Potential anti-inflammatory actions of the elmiric (lipoamino) acids
A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and tested for their possible use as anti-inflammatory agents. The compounds were assayed in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-05, Vol.15 (10), p.3345-3355 |
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| creator | Burstein, Sumner H. Adams, Jeffrey K. Bradshaw, Heather B. Fraioli, Cristian Rossetti, Ronald G. Salmonsen, Rebecca A. Shaw, John W. Walker, J. Michael Zipkin, Robert E. Zurier, Robert B. |
| description | A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and tested for their possible use as anti-inflammatory agents. The compounds were assayed in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation.
A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ
2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the
J series predominates over the
E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them. |
| doi_str_mv | 10.1016/j.bmc.2007.03.026 |
| format | Article |
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A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ
2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the
J series predominates over the
E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.03.026</identifier><identifier>PMID: 17383881</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alanine - chemistry ; Animals ; Anti-inflammatory ; Anti-Inflammatory Agents ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cell Line ; Cell Proliferation - drug effects ; Chromatography, Thin Layer ; Drug Evaluation, Preclinical ; Ear edema ; Edema - chemically induced ; Edema - prevention & control ; Endocannabinoid ; Fatty Acids - chemistry ; Glycine - chemistry ; Indicators and Reagents ; Macrophages - drug effects ; Magnetic Resonance Spectroscopy ; Male ; Medical sciences ; Mice ; Pharmacology. Drug treatments ; Phorbol Esters ; Prostaglandin ; Prostaglandin Antagonists - chemical synthesis ; Prostaglandin Antagonists - pharmacology ; Spectrophotometry, Ultraviolet ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2007-05, Vol.15 (10), p.3345-3355</ispartof><rights>2007 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c479t-9912d318d5e75152af661f77dda8896f1506c4b004865aa2c78aa0df2d82e0f63</citedby><cites>FETCH-LOGICAL-c479t-9912d318d5e75152af661f77dda8896f1506c4b004865aa2c78aa0df2d82e0f63</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.2007.03.026$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,315,781,785,886,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18683672$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17383881$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Burstein, Sumner H.</creatorcontrib><creatorcontrib>Adams, Jeffrey K.</creatorcontrib><creatorcontrib>Bradshaw, Heather B.</creatorcontrib><creatorcontrib>Fraioli, Cristian</creatorcontrib><creatorcontrib>Rossetti, Ronald G.</creatorcontrib><creatorcontrib>Salmonsen, Rebecca A.</creatorcontrib><creatorcontrib>Shaw, John W.</creatorcontrib><creatorcontrib>Walker, J. Michael</creatorcontrib><creatorcontrib>Zipkin, Robert E.</creatorcontrib><creatorcontrib>Zurier, Robert B.</creatorcontrib><title>Potential anti-inflammatory actions of the elmiric (lipoamino) acids</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and tested for their possible use as anti-inflammatory agents. The compounds were assayed in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation.
A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ
2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the
J series predominates over the
E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.</description><subject>Alanine - chemistry</subject><subject>Animals</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cell Line</subject><subject>Cell Proliferation - drug effects</subject><subject>Chromatography, Thin Layer</subject><subject>Drug Evaluation, Preclinical</subject><subject>Ear edema</subject><subject>Edema - chemically induced</subject><subject>Edema - prevention & control</subject><subject>Endocannabinoid</subject><subject>Fatty Acids - chemistry</subject><subject>Glycine - chemistry</subject><subject>Indicators and Reagents</subject><subject>Macrophages - drug effects</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Phorbol Esters</subject><subject>Prostaglandin</subject><subject>Prostaglandin Antagonists - chemical synthesis</subject><subject>Prostaglandin Antagonists - pharmacology</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9r3DAQxUVpSTZpP0AvxZdCc7A7I9myTCFQ0qQtBJJDexaz-tNosa1FcgL59tWyS5JeenqHee_N48fYe4QGAeXnTbOeTMMB-gZEA1y-YitsZVsLMeBrtoJBqhrUII_ZSc4bAODtgEfsGHuhhFK4Yt9u4-LmJdBYUZE6zH6kaaIlpseKzBLinKvoq-XOVW6cQgqm-jSGbaQpzPGsWILNb9kbT2N27w56yn5fXf66-FFf33z_efH1ujZtPyz1MCC3ApXtXN9hx8lLib7vrSVVRnrsQJp2DdAq2RFx0ysisJ5bxR14KU7Z-b53e7-enDVleKJRb1OYKD3qSEH_e5nDnf4THzSWegReCnBfYFLMOTn_lEXQO6R6owtSvUOqQeiCtGQ-vHz6nDgwLIaPBwNlQ6NPNJuQn31KKiH73fMve58riB6CSzqb4GbjbEjOLNrG8J8ZfwGT3ZTW</recordid><startdate>20070515</startdate><enddate>20070515</enddate><creator>Burstein, Sumner H.</creator><creator>Adams, Jeffrey K.</creator><creator>Bradshaw, Heather B.</creator><creator>Fraioli, Cristian</creator><creator>Rossetti, Ronald G.</creator><creator>Salmonsen, Rebecca A.</creator><creator>Shaw, John W.</creator><creator>Walker, J. Michael</creator><creator>Zipkin, Robert E.</creator><creator>Zurier, Robert B.</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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>5PM</scope></search><sort><creationdate>20070515</creationdate><title>Potential anti-inflammatory actions of the elmiric (lipoamino) acids</title><author>Burstein, Sumner H. ; Adams, Jeffrey K. ; Bradshaw, Heather B. ; Fraioli, Cristian ; Rossetti, Ronald G. ; Salmonsen, Rebecca A. ; Shaw, John W. ; Walker, J. Michael ; Zipkin, Robert E. ; Zurier, Robert B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c479t-9912d318d5e75152af661f77dda8896f1506c4b004865aa2c78aa0df2d82e0f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Alanine - chemistry</topic><topic>Animals</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cell Line</topic><topic>Cell Proliferation - drug effects</topic><topic>Chromatography, Thin Layer</topic><topic>Drug Evaluation, Preclinical</topic><topic>Ear edema</topic><topic>Edema - chemically induced</topic><topic>Edema - prevention & control</topic><topic>Endocannabinoid</topic><topic>Fatty Acids - chemistry</topic><topic>Glycine - chemistry</topic><topic>Indicators and Reagents</topic><topic>Macrophages - drug effects</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Phorbol Esters</topic><topic>Prostaglandin</topic><topic>Prostaglandin Antagonists - chemical synthesis</topic><topic>Prostaglandin Antagonists - pharmacology</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burstein, Sumner H.</creatorcontrib><creatorcontrib>Adams, Jeffrey K.</creatorcontrib><creatorcontrib>Bradshaw, Heather B.</creatorcontrib><creatorcontrib>Fraioli, Cristian</creatorcontrib><creatorcontrib>Rossetti, Ronald G.</creatorcontrib><creatorcontrib>Salmonsen, Rebecca A.</creatorcontrib><creatorcontrib>Shaw, John W.</creatorcontrib><creatorcontrib>Walker, J. Michael</creatorcontrib><creatorcontrib>Zipkin, Robert E.</creatorcontrib><creatorcontrib>Zurier, Robert B.</creatorcontrib><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>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Burstein, Sumner H.</au><au>Adams, Jeffrey K.</au><au>Bradshaw, Heather B.</au><au>Fraioli, Cristian</au><au>Rossetti, Ronald G.</au><au>Salmonsen, Rebecca A.</au><au>Shaw, John W.</au><au>Walker, J. Michael</au><au>Zipkin, Robert E.</au><au>Zurier, Robert B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potential anti-inflammatory actions of the elmiric (lipoamino) acids</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-05-15</date><risdate>2007</risdate><volume>15</volume><issue>10</issue><spage>3345</spage><epage>3355</epage><pages>3345-3355</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and tested for their possible use as anti-inflammatory agents. The compounds were assayed in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation.
A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ
2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the
J series predominates over the
E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17383881</pmid><doi>10.1016/j.bmc.2007.03.026</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Alanine - chemistry Animals Anti-inflammatory Anti-Inflammatory Agents Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cell Line Cell Proliferation - drug effects Chromatography, Thin Layer Drug Evaluation, Preclinical Ear edema Edema - chemically induced Edema - prevention & control Endocannabinoid Fatty Acids - chemistry Glycine - chemistry Indicators and Reagents Macrophages - drug effects Magnetic Resonance Spectroscopy Male Medical sciences Mice Pharmacology. Drug treatments Phorbol Esters Prostaglandin Prostaglandin Antagonists - chemical synthesis Prostaglandin Antagonists - pharmacology Spectrophotometry, Ultraviolet Structure-Activity Relationship |
| title | Potential anti-inflammatory actions of the elmiric (lipoamino) acids |
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