Antinociceptive properties of caffeic acid derivatives in mice
Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID 50 value of 15.1 (11.9–19.1) μmol/kg an...
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| Veröffentlicht in: | European journal of medicinal chemistry 2009-11, Vol.44 (11), p.4596-4602 |
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| container_title | European journal of medicinal chemistry |
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| creator | de Campos Buzzi, Fátima Franzoi, Caroline Liandra Antonini, Graziele Fracasso, Mauricio Filho, Valdir Cechinel Yunes, Rosendo Augusto Niero, Rivaldo |
| description | Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID
50 value of 15.1 (11.9–19.1)
μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.
[Display omitted] Caffeic acid derivatives have been synthesized and tested for their antinociceptive activity in different models of pain and compared with some drugs used clinically. Some structural aspects are also discussed. |
| doi_str_mv | 10.1016/j.ejmech.2009.06.029 |
| format | Article |
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50 value of 15.1 (11.9–19.1)
μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.
[Display omitted] Caffeic acid derivatives have been synthesized and tested for their antinociceptive activity in different models of pain and compared with some drugs used clinically. Some structural aspects are also discussed.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2009.06.029</identifier><identifier>PMID: 19628311</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Analgesics ; Analgesics - chemistry ; Analgesics - therapeutic use ; Animals ; Antinociceptive action ; Biological and medical sciences ; Caffeic acid derivatives ; Caffeic Acids - chemistry ; Caffeic Acids - therapeutic use ; Medical sciences ; Mice ; Molecular Structure ; Neuropharmacology ; Pain - chemically induced ; Pain - drug therapy ; Pharmacology. Drug treatments ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2009-11, Vol.44 (11), p.4596-4602</ispartof><rights>2009 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c462t-fb075158553807ef9de18b58c679b6c963869575bf2ef9fdfd3a7484aa58c4483</citedby><cites>FETCH-LOGICAL-c462t-fb075158553807ef9de18b58c679b6c963869575bf2ef9fdfd3a7484aa58c4483</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2009.06.029$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22124214$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19628311$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>de Campos Buzzi, Fátima</creatorcontrib><creatorcontrib>Franzoi, Caroline Liandra</creatorcontrib><creatorcontrib>Antonini, Graziele</creatorcontrib><creatorcontrib>Fracasso, Mauricio</creatorcontrib><creatorcontrib>Filho, Valdir Cechinel</creatorcontrib><creatorcontrib>Yunes, Rosendo Augusto</creatorcontrib><creatorcontrib>Niero, Rivaldo</creatorcontrib><title>Antinociceptive properties of caffeic acid derivatives in mice</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID
50 value of 15.1 (11.9–19.1)
μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.
[Display omitted] Caffeic acid derivatives have been synthesized and tested for their antinociceptive activity in different models of pain and compared with some drugs used clinically. Some structural aspects are also discussed.</description><subject>Analgesics</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - therapeutic use</subject><subject>Animals</subject><subject>Antinociceptive action</subject><subject>Biological and medical sciences</subject><subject>Caffeic acid derivatives</subject><subject>Caffeic Acids - chemistry</subject><subject>Caffeic Acids - therapeutic use</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>Pain - chemically induced</subject><subject>Pain - drug therapy</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1rGzEQhkVJqB23_6CUvYScdjP61l4MIaRpwZBLehZa7YjKeHcdaW3ov4-MTXrraQ7zvDMvDyHfKDQUqLrfNrgd0P9pGEDbgGqAtZ_Ikmplas6kuCJLYIzXknGxIDc5bwFAKoDPZEFbxQyndEnWD-Mcx8lHj_s5HrHap2mPaY6YqylU3oWA0VfOx77qMcWjO1G5imM1lMwXch3cLuPXy1yR3z-eXh9_1puX51-PD5vaC8XmOnSgJZVGSm5AY2h7pKaTxivddsq3ihvVSi27wMoy9KHnTgsjnCuMEIavyN35bqn3dsA82yFmj7udG3E6ZKu5AG1argspzqRPU84Jg92nOLj011KwJ3F2a8_i7EmcBWWLuBL7fnlw6Abs_4UupgpwewFc9m4Xkht9zB8cY5QJRkXh1mcOi45jxGSzjzh67GNCP9t-iv9v8g7rgYzf</recordid><startdate>20091101</startdate><enddate>20091101</enddate><creator>de Campos Buzzi, Fátima</creator><creator>Franzoi, Caroline Liandra</creator><creator>Antonini, Graziele</creator><creator>Fracasso, Mauricio</creator><creator>Filho, Valdir Cechinel</creator><creator>Yunes, Rosendo Augusto</creator><creator>Niero, Rivaldo</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20091101</creationdate><title>Antinociceptive properties of caffeic acid derivatives in mice</title><author>de Campos Buzzi, Fátima ; Franzoi, Caroline Liandra ; Antonini, Graziele ; Fracasso, Mauricio ; Filho, Valdir Cechinel ; Yunes, Rosendo Augusto ; Niero, Rivaldo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c462t-fb075158553807ef9de18b58c679b6c963869575bf2ef9fdfd3a7484aa58c4483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Analgesics</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - therapeutic use</topic><topic>Animals</topic><topic>Antinociceptive action</topic><topic>Biological and medical sciences</topic><topic>Caffeic acid derivatives</topic><topic>Caffeic Acids - chemistry</topic><topic>Caffeic Acids - therapeutic use</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Neuropharmacology</topic><topic>Pain - chemically induced</topic><topic>Pain - drug therapy</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>de Campos Buzzi, Fátima</creatorcontrib><creatorcontrib>Franzoi, Caroline Liandra</creatorcontrib><creatorcontrib>Antonini, Graziele</creatorcontrib><creatorcontrib>Fracasso, Mauricio</creatorcontrib><creatorcontrib>Filho, Valdir Cechinel</creatorcontrib><creatorcontrib>Yunes, Rosendo Augusto</creatorcontrib><creatorcontrib>Niero, Rivaldo</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>de Campos Buzzi, Fátima</au><au>Franzoi, Caroline Liandra</au><au>Antonini, Graziele</au><au>Fracasso, Mauricio</au><au>Filho, Valdir Cechinel</au><au>Yunes, Rosendo Augusto</au><au>Niero, Rivaldo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antinociceptive properties of caffeic acid derivatives in mice</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2009-11-01</date><risdate>2009</risdate><volume>44</volume><issue>11</issue><spage>4596</spage><epage>4602</epage><pages>4596-4602</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID
50 value of 15.1 (11.9–19.1)
μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.
[Display omitted] Caffeic acid derivatives have been synthesized and tested for their antinociceptive activity in different models of pain and compared with some drugs used clinically. Some structural aspects are also discussed.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>19628311</pmid><doi>10.1016/j.ejmech.2009.06.029</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2009-11, Vol.44 (11), p.4596-4602 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Analgesics Analgesics - chemistry Analgesics - therapeutic use Animals Antinociceptive action Biological and medical sciences Caffeic acid derivatives Caffeic Acids - chemistry Caffeic Acids - therapeutic use Medical sciences Mice Molecular Structure Neuropharmacology Pain - chemically induced Pain - drug therapy Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Antinociceptive properties of caffeic acid derivatives in mice |
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