Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors
In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both en...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2013-11, Vol.346 (11), p.775-782 |
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| creator | Granica, Sebastian Kiss, Anna K. Jarończyk, Małgorzata Maurin, Jan K. Mazurek, Aleksander P. Czarnocki, Zbigniew |
| description | In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments. All active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active ones were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively. The results of our study may be considered as the beginning of a search for potential anti‐Alzheimer's disease drugs based on the structure of natural furocoumarins.
Several imperatorin analogs were synthesized using imperatorin and xanthotoxin as substrates. Their anti‐cholinesterase activities were evaluated, and all active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active compounds were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively. |
| doi_str_mv | 10.1002/ardp.201300259 |
| format | Article |
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Several imperatorin analogs were synthesized using imperatorin and xanthotoxin as substrates. Their anti‐cholinesterase activities were evaluated, and all active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active compounds were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201300259</identifier><identifier>PMID: 24123207</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Acetylcholinesterase ; Acetylcholinesterase - metabolism ; Alzheimer Disease - drug therapy ; Alzheimer Disease - enzymology ; Alzheimer's disease ; Angelica archangelica ; Animals ; Binding Sites ; Butyrylcholinesterase ; Butyrylcholinesterase - metabolism ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - pharmacology ; Furocoumarins ; Furocoumarins - chemical synthesis ; Furocoumarins - pharmacology ; Galantamine - pharmacology ; Molecular Docking Simulation ; Structure-Activity Relationship</subject><ispartof>Archiv der Pharmazie (Weinheim), 2013-11, Vol.346 (11), p.775-782</ispartof><rights>2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4119-6b88cf9ed826e25be711027f0ed43b7fb9b697a774e8a0d12db85c05e98818373</citedby><cites>FETCH-LOGICAL-c4119-6b88cf9ed826e25be711027f0ed43b7fb9b697a774e8a0d12db85c05e98818373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.201300259$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.201300259$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24123207$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Granica, Sebastian</creatorcontrib><creatorcontrib>Kiss, Anna K.</creatorcontrib><creatorcontrib>Jarończyk, Małgorzata</creatorcontrib><creatorcontrib>Maurin, Jan K.</creatorcontrib><creatorcontrib>Mazurek, Aleksander P.</creatorcontrib><creatorcontrib>Czarnocki, Zbigniew</creatorcontrib><title>Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><description>In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments. All active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active ones were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively. The results of our study may be considered as the beginning of a search for potential anti‐Alzheimer's disease drugs based on the structure of natural furocoumarins.
Several imperatorin analogs were synthesized using imperatorin and xanthotoxin as substrates. Their anti‐cholinesterase activities were evaluated, and all active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active compounds were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively.</description><subject>Acetylcholinesterase</subject><subject>Acetylcholinesterase - metabolism</subject><subject>Alzheimer Disease - drug therapy</subject><subject>Alzheimer Disease - enzymology</subject><subject>Alzheimer's disease</subject><subject>Angelica archangelica</subject><subject>Animals</subject><subject>Binding Sites</subject><subject>Butyrylcholinesterase</subject><subject>Butyrylcholinesterase - metabolism</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Furocoumarins</subject><subject>Furocoumarins - chemical synthesis</subject><subject>Furocoumarins - pharmacology</subject><subject>Galantamine - pharmacology</subject><subject>Molecular Docking Simulation</subject><subject>Structure-Activity Relationship</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v0zAchi3ExMrGlSOKxIVLOn_G9rGMfXQabGKDHS0n-YV6pHFnJ0D--7nrViF24GRZft5H1vsi9JbgKcGYHthQr6YUE5YuQr9AEyIoyTlR_CWaYFaIvKCM7aLXMd5ijFmiXqFdygllFMsJCldj1y8gupj5JpsvVxBs74PrsllnW_8jZrars-sFuJAd_bLtYHvnu8zGbFZBP7bVwreug9inXIQH-OPQj-HZy7xbuNIlddxHO41tI7x5PPfQt-Oj68PT_PziZH44O88rTojOi1KpqtFQK1oAFSVIQjCVDYaas1I2pS4LLa2UHJTFNaF1qUSFBWiliGKS7aEPG-8q-LshfcQsXaygbW0HfoiGCMy5EKmehL7_B731Q0gFJIpzRZmmfE1NN1QVfIwBGrMKbmnDaAg26zXMeg2zXSMF3j1qh3IJ9RZ_qj8BegP8di2M_9GZ2ddPl3_L803WpYr_bLM2_DSFZFKYmy8n5uzs5jO_0sp8Z_fUaKb5</recordid><startdate>201311</startdate><enddate>201311</enddate><creator>Granica, Sebastian</creator><creator>Kiss, Anna K.</creator><creator>Jarończyk, Małgorzata</creator><creator>Maurin, Jan K.</creator><creator>Mazurek, Aleksander P.</creator><creator>Czarnocki, Zbigniew</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>K9.</scope><scope>7X8</scope></search><sort><creationdate>201311</creationdate><title>Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors</title><author>Granica, Sebastian ; Kiss, Anna K. ; Jarończyk, Małgorzata ; Maurin, Jan K. ; Mazurek, Aleksander P. ; Czarnocki, Zbigniew</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4119-6b88cf9ed826e25be711027f0ed43b7fb9b697a774e8a0d12db85c05e98818373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Acetylcholinesterase</topic><topic>Acetylcholinesterase - metabolism</topic><topic>Alzheimer Disease - drug therapy</topic><topic>Alzheimer Disease - enzymology</topic><topic>Alzheimer's disease</topic><topic>Angelica archangelica</topic><topic>Animals</topic><topic>Binding Sites</topic><topic>Butyrylcholinesterase</topic><topic>Butyrylcholinesterase - metabolism</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Furocoumarins</topic><topic>Furocoumarins - chemical synthesis</topic><topic>Furocoumarins - pharmacology</topic><topic>Galantamine - pharmacology</topic><topic>Molecular Docking Simulation</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Granica, Sebastian</creatorcontrib><creatorcontrib>Kiss, Anna K.</creatorcontrib><creatorcontrib>Jarończyk, Małgorzata</creatorcontrib><creatorcontrib>Maurin, Jan K.</creatorcontrib><creatorcontrib>Mazurek, Aleksander P.</creatorcontrib><creatorcontrib>Czarnocki, Zbigniew</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Granica, Sebastian</au><au>Kiss, Anna K.</au><au>Jarończyk, Małgorzata</au><au>Maurin, Jan K.</au><au>Mazurek, Aleksander P.</au><au>Czarnocki, Zbigniew</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><date>2013-11</date><risdate>2013</risdate><volume>346</volume><issue>11</issue><spage>775</spage><epage>782</epage><pages>775-782</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments. All active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active ones were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively. The results of our study may be considered as the beginning of a search for potential anti‐Alzheimer's disease drugs based on the structure of natural furocoumarins.
Several imperatorin analogs were synthesized using imperatorin and xanthotoxin as substrates. Their anti‐cholinesterase activities were evaluated, and all active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active compounds were 8‐(3‐methylbutoxy)‐psoralen and 8‐hexoxypsoralen with IC50 values for BuChE of around 16.5 and 16.4 µM, respectively.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>24123207</pmid><doi>10.1002/ardp.201300259</doi><tpages>8</tpages></addata></record> |
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| ispartof | Archiv der Pharmazie (Weinheim), 2013-11, Vol.346 (11), p.775-782 |
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| subjects | Acetylcholinesterase Acetylcholinesterase - metabolism Alzheimer Disease - drug therapy Alzheimer Disease - enzymology Alzheimer's disease Angelica archangelica Animals Binding Sites Butyrylcholinesterase Butyrylcholinesterase - metabolism Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - pharmacology Furocoumarins Furocoumarins - chemical synthesis Furocoumarins - pharmacology Galantamine - pharmacology Molecular Docking Simulation Structure-Activity Relationship |
| title | Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors |
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