Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids
A series of berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggrega...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-05, Vol.20 (9), p.3038-3048 |
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| creator | Huang, Ling Su, Tao Shan, Wenjun Luo, Zonghua Sun, Yang He, Feng Li, Xingshu |
| description | A series of berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively).
A series of berberine-phenyl-benzoheterocyclic (26–29) and tacrine-phenyl-benzoheterocyclic hybrids (44–46) were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. |
| doi_str_mv | 10.1016/j.bmc.2012.02.059 |
| format | Article |
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A series of berberine-phenyl-benzoheterocyclic (26–29) and tacrine-phenyl-benzoheterocyclic hybrids (44–46) were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2012.02.059</identifier><identifier>PMID: 22472046</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Acetylcholinesterase - metabolism ; Alzheimer Disease - drug therapy ; Alzheimer’s disease ; Amyloid ; Amyloid beta-Peptides - antagonists & inhibitors ; Amyloid beta-Peptides - metabolism ; Berberine - chemistry ; beta -Amyloid ; Binding Sites ; Biological and medical sciences ; Butyrylcholinesterase - metabolism ; chemistry ; Cholinesterase ; Cholinesterase Inhibitors - chemical synthesis ; Cholinesterase Inhibitors - chemistry ; Cholinesterase Inhibitors - pharmacology ; Cholinesterases - chemistry ; Cholinesterases - metabolism ; Drug development ; drugs ; Enzyme Activation - drug effects ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacology ; Humans ; Hybrids ; inhibitory concentration 50 ; Kinetics ; Medical sciences ; Molecular Dynamics Simulation ; Multifunctional drug ; Pharmacology. Drug treatments ; Protein Structure, Tertiary ; Spacer ; tacrine ; Tacrine - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2012-05, Vol.20 (9), p.3038-3048</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c440t-c86cbbaa5871f07fcfe442a7fd99002d5786475a67f0a0ce80126bd7f6ed29273</citedby><cites>FETCH-LOGICAL-c440t-c86cbbaa5871f07fcfe442a7fd99002d5786475a67f0a0ce80126bd7f6ed29273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2012.02.059$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25862808$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22472046$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Ling</creatorcontrib><creatorcontrib>Su, Tao</creatorcontrib><creatorcontrib>Shan, Wenjun</creatorcontrib><creatorcontrib>Luo, Zonghua</creatorcontrib><creatorcontrib>Sun, Yang</creatorcontrib><creatorcontrib>He, Feng</creatorcontrib><creatorcontrib>Li, Xingshu</creatorcontrib><title>Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively).
A series of berberine-phenyl-benzoheterocyclic (26–29) and tacrine-phenyl-benzoheterocyclic hybrids (44–46) were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.</description><subject>Acetylcholinesterase - metabolism</subject><subject>Alzheimer Disease - drug therapy</subject><subject>Alzheimer’s disease</subject><subject>Amyloid</subject><subject>Amyloid beta-Peptides - antagonists & inhibitors</subject><subject>Amyloid beta-Peptides - metabolism</subject><subject>Berberine - chemistry</subject><subject>beta -Amyloid</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Butyrylcholinesterase - metabolism</subject><subject>chemistry</subject><subject>Cholinesterase</subject><subject>Cholinesterase Inhibitors - chemical synthesis</subject><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Cholinesterases - chemistry</subject><subject>Cholinesterases - metabolism</subject><subject>Drug development</subject><subject>drugs</subject><subject>Enzyme Activation - drug effects</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacology</subject><subject>Humans</subject><subject>Hybrids</subject><subject>inhibitory concentration 50</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Molecular Dynamics Simulation</subject><subject>Multifunctional drug</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Structure, Tertiary</subject><subject>Spacer</subject><subject>tacrine</subject><subject>Tacrine - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU2P0zAQhiMEYsvCD-ACuSBxSRm7jj_ECa34WGklDrBny3bGjaskLna6UvgV_GTcbYHbCmmkuTzvOzPvVNVLAmsChL_bre3o1hQIXUOpVj2qVoRx1mw2ijyuVqC4bEAqflE9y3kHAJQp8rS6oJQJCoyvql_XUx9smEOc6uhr18chTJhnTCZjbdwc7sK81GbqajMuQwylb7cJt-ZeYpfaYipVRM2-x2kZGovTz9hjsYhucUNw9-rZuIehfrEpdPl59cSbIeOLc7-sbj99_H71pbn5-vn66sNN4xiDuXGSO2uNaaUgHoR3HhmjRvhOqXJm1wrJmWgNFx4MOJQlJG474Tl2VFGxuazennz3Kf44lIv1GLLDYTATxkPWJWBGgMuN_A8UFKFSAC0oOaEuxZwTer1PYTRpKdDRkuudLj_Tx59pKNWqonl1tj_YEbu_ij9PKsCbM2CyM4NPZnIh_-NayamE456vT5w3UZttKszttzKpBSAEKD-u9_5EYEn2LmDS2QWcHHYhoZt1F8MDi_4GsnfA9Q</recordid><startdate>20120501</startdate><enddate>20120501</enddate><creator>Huang, Ling</creator><creator>Su, Tao</creator><creator>Shan, Wenjun</creator><creator>Luo, Zonghua</creator><creator>Sun, Yang</creator><creator>He, Feng</creator><creator>Li, Xingshu</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</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>7X8</scope><scope>7QO</scope><scope>7TK</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20120501</creationdate><title>Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids</title><author>Huang, Ling ; Su, Tao ; Shan, Wenjun ; Luo, Zonghua ; Sun, Yang ; He, Feng ; Li, Xingshu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c440t-c86cbbaa5871f07fcfe442a7fd99002d5786475a67f0a0ce80126bd7f6ed29273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acetylcholinesterase - metabolism</topic><topic>Alzheimer Disease - drug therapy</topic><topic>Alzheimer’s disease</topic><topic>Amyloid</topic><topic>Amyloid beta-Peptides - antagonists & inhibitors</topic><topic>Amyloid beta-Peptides - metabolism</topic><topic>Berberine - chemistry</topic><topic>beta -Amyloid</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Butyrylcholinesterase - metabolism</topic><topic>chemistry</topic><topic>Cholinesterase</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Cholinesterases - chemistry</topic><topic>Cholinesterases - metabolism</topic><topic>Drug development</topic><topic>drugs</topic><topic>Enzyme Activation - drug effects</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - pharmacology</topic><topic>Humans</topic><topic>Hybrids</topic><topic>inhibitory concentration 50</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Molecular Dynamics Simulation</topic><topic>Multifunctional drug</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Structure, Tertiary</topic><topic>Spacer</topic><topic>tacrine</topic><topic>Tacrine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Ling</creatorcontrib><creatorcontrib>Su, Tao</creatorcontrib><creatorcontrib>Shan, Wenjun</creatorcontrib><creatorcontrib>Luo, Zonghua</creatorcontrib><creatorcontrib>Sun, Yang</creatorcontrib><creatorcontrib>He, Feng</creatorcontrib><creatorcontrib>Li, Xingshu</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Ling</au><au>Su, Tao</au><au>Shan, Wenjun</au><au>Luo, Zonghua</au><au>Sun, Yang</au><au>He, Feng</au><au>Li, Xingshu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2012-05-01</date><risdate>2012</risdate><volume>20</volume><issue>9</issue><spage>3038</spage><epage>3048</epage><pages>3038-3048</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively).
A series of berberine-phenyl-benzoheterocyclic (26–29) and tacrine-phenyl-benzoheterocyclic hybrids (44–46) were synthesised and evaluated as multifunctional anti-Alzheimer’s disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22472046</pmid><doi>10.1016/j.bmc.2012.02.059</doi><tpages>11</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2012-05, Vol.20 (9), p.3038-3048 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Acetylcholinesterase - metabolism Alzheimer Disease - drug therapy Alzheimer’s disease Amyloid Amyloid beta-Peptides - antagonists & inhibitors Amyloid beta-Peptides - metabolism Berberine - chemistry beta -Amyloid Binding Sites Biological and medical sciences Butyrylcholinesterase - metabolism chemistry Cholinesterase Cholinesterase Inhibitors - chemical synthesis Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - pharmacology Cholinesterases - chemistry Cholinesterases - metabolism Drug development drugs Enzyme Activation - drug effects Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Humans Hybrids inhibitory concentration 50 Kinetics Medical sciences Molecular Dynamics Simulation Multifunctional drug Pharmacology. Drug treatments Protein Structure, Tertiary Spacer tacrine Tacrine - chemistry |
| title | Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids |
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