New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress
We review the original rationale for the development and the chemistry of a series of new synthetic oleanane triterpenoids (SO), based on oleanolic acid (1) as a starting material. Many of the new compounds that have been made, such as 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (“CDDO”, 8), a...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2011-03, Vol.74 (3), p.537-545 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Sporn, Michael B Liby, Karen T Yore, Mark M Fu, Liangfeng Lopchuk, Justin M Gribble, Gordon W |
| description | We review the original rationale for the development and the chemistry of a series of new synthetic oleanane triterpenoids (SO), based on oleanolic acid (1) as a starting material. Many of the new compounds that have been made, such as 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (“CDDO”, 8), are highly potent (activities found at levels below 1 nM) anti-inflammatory agents, as measured by their ability to block the cellular synthesis of the enzyme inducible nitric oxide synthase (iNOS) in activated macrophages. Details of the organic synthesis of new SO and their chemical mechanisms of biological activity are reviewed, as is formation of biotin conjugates for investigation of protein targets. Finally, we give a brief summary of important biological activities of SO in many organ systems in numerous animal models. Clinical investigation of a new SO (methyl 2-cyano-3,12-dioxooleana-1,9(11)dien-28-oate, “CDDO-Me”, bardoxolone methyl, 13) is currently in progress. |
| doi_str_mv | 10.1021/np100826q |
| format | Article |
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Many of the new compounds that have been made, such as 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (“CDDO”, 8), are highly potent (activities found at levels below 1 nM) anti-inflammatory agents, as measured by their ability to block the cellular synthesis of the enzyme inducible nitric oxide synthase (iNOS) in activated macrophages. Details of the organic synthesis of new SO and their chemical mechanisms of biological activity are reviewed, as is formation of biotin conjugates for investigation of protein targets. Finally, we give a brief summary of important biological activities of SO in many organ systems in numerous animal models. Clinical investigation of a new SO (methyl 2-cyano-3,12-dioxooleana-1,9(11)dien-28-oate, “CDDO-Me”, bardoxolone methyl, 13) is currently in progress.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np100826q</identifier><identifier>PMID: 21309592</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - pharmacology ; Biological and medical sciences ; Medical sciences ; Miscellaneous ; Models, Animal ; Molecular Structure ; Nitric Oxide Synthase Type II - antagonists & inhibitors ; Oleanolic Acid - chemical synthesis ; Oleanolic Acid - chemistry ; Oleanolic Acid - pharmacology ; Oxidative Stress - physiology ; Pharmacology. Drug treatments ; Review ; Soft Tissue Injuries - drug therapy</subject><ispartof>Journal of natural products (Washington, D.C.), 2011-03, Vol.74 (3), p.537-545</ispartof><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a500t-4a386ecf88a760a60dd352bd281b5ec8fea9a266a5b0083932a9cc723c3196053</citedby><cites>FETCH-LOGICAL-a500t-4a386ecf88a760a60dd352bd281b5ec8fea9a266a5b0083932a9cc723c3196053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np100826q$$EPDF$$P50$$Gacs$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np100826q$$EHTML$$P50$$Gacs$$Hfree_for_read</linktohtml><link.rule.ids>230,315,782,786,887,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24024763$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21309592$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sporn, Michael B</creatorcontrib><creatorcontrib>Liby, Karen T</creatorcontrib><creatorcontrib>Yore, Mark M</creatorcontrib><creatorcontrib>Fu, Liangfeng</creatorcontrib><creatorcontrib>Lopchuk, Justin M</creatorcontrib><creatorcontrib>Gribble, Gordon W</creatorcontrib><title>New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>We review the original rationale for the development and the chemistry of a series of new synthetic oleanane triterpenoids (SO), based on oleanolic acid (1) as a starting material. Many of the new compounds that have been made, such as 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (“CDDO”, 8), are highly potent (activities found at levels below 1 nM) anti-inflammatory agents, as measured by their ability to block the cellular synthesis of the enzyme inducible nitric oxide synthase (iNOS) in activated macrophages. Details of the organic synthesis of new SO and their chemical mechanisms of biological activity are reviewed, as is formation of biotin conjugates for investigation of protein targets. Finally, we give a brief summary of important biological activities of SO in many organ systems in numerous animal models. Clinical investigation of a new SO (methyl 2-cyano-3,12-dioxooleana-1,9(11)dien-28-oate, “CDDO-Me”, bardoxolone methyl, 13) is currently in progress.</description><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Models, Animal</subject><subject>Molecular Structure</subject><subject>Nitric Oxide Synthase Type II - antagonists & inhibitors</subject><subject>Oleanolic Acid - chemical synthesis</subject><subject>Oleanolic Acid - chemistry</subject><subject>Oleanolic Acid - pharmacology</subject><subject>Oxidative Stress - physiology</subject><subject>Pharmacology. Drug treatments</subject><subject>Review</subject><subject>Soft Tissue Injuries - drug therapy</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>EIF</sourceid><recordid>eNptkU1v1DAQhi0EokvhwB9AviDEIeCPxJtwQKpWfFSqaKUuZ2viTFqvEntrOwt754fjqMsWJC7-GD_zvuMZQl5y9o4zwd-7LWesFuruEVnwSrBCMVE9JgvGlSxkrcoT8izGDWNMsqZ6Sk4Enw-NWJBf3_AHvd67dIvJGroONmHYovO2ix_olU_oEj27yWukvQ_0KuAuX6x3FFyXeYQ0zozv6drGOCE9d5sp7OkKpogdbfc50A8wjpB8Ds9Zlz9tB8nukF6ngDE-J096GCK-OOyn5PvnT-vV1-Li8sv56uyigIqxVJSQ_4Kmr2tYKgaKdZ2sRNuJmrcVmrpHaEAoBVWb2yEbKaAxZimkkbxRrJKn5OO97nZqR-xMrjvAoLfBjhD22oPV_744e6tv_E5LpkrOyyzw5iAQ_N2EMenRRoPDAA79FHVd1ctaMDlbvb0nTfAxBuyPLpzpeWj6OLTMvvq7rCP5Z0oZeH0AIBoY-gDO2PjAlUyUSyUfODBRb_wUXO7mfwx_A2xqrgI</recordid><startdate>20110325</startdate><enddate>20110325</enddate><creator>Sporn, Michael B</creator><creator>Liby, Karen T</creator><creator>Yore, Mark M</creator><creator>Fu, Liangfeng</creator><creator>Lopchuk, Justin M</creator><creator>Gribble, Gordon W</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>N~.</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>5PM</scope></search><sort><creationdate>20110325</creationdate><title>New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress</title><author>Sporn, Michael B ; Liby, Karen T ; Yore, Mark M ; Fu, Liangfeng ; Lopchuk, Justin M ; Gribble, Gordon W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a500t-4a386ecf88a760a60dd352bd281b5ec8fea9a266a5b0083932a9cc723c3196053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Models, Animal</topic><topic>Molecular Structure</topic><topic>Nitric Oxide Synthase Type II - antagonists & inhibitors</topic><topic>Oleanolic Acid - chemical synthesis</topic><topic>Oleanolic Acid - chemistry</topic><topic>Oleanolic Acid - pharmacology</topic><topic>Oxidative Stress - physiology</topic><topic>Pharmacology. Drug treatments</topic><topic>Review</topic><topic>Soft Tissue Injuries - drug therapy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sporn, Michael B</creatorcontrib><creatorcontrib>Liby, Karen T</creatorcontrib><creatorcontrib>Yore, Mark M</creatorcontrib><creatorcontrib>Fu, Liangfeng</creatorcontrib><creatorcontrib>Lopchuk, Justin M</creatorcontrib><creatorcontrib>Gribble, Gordon W</creatorcontrib><collection>American Chemical Society (ACS) Open Access</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sporn, Michael B</au><au>Liby, Karen T</au><au>Yore, Mark M</au><au>Fu, Liangfeng</au><au>Lopchuk, Justin M</au><au>Gribble, Gordon W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2011-03-25</date><risdate>2011</risdate><volume>74</volume><issue>3</issue><spage>537</spage><epage>545</epage><pages>537-545</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>We review the original rationale for the development and the chemistry of a series of new synthetic oleanane triterpenoids (SO), based on oleanolic acid (1) as a starting material. Many of the new compounds that have been made, such as 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (“CDDO”, 8), are highly potent (activities found at levels below 1 nM) anti-inflammatory agents, as measured by their ability to block the cellular synthesis of the enzyme inducible nitric oxide synthase (iNOS) in activated macrophages. Details of the organic synthesis of new SO and their chemical mechanisms of biological activity are reviewed, as is formation of biotin conjugates for investigation of protein targets. Finally, we give a brief summary of important biological activities of SO in many organ systems in numerous animal models. Clinical investigation of a new SO (methyl 2-cyano-3,12-dioxooleana-1,9(11)dien-28-oate, “CDDO-Me”, bardoxolone methyl, 13) is currently in progress.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21309592</pmid><doi>10.1021/np100826q</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2011-03, Vol.74 (3), p.537-545 |
| issn | 0163-3864 1520-6025 |
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| subjects | Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Biological and medical sciences Medical sciences Miscellaneous Models, Animal Molecular Structure Nitric Oxide Synthase Type II - antagonists & inhibitors Oleanolic Acid - chemical synthesis Oleanolic Acid - chemistry Oleanolic Acid - pharmacology Oxidative Stress - physiology Pharmacology. Drug treatments Review Soft Tissue Injuries - drug therapy |
| title | New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress |
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