Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents
Stellatin ( 4), isolated from Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibitio...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-03, Vol.21 (6), p.1612-1616 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Gautam, Raju Jachak, Sanjay M. Kumar, Vivek Mohan, C. Gopi |
| description | Stellatin (
4), isolated from
Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and,
17 and
21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5
mg/ear. The derivatives were further evaluated for antioxidant activity wherein
16 and
17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors. |
| doi_str_mv | 10.1016/j.bmcl.2011.01.116 |
| format | Article |
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4), isolated from
Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and,
17 and
21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5
mg/ear. The derivatives were further evaluated for antioxidant activity wherein
16 and
17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.01.116</identifier><identifier>PMID: 21345672</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>active sites ; Animals ; Anti-inflammatory ; anti-inflammatory activity ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - pharmacology ; Antioxidant ; antioxidant activity ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Catalytic Domain ; Chromones ; Coumarins - chemistry ; Coumarins - pharmacology ; Cyclooxygenase (COX)-1 and -2 ; Cyclooxygenase Inhibitors - chemistry ; Cyclooxygenase Inhibitors - pharmacology ; ears ; edema ; free radical scavengers ; free radicals ; indomethacin ; Medical sciences ; Mice ; Models, Molecular ; Molecular docking ; Pharmacology. Drug treatments ; prostaglandin synthase ; Stellatin</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1612-1616</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-d1cc2ccea11d94ac4a48e329749bfebabeb507dc7974cb8a749f4f71da17b7c13</citedby><cites>FETCH-LOGICAL-c441t-d1cc2ccea11d94ac4a48e329749bfebabeb507dc7974cb8a749f4f71da17b7c13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2011.01.116$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23965631$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21345672$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gautam, Raju</creatorcontrib><creatorcontrib>Jachak, Sanjay M.</creatorcontrib><creatorcontrib>Kumar, Vivek</creatorcontrib><creatorcontrib>Mohan, C. Gopi</creatorcontrib><title>Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Stellatin (
4), isolated from
Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and,
17 and
21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5
mg/ear. The derivatives were further evaluated for antioxidant activity wherein
16 and
17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors.</description><subject>active sites</subject><subject>Animals</subject><subject>Anti-inflammatory</subject><subject>anti-inflammatory activity</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Antioxidant</subject><subject>antioxidant activity</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Catalytic Domain</subject><subject>Chromones</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - pharmacology</subject><subject>Cyclooxygenase (COX)-1 and -2</subject><subject>Cyclooxygenase Inhibitors - chemistry</subject><subject>Cyclooxygenase Inhibitors - pharmacology</subject><subject>ears</subject><subject>edema</subject><subject>free radical scavengers</subject><subject>free radicals</subject><subject>indomethacin</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Molecular docking</subject><subject>Pharmacology. Drug treatments</subject><subject>prostaglandin synthase</subject><subject>Stellatin</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFks1u1DAQxyMEokvhBTiAL6ggNYsncZKNxKVa8SVV6qFU6s2a2JOtF8cudrJi34ZHxWEXuMFpRuPffP6dZc-BL4FD_Xa77AZllwUHWHJYAtQPsgWIWuSl4NXDbMHbmuerVtyeZE9i3HIOggvxODspoBRV3RSL7Mf13o13FE08Z53x1m-MQstoh3bC0XjH0Gk2eEtqshiY9uqrcRsWx0kbisz3ySVrE-uYpmB2ydulB4xM7ZX1_vt-Qw4jsdfrq9scztlsijfMuDvTmdGH-KsFutHkxvUWhwFTdM8w5Y3xafaoRxvp2dGeZjcf3n9Zf8ovrz5-Xl9c5koIGHMNShVKEQLoVqASKFZUFm0j2q6nDjvqKt5o1aSI6laY4r3oG9AITdcoKE-zs0Pd--C_TRRHOZio5s0c-SnKljdQrVpe_ZdcVVWbLl_UiSwOpAo-xkC9vA9mwLCXwOUsodzKWUI5Syg5yCRhSnpxLD91A-k_Kb81S8CrI4AxadUHdMrEv1zZ1lVdzhu9PHA9eombkJib69SpSv9gLiUS8e5AUDrszlCQURlyirQJpEapvfnXpD8BXXPGgw</recordid><startdate>20110315</startdate><enddate>20110315</enddate><creator>Gautam, Raju</creator><creator>Jachak, Sanjay M.</creator><creator>Kumar, Vivek</creator><creator>Mohan, C. Gopi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110315</creationdate><title>Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents</title><author>Gautam, Raju ; Jachak, Sanjay M. ; Kumar, Vivek ; Mohan, C. Gopi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-d1cc2ccea11d94ac4a48e329749bfebabeb507dc7974cb8a749f4f71da17b7c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>active sites</topic><topic>Animals</topic><topic>Anti-inflammatory</topic><topic>anti-inflammatory activity</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Antioxidant</topic><topic>antioxidant activity</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Catalytic Domain</topic><topic>Chromones</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - pharmacology</topic><topic>Cyclooxygenase (COX)-1 and -2</topic><topic>Cyclooxygenase Inhibitors - chemistry</topic><topic>Cyclooxygenase Inhibitors - pharmacology</topic><topic>ears</topic><topic>edema</topic><topic>free radical scavengers</topic><topic>free radicals</topic><topic>indomethacin</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Molecular docking</topic><topic>Pharmacology. Drug treatments</topic><topic>prostaglandin synthase</topic><topic>Stellatin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gautam, Raju</creatorcontrib><creatorcontrib>Jachak, Sanjay M.</creatorcontrib><creatorcontrib>Kumar, Vivek</creatorcontrib><creatorcontrib>Mohan, C. 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4), isolated from
Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and,
17 and
21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5
mg/ear. The derivatives were further evaluated for antioxidant activity wherein
16 and
17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21345672</pmid><doi>10.1016/j.bmcl.2011.01.116</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1612-1616 |
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| subjects | active sites Animals Anti-inflammatory anti-inflammatory activity Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Antioxidant antioxidant activity Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Catalytic Domain Chromones Coumarins - chemistry Coumarins - pharmacology Cyclooxygenase (COX)-1 and -2 Cyclooxygenase Inhibitors - chemistry Cyclooxygenase Inhibitors - pharmacology ears edema free radical scavengers free radicals indomethacin Medical sciences Mice Models, Molecular Molecular docking Pharmacology. Drug treatments prostaglandin synthase Stellatin |
| title | Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents |
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