Novel X-linked inhibitor of apoptosis protein inhibitors as probes of apoptosis in biology and medicine
We report here a series of new inhibitors of the X-linked inhibitor of apoptosis protein (XIAP protein) based on the SMAC-tetrapeptide AVPI. The structural novelty of these molecules is the presence of the proline mimetic exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, leading to analogs with simi...
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| Veröffentlicht in: | Experimental biology and medicine (Maywood, N.J.) N.J.), 2011-02, Vol.236 (2), p.247-251 |
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| container_title | Experimental biology and medicine (Maywood, N.J.) |
| container_volume | 236 |
| creator | Hu, Qi Nie, Aihua Welsh, Kate Pinacho Crisóstomo, Fernando R Zhu, Xuejun Li, Zhengxiang An, Jing Reed, John C Zhang, Liangren Huang, Ziwei |
| description | We report here a series of new inhibitors of the X-linked inhibitor of apoptosis protein (XIAP protein) based on the SMAC-tetrapeptide AVPI. The structural novelty of these molecules is the presence of the proline mimetic exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, leading to analogs with similar activity to the natural ligand peptide. The structure–activity relationship and computational docking studies support the convenience of this unnatural amino acid as a building block to develop new peptides or small molecules targeting the XIAP-BIR3 domain. |
| doi_str_mv | 10.1258/ebm.2010.010284 |
| format | Article |
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The structural novelty of these molecules is the presence of the proline mimetic exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, leading to analogs with similar activity to the natural ligand peptide. The structure–activity relationship and computational docking studies support the convenience of this unnatural amino acid as a building block to develop new peptides or small molecules targeting the XIAP-BIR3 domain.</description><identifier>ISSN: 1535-3702</identifier><identifier>EISSN: 1535-3699</identifier><identifier>DOI: 10.1258/ebm.2010.010284</identifier><identifier>PMID: 21321323</identifier><language>eng</language><publisher>London, England: SAGE Publications</publisher><subject>Apoptosis ; Bridged Bicyclo Compounds - metabolism ; Humans ; Models, Molecular ; Molecular Biology - methods ; Molecular Dynamics Simulation ; Peptides - chemistry ; Peptides - metabolism ; Proline - analogs & derivatives ; Structure-Activity Relationship ; X-Linked Inhibitor of Apoptosis Protein - antagonists & inhibitors ; X-Linked Inhibitor of Apoptosis Protein - metabolism</subject><ispartof>Experimental biology and medicine (Maywood, N.J.), 2011-02, Vol.236 (2), p.247-251</ispartof><rights>2011 by the Society for Experimental Biology and Medicine</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c333t-4ca0f85e244e0943b1c0fe99f485db8423467af91dcbc1131ff5258361f3262d3</citedby><cites>FETCH-LOGICAL-c333t-4ca0f85e244e0943b1c0fe99f485db8423467af91dcbc1131ff5258361f3262d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21321323$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, Qi</creatorcontrib><creatorcontrib>Nie, Aihua</creatorcontrib><creatorcontrib>Welsh, Kate</creatorcontrib><creatorcontrib>Pinacho Crisóstomo, Fernando R</creatorcontrib><creatorcontrib>Zhu, Xuejun</creatorcontrib><creatorcontrib>Li, Zhengxiang</creatorcontrib><creatorcontrib>An, Jing</creatorcontrib><creatorcontrib>Reed, John C</creatorcontrib><creatorcontrib>Zhang, Liangren</creatorcontrib><creatorcontrib>Huang, Ziwei</creatorcontrib><title>Novel X-linked inhibitor of apoptosis protein inhibitors as probes of apoptosis in biology and medicine</title><title>Experimental biology and medicine (Maywood, N.J.)</title><addtitle>Exp Biol Med (Maywood)</addtitle><description>We report here a series of new inhibitors of the X-linked inhibitor of apoptosis protein (XIAP protein) based on the SMAC-tetrapeptide AVPI. The structural novelty of these molecules is the presence of the proline mimetic exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, leading to analogs with similar activity to the natural ligand peptide. The structure–activity relationship and computational docking studies support the convenience of this unnatural amino acid as a building block to develop new peptides or small molecules targeting the XIAP-BIR3 domain.</description><subject>Apoptosis</subject><subject>Bridged Bicyclo Compounds - metabolism</subject><subject>Humans</subject><subject>Models, Molecular</subject><subject>Molecular Biology - methods</subject><subject>Molecular Dynamics Simulation</subject><subject>Peptides - chemistry</subject><subject>Peptides - metabolism</subject><subject>Proline - analogs & derivatives</subject><subject>Structure-Activity Relationship</subject><subject>X-Linked Inhibitor of Apoptosis Protein - antagonists & inhibitors</subject><subject>X-Linked Inhibitor of Apoptosis Protein - metabolism</subject><issn>1535-3702</issn><issn>1535-3699</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kEtLAzEURoMotlbX7iQ7N06b5zyWUnxB0Y2Cu5Bkkpo6M6mTGaH_3tRpFRdCQl7nfuQeAM4xmmLC85lR9ZSgeIqT5OwAjDGnPKFpURzu9xkiI3ASwgohzDOSHoMRwXQ76BgsH_2nqeBrUrnm3ZTQNW9Ouc630Fso137d-eACXLe-M675fQ5Qft8qE_6SEVLOV365gbIpYW1Kp11jTsGRlVUwZ7t1Al5ub57n98ni6e5hfr1INKW0S5iWyObcEMYMKhhVWCNrisKynJcqZ4SyNJO2wKVWGmOKreXRA02xpSQlJZ2AyyE3_u2jN6ETtQvaVJVsjO-DyDkuKGc4i-RsIHXrQ2iNFevW1bLdCIzEVq6IcsVWrhjkxoqLXXavYl8__N5mBK4GIMilESvft03s9d-8Lwbqg74</recordid><startdate>201102</startdate><enddate>201102</enddate><creator>Hu, Qi</creator><creator>Nie, Aihua</creator><creator>Welsh, Kate</creator><creator>Pinacho Crisóstomo, Fernando R</creator><creator>Zhu, Xuejun</creator><creator>Li, Zhengxiang</creator><creator>An, Jing</creator><creator>Reed, John C</creator><creator>Zhang, Liangren</creator><creator>Huang, Ziwei</creator><general>SAGE Publications</general><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>201102</creationdate><title>Novel X-linked inhibitor of apoptosis protein inhibitors as probes of apoptosis in biology and medicine</title><author>Hu, Qi ; Nie, Aihua ; Welsh, Kate ; Pinacho Crisóstomo, Fernando R ; Zhu, Xuejun ; Li, Zhengxiang ; An, Jing ; Reed, John C ; Zhang, Liangren ; Huang, Ziwei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c333t-4ca0f85e244e0943b1c0fe99f485db8423467af91dcbc1131ff5258361f3262d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Apoptosis</topic><topic>Bridged Bicyclo Compounds - metabolism</topic><topic>Humans</topic><topic>Models, Molecular</topic><topic>Molecular Biology - methods</topic><topic>Molecular Dynamics Simulation</topic><topic>Peptides - chemistry</topic><topic>Peptides - metabolism</topic><topic>Proline - analogs & derivatives</topic><topic>Structure-Activity Relationship</topic><topic>X-Linked Inhibitor of Apoptosis Protein - antagonists & inhibitors</topic><topic>X-Linked Inhibitor of Apoptosis Protein - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Qi</creatorcontrib><creatorcontrib>Nie, Aihua</creatorcontrib><creatorcontrib>Welsh, Kate</creatorcontrib><creatorcontrib>Pinacho Crisóstomo, Fernando R</creatorcontrib><creatorcontrib>Zhu, Xuejun</creatorcontrib><creatorcontrib>Li, Zhengxiang</creatorcontrib><creatorcontrib>An, Jing</creatorcontrib><creatorcontrib>Reed, John C</creatorcontrib><creatorcontrib>Zhang, Liangren</creatorcontrib><creatorcontrib>Huang, Ziwei</creatorcontrib><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>Experimental biology and medicine (Maywood, N.J.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Qi</au><au>Nie, Aihua</au><au>Welsh, Kate</au><au>Pinacho Crisóstomo, Fernando R</au><au>Zhu, Xuejun</au><au>Li, Zhengxiang</au><au>An, Jing</au><au>Reed, John C</au><au>Zhang, Liangren</au><au>Huang, Ziwei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel X-linked inhibitor of apoptosis protein inhibitors as probes of apoptosis in biology and medicine</atitle><jtitle>Experimental biology and medicine (Maywood, N.J.)</jtitle><addtitle>Exp Biol Med (Maywood)</addtitle><date>2011-02</date><risdate>2011</risdate><volume>236</volume><issue>2</issue><spage>247</spage><epage>251</epage><pages>247-251</pages><issn>1535-3702</issn><eissn>1535-3699</eissn><abstract>We report here a series of new inhibitors of the X-linked inhibitor of apoptosis protein (XIAP protein) based on the SMAC-tetrapeptide AVPI. The structural novelty of these molecules is the presence of the proline mimetic exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, leading to analogs with similar activity to the natural ligand peptide. The structure–activity relationship and computational docking studies support the convenience of this unnatural amino acid as a building block to develop new peptides or small molecules targeting the XIAP-BIR3 domain.</abstract><cop>London, England</cop><pub>SAGE Publications</pub><pmid>21321323</pmid><doi>10.1258/ebm.2010.010284</doi><tpages>5</tpages></addata></record> |
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| ispartof | Experimental biology and medicine (Maywood, N.J.), 2011-02, Vol.236 (2), p.247-251 |
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| language | eng |
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| source | MEDLINE; EZB Electronic Journals Library |
| subjects | Apoptosis Bridged Bicyclo Compounds - metabolism Humans Models, Molecular Molecular Biology - methods Molecular Dynamics Simulation Peptides - chemistry Peptides - metabolism Proline - analogs & derivatives Structure-Activity Relationship X-Linked Inhibitor of Apoptosis Protein - antagonists & inhibitors X-Linked Inhibitor of Apoptosis Protein - metabolism |
| title | Novel X-linked inhibitor of apoptosis protein inhibitors as probes of apoptosis in biology and medicine |
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