Convolutamydine A and synthetic analogues have antinociceptive properties in mice
Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues. Convolutamydine A and the two analogues were given orally to assess their ab...
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| Veröffentlicht in: | Pharmacology, biochemistry and behavior biochemistry and behavior, 2013-01, Vol.103 (3), p.431-439 |
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| creator | Figueiredo, Gabriela S.M. Zardo, Renata S. Silva, Bárbara V. Violante, Flávio A. Pinto, Angelo C. Fernandes, Patricia D. |
| description | Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues.
Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues.
Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug.
In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.
► Convolutamydine A and two analogues were evaluated in nociceptive models. ► Substances demonstrated peripheral antinociceptive effects. ► A supraspinal analgesic effect was observed in the hot plate model. ► The effects of convolutamydine A are mediated by all three systems. ► Analogues action involves the cholinergic and nitric oxide systems. |
| doi_str_mv | 10.1016/j.pbb.2012.09.023 |
| format | Article |
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Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues.
Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug.
In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.
► Convolutamydine A and two analogues were evaluated in nociceptive models. ► Substances demonstrated peripheral antinociceptive effects. ► A supraspinal analgesic effect was observed in the hot plate model. ► The effects of convolutamydine A are mediated by all three systems. ► Analogues action involves the cholinergic and nitric oxide systems.</description><identifier>ISSN: 0091-3057</identifier><identifier>EISSN: 1873-5177</identifier><identifier>DOI: 10.1016/j.pbb.2012.09.023</identifier><identifier>PMID: 23046852</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Analgesia ; Analgesics - adverse effects ; Analgesics - chemical synthesis ; Analgesics - pharmacology ; Analgesics - therapeutic use ; Animals ; Antinociceptive activity ; Behavior, Animal - drug effects ; Convolutamydine ; Disease Models, Animal ; Dose-Response Relationship, Drug ; Female ; Isatin ; Isatin - adverse effects ; Isatin - analogs & derivatives ; Isatin - pharmacology ; Isatin - therapeutic use ; Male ; Mice ; Motor Activity - drug effects ; Pain ; Pain - drug therapy ; Pain Measurement - drug effects</subject><ispartof>Pharmacology, biochemistry and behavior, 2013-01, Vol.103 (3), p.431-439</ispartof><rights>2012 Elsevier Inc.</rights><rights>Copyright © 2012 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-1f144d928312bd7cd109632e1e828c8bf23c1176926a1f44556b74608c2cd0f23</citedby><cites>FETCH-LOGICAL-c396t-1f144d928312bd7cd109632e1e828c8bf23c1176926a1f44556b74608c2cd0f23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.pbb.2012.09.023$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23046852$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Figueiredo, Gabriela S.M.</creatorcontrib><creatorcontrib>Zardo, Renata S.</creatorcontrib><creatorcontrib>Silva, Bárbara V.</creatorcontrib><creatorcontrib>Violante, Flávio A.</creatorcontrib><creatorcontrib>Pinto, Angelo C.</creatorcontrib><creatorcontrib>Fernandes, Patricia D.</creatorcontrib><title>Convolutamydine A and synthetic analogues have antinociceptive properties in mice</title><title>Pharmacology, biochemistry and behavior</title><addtitle>Pharmacol Biochem Behav</addtitle><description>Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues.
Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues.
Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug.
In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.
► Convolutamydine A and two analogues were evaluated in nociceptive models. ► Substances demonstrated peripheral antinociceptive effects. ► A supraspinal analgesic effect was observed in the hot plate model. ► The effects of convolutamydine A are mediated by all three systems. ► Analogues action involves the cholinergic and nitric oxide systems.</description><subject>Analgesia</subject><subject>Analgesics - adverse effects</subject><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - pharmacology</subject><subject>Analgesics - therapeutic use</subject><subject>Animals</subject><subject>Antinociceptive activity</subject><subject>Behavior, Animal - drug effects</subject><subject>Convolutamydine</subject><subject>Disease Models, Animal</subject><subject>Dose-Response Relationship, Drug</subject><subject>Female</subject><subject>Isatin</subject><subject>Isatin - adverse effects</subject><subject>Isatin - analogs & derivatives</subject><subject>Isatin - pharmacology</subject><subject>Isatin - therapeutic use</subject><subject>Male</subject><subject>Mice</subject><subject>Motor Activity - drug effects</subject><subject>Pain</subject><subject>Pain - drug therapy</subject><subject>Pain Measurement - drug effects</subject><issn>0091-3057</issn><issn>1873-5177</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LxDAQhoMoun78AC_So5fWmaRNWjzJ4hcIIug5tMlUs_TLJruw_97IqkdPwzvzzsvMw9g5QoaA8mqVTU2TcUCeQZUBF3tsgaUSaYFK7bMFQIWpgEIdsWPvVwCQc6kO2REXkMuy4Av2shyHzditQ91vrRsouUnqwSZ-O4QPCs5EVXfj-5p88lFvKMrghtE4Q1NwUU_zONEcXJy7Ielj_5QdtHXn6eynnrC3u9vX5UP69Hz_uLx5So2oZEixxTy3FS8F8sYqYxEqKTghlbw0ZdNyYRCVrLissc3zopCNyiWUhhsLcXrCLne58YTPeF_QvfOGuq4eaFx7jVyJAlGqPFpxZzXz6P1MrZ5m19fzViPob5J6pSNJ_U1SQ6Ujybhz8RO_bnqyfxu_6KLhemeg-OTG0ay9cTQYsm4mE7Qd3T_xX1SLg2o</recordid><startdate>201301</startdate><enddate>201301</enddate><creator>Figueiredo, Gabriela S.M.</creator><creator>Zardo, Renata S.</creator><creator>Silva, Bárbara V.</creator><creator>Violante, Flávio A.</creator><creator>Pinto, Angelo C.</creator><creator>Fernandes, Patricia D.</creator><general>Elsevier Inc</general><scope>6I.</scope><scope>AAFTH</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>201301</creationdate><title>Convolutamydine A and synthetic analogues have antinociceptive properties in mice</title><author>Figueiredo, Gabriela S.M. ; Zardo, Renata S. ; Silva, Bárbara V. ; Violante, Flávio A. ; Pinto, Angelo C. ; Fernandes, Patricia D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-1f144d928312bd7cd109632e1e828c8bf23c1176926a1f44556b74608c2cd0f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Analgesia</topic><topic>Analgesics - adverse effects</topic><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - pharmacology</topic><topic>Analgesics - therapeutic use</topic><topic>Animals</topic><topic>Antinociceptive activity</topic><topic>Behavior, Animal - drug effects</topic><topic>Convolutamydine</topic><topic>Disease Models, Animal</topic><topic>Dose-Response Relationship, Drug</topic><topic>Female</topic><topic>Isatin</topic><topic>Isatin - adverse effects</topic><topic>Isatin - analogs & derivatives</topic><topic>Isatin - pharmacology</topic><topic>Isatin - therapeutic use</topic><topic>Male</topic><topic>Mice</topic><topic>Motor Activity - drug effects</topic><topic>Pain</topic><topic>Pain - drug therapy</topic><topic>Pain Measurement - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Figueiredo, Gabriela S.M.</creatorcontrib><creatorcontrib>Zardo, Renata S.</creatorcontrib><creatorcontrib>Silva, Bárbara V.</creatorcontrib><creatorcontrib>Violante, Flávio A.</creatorcontrib><creatorcontrib>Pinto, Angelo C.</creatorcontrib><creatorcontrib>Fernandes, Patricia D.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>Pharmacology, biochemistry and behavior</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Figueiredo, Gabriela S.M.</au><au>Zardo, Renata S.</au><au>Silva, Bárbara V.</au><au>Violante, Flávio A.</au><au>Pinto, Angelo C.</au><au>Fernandes, Patricia D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Convolutamydine A and synthetic analogues have antinociceptive properties in mice</atitle><jtitle>Pharmacology, biochemistry and behavior</jtitle><addtitle>Pharmacol Biochem Behav</addtitle><date>2013-01</date><risdate>2013</risdate><volume>103</volume><issue>3</issue><spage>431</spage><epage>439</epage><pages>431-439</pages><issn>0091-3057</issn><eissn>1873-5177</eissn><abstract>Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues.
Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues.
Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug.
In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.
► Convolutamydine A and two analogues were evaluated in nociceptive models. ► Substances demonstrated peripheral antinociceptive effects. ► A supraspinal analgesic effect was observed in the hot plate model. ► The effects of convolutamydine A are mediated by all three systems. ► Analogues action involves the cholinergic and nitric oxide systems.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>23046852</pmid><doi>10.1016/j.pbb.2012.09.023</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Analgesia Analgesics - adverse effects Analgesics - chemical synthesis Analgesics - pharmacology Analgesics - therapeutic use Animals Antinociceptive activity Behavior, Animal - drug effects Convolutamydine Disease Models, Animal Dose-Response Relationship, Drug Female Isatin Isatin - adverse effects Isatin - analogs & derivatives Isatin - pharmacology Isatin - therapeutic use Male Mice Motor Activity - drug effects Pain Pain - drug therapy Pain Measurement - drug effects |
| title | Convolutamydine A and synthetic analogues have antinociceptive properties in mice |
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