8-Hydroxyquinoline-based anti-Alzheimer multimodal agents
The concept of multitarget-directed ligands (MTDLs) has attracted considerable interest in the development of agents against Alzheimer’s disease. Cathepsin B, a cysteine protease, and butyrylcholinesterase, a serine hydrolase, play important function in the development and progression of Alzheimer’s...
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| Veröffentlicht in: | Monatshefte für Chemie 2020-07, Vol.151 (7), p.1111-1120 |
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| creator | Knez, Damijan Sosič, Izidor Mitrović, Ana Pišlar, Anja Kos, Janko Gobec, Stanislav |
| description | The concept of multitarget-directed ligands (MTDLs) has attracted considerable interest in the development of agents against Alzheimer’s disease. Cathepsin B, a cysteine protease, and butyrylcholinesterase, a serine hydrolase, play important function in the development and progression of Alzheimer’s disease. We present herein the evaluation of 8-hydroxyquinoline-based analogues with activities against butyrylcholinesterase and β-secretase activity of cathepsin B. Furthermore, inhibition of amyloid β aggregation, chelation of copper and zinc ions coupled with antioxidative properties and safe cytotoxicity profile of (
1R
,
2S
)-
N
-ethyl-2-[[(8-hydroxy-5-nitroquinolin-7-yl)methyl]amino]cyclohexane-1-carboxamide suggest that this derivative is a good starting point for optimization towards an effective multifunctional ligand.
Graphic abstract |
| doi_str_mv | 10.1007/s00706-020-02651-0 |
| format | Article |
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1R
,
2S
)-
N
-ethyl-2-[[(8-hydroxy-5-nitroquinolin-7-yl)methyl]amino]cyclohexane-1-carboxamide suggest that this derivative is a good starting point for optimization towards an effective multifunctional ligand.
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1R
,
2S
)-
N
-ethyl-2-[[(8-hydroxy-5-nitroquinolin-7-yl)methyl]amino]cyclohexane-1-carboxamide suggest that this derivative is a good starting point for optimization towards an effective multifunctional ligand.
Graphic abstract</description><subject>Analytical Chemistry</subject><subject>Cathepsin B</subject><subject>Chelation</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Cyclohexane</subject><subject>Hydroxyquinoline</subject><subject>Inorganic Chemistry</subject><subject>Ligands</subject><subject>Optimization</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Theoretical and Computational Chemistry</subject><subject>Toxicity</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kE1Lw0AQhhdRsFb_gKeA59XZj8wmx1LUCgUvel42ybSm5KPdTcD6610bwZuHmWGG930HHsZuBdwLAPMQYgPkICEWpoLDGZsJrTTX2qTnbAbxzHOpzSW7CmEHcdegZizP-OpY-f7zeBjrrm_qjnjhAlWJ64aaL5qvD6pb8kk7NkPd9pVrErelbgjX7GLjmkA3v3PO3p8e35Yrvn59flku1rxUKQ4csRCpSxEUQWUMlq6oFGy0QSN0RVmOORW5ECgkyUI7YUpIyxzQSCeQSjVnd1Pu3veHkcJgd_3ou_jSSi1VJhCNiSo5qUrfh-BpY_e-bp0_WgH2B5GdENmIyJ4QWYgmNZlCFHdb8n_R_7i-AS8iZ_o</recordid><startdate>20200701</startdate><enddate>20200701</enddate><creator>Knez, Damijan</creator><creator>Sosič, Izidor</creator><creator>Mitrović, Ana</creator><creator>Pišlar, Anja</creator><creator>Kos, Janko</creator><creator>Gobec, Stanislav</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9678-3083</orcidid></search><sort><creationdate>20200701</creationdate><title>8-Hydroxyquinoline-based anti-Alzheimer multimodal agents</title><author>Knez, Damijan ; Sosič, Izidor ; Mitrović, Ana ; Pišlar, Anja ; Kos, Janko ; Gobec, Stanislav</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-66b15a5603e0d776cabd30f476714de8969eb911612e2b4a17c05c90672a16ec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Analytical Chemistry</topic><topic>Cathepsin B</topic><topic>Chelation</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Cyclohexane</topic><topic>Hydroxyquinoline</topic><topic>Inorganic Chemistry</topic><topic>Ligands</topic><topic>Optimization</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Theoretical and Computational Chemistry</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Knez, Damijan</creatorcontrib><creatorcontrib>Sosič, Izidor</creatorcontrib><creatorcontrib>Mitrović, Ana</creatorcontrib><creatorcontrib>Pišlar, Anja</creatorcontrib><creatorcontrib>Kos, Janko</creatorcontrib><creatorcontrib>Gobec, Stanislav</creatorcontrib><collection>CrossRef</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Knez, Damijan</au><au>Sosič, Izidor</au><au>Mitrović, Ana</au><au>Pišlar, Anja</au><au>Kos, Janko</au><au>Gobec, Stanislav</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>8-Hydroxyquinoline-based anti-Alzheimer multimodal agents</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><date>2020-07-01</date><risdate>2020</risdate><volume>151</volume><issue>7</issue><spage>1111</spage><epage>1120</epage><pages>1111-1120</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>The concept of multitarget-directed ligands (MTDLs) has attracted considerable interest in the development of agents against Alzheimer’s disease. Cathepsin B, a cysteine protease, and butyrylcholinesterase, a serine hydrolase, play important function in the development and progression of Alzheimer’s disease. We present herein the evaluation of 8-hydroxyquinoline-based analogues with activities against butyrylcholinesterase and β-secretase activity of cathepsin B. Furthermore, inhibition of amyloid β aggregation, chelation of copper and zinc ions coupled with antioxidative properties and safe cytotoxicity profile of (
1R
,
2S
)-
N
-ethyl-2-[[(8-hydroxy-5-nitroquinolin-7-yl)methyl]amino]cyclohexane-1-carboxamide suggest that this derivative is a good starting point for optimization towards an effective multifunctional ligand.
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| subjects | Analytical Chemistry Cathepsin B Chelation Chemistry Chemistry and Materials Science Chemistry/Food Science Cyclohexane Hydroxyquinoline Inorganic Chemistry Ligands Optimization Organic Chemistry Original Paper Physical Chemistry Theoretical and Computational Chemistry Toxicity |
| title | 8-Hydroxyquinoline-based anti-Alzheimer multimodal agents |
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