512</enddate><creator>García, Manuela E.</creator><creator>Borioni, José L.</creator><creator>Cavallaro, Valeria</creator><creator>Puiatti, Marcelo</creator><creator>Pierini, Adriana B.</creator><creator>Murray, Ana P.</creator><creator>Peñéñory, Alicia B.</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201512</creationdate><title>Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies</title><author>García, Manuela E. ; Borioni, José L. ; Cavallaro, Valeria ; Puiatti, Marcelo ; Pierini, Adriana B. ; Murray, Ana P. ; Peñéñory, Alicia B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-d934e4d942104f58566ceeedbcc80605d6ca810d9e7510ff3f1f7066c05b75903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetylcholinesterase - metabolism</topic><topic>Acetylcholinesterase inhibitors</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Electrophorus</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Solanocapsine derivatives</topic><topic>Solanum pseudocapsicum</topic><topic>Steroidal alkaloids</topic><topic>Steroids - chemical synthesis</topic><topic>Steroids - chemistry</topic><topic>Steroids - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>García, Manuela E.</creatorcontrib><creatorcontrib>Borioni, José L.</creatorcontrib><creatorcontrib>Cavallaro, Valeria</creatorcontrib><creatorcontrib>Puiatti, Marcelo</creatorcontrib><creatorcontrib>Pierini, Adriana B.</creatorcontrib><creatorcontrib>Murray, Ana P.</creatorcontrib><creatorcontrib>Peñéñory, Alicia B.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>García, Manuela E.</au><au>Borioni, José L.</au><au>Cavallaro, Valeria</au><au>Puiatti, Marcelo</au><au>Pierini, Adriana B.</au><au>Murray, Ana P.</au><au>Peñéñory, Alicia B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2015-12</date><risdate>2015</risdate><volume>104</volume><spage>95</spage><epage>110</epage><pages>95-110</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>[Display omitted]
•Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions with the enzyme and binding conformations were evaluated.
The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. Through this study valuable information was obtained of steroidal alkaloid-type compounds as a starting point for the synthesis of AChE inhibitors.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>26362598</pmid><doi>10.1016/j.steroids.2015.09.001</doi><tpages>16</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Acetylcholinesterase - metabolism Acetylcholinesterase inhibitors Alkaloids - chemical synthesis Alkaloids - chemistry Alkaloids - pharmacology Animals Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - pharmacology Dose-Response Relationship, Drug Electrophorus Molecular Docking Simulation Molecular Structure Solanocapsine derivatives Solanum pseudocapsicum Steroidal alkaloids Steroids - chemical synthesis Steroids - chemistry Steroids - pharmacology Structure-Activity Relationship |
title | Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies |
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