Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of N-Palmitoylethanolamine- Selective Acid Amidase
Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of “N-palmitoylethanolamine hydrolase” described so far. These compounds are devo...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-10, Vol.46 (21), p.4373-4376 |
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| container_issue | 21 |
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| container_title | Journal of medicinal chemistry |
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| creator | Vandevoorde, Séverine Tsuboi, Kazuhito Ueda, Natsuo Jonsson, Kent-Olov Fowler, Christopher J Lambert, Didier M |
| description | Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of “N-palmitoylethanolamine hydrolase” described so far. These compounds are devoid of affinity for CB1 and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide. |
| doi_str_mv | 10.1021/jm0340795 |
| format | Article |
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These compounds are devoid of affinity for CB1 and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0340795</identifier><identifier>PMID: 14521402</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amides - chemical synthesis ; Amides - pharmacology ; Amidohydrolases - antagonists & inhibitors ; Analytical, structural and metabolic biochemistry ; Animals ; Arachidonic Acids - metabolism ; Benzoxazines ; Binding, Competitive - drug effects ; Biological and medical sciences ; Brain - drug effects ; Brain - enzymology ; Calcium Channel Blockers - metabolism ; CHO Cells ; Cricetinae ; Cyclohexanols - metabolism ; Endocannabinoids ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - metabolism ; Enzyme Inhibitors - pharmacology ; Enzymes and enzyme inhibitors ; Esters - chemical synthesis ; Esters - pharmacology ; Fundamental and applied biological sciences. Psychology ; Humans ; Hydrolases ; Indicators and Reagents ; Lung - drug effects ; Lung - enzymology ; Medical sciences ; Miscellaneous ; Morpholines - metabolism ; Naphthalenes - metabolism ; Palmitates - chemical synthesis ; Palmitates - metabolism ; Palmitates - pharmacology ; Pharmacology. 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Med. Chem</addtitle><description>Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of “N-palmitoylethanolamine hydrolase” described so far. These compounds are devoid of affinity for CB1 and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.</description><subject>Amides - chemical synthesis</subject><subject>Amides - pharmacology</subject><subject>Amidohydrolases - antagonists & inhibitors</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>Arachidonic Acids - metabolism</subject><subject>Benzoxazines</subject><subject>Binding, Competitive - drug effects</subject><subject>Biological and medical sciences</subject><subject>Brain - drug effects</subject><subject>Brain - enzymology</subject><subject>Calcium Channel Blockers - metabolism</subject><subject>CHO Cells</subject><subject>Cricetinae</subject><subject>Cyclohexanols - metabolism</subject><subject>Endocannabinoids</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - metabolism</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Esters - chemical synthesis</subject><subject>Esters - pharmacology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Humans</subject><subject>Hydrolases</subject><subject>Indicators and Reagents</subject><subject>Lung - drug effects</subject><subject>Lung - enzymology</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Morpholines - metabolism</subject><subject>Naphthalenes - metabolism</subject><subject>Palmitates - chemical synthesis</subject><subject>Palmitates - metabolism</subject><subject>Palmitates - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Polyunsaturated Alkamides</subject><subject>Rats</subject><subject>Receptor, Cannabinoid, CB2</subject><subject>Receptors, Cannabinoid</subject><subject>Receptors, Drug - drug effects</subject><subject>Receptors, Drug - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAUhS1ERYeBBS-AvAEJqQH_xHHCbjRqZypVENHC1nKcG40HJ27tDKKvwRPjUaIOC1bWtb9zru89CL2h5CMljH7a94TnRFbiGVpQwUiWlyR_jhaEMJaxgvFz9DLGPSGEU8ZfoHOaC0Zzwhboz2UcIcQL_A3G4GEu9NBiPV3p3raAfYdr7Xo7WoNXxrafce29w50PeNwBvrIhjvgWHJjR_gJ8PexsY0cf4lH5JZu0_tHBuNODd8l0gOwfwdETr1IrHeEVOuu0i_B6Ppfo-9Xl3Xqb3XzdXK9XN5nOczFmhSwaLgvGyoY0wIgBJk0leNWBoLqscsJLLllTQslEQjstm6osqspo0laM8SV6P_neB_9wSKOr3kYDzukB_CEqKSSnVBYJ_DCBJvgYA3TqPtheh0dFiToGoJ4CSOzb2fTQ9NCeyHnjCXg3Azoa7bqgB2PjiUvxMZI6L1E2cTZl8vvpXYefqpBcCnVX36r1tt7U2x8bVZx8tYlq7w9hSLv7zwf_AmWKp_Y</recordid><startdate>20031009</startdate><enddate>20031009</enddate><creator>Vandevoorde, Séverine</creator><creator>Tsuboi, Kazuhito</creator><creator>Ueda, Natsuo</creator><creator>Jonsson, Kent-Olov</creator><creator>Fowler, Christopher J</creator><creator>Lambert, Didier M</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>20031009</creationdate><title>Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of N-Palmitoylethanolamine- Selective Acid Amidase</title><author>Vandevoorde, Séverine ; Tsuboi, Kazuhito ; Ueda, Natsuo ; Jonsson, Kent-Olov ; Fowler, Christopher J ; Lambert, Didier M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-676b376228b0be20ce27c9539fe51a894038372b8e8256b3fa7b98699ca0d9223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amides - chemical synthesis</topic><topic>Amides - pharmacology</topic><topic>Amidohydrolases - antagonists & inhibitors</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Animals</topic><topic>Arachidonic Acids - metabolism</topic><topic>Benzoxazines</topic><topic>Binding, Competitive - drug effects</topic><topic>Biological and medical sciences</topic><topic>Brain - drug effects</topic><topic>Brain - enzymology</topic><topic>Calcium Channel Blockers - metabolism</topic><topic>CHO Cells</topic><topic>Cricetinae</topic><topic>Cyclohexanols - metabolism</topic><topic>Endocannabinoids</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - metabolism</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Esters - chemical synthesis</topic><topic>Esters - pharmacology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Humans</topic><topic>Hydrolases</topic><topic>Indicators and Reagents</topic><topic>Lung - drug effects</topic><topic>Lung - enzymology</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Morpholines - metabolism</topic><topic>Naphthalenes - metabolism</topic><topic>Palmitates - chemical synthesis</topic><topic>Palmitates - metabolism</topic><topic>Palmitates - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Polyunsaturated Alkamides</topic><topic>Rats</topic><topic>Receptor, Cannabinoid, CB2</topic><topic>Receptors, Cannabinoid</topic><topic>Receptors, Drug - drug effects</topic><topic>Receptors, Drug - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vandevoorde, Séverine</creatorcontrib><creatorcontrib>Tsuboi, Kazuhito</creatorcontrib><creatorcontrib>Ueda, Natsuo</creatorcontrib><creatorcontrib>Jonsson, Kent-Olov</creatorcontrib><creatorcontrib>Fowler, Christopher J</creatorcontrib><creatorcontrib>Lambert, Didier M</creatorcontrib><collection>Istex</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vandevoorde, Séverine</au><au>Tsuboi, Kazuhito</au><au>Ueda, Natsuo</au><au>Jonsson, Kent-Olov</au><au>Fowler, Christopher J</au><au>Lambert, Didier M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of N-Palmitoylethanolamine- Selective Acid Amidase</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2003-10-09</date><risdate>2003</risdate><volume>46</volume><issue>21</issue><spage>4373</spage><epage>4376</epage><pages>4373-4376</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of “N-palmitoylethanolamine hydrolase” described so far. These compounds are devoid of affinity for CB1 and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14521402</pmid><doi>10.1021/jm0340795</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2003-10, Vol.46 (21), p.4373-4376 |
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| subjects | Amides - chemical synthesis Amides - pharmacology Amidohydrolases - antagonists & inhibitors Analytical, structural and metabolic biochemistry Animals Arachidonic Acids - metabolism Benzoxazines Binding, Competitive - drug effects Biological and medical sciences Brain - drug effects Brain - enzymology Calcium Channel Blockers - metabolism CHO Cells Cricetinae Cyclohexanols - metabolism Endocannabinoids Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - metabolism Enzyme Inhibitors - pharmacology Enzymes and enzyme inhibitors Esters - chemical synthesis Esters - pharmacology Fundamental and applied biological sciences. Psychology Humans Hydrolases Indicators and Reagents Lung - drug effects Lung - enzymology Medical sciences Miscellaneous Morpholines - metabolism Naphthalenes - metabolism Palmitates - chemical synthesis Palmitates - metabolism Palmitates - pharmacology Pharmacology. Drug treatments Polyunsaturated Alkamides Rats Receptor, Cannabinoid, CB2 Receptors, Cannabinoid Receptors, Drug - drug effects Receptors, Drug - metabolism |
| title | Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of N-Palmitoylethanolamine- Selective Acid Amidase |
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